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Multicomponent Reaction
Multicomponent Reaction
Multicomponent Reaction
Multicomponent reaction (MCR) is a synthetic methodology In 1891, an Italian chemist, P. Biginelli has reported the three-
in which three or more reactants come together in a single component MCR using b-keto esters such as ethyl acetoacetate
reaction vessel to form a new product. The characteristic aspect (A0649), aromatic aldehydes such as benzaldehyde (B2379),
of MCRs is that the final products contain almost all portions of and ureas (or thioureas) in the presence of acid catalyst
substrates, generating almost no by-products. That makes (Brönsted or Lewis acids), affording dihydropyrimidinone
MCRs an extremely ideal and eco-friendly reaction system. derivaties.4) Dihydropyrimidinones have been paid much
Target compounds can be obtained in one pot with much fewer attention because of their various bioactivities such as anti-
steps. Therefore, MCRs have been paid much attention in inflammatory or anti-bacterial activities. For an example of
various research fields, such as discovery of lead compounds in pharmaceuticals developed by using the reaction, several anti-
medicinal chemistry, or combinatorial chemistry. tubercular agents have been reported as below.5)
There have been a number of reports on MCRs so far, and Examples of Anti-tubercular Agents using Biginelli Reaction
typical examples are described as below.
NO2
1. Strecker reaction N N
(Three-component reaction: 3CR) O
F N NH
EtO2C H
NH
N O
Strecker Reaction (Amino Acid Synthesis) N O H
H
R H R CN R COOH
4. Passerini reaction (3CR)
2. Hantzsch dihydropyridine synthesis (3CR) In 1921, an Italian chemist, M. Passerini et al. have reported
the three-component reaction using carboxylic acids, aldehydes,
and isonitriles, affording a-acyloxy amides.6) The Passerini
Hantzsch Dihydropyridine Synthesis
O O R3 O reaction also has been applied into pharmaceutical research, for
O
2 R O
2
+ + NH3
R2O OR2 example, Hulme et al. have reported the library synthesis of
R3 H
R1 O R1 N
H
R1 novel norstatine derivatives bearing benzimidazole moieties.7)
NHBoc
This reaction was reported by A. R. Hantzsch in 1881, and is BocHN R2 CN
BocHN
O
R2
NHBoc
H
R1 COOH + + N
the best-known three-component MCR, which affords CHO CH2Cl2, rt, 18 h R1 O
O
1,4-dihydropyridine derivatives using b-keto esters, aldehydes,
Passerini Products
and ammonia.2) For an example, a calcium channel blocker,
H2N R2
3) O NH2 Acyl Migration
Nifedipine , is also synthesized by this reaction. H
N
R1 O
10% TFA / CH2Cl2, Et3N / MeOH (1 : 3),
rt, 24 h O rt, 2 h
R1 O
CHO NO2 HN R2 R2 N
O
MeO2C + + NH3 MeO2C CO2Me H
NH2
R1 N N
N 10% TFA / DCE,
O NO2 HO H H
MW, 100°C, 20 min OH
N O
H
Nifedipine
Biginelli reaction
CH3
O R3 Ph Ph
O O CH3 N O N O N
R3 X H+ N HN
R2O NR4 N N N N N N
2
R O + + R 4
N N
R5 H
OH
H H
OH
H H
OH
H
H O
1
H H R1 N5 X
R O (X = O or S) R
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Multicomponent reaction (MCR)
OMOM OMe
BnO Me
8) Me
5. Gröbcke-Blackburn-Bienaymé reaction CH3 CHO + NH2 + MeO NC + I
(3CR)
O
BocHN MeOH, reflux
O
OTBDPS
CO2H
OMe OMe
Gröbcke-Blackburn-Bienaymé Reaction HO Me
Me OBn
R3 MeO
OAc
NH H
I Me
H+ OMOM NH
NHBoc
N Me
N N S N
R1 + R2 CHO + R3 NC R1 R2 Me CH3
O O
NH2 N N O H OH
O O
O O O
TBDPSO MeO
NH
This reaction is a three-component MCR using aldehydes, Ugi Products (Y. 90%) HO
O O HN
R2 of its easy-handling property, TosMIC has been widely used for
OR3 O
+ R2 NH2 + H P OR3 the synthesis of nitrogen-containing aromatic heterocyclic
R1 H OR3 R1 P
OR3
compounds, such as oxazoles.14) TosMIC also has been used
for MCRs, for example, Tsoleridis et al. have reported the
In 1952, M. I. Kabachinik et al. have reported the three- synthesis of quinoxaline derivatives via the three-component
component MCR using aldehydes, amines, and dialkyl condensation of o-phenylenediamines, aromatic aldehydes and
phosphites in the presence of acid catalyst (Brønsted or Lewis TosMIC.15)
9)
acids), affording a-aminophosphonates. In recent years, much
attention has been paid to a-aminophoshonates since they can R1 NH2 O
be considered as structural analogues of the corresponding + ArCHO + CH3 S CH2NC
a-amino acids and transition state mimics of peptide hydrolysis. R2 NH2 O
T1046 (TosMIC)
Thus, a-aminophoshonates have been applied into several
research areas, such as development of renin inhibitors or HIV
Base R1 N Ar
protease inhibitors.10)
Toluene, reflux, 4 h R2 N
1 H H phenyl DABCO 91
2 H H 2,4-dimethylphenyl DABCO 81
Ugi Reaction
O R2 3 4-chlorophenyl DABCO 84
O H H
R3 N R4
R1 H
+ R2 NH2 + R3 NC + R4 COOH N
4 Me Me phenyl DBU 86
H
R1 O
5 Me Me 2-methylphenyl DBU 85
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Multicomponent reaction (MCR)
point of view, thus, the reaction above is an extremely useful and Ionic liquids can be generally recovered and recycled, which
eco-friendly MCR. can help to reduce the waste of traditional solvents which are
rarely reused. In addition, ionic liquids have attracted much
KF Me attention as excellent solvents due to their low volatility. Judging
TMS 18-Crown-6 N Ar
NMe
R + + CO2 R from these points, this reaction can be regarded as a more eco-
Ar H O
OTf THF, 0 °C
O
friendly reaction example.
Benzyne Precursor
Ar = 2,4,6-trimethyphenyl
OMe
Me
TMS N Ar
46
OTf
O References
OMe O (Y. 73%)
1) A. Strecker, Ann. 1850, 75, 27.
Me
TMS N Ar 2) A. Hantzsch, Ber. 1881, 14, 1637.
60
O
OTf 3) R. Alajarin, J. J. Vaquero, J. L. G. Navio, J. A-Builla, Synlett 1992, 297; R. Alajarin,
O (Y. 44%)
P. Jordan, J. J. Vaquero , J. A-Builla, Synthesis, 1995, 389; B. M. Khadilkar, A. A.
Chitnavis, Ind. J. Chem. 1995, 34B, 652; B. M. Khadilkar, V. G. Gaikar, A. A.
Thus, MCR is a strong synthetic methodology to enable Chitnavis, Tetrahedron Lett. 1995, 36, 8083.
condensation of various substrates in one pot, however, in some 4) P. Biginelli, Ber. 1891, 24, 1317; P. Biginelli, Ber. 1891, 24, 2962.
cases, reactions require long times for completion or result in 5) A. R. Trivedi, V. R. Bhuva, B. H. Dholariya, D. K. Dodiya, V. B. Kataria, V. H.
undesired side reactions even after optimization of reaction Shah, Bioorg. Med. Chem. Lett. 2010, 20, 6100; V. Virsodia, R. R. S. Pissurlenkar,
conditions such as solvents or Lewis acid catalysts. For resolving D. Manvar; C. Dholakia, P. Adlakha, A. Shah, E. Coutinho, Eur. J. Med. Chem.
these problems, there have been some successful reports on 2008, 43, 2103
accelerating MCRs. For example, Shaabani et al. have reported 6) M. Passerini, Gazz. Chim. Ital. 1921, 51, 181.
the ionic liquid promoted Gröbcke-Blackburn-Bienaymé 7) A. Y. Shaw, F. Medda, C. Hulme, Tetrahedron Lett. 2012, 53, 1313.
17)
reaction. As indicated in the table below, in the case of using 8) K. Gröbke, L. Weber, F. Mehlin, Synlett, 1998, 661; C. Blackburn, B. Guan, K.
ionic liquids as solvents, reactions proceed smoothly to afford Shiosaki, S. Tsai, Tetrahedron Lett. 1998, 39, 3635; H. Bienaymé, K. Bouzid,
the desired products in excellent yields. On the other hand, the Angew. Chem. 1998, 110, 2349; H. Bienaymé, K. Bouzid, Angew. Chem. Int. Ed.
yield of product is poor even in the prolonged reaction time 1998, 39, 2234.
(Entry 2 ). Moreover, as indicated in Entry 1, the ionic liquid can 9) M. I. Kabachnik, T. Y. Medved, Dokiady Akademii Nauk SSSR, 1952, 83, 689; E.
be reused for the same reactions, maintaining the high yields. K. Fields, J. Am. Chem. Soc. 1952, 74, 1528.
10) S. Shibuya, YAKUGAKU ZASSHI 2004, 124, 725; M. C. Allen, W. Fuhrer, B. Tuck,
R. Wade, J. M. Wood, J. Med. Chem. 1989, 32, 1652; M. K. Manthey, D. T. C.
R1
N [bmim]Br HN
+ R2 CHO + NC R1
Huang, W. A. Bubb, R. I. Christpherson, J. Med. Chem. 1998, 41, 4550.
NH2 rt, 3 h N
R2 11) I. Ugi, Angew. Chem. Int. Ed. 1962, 1, 8.
N
CH3
N 12) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem.
Br
[bmim]Br = N Soc. 2002, 124, 6552.
(CH2)3CH3
13) A. M. V. Leusen, Org. Synth. 1977, 57, 102.
Entry R1 R2 Yield (%) 14) O. Possel, A. M. V. Leusen, Heterocycles, 1977, 7, 77; A. M. V. Leusen, O. H.
1 Br Ph 98 (95, 92, 90, 85)a Oldenziel, Tetrahedron Lett. 1972, 23, 2373.
2 Me Ph 98 15) C. Neochoritis, J. Stephanidou-Stephanatou, C. A. Tsoleridis, Synlett 2009,
2'b Me Ph 25 302.
3 Me 4-CH3C6H4 99 16) H. Yoshida, H. Fukushima, J. Ohshita, A. Kunai, J. Am. Chem. Soc. 2006, 128,
4 Me 4-O2NC6H4 92 11040.
5 Me 4-Pyridyl 97 17) A. Shaabani, E. Soleimani, A. Maleki, Tetrahedron Lett. 2006, 47, 3031.
a
The same ionic liquid is used for each of the five runs.
b
Ionic liquid is not used. Reaction time is 12 h.
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The list of products
We introduce our products according to their structure and applications.
Thioureas・・・・・・・・・・・・・・ 11
A0479 25g 100g 500g A0478 25mL 100mL 500mL A0480 25mL 500mL
O O O
C H C H C H
Aldehydes OCH3
OCH3
OCH3
o-Anisaldehyde [135-02-4] m-Anisaldehyde [591-31-1] p-Anisaldehyde [123-11-5]
B2379 500g B0836 25g 100g 500g B0548 25g 100g 500g B0549 25g 250g C0561 25g 500g
O O O O O
C H C H C H C H C H
Br Cl
Br
Br
2-Bromobenzaldehyde 3-Bromobenzaldehyde 4-Bromobenzaldehyde 2-Chlorobenzaldehyde
Benzaldehyde [100-52-7] [6630-33-7] [3132-99-8] [1122-91-4] [89-98-5]
C0124 25g 100g 500g C0125 25g 100g 500g C1465 1g 5g C0352 25mL 500mL C0443 5g 25g
O O O O
C H C H C H O C H
Cl
H
Cl
Cl F CN
3-Chlorobenzaldehyde 4-Chlorobenzaldehyde 2-Chloro-4-fluoro- trans-Cinnamaldehyde 4-Cyanobenzaldehyde
[587-04-2] [104-88-1] benzaldehyde [84194-36-5] [14371-10-9] [105-07-7]
C0880 25mL 100mL D1666 25g 500g D0564 25g 100g 500g B2019 1g 5g F0073 25g 500g
O O O
C H C H C H O
Cl OH H C O
O
O C H
Cl O
OH
Cyclohexanecarboxaldehyde 2,3-Dichlorobenzaldehyde 2,4-Dihydroxybenzaldehyde 3,4-Ethylenedioxybenzaldehyde
[2043-61-0] [6334-18-5] [95-01-2] [29668-44-8] Furfural [98-01-1]
H0197 25g 100g 500g H0198 25g 100g 500g I0101 25mL 500mL I0153 25g 250g N0002 25mL 100mL 500mL
O O O O
C H C H C H C H
O
CH3
H O
OH CH3 C H
OH
3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde Isobutyraldehyde Isophthalaldehyde 1-Naphthaldehyde
[100-83-4] [123-08-0] [78-84-2] [626-19-7] [66-77-3]
N0003 5g 25g N0130 25g 100g 500g N0129 25g 500g N0559 25g 100g 500g P0746 5g 25g
O O O O
O C H C H C H C H
C H NO2 F F
NO2 F F
NO2 F
2-Naphthaldehyde 2-Nitrobenzaldehyde 3-Nitrobenzaldehyde 4-Nitrobenzaldehyde Pentafluorobenzaldehyde
[66-99-9] [552-89-6] [99-61-6] [555-16-8] [653-37-2]
B0242 5g 25g 250g P0456 25g 500g P0847 5mL 25mL P0425 25g 100g 500g N0090 25mL 100mL 500mL
O O
O H C H3C O C H
O
C H H3C C C H O
O H3C N C H N
O
S C H
N
C H CH3 CH3
4-Pyridinecarboxaldehyde O 2-Thiophenecarboxaldehyde
[872-85-5] Terephthalaldehyde [623-27-8] (stabilized with HQ) [98-03-3] p-Tolualdehyde [104-87-0] p-Tolualdehyde [104-87-0]
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Multicomponent reaction (MCR)
T1281 25g T1091 5g 25g 250g T2651 5g 25g T1368 25mL O0453 200mg 1g
O O O O
O
C H C H C H C H
H C
CF3 CH3O OCH3 CH3 CH3 N
CH3O OCH3
OCH3
3,4,5-Trimethoxybenzaldehyde
[86-81-7]
A0219 25mL 500mL A0850 5g 25g A0989 5g 25g
Amines
N
CH2
NH2
N NH2 N NH2
H
2-Aminobenzimidazole 2-Aminopyrazine
Allylamine [107-11-9] [934-32-7] [5049-61-6]
A1859 5g 25g A0411 25g 100g 500g A0412 25g A1060 5g 25g A0633 25g 100g 500g
NH2
N N N
N
N
N S NH2 S NH2
H N NH2 N NH2
3-Amino-1,2,4-triazole
[61-82-5] Amylamine [110-58-7] Aniline [62-53-3] Benzylamine [100-46-9] 2-Bromoaniline [615-36-1]
B0709 25mL 100mL 500mL B0707 25mL 500mL C0494 25mL 500mL C0887 25mL 500mL F0091 25mL 100mL 500mL
NH2
CH3
CH3 C NH2 CH3 NH2
O CH2NH2
CH3 NH2
tert-Butylamine [75-64-9] Butylamine [109-73-9] Cyclohexylamine [108-91-8] Cyclopentylamine [1003-03-8] Furfurylamine [617-89-0]
I0095 25mL 500mL I0165 25mL 500mL P0085 25mL 100mL 500mL A1161 25g 250g P0911 5mL 25mL
CH3 CH3
NH2 HC CCH2NH2
CH3 CH3 NH2 NH2
N CH2NH2
Isobutylamine [78-81-9] Isopropylamine [75-31-0] 2-Phenylethylamine [64-04-0] 2-Picolylamine [3731-51-9] Propargylamine [2450-71-7]
D4736 5g 25g M2726 1mL 5mL P0168 25g 100g 500g
NH2 NH2
I I NH2
CH2
NH2
CH3
NO2
2,6-Diiodo-4-nitroaniline 2-Methylallylamine 1,2-Phenylenediamine
[5398-27-6] [2878-14-0] [95-54-5]
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Multicomponent reaction (MCR)
CF3
4-(Trifluoromethyl)-
benzoic Acid [455-24-3]
A1981 25g 500g A0811 25mL 500mL A1080 25mL 100mL 500mL
b - Keto Esters
O O O O O O
CH2 CH3
CH3 O CH3 O CH3 O
O O CH3 O O O O O O O O O
CH3 CH3 O
CH3 CH3 O O CH3
CH3 O CH3 OC(CH3)3 CH3 O CH3 O
O
sec-Butyl Acetoacetate tert-Butyl Acetoacetate Butyl Acetoacetate Diethyl Oxalacetate Diethyl 3-Oxopimelate
[13562-76-0] [1694-31-1] [591-60-6] [108-56-5] [40420-22-2]
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Multicomponent reaction (MCR)
A0649 25g 500g B0097 25g 100g 500g C0911 25g 500g E0811 5g 25g D1891 5mL 25mL
O O
O O O O O O F O O
O CH3
Cl
CH3 O CH3 O CH3 O CH3 (CH3)3C O CH3
Cl N Cl
Ethyl 3-(2,6-Dichloro-
Ethyl Acetoacetate Ethyl Benzoylacetate Ethyl 4-Chloroacetoacetate 5-fluoro-3-pyridyl)-3- Ethyl 4,4-Dimethyl-3-
[141-97-9] [94-02-0] [638-07-3] oxopropionate [96568-04-6] oxovalerate [17094-34-7]
E0489 25g 500g F0435 1g 5g 25g E0882 5g 25g E0484 5g 25g M1380 25g
CH2 O O
O O O O O O O O O
CH3 O CH3
CH3
O O CH3 O CH3 O CH3
CH3 O Cl
Ethylene Glycol CH3
Monoacetoacetate F CH3O
Monomethacrylate (stabilized Ethyl (4-Fluorobenzoyl)- Ethyl Isobutyrylacetate Ethyl Malonyl Chloride Ethyl 4-Methoxybenzoyl-
with BHT) [21282-97-3] acetate [1999-00-4] [7152-15-0] [36239-09-5] acetate [2881-83-6]
N0513 5g 25g O0216 10g 25g K0030 25mL 500mL K0031 5g 25g P1062 5g
O O O O O O O O O O
O CH3
CH3 CH3
O CH3 CH3 O CH3 O CH3 CF3CF2 O CH3
O2N
Ethyl 4-Nitrobenzoylacetate Ethyl 3-Oxoheptanoate Ethyl 3-Oxohexanoate Ethyl 3-Oxovalerate Ethyl 4,4,5,5,5-Pentafluoro-
[838-57-3] [7737-62-4] [3249-68-1] [4949-44-4] 3-oxovalerate [663-35-4]
E0759 25g T1285 10g 25g T0810 25g 100g 500g A0916 25mL A0913 25mL
F O O
F O O O O O O
O O
O CH3
CH3
CF3 O CH3 CH3 O CH3 O CH3
F
Cl3C O CH3
F Ethyl Ethyl
Ethyl (2,3,4,5-Tetrafluoro- 4,4,4-Trichloroacetoacetate 4,4,4-Trifluoroacetoacetate Heptyl Acetoacetate Hexyl Acetoacetate
benzoyl)acetate [94695-50-8] [3702-98-5] [372-31-6] [42598-96-9] [13562-84-0]
A0812 25mL 500mL A0814 25mL I0826 25g 500g T1530 25g M0799 25g 100g 500g
O O O O O O O O
O O
OCH3
CH3 O OCH3 CH3O Cl CH3 O CH3 O CH3
NO2
2-Methoxyethyl Methyl 3-Cyclopropyl-3- Methyl Malonyl Chloride 4-Nitrobenzyl n-Octyl Acetoacetate
Acetoacetate [22502-03-0] oxopropionate [32249-35-7] [37517-81-0] Acetoacetate [61312-84-3] [16436-00-3]
A0813 25mL A0817 25mL 500mL E1018 5g 25g E1059 1g 5g E1071 1g 5g
CH3
O O O O O O O O O O
CH3 CH3 F
CH3 O CH3 O O CH3 O CH3 O CH3
CH3
F Cl
3-Pentyl Acetoacetate Propyl Acetoacetate Ethyl 4,4-Difluoro- Ethyl 3-Oxo-3-(4-chlorophenyl)- Ethyl 2-Benzoylpropionate
[13562-81-7] [1779-60-8] acetoacetate [352-24-9] propionate [2881-63-2] [10488-87-6]
E1073 200mg 1g E1080 200mg 1g E1097 5g 25g E1117 1g 5g E1120 1g
O O
O O F O O O O O O
O CH3
S O CH3 O CH3
O CH3 O CH3
NC
Ethyl 3-(4-Cyanophenyl)- Br OCH3
Ethyl 3-Oxo-3-(2-thienyl)- 3-oxopropionate Ethyl (2-Fluorobenzoyl)- Ethyl (4-Bromobenzoyl)- Ethyl (2-Methoxybenzoyl)-
propionate [13669-10-8] [49744-93-6] acetate [1479-24-9] acetate [26510-95-2] acetate [41607-95-8]
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Multicomponent reaction (MCR)
O O
O O CH3 O O F O2N
O CH3 O O O O
CH3O
OCH2CH3 O CH3
N CH3 N CH3
H H
Ethyl 3-Cyclohexyl-
Ethyl (3-Methoxybenzoyl)- Ethyl (2-Methylbenzoyl)- 3-oxopropionate 2'-Fluoroacetoacetanilide 4'-Nitroacetoacetanilide
acetate [27834-99-7] acetate [51725-82-7] [15971-92-3] [5279-85-6] [4835-39-6]
O0444 200mg 1g R0165 5g 25g T1245 5g 25g
CF3 O O O
O O
CH3
O CH3 CF3 OCH3
N CH3
H O O
4'-(Trifluoromethyl)- Ethyl 2,4-Dioxovalerate Methyl 4,4,4-Trifluoro-
acetoacetanilide [351-87-1] [615-79-2] acetoacetate [83643-84-9]
B2185 1g 5g B1274 5mL 25mL C1438 1g 5g
CH2NC NC
CH3
Isonitriles CH3 C NC
CH3
Benzyl Isocyanide tert-Butyl Isocyanide Cyclohexyl Isocyanide
[10340-91-7] [7188-38-7] [931-53-3]
I0562 5g 25g I0824 1g 5g I0455 1g 5g T1054 1mL 5mL T1046 5g 25g
NC
O N CH3 CH3 O
CN N CH3 C CH2 C NC CH3 S CH2NC
O CH3 N
CH3 CH3 O
CH2NC p-Toluenesulfonylmethyl
Ethyl Isocyanoacetate 1-Isocyanoadamantane 1-(Isocyanomethyl)-1H- 1,1,3,3-Tetramethylbutyl Isocyanide
[2999-46-4] [22110-53-8] benzotriazole [87022-42-2] Isocyanide [14542-93-9] (= TosMIC) [36635-61-7]
C2959 1g N0982 200mg 1g T3157 1g 5g
NC
CN O
S CH3
O
NC
NO2
Cyclopentyl Isocyanide 4-Nitrophenyl Isocyanide α-Tosylbenzyl Isocyanide
[68498-54-4] [1984-23-2] [36635-66-2]
A0101 25g A0124 25g A0237 25g 250g
O O O O O
Ureas CH3 N N
CH3
CH3 N NH2
CH2
N NH2
H H H H
1-Acetyl-3-methylurea
[623-59-6] Acetylurea [591-07-1] Allylurea [557-11-9]
B0449 25g D0767 25g 500g B1103 25g B2842 25g B2833 5g
O O O CH3 O O O
(CH3)3Si Si(CH3)3
N NH2 HO N N OH N N CH3 N NH2 N NH2
H H H H H
H H Br
Br
1,3-Bis(hydroxymethyl)- N,N'-Bis(trimethylsilyl)urea 1-(2-Bromoisovaleryl)urea (2-Bromophenyl)urea
Benzylurea [538-32-9] urea [140-95-4] [18297-63-7] [496-67-3] [13114-90-4]
B2834 5g 25g B1831 25g C0173 25g C1220 25g C2266 5g
Br
O O O O O
O O O O
Cl S CH3 S
N NH2 N N N NH2
CH3 N NH2 N NH2 H H H
H H H
Cl Cl
(4-Bromophenyl)urea 2-Chloroethylurea 1-(4-Chlorophenylsulfonyl)- (4-Chlorophenylsulfonyl)-
[1967-25-5] Butylurea [592-31-4] [6296-42-0] 3-propylurea [94-20-2] urea [22663-37-2]
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Multicomponent reaction (MCR)
C0926 5g 25g C1101 25g 250g C2034 25g C2657 5g 25g D0441 25g 500g
O N O O O O O O
NC NOCH3
N N Cl N NH2 N NH2 CH3 N N N N
H H H H H H H H
CN
O O O O O
H
CH3 CH3 H2N N
CH3 N N CH3 N N N N CH3 N NH2 OH
H H H H H H H
O
1,3-Diethylurea [623-76-7] 1,3-Dimethylurea [96-31-1] 1,3-Diphenylurea [102-07-8] Ethylurea [625-52-5] Hydantoic Acid [462-60-2]
H0700 25g H0438 25g I0665 25g 250g M0455 25g 500g N0328 5g
O O H H H H O O
HOCH2 N N N N CH2OH
N N
HO O O O2N
N NH2 HO N NH2 O N
H
O O N
H
O H2N NHCH3 N NH2
H H H
O O O
O S CH3 Cl Cl
N NH2 O O O
H
CH3(CH2)17
N NH2 CH3 N NH2 N NH2 N N Cl
H H H H
H CH3
N-Octadecylurea p-Toluenesulfonylurea 3,4,4'-Trichlorocarbanilide
[2158-08-9] [1694-06-0] o-Tolylurea [614-77-7] p-Tolylurea [622-51-5] [101-20-2]
U0048 25mL T1915 25g 250g U0073 300g B4483 1g 5g B4517 1g 5g
O OCH2CH3 O OCH3 O F F
CH3O OCH3 O
H2N C NH(CH2)3 Si OCH2CH3 H2N C NH(CH2)3 Si OCH3 O
H2N NH2
OCH2CH3 OCH3 N N N N
H H H H
1-[3-(Triethoxysilyl)propyl]-
urea (40-52% in Methanol) 1-[3-(Trimethoxysilyl)- 1,3-Bis(4-methoxyphenyl)- 1,3-Bis(4-fluorophenyl)-
[23779-32-0] propyl]urea [23843-64-3] Urea [57-13-6] urea [1227-44-7] urea [370-22-9]
B4518 200mg 1g B4529 1g 5g E1171 200mg 1g F0950 1g 5g M2575 1g 5g
O2N
O O
N NH2 C N NH2
H HC H
(4-Nitrophenyl)urea
[556-10-5] 2-Propynylurea [5221-62-5]
A0117 25g A1403 5g A0230 25g 500g
S
NH C NH2
S
Thioureas
O S
CH2 OH
CH3 N NH2 N N
H H H
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Multicomponent reaction (MCR)
A0220 25g 100g 500g B0802 25g B3452 200mg 1g D0301 25g 500g D0440 5g 25g
CF3 CF3
S O S
S S S
CH2
N NH2 N NH2 CF3 N N CF3 H3C N N CH3
H H H H H H N N
H H
1,3-Bis[3,5-
1-Allyl-2-thiourea N-Benzoylthiourea bis(trifluoromethyl)phenyl]- 1,3-Dibutylthiourea 1,3-Dicyclohexylthiourea
[109-57-9] [614-23-3] thiourea [1060-92-0] [109-46-6] [1212-29-9]
D0530 25g 500g D0253 25g D0652 10g D0804 25g 100g 500g T0197 25g 500g
CH3 CH3 F
S S S NH S NH S
. HCl
N N N N CH3 N N NH2 N NH2 H2N N NH2
H H H H H H H H
CH3 CH3
S HN NH2 S NH S S
CH3
N NH2 N N NH2 N NH2 H2N NH2
H H H H
CH3 Cl Cl Br
S S CH3O OCH3
S S S
N NH2 N NH2 N N N N
H H N NH2
H H H H H
CH3
CF3 CF3 S Cl
S S S S
CH2NH C NH2 N N
N N Br N NH2 N NH2
H H H H
H H
1,3-Bis[4-(trifluoromethyl)-
phenyl]thiourea 1-Benzyl-3-phenyl- (3-Bromophenyl)thiourea (4-Chlorophenyl)thiourea
[1744-07-6] Benzylthiourea [621-83-0] thiourea [726-25-0] [21327-14-0] [3696-23-9]
C2966 200mg 1g C3137 1g 5g C3168 1g 5g D4861 1g 5g D4958 5g 25g
F F F CH3
S S S S S
OCH3 O2N
S S S S S
OCH3 CH3
N NH2 H2N N H2N N N N N NH2
H H H H H H
F
(2-Fluorophenyl)thiourea (4-Methoxyphenyl)- (2-Methoxyethyl)thiourea 1-Methyl-3-phenyl- (4-Nitrophenyl)thiourea
[656-32-6] thiourea [2293-07-4] [102353-42-4] thiourea [2724-69-8] [3696-22-8]
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Multicomponent reaction (MCR)
S S
O
N N NH2 H2N N
H H
[(Tetrahydrofuran-2-yl)-
(2-Pyridyl)thiourea methyl]thiourea
[14294-11-2] [66892-25-9]
P1016 25g 250g D0300 25g D0521 25g 100g 500g
Dialkyl Phosphites
O O O
CH2O P OCH2 CH3(CH2)3O P O(CH2)3CH3 CH3CH2O P OCH2CH3
H H H
O O O O
CH3 CH3 CH3 CH3
CHCH2O P OCH2CH CHO P OCH CH3O P OCH3 O P O
CH3 CH3 CH3 CH3
H H H H
O O Cl
Diketone Compounds
O O
CH3 O O
C C C C
Br N CH3
H
O O
O O F O2N CF3
CH3 O O O O O O
C C F
F N CH3 N CH3 N CH3
H H H
(4-Fluorobenzoyl)acetone 2'-Fluoroacetoacetanilide 4'-Nitroacetoacetanilide 4'-(Trifluoromethyl)-
4-Fluorobenzil [3834-66-0] [29681-98-9] [5279-85-6] [4835-39-6] acetoacetanilide [351-87-1]
A2941 5g 25g A2943 1g B1566 25g 250g
O O Br O
Isatins N O N O N O
H
C CH3 CH2 CH CH2
O
1-Acetylisatin [574-17-4] 1-Allylisatin [830-74-0] 5-Bromoisatin [87-48-9]
B2423 5g 25g B2424 5g 25g B3974 1g 5g B4779 1g 5g C1870 5g 25g
Br Cl
O O O Br O O
N O Br N O N O N O N O
H H H H
Br CH3
5-Bromo-1-methylisatin
4-Bromoisatin [20780-72-7] 6-Bromoisatin [6326-79-0] 7-Bromoisatin [20780-74-9] [2058-72-2] 4-Chloroisatin [6344-05-4]
C1871 5g 25g C2840 1g 5g C3195 200mg 1g D4039 1g 5g F0551 5g 25g
Cl
O O Cl O O O
Cl N O N O N O N O N O
H H H H
Cl CH3 Cl F
5-Chloro-1-methylisatin 4,7-Dichloroisatin
6-Chloroisatin [6341-92-0] 7-Chloroisatin [7477-63-6] [60434-13-1] [18711-13-2] 7-Fluoroisatin [317-20-4]
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Multicomponent reaction (MCR)
F0589 5g 25g I0080 25g 100g 500g I0640 5g M1362 5g 25g M1703 5g 25g
F O O I O CH3O O CH3 O
N O N O N O N O N O
H H H H H
5-Methoxyisatin
5-Fluoroisatin [443-69-6] Isatin [91-56-5] 5-Iodoisatin [20780-76-1] [39755-95-8] 5-Methylisatin [608-05-9]
M2706 1g 5g M2856 1g 5g N0572 5g 25g P2279 5g 25g T2457 1g 5g
O
O O O2N O O
N O
N O CH3O N O N O N O
H H H
CH3 CF3
6-Methoxyisatin 7-(Trifluoromethyl)isatin
1-Methylisatin [2058-74-4] [52351-75-4] 5-Nitroisatin [611-09-6] 1-Phenylisatin [723-89-7] [391-12-8]
T2774 1g 5g
CF3O O
N O
H
5-(Trifluoromethoxy)isatin
[169037-23-4]
A1464 1g 5g B3047 1g D2503 5g 25g
O
(CH3)3Si Si(CH3)3
C O
. H2O
N
Benzyne Precursors N
N CF3O2SO OSO2CF3
I
NH2
3,3'-Bis(trimethylsilyl)biphenyl- Diphenyliodonium-
1-Aminobenzotriazole 4,4'-diyl Bis(trifluoromethane- 2-carboxylate Monohydrate
[1614-12-6] sulfonate) [828282-80-0] [96195-89-0]
M1884 1g 5g M1885 1g 5g M1883 1g 5g M1882 1g 5g P1620 1g 5g
OSO2CF3 OSO2CF3 OSO2CF3 OSO2CF3
Si(CH3)3 Si(CH3)3 (CH3)3Si CH3 Si(CH3)3 I OSO2CF3
Si(CH3)3
OCH3
OCH3 CH3
3-Methoxy-2-(trimethylsilyl)- 4-Methoxy-2-(trimethylsilyl)- 2-Methyl-6-(trimethylsilyl)- 4-Methyl-2-(trimethylsilyl)- Phenyl[2-(trimethylsilyl)phenyl]-
phenyl Trifluoromethane- phenyl Trifluoromethane- phenyl Trifluoromethane- phenyl Trifluoromethane- iodonium Trifluoromethane-
sulfonate [217813-03-1] sulfonate [556812-41-0] sulfonate [556812-44-3] sulfonate [262373-15-9] sulfonate [164594-13-2]
T2465 1g 5g T2466 1g 5g T2089 1g 5g 25g T2467 1g
OSO2CF3
Si(CH3)3 OSO2CF3 Si(CH3)3
(CH3)3Si
Si(CH3)3
CF3O2SO OSO2CF3
1-(Trimethylsilyl)-2- 3-(Trimethylsilyl)-2- 2-(Trimethylsilyl)phenyl Si(CH3)3
CH3O
OCH3
4,5-Dimethoxy-
2-(trimethylsilyl)phenyl
Triflate [866252-52-0]
B0527 25mL 100mL 500mL B3546 25g 250g I0778 5g 25g
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Multicomponent reaction (MCR)
T1293 5g 25g L0210 25g 100g 500g N0850 25g 500g R0074 1g 5g T1663 1g 5g
O O
CF3 S O La3 CF3 S O Sc3
O 3 LiBr NiCl2 RuCl3 O 3
Lanthanum(III) Scandium(III)
Trifluoromethanesulfonate Lithium Bromide Nickel(II) Chloride Anhydrous Ruthenium(III) Chloride Trifluoromethanesulfonate
[52093-26-2] [7550-35-8] [7718-54-9] [10049-08-8] [144026-79-9]
T2052 100m 500mL T3238 100mL 500mL T1610 5g 25g Z0014 25g 300g
O
CF3 S O Yb3
TiCl4 TiCl4 O 3 . xH2O ZnCl2
Ionic Liquids
Br Cl PF6
N N N
(CH2)3CH3 (CH2)3CH3 (CH2)3CH3
1-Butyl-3-methylimidazolium
1-Butyl-3-methylimidazolium 1-Butyl-3-methylimidazolium Hexafluorophosphate
Bromide [85100-77-2] Chloride [79917-90-1] [174501-64-5]
B2195 5g 25g 100g B2337 5g 25g T0054 25g 100g 500g T0055 5g 25g 100g T1124 25g 100g 500g
CH3 CH3
N N
(CH2)3CH3 (CH2)3CH3 (CH2)3CH3
CF3SO3
N BF4 N CH3(CH2)3 N (CH2)3CH3 Br CH3(CH2)3 N (CH2)3CH3 Cl CH3(CH2)3 P (CH2)3CH3 Br
1-Butyl-3-methylimidazolium 1-Butyl-3-methylimidazolium
Tetrafluoroborate Trifluoromethanesulfonate Tetrabutylammonium Tetrabutylammonium Tetrabutylphosphonium
[174501-65-6] [174899-66-2] Bromide [1643-19-2] Chloride [1112-67-0] Bromide [3115-68-2]
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R5109E 20161021