Trimethylgallium

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Names

IUPAC name

trimethylgallane, trimethanidogallium

Identifiers
CAS Number 1445-79-0

3D model Interactive image

(JSmol)

ChemSpider 14323

ECHA InfoCard 100.014.452

PubChem CID 15051

CompTox DTXSID2061696
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Properties
Chemical Ga(CH3)3
formula

Molar mass 114.827 g/mol

Appearance colourless liquid

Melting point −15 °C (5 °F; 258 K)

Boiling point 55.7 °C (132.3 °F; 328.8 K)

Solubility in Reacts with water

water

Hazards

Occupational safety and health (OHS/OSH):

Main hazards Pyrophoric (can ignite

spontaneously in air),
reacts with water to
release methane

Except where otherwise noted, data are given

for materials in their standard state (at 25 °C
[77 °F], 100 kPa).

verify (what is ?)
 Infobox references

Trimethylgallium, often abbreviated to TMG or TMGa, is the organogallium

compound with the formula Ga(CH3)3. It is a colorless, pyrophoric liquid.[1] Unlike
trimethylaluminium, TMG adopts a monomeric structure.[2] When examined in
detail, the monomeric units are clearly linked by multiple weak Ga---C
interactions, reminiscent of the situation for trimethylindium.[3]

Preparation[edit]

Two forms of TMG are typically investigated: Lewis base adducts or TMG itself.
All are prepared by reactions of gallium trichloride with various methylating
agents. When the methylation is conducted with methylmagnesium iodide in
diethyl ether, the product is the poorly volatile diethyl ether adduct. As noted by
TMG discoverers Kraus and Toonder in 1933, the ether ligand is not readily lost,
although it may be displaced with liquid ammonia. [4] When the alkylation is
conducted with methyl lithium in the presence of a tertiary phosphine the air-
stable phosphine adduct is obtained:

GaCl3 + 3 MeLi + PR3 → R3P−GaMe3 + 3 LiCl

Heating the solid phosphine adduct under vacuum liberates the base-free TMG: [1]

R3P−GaMe3 → R3P + GaMe3

Other non-volatile bases have been described.[5] Other methylating agents for the
synthesis of TMG include dimethylzinc and trimethylaluminium.

Applications[edit]

TMG is the preferred metalorganic source of gallium for metalorganic vapour

phase epitaxy (MOVPE) of gallium-containing compound semiconductors, such
as GaAs, GaN, GaP, GaSb, InGaAs, InGaN, AlGaInP, InGaP, AlInGaNP and Ga2O3.
[6]
These material are used in the production of LED lighting and semiconductors
as a metalorganic chemical vapor deposition precursor.

References[edit]

1. ^
2. Jump up to:
ab
3. Bradley, D. C.; Chudzynska, H. C.; Harding, I. S. (1997). "Trimethylindium and
Trimethylgallium". Inorganic Syntheses. Vol. 31. pp. 67–74.
doi:10.1002/9780470132623.ch8. ISBN 978-0-470-13262-3.
4. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.).
Butterworth-Heinemann. ISBN 978-0-08-037941-8.
5. ^ Mitzel, Norbert W.; Lustig, Christian; Berger, Raphael J. F.; Runeberg, Nino (2002).
"Luminescence Phenomena and Solid-State Structures of Trimethyl- and
Triethylgallium". Angewandte Chemie International Edition. 41 (14): 2519–2522.
doi:10.1002/1521-3773(20020715)41:14<2519::AID-ANIE2519>3.0.CO;2-2. PMID
12203520.
6. ^ Kraus, C. A.; Toonder, F. E. (1933). "Trimethyl Gallium, Trimethyl Gallium Etherate
and Trimethyl Gallium Ammine". PNAS. 19 (3): 292–8. Bibcode:1933PNAS...19..292K.
doi:10.1073/pnas.19.3.292. PMC 1085965. PMID 16577510.
7. ^ Foster, Douglas F.; Cole-Hamilton, David J. (1997). "Electronic Grade Alkyls of Group
12 and 13 Elements". Inorganic Syntheses. Vol. 31. p. 29-66.
doi:10.1002/9780470132623.ch7. ISBN 978-0-471-15288-0.
8. ^ Shenai-Khatkhate, D. V.; Goyette, R. J.; Dicarlo, R. L. Jr; Dripps, G. (2004).
"Environment, health and safety issues for sources used in MOVPE growth of
compound semiconductors". Journal of Crystal Growth. 272 (1–4): 816–21.
Bibcode:2004JCrGr.272..816S. doi:10.1016/j.jcrysgro.2004.09.007.

show

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Gallium compounds

Categories:

Chemical vapour deposition precursors

Gallium compounds
Methyl complexes
Pyrophoric materials
This page was last edited on 2 May 2024, at 09:06 (UTC).
 Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may
apply. By using this site, you agree to the Terms of Use and

Trimethylgallium
13 languages
Article
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From Wikipedia, the free encyclopedia

Names

IUPAC name
trimethylgallane, trimethanidogallium

Identifiers

CAS Number 1445-79-0

3D model Interactive image

(JSmol)

ChemSpider 14323

ECHA InfoCard 100.014.452

PubChem CID 15051

CompTox DTXSID2061696
Dashboard
(EPA)

show

InChI

show

SMILES

Properties
Chemical Ga(CH3)3
formula

Molar mass 114.827 g/mol

Appearance colourless liquid

Melting point −15 °C (5 °F; 258 K)

Boiling point 55.7 °C (132.3 °F; 328.8 K)

Solubility in Reacts with water

water

Hazards

Occupational safety and health (OHS/OSH):

Main hazards Pyrophoric (can ignite

spontaneously in air),
reacts with water to
release methane

Except where otherwise noted, data are given

for materials in their standard state (at 25 °C
[77 °F], 100 kPa).
 verify (what is ?)

Infobox references

Trimethylgallium, often abbreviated to TMG or TMGa, is the organogallium

compound with the formula Ga(CH3)3. It is a colorless, pyrophoric liquid.[1] Unlike
trimethylaluminium, TMG adopts a monomeric structure.[2] When examined in
detail, the monomeric units are clearly linked by multiple weak Ga---C
interactions, reminiscent of the situation for trimethylindium.[3]

Preparation[edit]

Two forms of TMG are typically investigated: Lewis base adducts or TMG itself.
All are prepared by reactions of gallium trichloride with various methylating
agents. When the methylation is conducted with methylmagnesium iodide in
diethyl ether, the product is the poorly volatile diethyl ether adduct. As noted by
TMG discoverers Kraus and Toonder in 1933, the ether ligand is not readily lost,
although it may be displaced with liquid ammonia. [4] When the alkylation is
conducted with methyl lithium in the presence of a tertiary phosphine the air-
stable phosphine adduct is obtained:

GaCl3 + 3 MeLi + PR3 → R3P−GaMe3 + 3 LiCl

Heating the solid phosphine adduct under vacuum liberates the base-free TMG: [1]

R3P−GaMe3 → R3P + GaMe3

Other non-volatile bases have been described.[5] Other methylating agents for the
synthesis of TMG include dimethylzinc and trimethylaluminium.

Applications[edit]

TMG is the preferred metalorganic source of gallium for metalorganic vapour

phase epitaxy (MOVPE) of gallium-containing compound semiconductors, such
as GaAs, GaN, GaP, GaSb, InGaAs, InGaN, AlGaInP, InGaP, AlInGaNP and Ga2O3.
[6]
These material are used in the production of LED lighting and semiconductors
as a metalorganic chemical vapor deposition precursor.

References[edit]

1. ^
2. Jump up to:
ab
3. Bradley, D. C.; Chudzynska, H. C.; Harding, I. S. (1997). "Trimethylindium and
Trimethylgallium". Inorganic Syntheses. Vol. 31. pp. 67–74.
doi:10.1002/9780470132623.ch8. ISBN 978-0-470-13262-3.
4. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.).
Butterworth-Heinemann. ISBN 978-0-08-037941-8.
5. ^ Mitzel, Norbert W.; Lustig, Christian; Berger, Raphael J. F.; Runeberg, Nino (2002).
"Luminescence Phenomena and Solid-State Structures of Trimethyl- and
Triethylgallium". Angewandte Chemie International Edition. 41 (14): 2519–2522.
doi:10.1002/1521-3773(20020715)41:14<2519::AID-ANIE2519>3.0.CO;2-2. PMID
12203520.
6. ^ Kraus, C. A.; Toonder, F. E. (1933). "Trimethyl Gallium, Trimethyl Gallium Etherate
and Trimethyl Gallium Ammine". PNAS. 19 (3): 292–8. Bibcode:1933PNAS...19..292K.
doi:10.1073/pnas.19.3.292. PMC 1085965. PMID 16577510.
7. ^ Foster, Douglas F.; Cole-Hamilton, David J. (1997). "Electronic Grade Alkyls of Group
12 and 13 Elements". Inorganic Syntheses. Vol. 31. p. 29-66.
doi:10.1002/9780470132623.ch7. ISBN 978-0-471-15288-0.
8. ^ Shenai-Khatkhate, D. V.; Goyette, R. J.; Dicarlo, R. L. Jr; Dripps, G. (2004).
"Environment, health and safety issues for sources used in MOVPE growth of
compound semiconductors". Journal of Crystal Growth. 272 (1–4): 816–21.
Bibcode:2004JCrGr.272..816S. doi:10.1016/j.jcrysgro.2004.09.007.

show

● V
● T
● E

Gallium compounds

Categories:

Chemical vapour deposition precursors

Gallium compounds
Methyl complexes
Pyrophoric materials
This page was last edited on 2 May 2024, at 09:06 (UTC).
 Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may
apply. By using this site, you agree to the Terms of Use and

Trimethylgallium
13 languages
Article
Talk
Read
Edit
View history
Tools
From Wikipedia, the free encyclopedia

Names

IUPAC name
trimethylgallane, trimethanidogallium

Identifiers

CAS Number 1445-79-0

3D model Interactive image

(JSmol)

ChemSpider 14323

ECHA InfoCard 100.014.452

PubChem CID 15051

CompTox DTXSID2061696
Dashboard
(EPA)

show

InChI

show

SMILES

Properties
Chemical Ga(CH3)3
formula

Molar mass 114.827 g/mol

Appearance colourless liquid

Melting point −15 °C (5 °F; 258 K)

Boiling point 55.7 °C (132.3 °F; 328.8 K)

Solubility in Reacts with water

water

Hazards

Occupational safety and health (OHS/OSH):

Main hazards Pyrophoric (can ignite

spontaneously in air),
reacts with water to
release methane

Except where otherwise noted, data are given

for materials in their standard state (at 25 °C
[77 °F], 100 kPa).
 verify (what is ?)

Infobox references

Trimethylgallium, often abbreviated to TMG or TMGa, is the organogallium

compound with the formula Ga(CH3)3. It is a colorless, pyrophoric liquid.[1] Unlike
trimethylaluminium, TMG adopts a monomeric structure.[2] When examined in
detail, the monomeric units are clearly linked by multiple weak Ga---C
interactions, reminiscent of the situation for trimethylindium.[3]

Preparation[edit]

Two forms of TMG are typically investigated: Lewis base adducts or TMG itself.
All are prepared by reactions of gallium trichloride with various methylating
agents. When the methylation is conducted with methylmagnesium iodide in
diethyl ether, the product is the poorly volatile diethyl ether adduct. As noted by
TMG discoverers Kraus and Toonder in 1933, the ether ligand is not readily lost,
although it may be displaced with liquid ammonia. [4] When the alkylation is
conducted with methyl lithium in the presence of a tertiary phosphine the air-
stable phosphine adduct is obtained:

GaCl3 + 3 MeLi + PR3 → R3P−GaMe3 + 3 LiCl

Heating the solid phosphine adduct under vacuum liberates the base-free TMG: [1]

R3P−GaMe3 → R3P + GaMe3

Other non-volatile bases have been described.[5] Other methylating agents for the
synthesis of TMG include dimethylzinc and trimethylaluminium.

Applications[edit]

TMG is the preferred metalorganic source of gallium for metalorganic vapour

phase epitaxy (MOVPE) of gallium-containing compound semiconductors, such
as GaAs, GaN, GaP, GaSb, InGaAs, InGaN, AlGaInP, InGaP, AlInGaNP and Ga2O3.
[6]
These material are used in the production of LED lighting and semiconductors
as a metalorganic chemical vapor deposition precursor.

References[edit]

1. ^
2. Jump up to:
ab
3. Bradley, D. C.; Chudzynska, H. C.; Harding, I. S. (1997). "Trimethylindium and
Trimethylgallium". Inorganic Syntheses. Vol. 31. pp. 67–74.
doi:10.1002/9780470132623.ch8. ISBN 978-0-470-13262-3.
4. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.).
Butterworth-Heinemann. ISBN 978-0-08-037941-8.
5. ^ Mitzel, Norbert W.; Lustig, Christian; Berger, Raphael J. F.; Runeberg, Nino (2002).
"Luminescence Phenomena and Solid-State Structures of Trimethyl- and
Triethylgallium". Angewandte Chemie International Edition. 41 (14): 2519–2522.
doi:10.1002/1521-3773(20020715)41:14<2519::AID-ANIE2519>3.0.CO;2-2. PMID
12203520.
6. ^ Kraus, C. A.; Toonder, F. E. (1933). "Trimethyl Gallium, Trimethyl Gallium Etherate
and Trimethyl Gallium Ammine". PNAS. 19 (3): 292–8. Bibcode:1933PNAS...19..292K.
doi:10.1073/pnas.19.3.292. PMC 1085965. PMID 16577510.
7. ^ Foster, Douglas F.; Cole-Hamilton, David J. (1997). "Electronic Grade Alkyls of Group
12 and 13 Elements". Inorganic Syntheses. Vol. 31. p. 29-66.
doi:10.1002/9780470132623.ch7. ISBN 978-0-471-15288-0.
8. ^ Shenai-Khatkhate, D. V.; Goyette, R. J.; Dicarlo, R. L. Jr; Dripps, G. (2004).
"Environment, health and safety issues for sources used in MOVPE growth of
compound semiconductors". Journal of Crystal Growth. 272 (1–4): 816–21.
Bibcode:2004JCrGr.272..816S. doi:10.1016/j.jcrysgro.2004.09.007.

show

● V
● T
● E

Gallium compounds

Categories:

Chemical vapour deposition precursors

Gallium compounds
Methyl complexes
Pyrophoric materials
This page was last edited on 2 May 2024, at 09:06 (UTC).
 Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may
apply. By using this site, you agree to the Terms of Use and

Trimethylaluminium
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Names
IUPAC name

Trimethylalumane

Other names

Trimethylaluminum; aluminium trimethyl; aluminum trimethyl

Identifiers

CAS Number 75-24-1

3D model (JSmol) dimer: Interactive image

monomer: Interactive image

ChemSpider 10606585

ECHA InfoCard 100.000.776

PubChem CID 16682925

UNII AV210LG46J

CompTox DTXSID9058787
Dashboard (EPA)

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InChI

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SMILES

Properties

Chemical formula C6H18Al2

Molar mass 144.17 g/mol

72.09 g/mol (C3H9Al)

Appearance Colorless liquid

Density 3
0.752 g/cm

Melting point 15 °C (59 °F; 288 K)

Boiling point [1][2]

125–130 °C (257–266 °F; 398–403 K)

Solubility in water Reacts

Vapor pressure 1.2 kPa (20 °C)

[1]
9.24 kPa (60 °C)
Viscosity 1.12 cP (20 °C)
0.9 cP (30 °C)

Thermochemistry

Heat capacity (C) [2]

155.6 J/mol·K

Std molar [2]

209.4 J/mol·K

⦵
entropy (S 298)

Std enthalpy of [2]

−136.4 kJ/mol

formation

⦵
(ΔfH 298)

Gibbs free energy [2]

−9.9 kJ/mol
⦵
(ΔfG )

Hazards

Occupational safety and health (OHS/OSH):

Main hazards Pyrophoric

GHS labelling:
Pictograms

[1]

Signal word Danger

Hazard [1]
H250, H260, H314
statements

Precautionary P222, P223, P231+P232, P280, P370+P378,

statements [1]
P422

NFPA 704 (fire

diamond)

3
W

Flash point [1]

−17.0 °C (1.4 °F; 256.1 K)

Related compounds

Related Triethylaluminium
 compounds

Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ?)

Infobox references

Trimethylaluminium is one of the simplest examples of an organoaluminium

compound. Despite its name it has the formula Al2(CH3)6 (abbreviated as Al2Me6
or TMA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an
industrially important compound, closely related to triethylaluminium.[3][4]

Structure and bonding[edit]

The structure and bonding in Al2R6 and diborane are analogous (R = alkyl). In
Al2Me6, the Al-C(terminal) and Al-C(bridging) distances are 1.97 and 2.14 Å,
respectively. The Al center is tetrahedral.[5] The carbon atoms of the bridging
methyl groups are each surrounded by five neighbors: three hydrogen atoms and
two aluminium atoms. The methyl groups interchange readily intramolecularly. At
higher temperatures, the dimer cracks into monomeric AlMe3.[6]

Synthesis[edit]

TMA is prepared via a two-step process that can be summarized as follows:

2 Al + 6 CH3Cl + 6 Na → Al2(CH3)6 + 6 NaCl

Applications[edit]
Catalysis[edit]

Starting with the invention of Ziegler-Natta catalysis, organoaluminium

compounds have a prominent role in the production of polyolefins, such as
polyethylene and polypropylene. Methylaluminoxane, which is produced from
TMA, is an activator for many transition metal catalysts.

Semiconductor applications[edit]

TMA is also used in semiconductor fabrication to deposit thin film, high-k

dielectrics such as Al2O3 via the processes of chemical vapor deposition or
atomic layer deposition. TMA is the preferred precursor for metalorganic vapour
phase epitaxy (MOVPE) of aluminium-containing compound semiconductors,
such as AlAs, AlN, AlP, AlSb, AlGaAs, AlInGaAs, AlInGaP, AlGaN, AlInGaN,
AlInGaNP, etc. Criteria for TMA quality focus on (a) elemental impurities, (b)
oxygenated and organic impurities.

Photovoltaic applications[edit]

In deposition processes very similar to semiconductor processing, TMA is used

to deposit thin film, low-k (non-absorbing) dielectric layer stacks with Al 2O3 via
the processes of chemical vapor deposition or atomic layer deposition. The Al2O3
provides excellent surface passivation of p-doped silicon surfaces. The Al 2O3
layer is typically the bottom layer with multiple silicon nitride (Si xNy) layers for
capping.

Reactions[edit]

Hydrolysis and related protonolysis reactions[edit]

Trimethylaluminium is hydrolyzed readily, even dangerously:

Al2Me6 + 3 H2O → Al2O3 + 6 CH4

Under controlled conditions, the reaction can be stopped to give
methylaluminoxane:

AlMe3 + H2O → 1/n [AlMeO]n + 2 CH4

Alcoholysis and aminolysis reactions proceed comparably. For example,

dimethylamine gives the dialuminium diamide dimer:[7]

2 AlMe3 + 2 HNMe2 → [AlMe2NMe2]2 + 2 CH4

Reactions with metal chlorides[edit]

TMA reacts with many metal halides to install alkyl groups. When combined with
gallium trichloride, it gives trimethylgallium.[8] Al2Me6 reacts with aluminium
trichloride to give (AlMe2Cl)2.

TMA/metal halide reactions have emerged as reagents in organic synthesis.

Tebbe's reagent, which is used for the methylenation of esters and ketones, is
prepared from TMA and titanocene dichloride.[9] In combination with 20 to 100
mol % Cp2ZrCl2 (zirconocene dichloride), the (CH3)2Al-CH3 adds "across" alkynes
to give vinyl aluminium species that are useful in organic synthesis in a reaction
known as carboalumination.[10]

Adducts[edit]

As for other "electron-deficient" compounds, trimethylaluminium gives adducts

R3N.AlMe3. The Lewis acid properties of AlMe3 have been quantified.[11] The
enthalpy data show that AlMe3 is a hard acid and its acid parameters in the ECW
model are EA =8.66 and CA = 3.68.

These adducts, e.g. the complex with the tertiary amine DABCO, are safer to
handle than TMA itself.[12]

The NASA ATREX mission (Anomalous Transport Rocket Experiment) employed

the white smoke that TMA forms on air contact to study the high altitude jet
stream.

Synthetic reagent[edit]
TMA is a source of methyl nucleophiles, akin to methyl lithium, but less reactive.
It reacts with ketones to give, after a hydrolytic workup, tertiary alcohols.

Safety[edit]

Trimethylaluminium is pyrophoric, reacting violently with air and water.

References[edit]

● ^
● Jump up to:
abcdef
● Sigma-Aldrich Co., Trimethylaluminum. Retrieved on 2014-05-05.
● ^
● Jump up to:
abcde
● "Trimethyl aluminum".
● ^ Krause, Michael J.; Orlandi, Frank; Saurage, Alfred T.; Zietz, Joseph R. (2000).
"Aluminum Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry.
Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_543. ISBN 978-3527306732.
● ^ C. Elschenbroich (2006). Organometallics. VCH. ISBN 978-3-527-29390-2.
● ^ Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press.
ISBN 0-12-352651-5.
● ^ Vass, Gábor; Tarczay, György; Magyarfalvi, Gábor; Bödi, András; Szepes, László
(2002). "HeI Photoelectron Spectroscopy of Trialkylaluminium and Dialkylaluminium
Hydride Compounds and Their Oligomers". Organometallics. 21 (13): 2751–2757.
doi:10.1021/om010994h.
● ^ Lipton, Michael F.; Basha, Anwer; Weinreb, Steven M. (1979). "Conversion of Esters to
Amides with Dimethylaluminium Amides: N,N-Dimethylcyclohexanecarboxamide".
Organic Syntheses. 59: 49. doi:10.15227/orgsyn.059.0049.
● ^ Gaines, D. F.; Borlin, Jorjan; Fody, E. P. (1974). "Trimethylgallium". Inorganic
Syntheses. Vol. 15. pp. 203–207. doi:10.1002/9780470132463.ch45. ISBN 978-0-470-13246-
3.
● ^ Pine, S. H.; Kim, V.; Lee, V. (1990). "Enol ethers by methylenation of esters: 1-Phenoxy-
1-phenylethene and 3,4-dihydro-2-methylene-2H-1-benzopyran". Org. Synth. 69: 72.
doi:10.15227/orgsyn.069.0072.
● ^ Negishi, E.; Matsushita, H. (1984). "Palladium-Catalyzed Synthesis of 1,4-Dienes by
Allylation of Alkenyalane: α-Farnesene [1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-]".
Organic Syntheses. 62: 31. doi:10.15227/orgsyn.062.0031.
● ^ Henrickson, C. H.; Duffy, D.; Eyman, D. P. (1968). "Lewis acidity of Alanes. Interactions
of Trimethylalane with Amines, Ethers, and Phosphines". Inorganic Chemistry. 7 (6):
1047–1051. doi:10.1021/ic50064a001.
● ^ Vinogradov, Andrej; Woodward, S. (2010). "Palladium-Catalyzed Cross-Coupling Using
an Air-Stable Trimethylaluminium Source. Preparation of Ethyl 4-Methylbenzoate".
Organic Syntheses. 87: 104. doi:10.15227/orgsyn.087.0104.

External links[edit]
 Wikimedia Commons has media related to Trimethylaluminium.

● NASA ATREX mission article.

show

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● E

Aluminium compounds

Authority control
● Germany
databases: National

Categories:

Organoaluminium compounds
Coordination complexes
Methyl complexes
Pyrophoric materials
This page was last edited on 1 March 2024, at 09:50 (UTC).

Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may
apply. By using this site, you ag