Diphenyl ether

Diphenyl ether is the organic compound

with the formula (C6H5)2O. It is a colorless
solid. This, the simplest diaryl ether, enjoys
a variety of niche applications.[5]
 Diphenyl ether

Names

Preferred IUPAC name

1,1'-Oxydibenzene[1]

Other names
Oxydibenzene
Diphenyl ether[1]
Diphenyl oxide
1,1'-Oxybisbenzene
Phenoxybenzene[1]

Identifiers
CAS Number 101-84-8  

3D model (JSmol) Interactive image

Beilstein Reference 1364620

ChEBI CHEBI:39258  

ChEMBL ChEMBL38934  

ChemSpider 7302  

ECHA InfoCard 100.002.711

EC Number 202-981-2

Gmelin Reference 165477

PubChem CID 7583

RTECS number KN8970000

UNII 3O695R5M1U  

UN number 3077

InChI
InChI=1S/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H 
Key: USIUVYZYUHIAEV-UHFFFAOYSA-N 

InChI=1/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
Key: USIUVYZYUHIAEV-UHFFFAOYAV

SMILES
O(c1ccccc1)c2ccccc2
 Properties
Chemical formula C12H10O

Molar mass 170.211 g·mol−1

Appearance Colorless solid or liquid

Odor geranium-like

Density 1.08 g/cm3 (20°C)[2]

Melting point 25 to 26 °C (77 to 79 °F;

298 to 299 K)

Boiling point 121 °C (250 °F; 394 K)[3]

at 1.34 kPa (10.05 mm
Hg), 258.55 °C at 100
kPa (1 bar)

Solubility in water Insoluble

Vapor pressure 0.02 mmHg (25°C)[2]

Magnetic susceptibility -108.1·10−6 cm3/mol

(χ)

Hazards
Safety data sheet Aldrich MSDS

GHS pictograms

GHS signal word Warning

GHS hazard statements H319, H400, H411

GHS precautionary P264, P273, P280,

statements
P305+351+338,
P337+313, P391, P501

NFPA 704 1
2

Flash point 115 °C (239 °F; 388 K)

Explosive limits 0.7%-6.0%[2]

Lethal dose or concentration (LD, LC):

LD50 (median dose) 3370 mg/kg (rat, oral)
4000 mg/kg (rat, oral)

4000 mg/kg (guinea

 pig, oral)[4]

US health exposure limits (NIOSH):

PEL (Permissible) TWA 1 ppm (7
mg/m3)[2]
REL (Recommended) TWA 1 ppm (7
mg/m3)[2]
IDLH (Immediate 100 ppm[2]
danger)
Except where otherwise noted, data are given for
materials in their standard state (at 25 °C [77 °F],
100 kPa).

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Infobox references

Synthesis and reactions

Diphenyl ether and many of its properties
were first reported as early as 1901.[6] It is
synthesized by a modification of the
Williamson ether synthesis, here the
reaction of phenol and bromobenzene in
the presence of base and a catalytic
amount of copper:

PhONa + PhBr → PhOPh + NaBr

Involving similar reactions, diphenyl ether
is a significant side product in the high-
pressure hydrolysis of chlorobenzene in
the production of phenol.[7]

Related compounds are prepared by

Ullmann reactions.[8]
The compound undergoes reactions
typical of other phenyl rings, including
hydroxylation, nitration, halogenation,
sulfonation, and Friedel–Crafts alkylation
or acylation.[5]

Uses
The main application of diphenyl ether is
as a eutectic mixture with biphenyl, used
as a heat transfer medium. Such a mixture
is well-suited for heat transfer applications
because of the relatively large temperature
range of its liquid state. A eutectic mixture
[commercially, Dowtherm A] is 73.5%
diphenyl ether (diphenyl oxide) and 26.5%
biphenyl (diphenyl).[9][10]

Diphenyl ether is a starting material in the

production of phenoxathiin via the Ferrario
reaction.[11] Phenoxathiin is used in
polyamide and polyimide production.[12]

Because of its odor reminiscent of

scented geranium, as well as its stability
and low price, diphenyl ether is used
widely in soap perfumes. Diphenyl ether is
also used as a processing aid in the
production of polyesters.[5]

Related compounds
Several polybrominated diphenyl ethers
(PBDEs) are useful flame retardants. Of
penta-, octa-, and decaBDE, the three most
common PBDEs, only decaBDE is still in
widespread use since its ban in the
European Union in 2003.[13] DecaBDE, also
known as decabromodiphenyl oxide,[14] is
a high-volume industrial chemical with
over 450,000 kilograms produced annually
in the United States. Decabromodiphenyl
oxide is sold under the trade name Saytex
102 as a flame retardant in the
manufacture of paints and reinforced
plastics.
References
1. "CHAPTER P-6. Applications to Specific
Classes of Compounds". Nomenclature of
Organic Chemistry : IUPAC
Recommendations and Preferred Names
2013 (Blue Book). Cambridge: The Royal
Society of Chemistry. 2014. p. 705.
doi:10.1039/9781849733069-00648 .
ISBN 978-0-85404-182-4.
2. "NIOSH Pocket Guide to Chemical
Hazards #0496" . National Institute for
Occupational Safety and Health (NIOSH).
3. Byers, Charles H.; Williams, David F. (July
1987). "Viscosities of pure polyaromatic
hydrocarbons". Journal of Chemical &
Engineering Data. 32 (3): 344–348.
doi:10.1021/je00049a018 . ISSN 0021-
9568 .
4. "Phenyl ether" . Immediately Dangerous
to Life and Health Concentrations (IDLH).
National Institute for Occupational Safety
and Health (NIOSH).
5. Fiege, H.; Voges, H.-M.; Hamamoto, T;
Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.;
Buysch, H.-J.; Garbe, D.; Paulus, W. (2000).
Phenol Derivatives. Ullmann's Encyclopedia
of Industrial Chemistry. Weinheim: Wiley-
VCH. doi:10.1002/14356007.a19_313 .
ISBN 978-3-527-30673-2.
6. Cook, A. N. (1901). "Derivatives of
Phenylether". Journal of the American
Chemical Society. 23 (11): 806–813.
doi:10.1021/ja02037a005 .
7. Fahlbusch, K.-G.; Hammerschmidt, F.-J.;
Panten, J.; Pickenhagen, W.; Schatkowski,
D.; Bauer, K.; Garbe, D.; Surburg, H. (2003).
Flavor and Fragrances. Ullmann's
Encyclopedia of Industrial Chemistry.
Weinheim: Wiley-VCH.
doi:10.1002/14356007.a11_141 . ISBN 978-
3-527-30673-2.
8. Ungnade, H. E.; Orwoll, E. F. (1946). "2-
Methoxy Diphenyl Ether". Org. Synth. 26: 50.
doi:10.15227/orgsyn.026.0050 .
9. Patent Appeal No. 7555 United States
Court of Customs and Patent Appeals 7
April 1966
http://openjurist.org/358/f2d/750/applicati
on-of-edward-s-blake-and-william-c-
hammann
10. "Dowtherm® A 44570" .
11. Suter, C. M.; Maxwell, C. E. (1943).
"Phenoxthin" . Organic Syntheses.;
Collective Volume, 2, p. 485
12. Mitsuru Ueoda; Tatsuo Aizawa; Yoshio
Imai (1977). "Preparation and properties of
polyamides and polyimides containing
phenoxathiin units". Journal of Polymer
Science: Polymer Chemistry Edition. 15
(11): 2739–2747.
doi:10.1002/pol.1977.170151119 .
13. DIRECTIVE 2003/11/EC of the European
Parliament and of the Council
14. Sutker, B. J. (2005). Flame Retardants.
Ullmann's Encyclopedia of Industrial
Chemistry. Weinheim: Wiley-VCH.
doi:10.1002/14356007.a11_123 . ISBN 978-
3-527-30673-2.
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