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 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1364620
ChEBI |

* CHEBI:39258 Y

ChEMBL |

* ChEMBL38934 Y

ChemSpider |

* 7302 Y

EC Number |

* 202-981-2

Gmelin Reference

| 165477

PubChem CID

* 7583

RTECS number |

* KN8970000

UNII |

* 3O695R5M1U Y

UN number | 3077

InChI

* InChI=1S/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H Y

Key: USIUVYZYUHIAEV-UHFFFAOYSA-N Y

* 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 |  258.55 °C (497.39 °F; 531.70 K)[3] at 100 kPa (1 bar),
121 °C at 1.34 kPa (10.05 mm Hg)

Solubility in water

| Insoluble
Vapor pressure | 0.02 mmHg (25 °C)[2]

Magnetic susceptibility (χ)

| -108.1·10−6 cm3/mol
Hazards
Safety data sheet | Aldrich MSDS
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H319, H400, H411

GHS precautionary statements

| P264, P273, P280, P305+351+338, P337+313, P391, P501
NFPA 704 (fire diamond)  |

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]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 1 ppm (7 mg/m3)[2]

REL (Recommended)

| TWA 1 ppm (7 mg/m3)[2]

IDLH (Immediate danger)

| 100 ppm[2]

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

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Diphenyl ether is the organic compound with the formula (C6H5)2O. It is a colorless, low-melting solid. This, the simplest diaryl ether, has a variety of niche applications.[5]

## Contents

* 1 Synthesis and reactions
* 2 Uses
* 3 Related compounds
* 4 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:

PhOH + PhBr → PhOPh + HBr

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 fluid. 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 and 26.5% biphenyl.[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

It is a component of important hormone T3 or triiodothyronine.

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. ↑ 1.0 1.1 1.2 "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. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 NIOSH Pocket Guide to Chemical Hazards. "#0496". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0496.html.
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). https://www.cdc.gov/niosh/idlh/101848.html.
5. ↑ 5.0 5.1 5.2 Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J. et al. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
6. ↑ Cook, A. N. (1901). "Derivatives of Phenylether". Journal of the American Chemical Society 23 (10): 806–813. doi:10.1021/ja02037a005. https://zenodo.org/record/1428908.
7. ↑ Fahlbusch, K.-G.; Hammerschmidt, F.-J.; Panten, J.; Pickenhagen, W.; Schatkowski, D.; Bauer, K.; Garbe, D.; Surburg, H. (2003). Flavor and Fragrances. 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/application-of-edward-s-blake-and-william-c-hammann
10. ↑ "Dowtherm® A 44570". http://www.sigmaaldrich.com/catalog/product/aldrich/44570.
11. ↑ Suter, C. M.; Maxwell, C. E. (1943). "Phenoxthin". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv2p0485. ;  Collective Volume, 2, pp. 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". Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_123. ISBN 978-3-527-30673-2.

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*[CID]: Compound ID
*[H319]: Causes serious eye irritation
*[H400]: Very toxic to aquatic life
*[H411]: Toxic to aquatic life with long lasting effects
*[P264]: Wash … thoroughly after handling
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P337+313]: Get medical advice/attention
*[P391]: Collect spillage
*[P501]: Dispose of contents/container to …