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101-84-8

Basic Information
CAS No.: 101-84-8
Name: Diphenyl ether
Article Data: 393
Cas Database
Molecular Structure:
Molecular Structure of 101-84-8 (Diphenyl ether)
Formula: C12H10O
Molecular Weight: 170.211
Synonyms: Phenylether (8CI);1,1'-Oxybis[benzene];Barrel Therm 330;Benzene, phenoxy-;Biphenyl oxide;Chemcryl JK-EB;Diphenyl oxide;NSC 19311;Oxybisbenzene;Phenoxybenzene;Phenyl oxide;Benzene, 1,1'-oxybis-;
EINECS: 202-981-2
Density: 1.063 g/cm3
Melting Point: 26 °C
Boiling Point: 258.3 °C at 760 mmHg
Flash Point: 99.3 °C
Solubility: Insoluble in water
Appearance: clear pale yellowish liquid after melting
Hazard Symbols: DangerousN,IrritantXi,ToxicT
Risk Codes: 51/53-36/37/38-39/23/24/25-23/24/25-36/38
Safety: 60-61-57-37/39-26-45-36/37
Transport Information: UN 3077 9/PG 3
PSA: 9.23000
LogP: 3.47890
Synthetic route
83566-43-2

tetraphenyl-bismuth trifluoroacetate

101-84-8

diphenylether

Conditions
ConditionsYield
With phenol In benzene refluxing overnight (Ar); t.l.c.;100%
In benzene 24 h at 80°C; filtn., evapn., addn. of Cl3CCO2H in CH2Cl2, reflux for 2 h, cooling, washing, drying, t.l.c.;38%
With water In water; benzene 24 h at 80°C, addn. of water; filtn., evapn., addn. of Cl3CCO2H in CH2Cl2, reflux for 2 h, cooling, washing, drying., t.l.c.;34%
591-50-4

iodobenzene

108-95-2

phenol

101-84-8

diphenylether

Conditions
ConditionsYield
With copper(I) oxide; caesium carbonate; hydroxybenzaldoxime; 3 A molecular sieve In acetonitrile at 82℃; for 24h; Ullmann-type coupling;100%
With caesium carbonate; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine In acetonitrile at 82℃; for 24h; Conversion of starting material; activated 3 A molecular sieve (KnNa12-n[(AlO2)12(SiO2)12]);100%
Stage #1: phenol With caesium carbonate; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine at 100℃; Molecular sieve 3 Å;
Stage #2: iodobenzene In acetonitrile at 82℃; for 24h;
100%
83566-43-2

tetraphenyl-bismuth trifluoroacetate

108-95-2

phenol

101-84-8

diphenylether

Conditions
ConditionsYield
In benzene Heating;100%
In benzene at 80℃; for 12h;100%

4-phenoxybenzenediazonium o-benzenedisulfonimide

101-84-8

diphenylether

Conditions
ConditionsYield
With dihydrogen peroxide In tetrahydrofuran for 3h; Heating;100%
108-86-1

bromobenzene

108-95-2

phenol

101-84-8

diphenylether

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; Raney Ni-Al alloy In 1,4-dioxane at 110℃; for 24h;99%
With caesium carbonate; copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 18h; Ullmann condensation;98%
With 2-[(dimethylamino)methyl]-1-thiophenolato-copper(I); caesium carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 16h; Inert atmosphere;98%
7005-72-3

4-chlorodiphenyl ether

101-84-8

diphenylether

Conditions
ConditionsYield
With C60H48BP3Pd; potassium formate; [2.2.2]cryptande In tetrahydrofuran at 60℃; for 72h; Schlenk technique; Inert atmosphere;99%
With N-tert-butylaminoborane; palladium on activated charcoal In methanol at 20℃; for 120h;82%
With tributyl-amine; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.8h; Inert atmosphere; Electrolysis;80%
With C8K In tetrahydrofuran Product distribution; Ambient temperature;
With N-ethyl-N,N-diisopropylamine In acetonitrile for 16h; Irradiation;95 %Spectr.
144150-76-5

4-phenoxyphenyl 4-methylbenzenesulfonate

101-84-8

diphenylether

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol; chloroform ice-cooling;94%
With sodium tetrahydroborate; bis(triphenylphosphine)nickel(II) chloride; tricyclohexylphosphine In tetrahydrofuran at 60℃; for 14h;70%
108-86-1

bromobenzene

100-67-4

potassium phenolate

101-84-8

diphenylether

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one at 120℃; for 5h; Ullmann diaryl etherification; Inert atmosphere;93%
With 1-butyl-3-methylimidazolium Tetrafluoroborate; copper(l) chloride at 100℃; for 10h;72%
With copper at 180 - 190℃;
With copper at 210 - 230℃;
591-50-4

iodobenzene

100-67-4

potassium phenolate

101-84-8

diphenylether

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one at 120℃; for 4h; Ullmann diaryl etherification; Inert atmosphere;93%
With 1-butyl-3-methylimidazolium Tetrafluoroborate; copper(l) chloride at 100℃;82%
6293-66-9

diphenyliodonium p-toluenesulfonate

108-95-2

phenol

101-84-8

diphenylether

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 6h;93%
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History

Diphenyl ether(CAS NO.101-84-8) and many of its properties were first reported as early as 1901.

Consensus Reports

Diphenyl ether and many of its properties were first reported as early as 1901.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

Specification

The Diphenyl ether with CAS registry number of 101-84-8 is also known as Benzene, phenoxy-. The IUPAC name is Phenoxybenzene. It belongs to product categories of Pharmaceutical Intermediates; Fine Chemical & Intermediates; Organics; Biphenyl & Diphenyl ether. Its EINECS registry number is 202-981-2. In addition, the formula is C12H10O and the molecular weight is 170.21. This chemical is a clear pale yellowish liquid after melting and insoluble in water. It should be sealed in ventilated and dry place away from fire, heat, oxidants. What's more, it can be used as heat transfer medium and used for organic synthesis, manufacture of perfume and dyes.

Physical properties about Diphenyl ether are: (1)ACD/LogP: 4.21; (2)ACD/LogD (pH 5.5): 4.21; (3)ACD/LogD (pH 7.4): 4.21; (4)ACD/BCF (pH 5.5): 932.39; (5)ACD/BCF (pH 7.4): 932.39; (6)ACD/KOC (pH 5.5): 4647.71; (7)ACD/KOC (pH 7.4): 4647.71; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.572; (11)Molar Refractivity: 52.69 cm3; (12)Molar Volume: 160 cm3; (13)Surface Tension: 38.4 dyne/cm; (14)Density: 1.063 g/cm3; (15)Flash Point: 99.3 °C; (16)Enthalpy of Vaporization: 47.59 kJ/mol; (17)Boiling Point: 258.3 °C at 760 mmHg; (18)Vapour Pressure: 0.0223 mmHg at 25 °C.

Preparation of Diphenyl ether: it is prepared by condensation  reaction of chlorobenzene and phenol. The reaction needs catalyst copper and solvent caustic solution. When the reaction is complete, reactant is dealed with acid and the ether oil is vacuum distilled to obtain product.

(1) C6H5OH + NaOH → C6H5ONa + H2O
(2) C6H5ONa + C6H5Cl → C6H5OC6H5 + NaCl

Uses of Diphenyl ether: it is used to produce 4-phenoxy-benzaldehyde by reaction with tris(diformylamino)methane. The reaction occurs with reagent AlCl3 and solvent 1,2-dichloro-ethane at -13 - 1 °C for 16 hours. The yield is about 20%.

Diphenyl ether is used to produce 4-phenoxy-benzaldehyde by reaction with tris(diformylamino)methane.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. There is danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. It also is toxic to aquatic organisms that may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid release to the environment and use appropriate containment to avoid environmental contamination. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately. This material and its container must be disposed of as hazardous waste.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)OC2=CC=CC=C2
2. InChI: InChI=1S/C12H10O/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
3. InChIKey: USIUVYZYUHIAEV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 7940mg/kg (7940mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
National Technical Information Service. Vol. 0TS0518143,
rat LD50 oral 2450mg/kg (2450mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: OTHER CHANGES
National Technical Information Service. Vol. 0TS0518143,