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831-82-3

Basic Information
CAS No.: 831-82-3
Name: 4-Phenoxyphenol
Article Data: 67
Molecular Structure:
Molecular Structure of 831-82-3 (4-Phenoxyphenol)
Formula: C12H10O2
Molecular Weight: 186.21
Synonyms: Phenol,p-phenoxy- (6CI,7CI,8CI);4-Hydroxydiphenyl ether;Hydroquinone monophenyl ether;NSC25027;p-Hydroxydiphenyl ether;p-Phenoxyphenol;
EINECS: 212-611-1
Density: 1.175 g/cm3
Melting Point: 80-84 °C(lit.)
Boiling Point: 313.761 °C at 760 mmHg
Flash Point: 141.446 °C
Solubility: insoluble in water, solubel in benzene, diethyl ether
Appearance: beige crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 29.46000
LogP: 3.18450
Synthetic route
51067-38-0

4-phenoxyphenylboronic acid

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Irradiation;97%
With dihydrogen peroxide In ethanol at 20℃; for 0.166667h;89%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;73%
With tert.-butylhydroperoxide; oxygen; trichloroacetonitrile In decane; acetonitrile at 20℃; for 12h; Irradiation;57%
591-50-4

iodobenzene

123-31-9

hydroquinone

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Catalytic behavior;92%
With sodium hydroxide In neat (no solvent) at 90℃; for 9h; Green chemistry;60%
106-51-4

p-benzoquinone

98-80-6

phenylboronic acid

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With methanol; copper(II) ferrite at 20℃; for 24h;86%
1655-69-2

1-methoxy-4-phenoxy-benzene

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 185℃; for 12h; further reagent: NaN(SiMe3)2;84%
With hydrogen iodide
With aluminium trichloride at 130 - 150℃;
108-86-1

bromobenzene

123-31-9

hydroquinone

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With zinc In N,N-dimethyl-formamide for 0.0416667h; Williamson ether synthesis; microwave irradiation;81%
108-90-7

chlorobenzene

123-31-9

hydroquinone

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With zinc In N,N-dimethyl-formamide for 0.0583333h; Williamson ether synthesis; microwave irradiation;79%
108-95-2

phenol

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With sodium hypochlorite; copper(l) chloride In water at 100℃; for 16h;73.3%
Multi-step reaction with 2 steps
1: potassium methoxide, copper(I) chloride, copper bronze / 6 h / 230 °C
2: boron tribromide / CH2Cl2 / 4 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 71 percent / K2CO3 / N,N-dimethyl-acetamide / Heating
2: 3-chloroperoxybenzoic acid / CHCl3 / Ambient temperature
3: conc. HCl / methanol / 1 h / Ambient temperature
View Scheme
101-55-3

4-Bromodiphenyl ether

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;67%
With potassium hydroxide; copper at 250℃;
With alkaline solution; copper at 200℃;
7005-72-3

4-chlorodiphenyl ether

831-82-3

4-Phenoxyphenol

Conditions
ConditionsYield
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;67%
3379-38-2

1,3-diphenoxybenzene

A

831-82-3

4-Phenoxyphenol

B

108-93-0

cyclohexanol

C

71-43-2

benzene

Conditions
ConditionsYield
With hydrogen In Hexadecane at 260℃; under 7600.51 Torr; for 5h; Autoclave;A 8.3%
B 9.5%
C 53.8%
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Specification

4-Phenoxyphenol, with the CAS registry number 831-82-3, is also named as Hydroquinone monophenyl ether. It belongs to the product categories of Aromatic Phenols; Phenoles and thiophenoles; Building Blocks; C9 to C20+; Chemical Synthesis; Organic Building Blocks; Oxygen Compounds; Phenols. Its EINECS number is 212-611-1. This chemical's molecular formula is C12H10O2 and molecular weight is 186.21. What's more, its systematic name is 4-Phenoxyphenol. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from strong oxidants. It is used as an intermediate for pesticide.

Physical properties of 4-Phenoxyphenol are: (1)ACD/LogP: 3.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.35; (4)ACD/LogD (pH 7.4): 3.35; (5)ACD/BCF (pH 5.5): 207.01; (6)ACD/BCF (pH 7.4): 206.57; (7)ACD/KOC (pH 5.5): 1582.66; (8)ACD/KOC (pH 7.4): 1579.33; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.46 Å2; (13)Index of Refraction: 1.605; (14)Molar Refractivity: 54.578 cm3; (15)Molar Volume: 158.45 cm3; (16)Polarizability: 21.636×10-24cm3; (17)Surface Tension: 46.3 dyne/cm; (18)Density: 1.175 g/cm3; (19)Flash Point: 141.446 °C; (20)Enthalpy of Vaporization: 57.698 kJ/mol; (21)Boiling Point: 313.761 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-methoxy-4-phenoxy-benzene at the temperature of 185 °C. This reaction will need reagents lithium diisopropylamide, 1,3-dimethyl-2-imidazolidinone and solvents heptane, tetrahydrofuran, ethylbenzene with the reaction time of 12 hours. The yield is about 84%.

4-Phenoxypheno can be prepared by 1-methoxy-4-phenoxy-benzene at the temperature of 185 °C

Uses of 4-Phenoxyphenol: it can be used to produce 2-(4-phenoxy-phenoxy)-benzaldehyde by heating. It will need reagent K2CO3 and solvent N,N-dimethyl-acetamide with the reaction time of 2 hours. The yield is about 95%.

4-Phenoxyphenol can be used to produce 2-(4-phenoxy-phenoxy)-benzaldehyde by heating

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccccc1)c2ccc(O)cc2
(2)Std. InChI: InChI=1S/C12H10O2/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9,13H
(3)Std. InChIKey: ZSBDGXGICLIJGD-UHFFFAOYSA-N