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108-95-2

Basic Information
CAS No.: 108-95-2
Name: Phenol
Molecular Structure:
Molecular Structure of 108-95-2 (Phenol)
Formula: C6H6O
Molecular Weight: 94.12
Synonyms: Carbolic Acid;Benzenol;Phenylic Acid;Hydroxybenzene;Phenic acid;Monohydroxybenzene;Monophenol;Oxybenzene;Phenyl alcohol;Phenyl hydrate;Phenyl hydroxide;Phenylic alcohol;
EINECS: 203-632-7
Density: 1.07 g/cm3
Melting Point: 40-42 °C(lit.)
Boiling Point: 181.8 °C at 760 mmHg
Flash Point: 72.5 °C
Solubility: 8 g/100 mL in water
Appearance: transparent crystalline solid
Hazard Symbols: ToxicT,CorrosiveC,FlammableF,HarmfulXn
Risk Codes: 23/24/25-34-48/20/21/22-68-40-39/23/24/25-11-36-20/21/22-24/25
Safety: 26-36/37/39-45-36/37-28A-28-24/25-1/2-36-16
Transport Information: UN 1671 6.1/PG 2
PSA: 20.23000
LogP: 1.39220
Synthetic route
533-58-4

2-Iodophenol

108-95-2

phenol

Conditions
ConditionsYield
With potassium tert-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;100%
With tris-(trimethylsilyl)silane In acetonitrile for 24h; Schlenk technique; Inert atmosphere; Irradiation;98%
With aluminium trichloride In dichloromethane; ethanethiol for 0.15h; Mechanism; Ambient temperature; var. other halogenated phenols;86.7%
With potassium phosphate; palladium diacetate; hydrazine hydrate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry;68%
1529-17-5

phenyltrimethylsilyl ether

108-95-2

phenol

Conditions
ConditionsYield
montmorillonite K-10 for 0.0166667h; Product distribution; Further Variations:; Catalysts; Solid phase reaction; desilylation; microwave irradiation;100%
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;98%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;98%
637-27-4

phenyl propionate

A

74-85-1

ethene

B

96-22-0

pentan-3-one

C

108-95-2

phenol

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine at 54℃; for 20h; Product distribution; Rate constant; Thermodynamic data; other solvents, reagents, reagents ratio, time, temperature; activation energy, ΔH<*>, ΔS<*>;A 100%
B n/a
C 100%
7492-40-2

4-phenylbutyl acetate

A

3360-41-6

4-phenyl-butan-1-ol

B

108-95-2

phenol

Conditions
ConditionsYield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;A 5%
B 100%
50972-20-8

phenyl-α-chloroethyl-carbonate

ammonium thiocyanate

A

109548-52-9

phenyl 1-thiocyanoethylcarbonate

B

108-95-2

phenol

Conditions
ConditionsYield
In formamide for 72h; Ambient temperature;A 100%
B 35%
108-98-5

thiophenol

A

57340-80-4

thallium thiophenoxide

B

108-95-2

phenol

Conditions
ConditionsYield
With thallous phenoxide In diethyl ether for 24h;A 100%
B 94%
100-66-3

methoxybenzene

108-95-2

phenol

Conditions
ConditionsYield
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In cyclohexane for 0.3h; Heating;100%
With water; hydrogen bromide; Aliquat 336 at 105℃; for 5h; Catalytic behavior;96%
With monochloroborane dimethyl sulfide complex In benzene Heating;95%
106-48-9

4-chloro-phenol

108-95-2

phenol

Conditions
ConditionsYield
With hydrogen; sodium hydroxide In water under 760.051 Torr; for 0.833333h; Kinetics; Reagent/catalyst; Solvent; Green chemistry;100%
With hydrogen; sodium hydroxide In water at 20℃; for 2h; Kinetics; Catalytic behavior; Solvent; Reagent/catalyst;99.1%
With hydrogen; sodium hydroxide In water at 25℃; under 760.051 Torr; for 2h; Reagent/catalyst; Solvent;99.9%
105930-58-3

7,7,8,8-Tetramethyl-3-methylene-5-phenoxy-1,4,6,9-tetraoxa-5λ5-phospha-spiro[4.4]nonan-2-one

A

13882-05-8

2-hydroxy-4,4,5,5-tetramethyl<1,3,2>dioxaphospholane-2-oxide

B

127-17-3

2-oxo-propionic acid

C

108-95-2

phenol

Conditions
ConditionsYield
With water In acetone at 20℃; for 24h;A 100%
B n/a
C n/a
122-79-2

Phenyl acetate

108-95-2

phenol

Conditions
ConditionsYield
With HZSM-5(30) In water for 7h; Product distribution; Heating; var. catalysts; other acetylated alcohols;100%
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 6h;100%
With sodium hydrogen telluride; acetic acid In ethanol for 0.5h; Heating;100%
103-45-7

acetic acid phenethyl ester

A

60-12-8

2-phenylethanol

B

108-95-2

phenol

Conditions
ConditionsYield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;A 18%
B 100%
122-72-5

3-phenylpropyl acetate

A

122-97-4

3-Phenyl-1-propanol

B

108-95-2

phenol

Conditions
ConditionsYield
With phosphate buffer; Phenyl acetate In diethyl ether for 2.75h; Ambient temperature; pig liver acetone powder;A 9%
B 100%
1864-94-4

phenyl formate

108-95-2

phenol

Conditions
ConditionsYield
With perchloric acid In diethyl ether; water at 20℃; for 0.166667h;100%
With samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 0.0833333h; Etherification;99.3%
With sodium hydroxide In water at 20℃;91%
824-91-9

O-methoxymethylphenol

108-95-2

phenol

Conditions
ConditionsYield
H6P2W18O62; silica gel In tetrahydrofuran; methanol at 65℃; for 0.916667h; Product distribution; Further Variations:; Catalysts;100%
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; Reagent/catalyst; Solvent; Temperature;95%
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h;94%
1295-35-8

bis(1,5-cyclooctadiene)nickel (0)

15133-82-1

tetrakis(triphenylphosphine)nickel(0)

A

nickel(II) propionate

B

15376-83-7

(triphenylphosphine)3(CO)nickelk

C

74-85-1

ethene

D

108-95-2

phenol

Conditions
ConditionsYield
With triphenylphosphine In neat (no solvent) (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and Ni(PPh3)4, mixture stirred at 54°C for 20 h; GLC;A 73%
B n/a
C 100%
D 91%
1295-35-8

bis(1,5-cyclooctadiene)nickel (0)

637-27-4

phenyl propionate

A

15376-83-7

(triphenylphosphine)3(CO)nickelk

B

74-85-1

ethene

C

108-95-2

phenol

Conditions
ConditionsYield
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 10), mixture stirred at 54°C for 21 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;A 80%
B 100%
C 100%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 4),mixture stirred at 54°C for 20 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;A 60%
B 100%
C 100%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 3),mixture stirred at 54°C for 20 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;A 60%
B 90%
C 90%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 2),mixture stirred at 54°C for 12 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;A 30%
B 60%
C 60%
With triphenylphosphine In neat (no solvent) Kinetics; byproducts: diethyl ketone, 1,3-cyclooctadiene, 1,4-cyclooctadiene; further byproducts: 1,5-cyclooctadiene, bicyclooctene-1, bicyclooctene-2, (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and PPh3 (PPh3/Ni = 1),mixture stirred at 54°C for 12 h; gas chromy., volatile removed in vac., recrystd. from THF-hexane;A n/a
B 40%
C 50%
1295-35-8

bis(1,5-cyclooctadiene)nickel (0)

637-27-4

phenyl propionate

1038-95-5

Tri(p-tolyl)phosphine

A

74-85-1

ethene

B

74887-07-3

Ni(CO)(P(C6H4CH3)3)3

C

108-95-2

phenol

Conditions
ConditionsYield
In further solvent(s) Kinetics; (N2 or Ar or vac.), EtCOOPh added to Ni(cod)2 and P(C6H4CH3)3 (P(Ph-CH3)3/Ni = 3) in acetophenone, mixture stirred at 65°C for 50 h;A 80%
B 85%
C 100%
5296-56-0

cyclopropanecarboxylic acid phenyl ester

108-95-2

phenol

Conditions
ConditionsYield
With aluminum (III) chloride; diphenyl diselenide; zinc In acetonitrile at 70℃; for 19.25h;100%
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

108-95-2

phenol

Conditions
ConditionsYield
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.25h; Green chemistry; chemoselective reaction;100%
With dihydrogen peroxide; 1-butyl-3-methylimidazolium chloride In water at 20℃; for 0.5h; Green chemistry;97%
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;96%

potassium phenyltrifluoborate

108-95-2

phenol

Conditions
ConditionsYield
With urea hydrogen peroxide adduct In methanol at 27 - 29℃; for 0.25h; Green chemistry; chemoselective reaction;100%
With Oxone; water In acetone at 20℃; for 0.0333333h;96%
With LACTIC ACID; dihydrogen peroxide In water at 20℃; for 0.166667h; Green chemistry;89%
98-80-6

phenylboronic acid

108-95-2

phenol

Conditions
ConditionsYield
With C5H11N*Cu(2+)*2NO3(1-); water at 30℃; for 2h;100%
With water at 60℃; for 5h; Green chemistry;100%
With water; oxygen; sodium sulfite at 50℃; for 1h; Temperature; Green chemistry;100%
54897-52-8

phenyl 3,3-dimethylacrylate

108-95-2

phenol

Conditions
ConditionsYield
With perchloric acid In acetonitrile at 20℃; for 1.25h; photo-Fries rearrangement; Inert atmosphere; Irradiation;100%
16156-59-5

phenyl methanesulfonate

108-95-2

phenol

Conditions
ConditionsYield
With sodium phosphate In aq. phosphate buffer; water; dimethyl sulfoxide at 25℃; for 0.333333h; pH=7.5; Enzymatic reaction;100%
89466-08-0

2-hydroxyphenyl boronic acid

108-95-2

phenol

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 120℃; for 2h; Suzuki Coupling; Inert atmosphere;100%
In dimethyl sulfoxide at 120℃; for 4h; Solvent; Temperature;100%
In dimethyl sulfoxide at 120℃; for 4h; Solvent; Temperature; Time; Reagent/catalyst;95%
With N-methyliminodiacetic acid In dimethyl sulfoxide; toluene at 120℃; for 12h; Inert atmosphere; Molecular sieve;
With 3-methyl-5H-1,4,2-dioxazol-5-one; Cp*Rh(OAc)2*H2O In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;

C8H11BO

108-95-2

phenol

Conditions
ConditionsYield
With water In dimethyl sulfoxide at 120℃; for 24h; Time; Reagent/catalyst;100%
In dimethyl sulfoxide at 120℃; for 12h;96%
Multi-step reaction with 2 steps
1: dimethyl sulfoxide; toluene / 12 h / Molecular sieve; Reflux; Dean-Stark
2: dimethyl sulfoxide / 240 h / 120 °C
View Scheme
269409-97-4

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

108-95-2

phenol

Conditions
ConditionsYield
In dimethyl sulfoxide at 120℃; for 24h;100%
In dimethyl sulfoxide at 120℃; for 24h;96%
71597-85-8

(p-hydroxyphenyl)boronic acid

108-95-2

phenol

Conditions
ConditionsYield
With acetic acid In 1,4-dioxane at 100℃; Reagent/catalyst; Solvent; Enzymatic reaction;100%
In formic acid at 60℃; for 2h;82%
With acetic acid at 130℃; for 1h; Reagent/catalyst; Temperature; Green chemistry;81%
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In toluene at 70℃; for 1.5h; Temperature; Microwave irradiation; Green chemistry;65%
1132-66-7

1-phenoxyhexane

108-95-2

phenol

Conditions
ConditionsYield
With boron tribromide In dichloromethane100%
946-80-5

(benzyloxy)benzene

A

108-88-3

toluene

B

108-93-0

cyclohexanol

C

108-95-2

phenol

Conditions
ConditionsYield
With Ni0.85Rh0.15; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst;A 100%
B 5%
C 79%
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 48h; Inert atmosphere; Autoclave;A 100%
B 12.2%
C 87.5%
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 3h; Catalytic behavior; Temperature; Inert atmosphere; Autoclave;A 100%
B 73.1%
C 22.4%
With Ru0.6Ni0.4; hydrogen In water at 95℃; under 760.051 Torr; for 16h; Reagent/catalyst;A 98%
B 61%
C 6%
With hydrogen In n-heptane at 140℃; under 750.075 Torr; for 6h; Catalytic behavior;A 34 %Chromat.
B 12 %Chromat.
C 22 %Chromat.
110-87-2

3,4-dihydro-2H-pyran

108-95-2

phenol

4203-50-3

2-phenoxytetrahydropyran

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide at 25℃; for 26h;100%
With poly-p-styryl-acetonyltriphenylphosphonium bromide In dichloromethane at 20℃; for 3h;99%
With zirconium(IV) chloride In dichloromethane for 1h;99%
109-04-6

2-bromo-pyridine

108-95-2

phenol

4783-68-0

2-phenoxypyridine

Conditions
ConditionsYield
With copper; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Ullmann Condensation; Microwave irradiation; Inert atmosphere;100%
With 1,1,1,5,5,5-hexafluoroacetylacetone; copper(II) ferrite; caesium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Ullmann Condensation; Inert atmosphere; Schlenk technique;99%
With 2-acetonylpyridine; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 90℃; for 15h; Inert atmosphere; chemoselective reaction;98%
96-09-3

styrene oxide

108-95-2

phenol

53574-80-4

AB_0000810

Conditions
ConditionsYield
With erbium(III) triflate In diethyl ether at 25℃; for 24h;100%
With BiCl6(3-)*2C4H10N2*ClH*3H(1+)*H2O In neat (no solvent) at 20℃; for 0.166667h;90%
With toluene-4-sulfonic acid; toluene Trennung von (+-)-1-Phenoxy-1-phenyl-aethanol-(2) und (+-)-2-Phenoxy-1-phenyl-aethanol-(1) ueber die 2-Carboxy-benzoyl-Derivate;
In benzene
Stage #1: phenol With sodium hydroxide In water at 80℃; for 0.166667h;
Stage #2: styrene oxide In water at 100℃; for 3h; Reagent/catalyst;
15.0 g
13091-23-1

4-chloro-3-nitropyridine

108-95-2

phenol

132038-21-2

3-nitro-4-phenoxypyridine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃;100%
With sodium hydride In tetrahydrofuran at 20℃;99%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;97%
541-41-3

chloroformic acid ethyl ester

108-95-2

phenol

3878-46-4

ethyl phenyl carbonate

Conditions
ConditionsYield
With pyridine In toluene at 220℃; for 24h;100%
With pyridine97%
With pyridine In toluene at 20 - 100℃; for 1h;65.2%
108-24-7

acetic anhydride

108-95-2

phenol

122-79-2

Phenyl acetate

Conditions
ConditionsYield
With pyridine; aluminum oxide at 103 - 105℃; for 2h; microwave irradiation;100%
With 2,6-di-tert-butyl-pyridine; sodium tetracarbonyl cobaltate In acetonitrile for 12h;100%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.25h;100%
98-88-4

benzoyl chloride

108-95-2

phenol

93-99-2

benzoic acid phenyl ester

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;100%
zinc(II) chloride In toluene99%
With sodium hydride In tetrahydrofuran at 20℃; for 1h;98%
103-71-9

phenyl isocyanate

108-95-2

phenol

4930-03-4

phenyl N-phenylcarbamate

Conditions
ConditionsYield
at 20℃; for 2h;100%
With cesium fluoride93.1%
With triethylamine In acetonitrile for 24.5h; Esterification;89%
124-63-0

methanesulfonyl chloride

108-95-2

phenol

16156-59-5

phenyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In benzene at 10℃; Kinetics; Mechanism; Thermodynamic data; Various temperatures, various concentrations. E(act.), ΔS(act.);100%
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;100%
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry;97%
1423-60-5

methyl ethynyl ketone

108-95-2

phenol

72024-02-3

(E)-4-phenoxybut-3-en-2-one

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 12h; Inert atmosphere;100%
With dmap In dichloromethane at 20℃; for 3h; Inert atmosphere;99%
dmap In dichloromethane at 20℃; for 2h;81%
With diethyl ether; triethylamine
350-46-9

4-Fluoronitrobenzene

108-95-2

phenol

620-88-2

4-nitrophenyl phenyl ether

Conditions
ConditionsYield
With cesium fluoride/clinoptilolite In dimethyl sulfoxide at 110℃; for 0.15h; Reagent/catalyst; Solvent; Temperature; Ullmann Condensation;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;100%
With potassium fluoride on basic alumina; 18-crown-6 ether In acetonitrile for 1h; Heating;98%
p-toluenesulfonyl chloride

p-toluenesulfonyl chloride

108-95-2

phenol

640-60-8

toluene-4-sulfonic acid phenyl ester

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry;100%
With potassium carbonate for 0.05h; microwave irradiation;99%
With sodium carbonate In water at 20℃; for 3h; Catalytic behavior; Reagent/catalyst;99%
78-93-3

butanone

108-95-2

phenol

77-40-7

Bisphenol B

Conditions
ConditionsYield
With hydrogenchloride at 15 - 20℃; for 3h;100%
With hydrogenchloride
108-12-3

isopentanoyl chloride

108-95-2

phenol

15806-38-9

phenyl 3-methylbutanoate

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride; sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h;100%
106-89-8

epichlorohydrin

108-95-2

phenol

122-60-1

Phenyl glycidyl ether

Conditions
ConditionsYield
Stage #1: phenol With sodium hydroxide In water at 25℃; for 0.666667h;
Stage #2: epichlorohydrin In water at 30 - 35℃; for 16h;
100%
With n-Bu4NOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h;91%
With n-BuNOSO2OCH2CHOHCH3; potassium carbonate at 75 - 80℃; for 1.5h; other aryl alcohols, var. phase transfer catalysts, var. reaction time;91%
74-88-4

methyl iodide

108-95-2

phenol

100-66-3

methoxybenzene

Conditions
ConditionsYield
With potassium hydroxide; acyclic polyethylene oxides In dichloromethane; water for 0.5h;100%
With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide for 1h; Product distribution; Ambient temperature; other phenols and alcohols, other alkylating agents, other reagents and solvents, var. time;100%
With potassium hydroxide; Aliquat 336 at 20℃; for 5h;99%
1795-48-8

Isopropyl isocyanate

108-95-2

phenol

17614-10-7

phenyl N-isopropylcarbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 23℃; for 2h; Inert atmosphere;100%
With dmap In tetrahydrofuran at 60℃; for 24h;94%
With dmap In tetrahydrofuran Heating;94%
With aluminium trichloride
103-82-2

phenylacetic acid

108-95-2

phenol

722-01-0

phenyl phenylacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
Stage #1: phenylacetic acid With phosphoric acid; trifluoroacetic anhydride In acetonitrile at 25℃; for 0.5h;
Stage #2: phenol In acetonitrile at 25℃; for 20h;
93%
Stage #1: phenylacetic acid With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃;
Stage #2: phenol In dichloromethane at 25℃;
87%
870-63-3

prenyl bromide

108-95-2

phenol

14309-15-0

phenyl prenyl ether

Conditions
ConditionsYield
at 170℃;100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Williamson Ether Synthesis; Darkness; Inert atmosphere;97%
With sodium hydroxide In N-methyl-acetamide; water75%
507-20-0

tertiary butyl chloride

108-95-2

phenol

98-54-4

para-tert-butylphenol

Conditions
ConditionsYield
With ethylaluminum dichloride bis(2-chloroethyl) ether complex In hexane; Cyclohexane-d12 at 25℃; for 2.5h; Catalytic behavior; Friedel-Crafts Alkylation; Glovebox; Inert atmosphere; regioselective reaction;100%
bei Siedetemperatur;
at 75℃; unter Druck;
108-95-2

phenol

101-02-0

triphenyl phosphite

Conditions
ConditionsYield
With Hexamethylphosphorous triamide In toluene at 130℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;100%
With phosphorus trichloride at 35 - 160℃; under 7.50075 Torr; for 6h; Temperature; Flow reactor; Inert atmosphere;94%
With 1H-imidazole; carbon disulfide; Hexamethylphosphorous triamide In benzene at 20 - 25℃; for 24h;86%
108-95-2

phenol

106-41-2

4-bromo-phenol

Conditions
ConditionsYield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4.5h; Heating;100%
With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 1.33333h; Catalytic behavior;100%
With oxygen; sodium bromide In dibutyl ether at 45℃; under 760.051 Torr; for 5h; Schlenk technique;99%
108-95-2

phenol

42368-15-0

(4-hydroxyphenyl)tellurium trichloride

Conditions
ConditionsYield
With tellurium tetrachloride In tetrachloromethane for 3h; Substitution; Heating;100%
With tetrachloromethane; tellurium tetrachloride
With tellurium tetrachloride
108-95-2

phenol

100-67-4

potassium phenolate

Conditions
ConditionsYield
With potassium hydride In tetrahydrofuran at 70℃; Inert atmosphere;100%
With potassium hydroxide In water at 24℃; for 0.5h;98%
With potassium hydroxide In water for 0.25h;98%
108-95-2

phenol

120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
With dihydrogen peroxide; MgAlZr0.1-HT In Petroleum ether at 79.9℃; for 8h;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In methanol; chloroform at -25℃; for 0.333333h;97%
With tert.-butylhydroperoxide In water; acetonitrile at 70℃; for 6h; Catalytic behavior; Temperature; Solvent;89%
108-95-2

phenol

106-51-4

p-benzoquinone

Conditions
ConditionsYield
With CuCl2 In acetonitrile100%
With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 10h; Catalytic behavior; Inert atmosphere;99%
With manganese(IV) oxide; sulfuric acid; aniline at 10℃; for 1.5h;95%
108-95-2

phenol

108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; rhodium colloidal catalyst In water at 36℃; under 180018 Torr; for 62h; pH=7.5; Catalytic hydrogenation;100%
In methanol; water100%
With hydrogen In water at 70℃; under 7500.75 Torr; for 0.25h;100%
100-01-6

4-nitro-aniline

108-95-2

phenol

1435-60-5, 81944-71-0

4-(4'-hydroxyphenylazo)nitrobenzene

Conditions
ConditionsYield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 2℃; for 1.5h;
Stage #2: phenol With sodium hydroxide In water at 2 - 20℃; for 4h;
100%
Stage #1: 4-nitro-aniline With carboxyl- and nitrite- functionalized graphene quantum dots at 20℃; for 0.0833333h;
Stage #2: phenol In water at 20℃; for 0.166667h;
96%
Stage #1: 4-nitro-aniline With hydrogenchloride In water; acetone at 0℃; Inert atmosphere;
Stage #2: With sodium nitrite In water; acetone at 0℃; for 1h; Inert atmosphere;
Stage #3: phenol With sodium carbonate; sodium hydroxide In water; acetone at 0 - 20℃; for 3h; Inert atmosphere;
92%
15933-59-2

1,1,3,3-tetramethyldisilazane

108-95-2

phenol

18246-19-0

dimethylphenoxysilane

Conditions
ConditionsYield
100%
With dimethylmonochlorosilane; triethylamine for 1h; temp.: below 40 deg C;57%
With dimethylmonochlorosilane Heating;
at 20 - 160℃; for 2h; Inert atmosphere;
501-52-0

3-Phenylpropionic acid

108-95-2

phenol

726-26-1

phenyl 3-phenylpropanoate

Conditions
ConditionsYield
With dmap; trimethylsilylethoxyacetylene; mercury(II) oxide In 1,2-dichloro-ethane at 40℃; for 0.5h;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
With dmap; di-2-thienyl carbonate In dichloromethane at 20℃; for 2h;95%
Raw Materials
108-86-1
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    108-95-2

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Consensus Reports

NCI Carcinogenesis Bioassay (oral); No Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-203 ,1980. . EPA Extremely Hazardous Substances List. Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Standards and Recommendations

OSHA PEL: TWA 5 ppm (skin)
ACGIH TLV: TWA 5 ppm (skin); BEI: 250 mg(total phenol)/g creatinine in urine at end of shift; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans; BAT: 300 mg/L at end of shift
NIOSH REL: (Phenol) TWA 20 mg/m3; CL 60 mg/m3/15M
DOT Classification:  6.1; Label: Poison

Analytical Methods

For occupational chemical analysis use OSHA: #32 or NIOSH: Phenol, 3502; Phenol and p-Cresol in Urine, 8305.

Specification

The Phenol, monohydroxy derivative of benzene, is an organic compound with the chemical formula C6H5OH. It has the EINECS register number 203-632-7 and CAS register number 108-95-2. Phenol is appreciably soluble in water, with about 8.3 g dissolving in 100 mL (0.88 M). In addition, Phenol is a colourless crystals with a characteristic odour. It is stable which should be protected from strong oxidizing agents, strong bases, strong acids, alkalies and calcium hypochlorite. Phenol is flammable which may discolour in light. 

Physical properties about Phenol are: (1)ACD/LogP: 1.54; (2)ACD/LogD (pH 5.5): 1.54; (3)ACD/LogD (pH 7.4): 1.54; (4)ACD/BCF (pH 5.5): 8.72; (5)ACD/BCF (pH 7.4): 8.69; (6)ACD/KOC (pH 5.5): 164.00; (7)ACD/KOC (pH 7.4): 163.44; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.553; (12)Molar Refractivity: 28.134 cm3; (13)Molar Volume: 87.863 cm3; (14)Polarizability: 11.153 10-24cm3; (15)Surface Tension: 40.9669990539551 dyne/cm; (16)Density: 1.071 g/cm3; (17)Flash Point: 72.475 °C; (18)Enthalpy of Vaporization: 43.524 kJ/mol; (19)Boiling Point: 181.839 °C at 760 mmHg; (20)Vapour Pressure: 0.614000022411346 mmHg at 25°C

Preparation of Phenol: Phenol has been made, over the years, by a variety of processes. Historically, an important method was the sulfonation of benzene followed by desulfonation with caustic soda:

C6H6 + H2SO4 → C6H5SO3H + H2O
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO4

The above route to Phenol has no longer used. The principal process in use is the peroxidation of cumene (iso-propylbenzene) at 130 °C in the presence of air and a catalyst followed by decomposition of the peroxide at 55 to 65 °C in the presence of sulfuric acid. In the cumene process, cumene is oxidized to form cumene hydroperoxide that is then concentrated and cleaved to produce phenol and acetone. By-products of the oxidation reaction are acetophenone and dimethyl benzyl alcohol, which is dehydrated in the cleavage reaction to produce alpha-methylstyrene.

C6H6 + CH2=CH-CH3 → C6H5CH(CH3)2
C6H5CH(CH3)2 + O2 → C6H5C(CH3)2OOH
C6H5C(CH3)2OOH [H2SO4]→ C6H5OH + CH3COCH3

The toluene-benzoic acid process of preparation of Phenol involves three chemical reactions: (l) oxidation of toluene to form benzoic acid, (2) oxidation of benzoic acid to form phenyl benzoate, (3) hydrolysis of phenyl benzoate to form phenol.

2 C6H5CH3 + 3 O2 → 2 C3H5CO2H + 2 H2O
4 C6H5CO2H + O2 → 2 C6H5CO2C6H5 + 2 H2O + 2 CO2
C6H5CO2C6H5 + 2 OH- → 2 C6H5OH + CO2

Uses of  Phenol: Phenol was widely used as an antiseptic, especially as Carbolic soap. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. The major uses of Phenol involve its conversion to plastics or related materials. Condensation with acetone gives bisphenol-A. Phenol is also used as an oral anesthetic/analgesic, commonly used to temporarily treat pharyngitis. Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceuticals. Phenol is one of the chemicals for embalming bodies for study because of its ability to preserve tissues for extended periods of time.

When you are using Phenol, please be cautious about it. Phenol is toxic, harmful, corrosive and highly flammable. There will be a danger of serious damage to health by prolonged exposure through inhalation, and in contact with skin and if swallowed. In addition, Phenol is toxic by inhalation, in contact with skin and if swallowed. What's more, there is a danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact Phenol, you should wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you can seek medical advice immediately (show label where possible). Meanwhile, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)O
(2)InChI: InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
(3)InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N

Toxicity of Phenol:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 80mg/kg (80mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935.
cat LDLo subcutaneous 80mg/kg (80mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
cat LDLo unreported 250mg/kg (250mg/kg)   Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
dog LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935.
dog LDLo unreported 200mg/kg (200mg/kg)   Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
frog LDLo parenteral 290mg/kg (290mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
frog LDLo subcutaneous 75mg/kg (75mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1319, 1935.
frog LDLo subcutaneous 290mg/kg (290mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955.
guinea pig LDLo intraperitoneal 300mg/kg (300mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955.
guinea pig LDLo subcutaneous 450mg/kg (450mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 1, Pg. 228, 1955.
human LDLo oral 140mg/kg (140mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
"Practical Toxicology of Plastics," Lefaux, R., Cleveland, OH, Chemical Rubber Co., 1968Vol. -, Pg. 329, 1968.
human LDLo oral 14gm/kg (14000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 463, 1969.
infant LDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 463, 1969.
mammal (species unspecified) LD50 oral 500mg/kg (500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
man TDLo unreported 5714ug/kg (5.714mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Veterinary and Human Toxicology. Vol. 41, Pg. 151, 1999.
mouse LC50 inhalation 177mg/m3 (177mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(6), Pg. 103, 1976.
mouse LD50 intraperitoneal 180mg/kg (180mg/kg)   Pharmacologist. Vol. 10, Pg. 172, 1968.
mouse LD50 intravenous 112mg/kg (112mg/kg) BEHAVIORAL: TREMOR Quarterly Journal of Pharmacy & Pharmacology. Vol. 12, Pg. 212, 1939.
mouse LD50 oral 270mg/kg (270mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(8), Pg. 6, 1973.
mouse LD50 subcutaneous 344mg/kg (344mg/kg)   Industrial Health. Vol. 5, Pg. 143, 1967.
rabbit LD50 skin 630mg/kg (630mg/kg)   Union Carbide Data Sheet. Vol. 1/6/1966,
rabbit LDLo intraperitoneal 620mg/kg (620mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo intravenous 180mg/kg (180mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo oral 420mg/kg (420mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo subcutaneous 620mg/kg (620mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 80, Pg. 233, 1944.
rabbit LDLo unreported 150mg/kg (150mg/kg)   Revue Medicale de la Suisse Romande. Vol. 15, Pg. 561, 1895.
rat LC50 inhalation 316mg/m3 (316mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(6), Pg. 103, 1976.
rat LD50 intraperitoneal 127mg/kg (127mg/kg)   Food and Chemical Toxicology. Vol. 22, Pg. 665, 1984.
rat LD50 oral 317mg/kg (317mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Proceedings of the Society for Experimental Biology and Medicine. Vol. 32, Pg. 592, 1935.
rat LD50 skin 669mg/kg (669mg/kg) BEHAVIORAL: TREMOR

KIDNEY, URETER, AND BLADDER: HEMATURIA

SKIN AND APPENDAGES (SKIN): CUTANEOUS SENSITIZATION (EXPERIMENTAL): AFTER TOPICAL EXPOSURE
British Journal of Industrial Medicine. Vol. 27, Pg. 155, 1970.
rat LD50 subcutaneous 460mg/kg (460mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 10, Pg. 1, 1963.