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Properties of substance:
phenol
skc-file
Group of substances:
organic
Physical appearance:
colorless needles crystals
Empirical formula (Hill's system for organic substances):
C
6
H
6
O
Structural formula as text:
C6H5OH
Molar/atomic mass: 94.1112
Melting point (°C):
40.9
Boiling point (°C):
181.75
Solubility (g/100 g of solvent):
1,1,2-trichloro-1,2,2-trifluoroethane
: sparingly soluble [
Ref.
]
acetone
: very soluble [
Ref.
]
benzene
: 2.5 (16°C) [
Ref.
]
benzene
: 8.33 (21°C) [
Ref.
]
benzene
: 10 (25°C) [
Ref.
]
carbon disulphide
: very soluble [
Ref.
]
carbon tetrachloride
: very soluble [
Ref.
]
chloroform
: very soluble [
Ref.
]
deuterium oxide
: 6.6 (20°C) [
Ref.
]
diethyl ether
: very soluble [
Ref.
]
dimethylsulfoxide
: very soluble [
Ref.
]
ethanol
: very soluble [
Ref.
]
glycerol 99.04%
: 276.4 (20°C) [
Ref.
]
hydrogen fluoride
: very soluble [
Ref.
]
oils: soluble [
Ref.
]
petroleum ether: insoluble [
Ref.
]
sulfur dioxide
: 38.9 (20°C) [
Ref.
]
water
: 6.7 (16°C) [
Ref.
]
water
: 8 (20°C) [
Ref.
]
water
: 9.016 (35°C) [
Ref.
]
water
: 10.71 (50°C) [
Ref.
]
water
: 14.97 (60°C) [
Ref.
]
water
: miscible (65.85°C) [
Ref.
]
Density:
1.0576 (41°C, g/cm
3
)
1.5426 (41°C, g/cm
3
)
Reactions of synthesis:
Yeild 96%. [
Ref.1
]
HOC
6
H
5
Cl + NH
4
Cl + Zn → HOC
6
H
6
+ ZnCl
2
+ NH
3
Reactions:
Yeild 80%. [
Ref.1
]
C
6
H
5
OH + (CH
3
)
2
CHCH
2
OH → (CH
3
)
3
CC
6
H
4
OH + H
2
O
Yeild 50%. [
Ref.1
]
C
6
H
5
OH + C
6
H
11
OH → C
6
H
11
C
6
H
4
OH + H
2
O
[
Ref.1
]
C
6
H
5
OH + C
2
H
5
OH → C
2
H
5
C
6
H
4
OH + H
2
O
Yeild 75%. [
Ref.1
,
Ref.2
]
C
6
H
5
OH + 3H
2
→ C
6
H
11
OH
Yeild 90-96%. [
Ref.1
]
2C
6
H
5
OH + (CH
3
)
2
CO → HOC
6
H
4
C(CH
3
)
2
C
6
H
4
OH + H
2
O
Yeild 44%. [
Ref.1
]
C
6
H
5
OH + (CH
3
COO)
2
Hg → CH
3
COOHgC
6
H
4
OH + CH
3
COOH
CH
3
COOHgC
6
H
4
OH + NaCl → ClHgC
6
H
4
OH + CH
3
COONa
Yeild 33%. [
Ref.1
,
Ref.2
,
Ref.3
,
Ref.4
,
Ref.5
]
C
6
H
5
OH + H
3
AsO
4
→ HOC
6
H
4
As(O)(OH)
2
+ H
2
O
HOC
6
H
4
As(O)(OH)
2
+ NaOH → HOC
6
H
4
As(O)(OH)(ONa) + H
2
O
[
Ref.1
]
HOC
6
H
5
+ (CH
3
)
2
SO + HCl → HOC
6
H
4
S(CH
3
)
2
Cl + H
2
O
Vapour pressure (Torr):
10 (73.5°C)
25 (90°C)
100 (120.2°C)
Dissociation:
pK
a
(1) = 9.98 (25°C, water)
pK
a
(1) = 18 (25°C, dimethylsulfoxide)
Standard molar enthalpy (heat) of formation Δ
f
H
0
(298.15 K, kJ/mol):
-165.02 (s)
Standard molar Gibbs energy of formation Δ
f
G
0
(298.15 K, kJ/mol):
-50.42 (s)
Standard molar entropy S
0
(298.15 K, J/(mol·K)):
144.01 (s)
Standard molar enthalpy (heat) of formation Δ
f
H
0
(298.15 K, kJ/mol):
-90.36 (g)
Standard molar Gibbs energy of formation Δ
f
G
0
(298.15 K, kJ/mol):
-32.89 (g)
Standard molar entropy S
0
(298.15 K, J/(mol·K)):
315.6 (g)
Molar heat capacity at constant pressure C
p
(298.15 K, J/(mol·K)):
103.55 (g)
LD
50
(mg/kg):
512 (white rats, oral)
427 (mice, oral)
Spectral properties of the substance:
Ultraviolet/visible spectrum (maximum in nm, layer thickness 1 cm, in parentheses - extinction) = 287 (281)
Ultraviolet/visible spectrum (maximum in nm, layer thickness 1 cm, in parentheses - extinction) = 270 (172)
References:
Clarke's isolation and identification of drugs. - 2ed. - London: Pharmaceutical press, 1986. - pp. 884-885
Milne G.W.A. Gardner's Commercially Important Chemicals. - Wiley-Interscience, 2005. - pp. 483-484
Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 372-390
Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 255-257
Альберт А., Сержент Е. Константы ионизации кислот и оснований. - М.-Л.: Химия, 1964. - pp. 126 [Russian]
Ахметов Б.В. Задачи и упражнения по физической и коллоидной химии. - Л.: Химия, 1989. - pp. 230 [Russian]
Беликов В.Г. Учебное пособие по фармацевтической химии. - М.: Медицина, 1979. - pp. 160 [Russian]
Крамаренко В.Ф. Токсикологическая химия. - Киев: Выща школа, 1989. - pp. 149-152 [Russian]
Лабораторные работы по фармацевтической химии. - Под ред. Беликова В.Г. - М.: Высшая школа, 1989. - pp. 142 [Russian]
Неотложная помощь при острых отравлениях: Справочник по токсикологии. - Под ред. Голикова С.Н. - М.: Медицина, 1977. - pp. 174-175 [Russian]
Полюдек-Фабини Р., Бейрих Т. Органический анализ. - Л.: Химия, 1981. - pp. 80-81 [Russian]
Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 188-189 [Russian]
Руководство к лабораторным занятиям по фармацевтической химии. - Под ред. Арзамасцева А.П. - М.: Медицина, 1987. - pp. 173-174 [Russian]
Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 434-436 [Russian]
Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 967, 1406, 1452 [Russian]
Харлампович Г.Д., Чуркин Ю.В. Фенолы. - М.: Химия, 1974. - pp. 11-12 [Russian]
Химическая энциклопедия. - Т. 2. - М.: Советская энциклопедия, 1990. - pp. 393 [Russian]
Химическая энциклопедия. - Т. 5. - М.: Советская энциклопедия, 1999. - pp. 70-71 [Russian]
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© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru
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], Ref.2], Ref.3
, Ref.4, Ref.5]