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88-69-7

Basic Information
CAS No.: 88-69-7
Name: 2-Isopropylphenol
Article Data: 107
Molecular Structure:
Molecular Structure of 88-69-7 (2-Isopropylphenol)
Formula: C9H12 O
Molecular Weight: 136.194
Synonyms: Phenol,o-isopropyl- (8CI); 2-(1-Methylethyl)phenol; 2-Isopropylphenol; NSC 5103;o-Cumenol; o-Hydroxycumene; o-Isopropylphenol
EINECS: 201-852-8
Density: 1.012
Melting Point: 15 - 16 C
Boiling Point: 212 - 213 C
Flash Point: 107 ºC
Solubility: Insoluble SOLVENT
Appearance: clear to pale yellow liquid
Hazard Symbols:
Risk Codes: R34   
Safety: Poison by intravenous route. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating vapors.
Transport Information: UN 3145
PSA: 20.23000
LogP: 2.51560
Synthetic route
7073-94-1

1-bromo-2-isopropylbenzene

88-69-7

2-(1-methylethyl)phenol

Conditions
ConditionsYield
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 6h;96%
With potassium phosphate; tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 20h;38%
With cesiumhydroxide monohydrate; bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In tetrahydrofuran at 24℃; for 20h; Inert atmosphere;
89787-12-2

2-isopropylphenylboronic acid

88-69-7

2-(1-methylethyl)phenol

Conditions
ConditionsYield
With iron(III) oxide; oxygen In tetrahydrofuran Irradiation;90%
With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation;90%
With ozone In ethanol; water at 20 - 30℃; for 0.5h;90%
676-58-4

methylmagnesium chloride

346433-42-9

carbonic acid tert-butyl ester 2-formyl-phenyl ester

88-69-7

2-(1-methylethyl)phenol

Conditions
ConditionsYield
In diethyl ether at 0℃; Grignard reaction;86%
2944-47-0

o-isopropylanisole

88-69-7

2-(1-methylethyl)phenol

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 24h;80%
With hydrogen iodide
With boron tribromide

aluminium isopropoxide

2216-51-5

(-)-menthol

108-95-2

phenol

A

88-69-7

2-(1-methylethyl)phenol

B

99-89-8

4-Isopropylphenol

C

2741-16-4

isopropoxybenzene

D

618-45-1

3-isopropylhydroxybenzene

Conditions
ConditionsYield
at 120℃; for 15h;A 64%
B 23%
C 10%
D 3%
67-63-0

isopropyl alcohol

108-95-2

phenol

A

88-69-7

2-(1-methylethyl)phenol

B

99-89-8

4-Isopropylphenol

C

644-35-9

5-propylphenol

D

2078-54-8

2,6-diisopropylphenol

Conditions
ConditionsYield
With supercritical water at 399.84℃; for 1h; Kinetics; Further Variations:; Time;A 57.9%
B 2.4%
C 6.9%
D 5.9%
108-24-7

acetic anhydride

643-28-7

2-isopropylaniline

A

88-69-7

2-(1-methylethyl)phenol

B

19486-60-3

2-isopropylbiphenyl

C

1608-68-0

2-isopropyl-phenyl acetate

Conditions
ConditionsYield
With potassium acetate; isopentyl nitrite In benzene at 80℃; for 10h;A 14%
B 6.4%
C 46%
108-24-7

acetic anhydride

643-28-7

2-isopropylaniline

A

88-69-7

2-(1-methylethyl)phenol

B

19486-60-3

2-isopropylbiphenyl

C

1608-68-0

2-isopropyl-phenyl acetate

D

59341-22-9

3,3-dimethyl-3H-indazole

Conditions
ConditionsYield
With potassium acetate; isopentyl nitrite In benzene at 80℃; for 10h;A 14%
B 6.4%
C 46%
D 2%
67-63-0

isopropyl alcohol

108-95-2

phenol

A

88-69-7

2-(1-methylethyl)phenol

B

99-89-8

4-Isopropylphenol

C

2078-54-8

2,6-diisopropylphenol

D

2741-16-4

isopropoxybenzene

Conditions
ConditionsYield
With HMCM-49/MCM-41 composite at 180℃; under 760.051 Torr; for 1h; Flow reactor;A 41.6%
B 13.3%
C n/a
D n/a

aluminium isopropoxide

2216-51-5

(-)-menthol

108-95-2

phenol

A

88-69-7

2-(1-methylethyl)phenol

B

99-89-8

4-Isopropylphenol

C

618-45-1

3-isopropylhydroxybenzene

Conditions
ConditionsYield
at 160℃; for 15h;A 37%
B 26%
C 37%
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Chemistry

MF: C9H12O
MW: 136.19
EINECS: 201-852-8
Flash Point: 88.9 °C
Water Solubility: insoluble
Melting Point: 12-16 °C(lit.)
Refractive index: n20/D 1.526(lit.)
Density: 1.012 g/mL at 25 °C(lit.)
IUPAC Name: 2-propan-2-ylphenol
Boiling Point: 213.5 °C at 760 mmHg 
Enthalpy of Vaporization: 46.82 kJ/mol
vapor pressure: <0.05 mm Hg ( 25 °C) 
Appearance: Colourless liquid, phenolic odour
Stability: Stable under normal temperatures and pressures.
Product Categories: API intermediates ; Alphabetical Listings ; Flavors and Fragrances ; I-L ; Organic Building Blocks ; Oxygen Compounds ; Phenols
Synonyms: 1-Hydroxy-2-isopropylbenzene ; 2-(1-Methylethyl)-pheno ; 2-(1-Methylethyl)phenol ; 2-(1-Methylethyl)-Phenol ; Isopropylphenol, ortho ; O-Hydroxycumene ; O-isopropyl-phenol ; Phenol, o-isopropyl-
Following is the molecular structure of O-isopropylphenol (88-69-7):

Production

Phenols, such as 2-Isopropylphenol (88-69-7), do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.

Toxicity Data With Reference

1.    

ivn-mus LD50:100 mg/kg

    JMCMAR    Journal of Medicinal Chemistry. 23 (1980),1350.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intravenous route. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Information of O-isopropylphenol (88-69-7):
Hazard Codes  C,Xn
C: Corrosive   Xn: Harmful
Risk Statements: 34-22
34: Causes burns 
22: Harmful if swallowed 
Safety Statements: 26-36/37/39-45-28
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 
RIDADR: UN 3145 8/PG 2
WGK Germany: 3
RTECS: SL5900000
HazardClass: 8
PackingGroup: II
HS Code: 29071900

Standards and Recommendations

DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD