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108-93-0

Basic Information
CAS No.: 108-93-0
Name: Cyclohexanol
Article Data: 1857
Cas Database
Molecular Structure:
Molecular Structure of 108-93-0 (Cyclohexanol)
Formula: C6H12O
Molecular Weight: 100.161
Synonyms: 1-Cyclohexanol;Adronal;Adronol;Anol;Cyclohexyl alcohol;Hexahydrophenol;Hexalin;Hexalin(alcohol);Hydroxycyclohexane;NSC 403656;NSC 54711;Naxol;Phenol, hexahydro-;
EINECS: 203-630-6
Density: 0.968 g/cm3
Melting Point: 23 °C
Boiling Point: 159.552 °C at 760 mmHg
Flash Point: 67.778 °C
Solubility: 3.6 g/100 mL (20 °C)
Appearance: a colorless liquid with a camphor-like odor
Hazard Symbols: HarmfulXn
Risk Codes: 20/22-37/38
Safety: 24/25
Transport Information: UN 1993
PSA: 20.23000
LogP: 1.31140
Synthetic route
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen In decane at 349.84℃; under 22502.3 Torr; for 3h; Temperature; Autoclave;95.6%
With hydrogen In water at 160℃; for 6h;80%
Multi-step reaction with 3 steps
1: hydrogenchloride / 80 °C / 760.05 Torr / Electrochemical reaction
2: sodium hydroxide / 80 °C / Electrochemical reaction
3: hydrogenchloride / 80 °C / 760.05 Torr / Electrochemical reaction
View Scheme
156147-58-9

1-((cyclohexyloxy)methyl)-4-methoxybenzene

108-93-0

cyclohexanol

Conditions
ConditionsYield
With 4,4'-bipyridine; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; under 3000.3 Torr; for 10h; Reagent/catalyst; Autoclave; Green chemistry;96%
With 4,4'-bipyridine; (phthalocyaninato)iron(II); oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; under 3000.3 Torr; for 10h; Autoclave;91%
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In monoethylene glycol diethyl ether at 120℃; under 1500.15 Torr; for 1.5h;
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 100℃; under 760.051 Torr; for 3.5h;
62-53-3

aniline

108-93-0

cyclohexanol

Conditions
ConditionsYield
With water; hydrogen In tert-butyl alcohol at 180℃; under 33003.3 Torr; for 8h; Reagent/catalyst; Pressure; Temperature; Molecular sieve; Autoclave;99.9%
With water; hydrogen at 160℃; Hydrogenation.Leiten ueber Nickel/Bimsstein;
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%
4441-56-9

cyclohexylboronic acid

108-93-0

cyclohexanol

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; water; triethylamine In acetonitrile at 20℃; for 0.166667h;92%
With Fe2O3-SiO2 nanoparticles; air In water at 50℃; for 3h; Green chemistry;91%
With dihydrogen peroxide at 30℃; for 5h; Green chemistry;91%
108-94-1

cyclohexanone

108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen; 5 percent Rh/MgO; magnesium oxide In water at 323℃; under 15001.2 Torr; Product distribution;100%
With Triethoxysilane; benzoic acid ethyl ester; cesium fluoride at 25℃; for 0.0166667h;100%
With zinc(II) tetrahydroborate In acetonitrile for 0.166667h; Ambient temperature;100%
930-68-7

cyclohexenone

A

108-94-1

cyclohexanone

B

108-93-0

cyclohexanol

Conditions
ConditionsYield
With Geotrichum candidum CCT 1205 whole cells In aq. phosphate buffer at 28℃; for 24h; pH=6.5; Enzymatic reaction;A 100%
B n/a
With hydrogen; In methanol at 30℃; under 735.5 Torr; for 5h;A 0.8%
B 98.2%
With C8H13O2S2(3-)*Na(1+)*Rh(1+)*H(1+); hydrogen In water; toluene at 60℃; under 15001.5 Torr; for 4h; Inert atmosphere; Schlenk technique; Autoclave;A 90%
B 9%
110-82-7

cyclohexane

108-93-0

cyclohexanol

Conditions
ConditionsYield
With ferredoxin reductase; [2Fe–2S] ferredoxin; cytochrome P450 enzyme CYP101B1 In aq. buffer pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction;95%
With C44H34N8O9Ti; dihydrogen peroxide; sodium hydrogencarbonate In acetonitrile at 80℃; under 760.051 Torr; for 4h; Catalytic behavior; Reagent/catalyst;93%
With perchloric acid; dihydrogen peroxide In water; acetonitrile; tert-butyl alcohol at 60℃; for 1h; stereoselective reaction;92%
90-05-1

2-methoxy-phenol

A

110-82-7

cyclohexane

B

2979-24-0

2-methoxycyclohexanol

C

108-93-0

cyclohexanol

Conditions
ConditionsYield
With 5% active carbon-supported ruthenium; hydrogen; magnesium oxide In water at 159.84℃; under 11251.1 Torr; for 2h; Reagent/catalyst; Autoclave;A 7%
B 12%
C 79%
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Autoclave;A 16.8%
B 67.4%
C 8.9%
With hydrogen In decane at 20 - 250℃;A 25 %Chromat.
B 9 %Chromat.
C 8 %Chromat.
101-84-8

diphenylether

A

110-82-7

cyclohexane

B

4645-15-2

dicyclohexyl ether

C

108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen; nickel In methyl cyclohexane at 90℃; under 37503.8 Torr; for 2.5h; chemoselective reaction;
With hydrogen In decalin at 120℃; under 15001.5 Torr; for 2h;
With hydrogen In methyl cyclohexane at 200℃; under 37503.8 Torr; for 0.666667h; Glovebox; Inert atmosphere; Autoclave;
With carbon dioxide; rhodium on carbon; hydrogen In tetrahydrofuran; water at 80℃; for 5h;
With hydrogen In water at 250℃; under 30003 Torr; for 2h;
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    Product Name: Cyclohexanol CAS: 108-93-0 MF: C6H12O MW: 100.16 EINECS: 203-630-6 Mol File: 108-93-0.mol Cyclohexanol Structure Cyclohexanol Chemical Properties Melting point 20-22 °C (lit.) Boiling point 160-161 °C

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Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 50 ppm (skin)
ACGIH TLV: TWA 50 ppm (skin)
DFG MAK: 50 ppm (210 mg/m3)

Analytical Methods

For occupational chemical analysis use NIOSH: Alcohols III, 1402.

Specification

This chemical has the IUPAC name Cyclohexanol,  and it's also named as 1-cyclohexanol. With the CAS registry number 108-93-0, its product categories are Essential Chemicals; Reagent Plus; Routine Reagents; Alcohols; C2 to C6; Oxygen Compounds and its classification codes are Human Data; Mutation data; Reproductive Effect; Skin / Eye Irritant; TSCA Flag T [Subject to the Section 4 test rule under TSCA]. However, this chemical is an alcohol and it should be stored in the cool and dry place. Keep it away from the oxides, heat, fire and acid.

Other characteristics of the Cyclohexanol can be summarised as followings: (1)ACD/LogP: 1.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.282; (4)ACD/LogD (pH 7.4): 1.282; (5)ACD/BCF (pH 5.5): 5.551; (6)ACD/BCF (pH 7.4): 5.551; (7)ACD/KOC (pH 5.5): 118.699; (8)ACD/KOC (pH 7.4): 118.699; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.478; (14)Molar Refractivity: 29.261 cm3; (15)Molar Volume: 103.441 cm3; (16)Polarizability: 11.6×10-24cm3; (17)Surface Tension: 32.496 dyne/cm; (18)Density: 0.968 g/cm3; (19)Flash Point: 67.778 °C; (20)Enthalpy of Vaporization: 46.14 kJ/mol; (21)Boiling Point: 159.552 °C at 760 mmHg; (22)Vapour Pressure: 0.876 mmHg at 25°C.

The Cyclohexanol could be obtained by the method of phenol hydrogenation and cyclohexane oxidation: It could be made by the reactant of 1-cyclohexyloxy-1H-pyridine-2-thione. This reaction needs the reagents of tributylstannane, AIBN, and the solvent of benzene. The yield is 73 %. In addition, this reaction should be taken for 20 minutes at the temperature of 80 °C.

Cyclohexanol could be made by the reactant of 1-cyclohexyloxy-1H-pyridine-2-thione

Uses of the Cyclohexanol: It's mainly used for the production of adipic acid, hexamethylene diamine, cyclohexanone, caprolactam and as a soap stabilizing agent, disinfection medicated soap and detergent emulsion. It's also used as solvents such as rubber, resins, nitrocellulose, metallic soaps, oils, esters, ethers. Paint blending agent, leather degreasing agent, release agent, dry cleaners, polishes are also made from the material of this chemical.

When you are using this chemical, please be cautious about it as the following: This chemical is harmful by inhalation and if swallowed. It's irritating to respiratory system and skin. Please avoid contact with skin and eyes.

You can still convert the following datas into molecular structure: 
1.SMILES: C1CCC(CC1)O
2.InChI: InChI=1/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2
3.InChIKey: HPXRVTGHNJAIIH-UHFFFAOYAN

The toxicity data is as follows:   

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo parenteral 1914mg/kg (1914mg/kg) CARDIAC: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 24, Pg. 405, 1925.
human TCLo inhalation 75ppm (75ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
mouse LD50 intramuscular 1gm/kg (1000mg/kg)   Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962.
mouse LD50 intraperitoneal 1352mg/kg (1352mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1254, 1969.
mouse LD50 intravenous 272mg/kg (272mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 330, 1962.
rabbit LDLo oral 2200mg/kg (2200mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.
rabbit LDLo skin 794mg/kg (794mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: CHANGE IN GALL BLADDER STRUCTURE OR FUNCTION
National Technical Information Service. Vol. OTS0538617,
rat LC inhalation > 6500mg/m3/1H (6500mg/m3)   National Technical Information Service. Vol. OTS0572832,
rat LD50 oral 1400mg/kg (1400mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0538617,