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Cyclohexanemethanol

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Name

Cyclohexanemethanol

EINECS 202-857-8
CAS No. 100-49-2 Density 0.913 g/cm3
PSA 20.23000 LogP 1.55900
Solubility N/A Melting Point -43oC
Formula C7H14O Boiling Point 181.1 °C at 760 mmHg
Molecular Weight 114.188 Flash Point 71.1 °C
Transport Information N/A Appearance Colorless liquid
Safety 23-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 100-49-2 (Cyclohexanemethanol) Hazard Symbols N/A
Synonyms

(Hydroxymethyl)cyclohexane;Cyclohexanecarbinol;Cyclohexylcarbinol;Cyclohexylmethylalcohol;NSC 5288;

Article Data 408

Cyclohexanemethanol Synthetic route

100-51-6

benzyl alcohol

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 1h;100%
With hydrogen In water at 100℃; under 22502.3 Torr; for 3h;99%
With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; rhodium colloidal catalyst In water at 36℃; under 180018 Torr; for 62h; pH=7.5; Catalytic hydrogenation;73%
2043-61-0

cyclohexanecarbaldehyde

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 25℃; for 2h;100%
With isopropyl alcohol; zirconium(IV) oxide for 6h; Heating;99%
With isopropyl alcohol; zirconium(IV) oxide for 6h; Rate constant; Heating;99%
100-52-7

benzaldehyde

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen In water at 100℃; under 15001.5 Torr; for 1h;100%
With hydrogen In water at 75℃; under 22502.3 Torr; for 10h; Autoclave; Sealed tube; Ionic liquid; chemoselective reaction;100%
With hydrogen at 180℃; under 150015 Torr; for 10h; Conversion of starting material;
With hydrogen In water at 30℃; under 22502.3 Torr; for 1h; Autoclave; chemoselective reaction;
With hydrogen In water at 30℃; for 19h; Autoclave;
98-89-5

Cyclohexanecarboxylic acid

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With samarium diiodide; hexanal; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; potassium hydroxide at 20℃; for 0.075h; Reduction;99%
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;94%
With hydrogen; Rh/Al2O3; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 150℃; under 76000 Torr; for 16h;93%
88773-82-4

(tetrahydropyranoxymethyl)-cyclohexane

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
Nafion-H In methanol for 4h;99%
65-85-0

benzoic acid

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With hydrogen; Rh/Al2O3; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 150℃; under 76000 Torr; for 16h;99%
With hydrogen In hexane at 130℃; under 15001.5 Torr; for 18h; Molecular sieve; chemoselective reaction;72 %Chromat.
With hydrogen In water at 220℃; under 37503.8 Torr; for 24h; Autoclave;94.6 %Chromat.
937-55-3

cyclohexylmethyl acetate

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With methanol; potassium permanganate; trimethylsulphonium iodide at 25℃; under 760.051 Torr; chemoselective reaction;99%
With ((N-((6-((di-tert-butylphosphino)methyl)pyridin-2-yl)methyl)-2-methylpropan-2-amine))CoCl2; potassium tert-butylate; hydrogen; sodium triethylborohydride In tetrahydrofuran at 130℃; under 37503.8 Torr; for 48h; Inert atmosphere; Autoclave; High pressure;51 %Chromat.
With C21H35BrMnN2O2P; hydrogen; potassium hydride; 1,3,5-trimethyl-benzene In toluene at 100℃; under 15001.5 Torr; for 43h; Autoclave; Inert atmosphere;99 %Spectr.
3289-28-9

ethyl cyclohexanecarboxylate

A

64-17-5

ethanol

B

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;A n/a
B 99%
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube; Overall yield = 99 %;
4630-82-4

methyl cyclohexylcarboxylate

A

67-56-1

methanol

B

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;A n/a
B 99%
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube; Overall yield = >99 %;
18448-47-0

methyl cyclohex-1-ene-1-carboxylate

100-49-2

cyclohexylmethyl alcohol

Conditions
ConditionsYield
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 100℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere;98%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); hydrogen In tetrahydrofuran at 120℃; under 22502.3 Torr; for 19h; Autoclave;85 %Chromat.

Cyclohexanemethanol Consensus Reports

Reported in EPA TSCA Inventory.

Cyclohexanemethanol Specification

The Hexahydrobenzyl alcohol is an organic compound with the formula C7H14O. The IUPAC name of this chemical is cyclohexylmethanol. With the CAS registry number 100-49-2, it is also named as 1,2,3, 6-Tetrahydrobenzaldehyde. The product's category is Alcohol Aldehyde & Acid Series. Besides, it is a colorless liquid, which should be stored in a cool and ventilated place. It is an organic synthesis intermediate.

Physical properties about Hexahydrobenzyl alcohol are: (1)ACD/LogP: 1.87; (2)ACD/LogD (pH 5.5): 1.87; (3)ACD/LogD (pH 7.4): 1.87; (4)ACD/BCF (pH 5.5): 15.59; (5)ACD/BCF (pH 7.4): 15.59; (6)ACD/KOC (pH 5.5): 248.55; (7)ACD/KOC (pH 7.4): 248.55; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 9.23 Å2; (12)Index of Refraction: 1.454; (13)Molar Refractivity: 33.89 cm3; (14)Molar Volume: 125 cm3; (15)Polarizability: 13.43×10-24cm3; (16)Surface Tension: 33.7 dyne/cm; (17)Density: 0.913 g/cm3; (18)Flash Point: 71.1 °C; (19)Enthalpy of Vaporization: 48.58 kJ/mol; (20)Boiling Point: 181.1 °C at 760 mmHg; (21)Vapour Pressure: 0.254 mmHg at 25°C.

Preparation: this chemical can be prepared by cyclohexanecarbonyl chloride. This reaction is a kind of Reduction. It will need reagent Bu3SnH, Ph3P, catalyst InCl3 and solvent tetrahydrofuran. The reaction time is 2 hours with reaction temperature of 20 °C. The yield is about 62%.



Uses of Hexahydrobenzyl alcohol: it can be used to produce acetic acid cyclohexylmethyl ester at temperature of 25 - 30 °C. It will need reagent Woelm-200-N alumina with reaction time of 1 hour. The yield is about 85%.

You can still convert the following datas into molecular structure:
(1)SMILES: OCC1CCCCC1
(2)InChI: InChI=1/C7H14O/c8-6-7-4-2-1-3-5-7/h7-8H,1-6H2
(3)InChIKey: VSSAZBXXNIABDN-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C7H14O/c8-6-7-4-2-1-3-5-7/h7-8H,1-6H2
(5)Std. InChIKey: VSSAZBXXNIABDN-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   National Technical Information Service. Vol. AD277-689,

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