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(1R,2R)-1,2-Cyclohexanedimethanol

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Name

(1R,2R)-1,2-Cyclohexanedimethanol

EINECS 692-053-7
CAS No. 65376-05-8 Density 1.004 g/cm3
PSA 40.46000 LogP 0.77740
Solubility N/A Melting Point 63.0 to 67.0 °C
Formula C8H16O2 Boiling Point 270.1 °C at 760 mmHg
Molecular Weight 144.214 Flash Point 129 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 65376-05-8 ((1R,2R)-1,2-Cyclohexanedimethanol) Hazard Symbols N/A
Synonyms

(1R,2R)-Cyclohexane-1,2-diyldimethanol;(1R,2R)-1,2-Bis(hydroxymethyl)cyclohexane;

Article Data 14

(1R,2R)-1,2-Cyclohexanedimethanol Synthetic route

140459-96-7

(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In methanol at 190℃; under 52505.3 Torr; Temperature; Pressure; Solvent;94%
Stage #1: (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester With diisobutylaluminium hydride In toluene at -5 - 20℃; for 6h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In toluene at -5 - 40℃; for 13h;
74%
With lithium aluminium tetrahydride In diethyl ether
Stage #1: (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester With diisobutylaluminium hydride In toluene at 0 - 20℃; for 4h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 0 - 40℃; for 18h;
With methanol; sodium tetrahydroborate In tetrahydrofuran at 40℃; for 3h; Temperature; Reflux;
46022-05-3

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 5h; Reflux;88.4%
With Red-Al In tetrahydrofuran; toluene for 5h; Inert atmosphere; Reflux;85.2%
Multi-step reaction with 2 steps
1: diethyl ether
2: LiAlH4 / diethyl ether
View Scheme
65376-04-7

(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 12h; Heating;80%
With lithium aluminium tetrahydride

bis(D-menthyl) (1R,2R)-cyclohexane-1,2-dicarboxylate

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 19h; Inert atmosphere;76%
76155-27-6

(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With C11H19NO
76155-27-6

(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol

A

57280-65-6, 65376-04-7, 80795-84-2, 93379-40-9

trans-2-(hydroxymethyl)cyclohexanecarboxylic acid

B

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

C

3205-34-3

(1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane

D

65376-04-7

(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid

Conditions
ConditionsYield
With sodium hydroxide; NAD; silver nitrate; glycine; Flavin mononucleotide Product distribution; multistep reaction, other trans-diols, stereospecificity;
96946-89-3

diethyl trans-1,2,3,6-tetrahydrophthalate

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Stage #1: diethyl trans-1,2,3,6-tetrahydrophthalate With hydrogen; palladium on activated charcoal
Stage #2: With lithium aluminium tetrahydride
65376-03-6

(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / H2 / Pd/C / methanol
2: 34 percent / NaOH / H2O / 192 h / 130 °C
3: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating
View Scheme
15753-50-1

cis-1,2-cyclohexanedimethanol

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / Ambient temperature
2: 34 percent / NaOH / H2O / 192 h / 130 °C
3: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating
View Scheme
439919-46-7

cis-1,6-dihydroxymethyl-3-cyclohexene

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / NAD+, FMN, pH 9, HLADH, NaOH, glycine / 48 h / 20 °C
2: 86 percent / H2 / Pd/C / methanol
3: 34 percent / NaOH / H2O / 192 h / 130 °C
4: 80 percent / LiAlH4 / diethyl ether / 12 h / Heating
View Scheme

(1R,2R)-1,2-Cyclohexanedimethanol Specification

The (1R,2R)-1,2-Cyclohexanedimethanol, with the CAS registry number of 65376-05-8, is also known as (1R,2R)-1,2-Bis(hydroxymethyl)cyclohexane. The molecular formula of this chemical is C8H16O2 and its molecular weight is 144.21144. What's more, its systematic name is (1R,2R)-Cyclohexane-1,2-diyldimethanol.

Physical properties about (1R,2R)-1,2-Cyclohexanedimethanol are: (1)ACD/LogP: 0.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.53; (4)ACD/LogD (pH 7.4): 0.53; (5)ACD/BCF (pH 5.5): 1.48; (6)ACD/BCF (pH 7.4): 1.48; (7)ACD/KOC (pH 5.5): 46.15; (8)ACD/KOC (pH 7.4): 46.15; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.47; (14)Molar Refractivity: 40.12 cm3; (15)Molar Volume: 143.5 cm3; (16)Polarizability: 15.9×10-24 cm3; (17)Surface Tension: 40.5 dyne/cm; (18)Density: 1.004 g/cm3; (19)Flash Point: 129 °C; (20)Enthalpy of Vaporization: 59.01 kJ/mol; (21)Boiling Point: 270.1 °C at 760 mmHg; (22)Vapour Pressure: 0.000923 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: OC[C@@H]1CCCC[C@H]1CO
(2) InChI: InChI=1/C8H16O2/c9-5-7-3-1-2-4-8(7)6-10/h7-10H,1-6H2/t7-,8-/m0/s1
(3) InChIKey: XDODWINGEHBYRT-YUMQZZPRBI

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