57794-08-8

Basic information

• Product Name: (1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL
• Synonyms: (S,S)-(+)-1,2-CYCLOHEXANEDIOL;(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL;(1S)-TRANS-1,2-CYCLOHEXANEDIOL;(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL, 99% ( 99% EE/GLC);(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL 98%;(1S,2S)-1α,2β-Cyclohexanediol;[1S,2S,(+)]-1,2-Cyclohexanediol;(1S,2S)-trans-1,2-Cyclohexanediol,98%
• CAS NO: 57794-08-8
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• Mol File: 57794-08-8.mol
• Article Data: 108

Chemical Properties

• Melting Point: 107-109 °C(lit.)
• Boiling Point: 177.22°C (rough estimate)
• Flash Point: 134 °C
• Appearance: /
• Density: 0.9958 (rough estimate)
• Refractive Index: 1.4270 (estimate)
• PKA: 14.49±0.40(Predicted)
• BRN: 1901343
• CAS DataBase Reference: (1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL(57794-08-8)
• EPA Substance Registry System: (1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL(57794-08-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 57794-08-8(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystals

Uses

(1S,2S)-trans-1,2-Cyclohexanediol may be used in the preparation of (1S,2S)-1,2-cyclohexanediyl bis(4-vinylbenzoate) by reacting with 4-vinylbenzoyl chloride. It may also be used as a chiral ligand for the preparation of non-racemic hydroxy phosphonates via titanium alkoxide-catalyzed addition of dimethyl phosphite to the corresponding aldehydes.

Purification Methods

The enantiomers have been recrystallised from *C6H6 or EtOAc. The (±) diol has been resolved via the distrychnine salt of the hemisulfate [Hayward et al. J Chem Soc Perkin Trans 1 2413 1976], or the 1-menthoxy acetates. {l-trans-diastereoisomer has m 64o, []D -91.7o (c 1.4 EtOH) from pet ether or aqueous EtOH and yields the (-)-trans-diol } and {d-trans-diastereoisomer has m 126-127o, []D -32.7o (c 0.8 EtOH) from pet ether or aqueous EtOH and yields the (+)-trans diol}. The bis-4-nitrobenzoate has m 126.5o []D (-) and (+) 25.5o (c 1.1 CHCl3), and the bis-3,5-dinitrobenzoate has m 160o []D ± 83.0o (c 1.8 CHCl3) [Wilson & Read J Chem Soc 1269 1935]. [Beilstein 6 III 4060.]

Upstream product

• 85761-38-2 (+)-(R,R)-benzylcyclohexan-1,2-diol 
• 1759-71-3 trans-1,2-cyclohexanediol diacetate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 765-87-7 cyclohexane-1,2-dione 
• 286-20-4 cyclohexene oxide 
• 1225376-11-3 2-hexanoyloxy-2-cyclohexenone 
• 5011-76-7 2-acetoxy-2-cyclohexen-1-one 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 108-24-7 acetic anhydride 
• 97-72-3 2-Methylpropionic anhydride 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 75-36-5 acetyl chloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 69501-36-6 (1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside 

Downstream Products

• 113712-84-8 trans-1,2-dipicryloxycyclohexane 
• 98966-21-3 trans-2-picryloxy-1-cyclohexanole 
• 145222-66-8 ((1S,5S,6S)-3-Methyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145222-66-8 ((1R,5R,6R)-3-Methyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145222-68-0 ((1R,5R,6R)-3-Butyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145222-68-0 ((1S,5S,6S)-3-Butyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145264-93-3 2-((1S,5S,6S)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-77-1 2-((1R,5R,6R)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-72-6 ((1S,5S,6S)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145222-72-6 ((1R,5R,6R)-3-Phenyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145511-67-7 2-((1S,5S,6S)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-76-0 2-((1R,5R,6R)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-ethanol 
• 145222-70-4 ((1S,5S,6S)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 
• 145222-70-4 ((1R,5R,6R)-3-Cyclohexyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester 

Relevant articles and documents

Enantiotopic Discrimination by Coordination-Desymmetrized meso-Ligands

The first examples of enantiopure catalysts that are chiral merely due to coordination of different metal ions at enantiotopic positions of an achiral meso-ligand are reported. These catalysts exhibit a pseudo-Cs symmetry and are able to catalyze reactions demanding simultaneous involvement of two catalytic sites. The latter was demonstrated by application in the asymmetric ring-opening of meso-epoxides.

Olefin reaction in the catalyst and the olefin production

PROBLEM TO BE SOLVED: To provide a catalyst for obtaining an olefin in high selectivity with a vicinal diol as a raw material.SOLUTION: A catalyst for olefination reaction for use in a reaction to produce an olefin by a reaction of a polyol, having two adjacent carbon atoms each having a hydroxy group, with hydrogen comprises: a carrier; at least one oxide selected from the group consisting of oxides of the group 6 elements and oxides of the group 7 elements supported on the carrier; and at least one metal selected from the group consisting of silver, iridium, and gold supported on the carrier.SELECTED DRAWING: None

Organic salts and merrifield resin supported [PM12O40]3? (M = Mo or W) as catalysts for adipic acid synthesis

Adipic acid (AA) was obtained by catalyzed oxidation of cyclohexene, epoxycyclohexane, or cyclohexanediol under organic solvent-free conditions using aqueous hydrogen peroxide (30%) as an oxidizing agent and molybdenum- or tungsten-based Keggin polyoxometalates (POMs) surrounded by organic cations or ionically supported on functionalized Merrifield resins. Operating under these environmentally friendly, greener conditions and with low catalyst loading (0.025% for the molecular salts and 0.001–0.007% for the supported POMs), AA could be produced in interesting yields.