| Identification | Back Directory | [Name]
(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL | [CAS]
57794-08-8 | [Synonyms]
(1S,2S)-cyclohexane-1,2-diol
(1S,2S)-1α,2β-Cyclohexanediol
(S,S)-(+)-1,2-CYCLOHEXANEDIOL
(1S)-TRANS-1,2-CYCLOHEXANEDIOL
[1S,2S,(+)]-1,2-Cyclohexanediol
(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL
(1S,2S)-trans-1,2-Cyclohexanediol,98%
(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL 98%
(1S,2S)-TRANS-1,2-CYCLOHEXANEDIOL, 99% ( 99% EE/GLC) | [Molecular Formula]
C6H12O2 | [MDL Number]
MFCD00066431 | [MOL File]
57794-08-8.mol | [Molecular Weight]
116.16 |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystals | [Melting point ]
107-109 °C(lit.)
| [Boiling point ]
177.22°C (rough estimate) | [density ]
0.9958 (rough estimate) | [refractive index ]
1.4270 (estimate) | [Fp ]
134 °C
| [pka]
14.49±0.40(Predicted) | [optical activity]
[α]20/D +39°, c = 1.6 in H2O | [BRN ]
1901343 |
| Hazard Information | Back Directory | [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.] |
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