421804
(1S,2S)-trans-1,2-Cyclohexanediol
99%
Synonym(s):
(1S)-trans-1,2-Cyclohexanediol
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About This Item
Linear Formula:
C6H10(OH)2
CAS Number:
Molecular Weight:
116.16
Beilstein:
1901343
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22
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Assay
99%
optical activity
[α]20/D +39°, c = 1.6 in H2O
optical purity
ee: 99% (GLC)
mp
107-109 °C (lit.)
functional group
hydroxyl
SMILES string
O[C@H]1CCCC[C@@H]1O
InChI
1S/C6H12O2/c7-5-3-1-2-4-6(5)8/h5-8H,1-4H2/t5-,6-/m0/s1
InChI key
PFURGBBHAOXLIO-WDSKDSINSA-N
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Application
(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.
C2-symmetric chiral diol with versatile applications as a chiral auxiliary, building block, and chiral ligand.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - STOT SE 3
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Chirality induction in cyclocopolymerization. 14. Template effect of 1, 2-cycloalkanediol in the cyclocopolymerization of bis (4-vinylbenzoate) s with styrene.
Kakuchi T, et al.
Macromolecules, 34(1), 38-43 (2001)
The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: titanium alkoxide-catalyzed P C bond formation and kinetic resolution.
Rowe BJ and Spilling CD.
Tetrahedron Asymmetry, 12(12), 1701-1708 (2001)
Burk, M.J. et al.
Tetrahedron Asymmetry, 2, 569-569 (1991)
Pichon, M. Figadere, B.
Tetrahedron Asymmetry, 7, 927-927 (1996)
Matteson, D.S. Man, H.-W.
The Journal of Organic Chemistry, 59, 5734-5734 (1994)
Chromatograms
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