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421804

Sigma-Aldrich

(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:
57794-08-8
Molecular Weight:
116.16
Beilstein/REAXYS Number:
1901343
MDL number:
MFCD00066431
UNSPSC Code:
12352001
PubChem Substance ID:
24866402
NACRES:
NA.22

Quality Level

200

assay

99%

optical activity

[α]20/D +39°, c = 1.6 in H2O

optical purity

ee: 99% (GLC)

mp

107-109 °C (lit.)

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - STOT SE 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Marshall, J.A. Xie, S.
The Journal of Organic Chemistry, 60, 7230-7230 (1995)
Stolle, A. et al.
Tetrahedron Letters, 35, 3521-3521 (1994)
Pichon, M. Figadere, B.
Tetrahedron Asymmetry, 7, 927-927 (1996)
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