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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:
1901343
MDL number:
MFCD00066431
UNSPSC Code:
12352001
PubChem Substance ID:
24866402
NACRES:
NA.22

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

Signal Word

Danger

Hazard Statements

H318,H335

Precautionary Statements

P261 - P280 - P305 + P351 + P338

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

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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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)
Stolle, A. et al.
Tetrahedron Letters, 35, 3521-3521 (1994)
Burk, M.J. et al.
Journal of the American Chemical Society, 115, 10125-10125 (1993)
Burk, M.J. et al.
Tetrahedron Asymmetry, 2, 569-569 (1991)
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