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Merck
CN

282367

(1S,2S,3R,5S)-(+)-Pinanediol

99%

Synonym(s):

(+)-2-Hydroxyisopinocampheol, (1S,2S,3R,5S)-2,3-Pinanediol, (1S,2S,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol, [1S-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol

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About This Item

Empirical Formula (Hill Notation):
C10H18O2
CAS Number:
18680-27-8
Molecular Weight:
170.25
Beilstein:
1853591
MDL number:
MFCD00077851
UNSPSC Code:
12352001
PubChem Substance ID:
24857043
NACRES:
NA.22

Key Documents

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Assay

99%

form

solid

optical activity

[α]20/D +8.5°, c = 6.5 in toluene

optical purity

ee: 99% (GLC)

mp

57-59 °C (lit.)

functional group

hydroxyl

SMILES string

CC1(C)C2C[C@@H](O)[C@@](C)(O)C1C2

InChI

1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m0/s1

InChI key

MOILFCKRQFQVFS-OORONAJNSA-N

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Application

(1S,2S,3R,5S)-(+)-Pinanediol can be used as a chiral reagent in the synthesis of homochiral α-hydroxyketones and in the resolution of prolineboronate esters.

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCN0944
MKCM5472
MKCC6674
MKBP2670V
MKBN5014V

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Ricardo Lira et al.
Organic letters, 9(21), 4315-4318 (2007-09-18)
syn-beta-Hydroxyallylsilanes of general structure 11 and 28 are prepared in 50-86% yield and 91-95% ee (for aliphatic aldehydes; 50% ee for benzaldehyde) via the BF(3).Et(2)O-promoted gamma-silylallylboration reactions, using reagents 14 and 15.
Selective oxidation of optically active sec,sec-1,2-diols by dioxiranes. A practical method for the synthesis of homochiral .alpha.-hydroxy ketones in high optical purity
Lucia D'Accolti, et al.
The Journal of Organic Chemistry, 58, 14, 3600-3601 (1993)
The efficient synthesis and simple resolution of a prolineboronate ester suitable for enzyme-inhibition studies
Terence A.K, et al.
Tetrahedron, 49, 5, 1009-1016 (1993)

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