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287784

Sigma-Aldrich

(1R,2R,3S,5R)-(−)-Pinanediol

99%

Synonym(s):

(−)-2-Hydroxyisopinocampheol, [1R-(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:
22422-34-0
Molecular Weight:
170.25
Beilstein:
2039144
MDL number:
MFCD09955216
UNSPSC Code:
12352001
PubChem Substance ID:
24857292
NACRES:
NA.22

Assay

99%

optical activity

[α]21/D −8.6°, c = 6.5 in toluene

optical purity

ee: 97% (GLC)

bp

101-102 °C/1 mmHg (lit.)

mp

57-59 °C (lit.)

SMILES string

CC1(C)[C@H]2C[C@H](O)[C@](C)(O)[C@@H]1C2

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-/m1/s1

InChI key

MOILFCKRQFQVFS-BDNRQGISSA-N

Application

Used to prepare chiral double allylation reagents.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Simple, stable, and versatile double-allylation reagents for the stereoselective preparation of skeletally diverse compounds.
Feng Peng et al.
Journal of the American Chemical Society, 129(11), 3070-3071 (2007-02-24)
Gerald I Richard et al.
Applied spectroscopy, 62(5), 476-480 (2008-05-24)
The spectroscopic properties of a chiral boronic acid based resorcinarene macrocycle employed for chiral analysis were investigated. Specifically, the emission and excitation characteristics of tetraarylboronate resorcinarene macrocycle (TBRM) and its quantum yield were evaluated. The chiral selector TBRM was investigated

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