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287784

Sigma-Aldrich

(1R,2R,3S,5R)-(−)-Pinanediol

99%

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Synonym(s):
(−)-2-Hydroxyisopinocampheol, [1R-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol
Empirical Formula (Hill Notation):
C10H18O2
CAS Number:
Molecular Weight:
170.25
Beilstein/REAXYS Number:
2039144
MDL number:
PubChem Substance ID:
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

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1 of 4

This Item
2823678.18632H156
vibrant-m

287784

(1R,2R,3S,5R)-(−)-Pinanediol

vibrant-m

282367

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

vibrant-m

8.18632

(1R)-(+)-α-Pinene

vibrant-m

H156

(+)-3-Hydroxymorphinan hydrobromide

assay

99%

assay

99%

assay

≥97.0% (GC)

assay

≥98% (HPLC)

bp

101-102 °C/1 mmHg (lit.)

bp

-

bp

155-156 °C/1013 hPa

bp

-

mp

57-59 °C (lit.)

mp

57-59 °C (lit.)

mp

-62 °C

mp

-

optical activity

[α]21/D −8.6°, c = 6.5 in toluene

optical activity

[α]20/D +8.5°, c = 6.5 in toluene

optical activity

-

optical activity

-

optical purity

ee: 97% (GLC)

optical purity

ee: 99% (GLC)

optical purity

-

optical purity

-

Application

Used to prepare chiral double allylation reagents.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)


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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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