268070

Sigma-Aldrich

(+)-α-Pinene

≥99%

Synonym(s):
(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, (1R,5R)-2-Pinene
Empirical Formula (Hill Notation):
C10H16
CAS Number:
Molecular Weight:
136.23
Beilstein/REAXYS Number:
2038653
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

≥99%

optical activity

[α]21/D +50.7°, neat

optical purity

ee: 97% (GLC)

autoignition temp.

491 °F

refractive index

n20/D 1.465 (lit.)

bp

155-156 °C (lit.)

mp

−62 °C (lit.)

density

0.858 g/mL at 20 °C (lit.)

SMILES string

CC1=CC[C@@H]2C[C@H]1C2(C)C

InChI

1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1

InChI key

GRWFGVWFFZKLTI-RKDXNWHRSA-N

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General description

(+)-α-Pinene is a monoterpenoid compound mainly found in Pinus species.

Application

Employed in the preparation of chiral hydroboration reagents.
(+)-α-Pinene may be used as precursors to prepare primary, secondary and tertiary γ-amino alcohols and 1,3-diamines, which can be used as chiral catalysts for the addition of diethylzinc to aromatic aldehydes, resulting in chiral 1-aryl-1-propanols with high enantioselectivity.

Packaging

5, 25 g in glass bottle

signalword

Danger

hazcat

Aquatic Acute 1 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 3

Flash Point F

91.4 °F - closed cup

Flash Point C

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

The Journal of Organic Chemistry, 59, 2365-2365 (1994)
Aldrichimica Acta, 20, 24-24 (1987)
Se-Eun Kim et al.
Scientific reports, 10(1), 9547-9547 (2020-06-14)
For centuries, herbs have been used by traditional therapists around the world to treat gastrointestinal tract disorders, such as gastritis. We hypothesized that the anti-Helicobacter pylori properties of phytoncide, which is extracted from pinecone waste, would facilitate use as a...
Enantioselective addition of diethylzinc to aldehydes catalyzed by ?-amino alcohols derived from (+)-and (-)-a-pinene.
Szakonyi Z, et al.
Tetrahedron Asymmetry, 17(2), 199-204 (2006)
Zheng Wu et al.
Neuron, 106(2), 316-328 (2020-02-28)
Cognitive capacities afford contingent associations between sensory information and behavioral responses. We studied this problem using an olfactory delayed match to sample task whereby a sample odor specifies the association between a subsequent test odor and rewarding action. Multi-neuron recordings...

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