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P45680
(+)-α-Pinene
98%
Synonym(s):
(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, (1R,5R)-2-Pinene
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About This Item
Empirical Formula (Hill Notation):
C10H16
CAS Number:
Molecular Weight:
136.23
Beilstein:
2038653
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
optical activity
[α]/D 35 to 54, neat
optical purity
ee: ≥85% (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
Application
(+)-α-Pinene can be used:
- To prepare chiral organoboranes, which are used in the synthesis of optically active compounds and in Suzuki coupling.[3][4]
- In the synthesis of chiral pyridine-type N-oxides as catalysts for the allylation of aromatic aldehydes.[5]
- To synthesize 2,3-pinane diamine, a chiral auxiliary in several catalysts and reagents.[6]
(+)-α-Pinene has been used in a tolerance testing procedure to detect the genes in Marinobacter aquaeolei, for engineering a pinene tolerant Escherichia coli.[1]
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1
Storage Class Code
3 - Flammable liquids
WGK
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
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Coating of soot and (NH4)2SO4 particles by ozonolysis products of a-pinene.
Saathoff, H., et al.
Journal of Aerosol Science, 34(10), 1297-1321 (2003)
Synthesis and characterization of novel chiral 1, 2-diamines derived from α-pinene.
Suzuki T, et al.
Chemistry Letters (Jpn), 34(11), 1476-1477 (2005)
Chiral synthesis via organoboranes. 18. Selective reductions. 43. Diisopinocampheylchloroborane as an excellent chiral reducing reagent for the synthesis of halo alcohols of high enantiomeric purity. A highly enantioselective synthesis of both optical isomers of Tomoxetine, Fluoxetine, and Nisoxetine.
Srebnik M, et al.
The Journal of Organic Chemistry, 53(13), 2916-2920 (1988)
New pyridine-derived N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes.
Malkov A V, et al.
J. Mol. Catal. A: Chem., 196(1-2), 179-186 (2003)
Engineering improved bio-jet fuel tolerance in Escherichia coli using a transgenic library from the hydrocarbon-degrader Marinobacter aquaeolei.
Tomko TA and Dunlop MJ.
Biotechnology for Biofuels, 8(1), 165-165 (2015)
Chromatograms
suitable for GCsuitable for GCsuitable for GC-
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