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305715

Sigma-Aldrich

(−)-α-Pinene

99%, optical purity ee: 97% (GLC)

Synonym(s):

(-)-alpha-Pinene, (1S)-(−)-α-Pinene, (1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, (1S,5S)-2-Pinene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
7785-26-4
Molecular Weight:
136.23
Beilstein:
1903790
EC Number:
232-077-3
MDL number:
MFCD00064145
UNSPSC Code:
12352002
eCl@ss:
39011007
PubChem Substance ID:
24858450
NACRES:
NA.22

vapor density

4.7 (vs air)

vapor pressure

~3 mmHg ( 20 °C)

Assay

99%

form

liquid

optical activity

[α]20/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

-64 °C (lit.)

density

0.855 g/mL at 25 °C

SMILES string

CC1=CCC2CC1C2(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-/m0/s1

InChI key

GRWFGVWFFZKLTI-IUCAKERBSA-N

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Application

(−)-α-Pinene can be used as a precursor for the preparation of:
  • Dichloro[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane by the in situ reduction and hydroboration reaction.
  • α-Pinene oxide by epoxidation using polymer supported by a molybdenum carbonyl catalyst.
  • Diisopinocampheylborane (Ipc2BH), which is used for the asymmetric hydroboration prochiral alkenes.

Signal Word

Danger

Hazard Statements

H226,H302,H304,H315,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 2 - Asp. Tox. 1 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

88.3 °F

Flash Point(C)

31.3 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

305715-5G:
305715-25G:
305715-BULK:
305715-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hydroboration. 93. Convenient Conversion of Optically Pure 2-Organylapopinenes into the (2-Organylapoisopinyl) dihaloboranes Potentially Valuable for Asymmetric Synthesis via Chiral Organoboranes
Dhokte UP and Brown HC
Organometallics, 15(16), 3504-3508 (1996)
Epoxidation of alkenes by a highly reusable and efficient polymer-supported molybdenum carbonyl catalyst
Grivani G, et al.
Catalysis Communications, 6(6), 375-378 (2005)

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