(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane

• ChemBase ID: 112297
• Molecular Formular: C10H16
• Molecular Mass: 136.23404
• Monoisotopic Mass: 136.12520051
• SMILES: [C@H]12CCC(=C)[C@H](C1)C2(C)C
• Canonical SMILES: C=C1CC[C@H]2C[C@@H]1C2(C)C
• InChI: InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3
• InChIKey: WTARULDDTDQWMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane
• IUPAC Traditional name: (-)-β-pinene
• Synonyms: (1S)-(-)-beta-Pinene; (1S)-(-)-β-Pinene; (1S,5S)-2(10)-Pinene; (-)-β-Pinene; (1S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane; (1S,5S)-2-(10)-Pinene; (-)-b-Pinene; (1S)-(-)-b-Pinene; β-PINENE; (-)-beta-Pinene; (1S)-(-)-β-蒎烯; (1S)-(-)-β-蒎烯; (1S,5S)-2(10)-蒎烯; (1S,5S)-6,6-二甲基-2-亚甲基二环[3.1.1]庚烷; (-)-β-蒎烯

Database IDs

• CAS Number: 18172-67-3
• EC Number: 242-060-2
• MDL Number: MFCD00001345
• Beilstein Number: 2038282
• Merck Index: 147446
• PubChem SID: 24865115; 162097418; 24901386; 24847064; 24887565
• PubChem CID: 440967
• FEMA ID: 2903
• Council of Europe Number: 2114

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.859595
• LogD (pH = 7.4): 2.859595
• Log P: 2.859595
• Molar Refractivity: 43.6498 cm^3
• Polarizability: 17.495043 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165°C; -61 °C(lit.); -61°C
• Boiling Point: 155°C; 164-165 °C(lit.); 164-165°C; 165-167 °C(lit.)
• Flash Point: 36 °C; 36°C(96°F); 96.8 °F
• Density: 0.858 g/ml; 0.859 g/mL at 25 °C; 0.860; 0.866 g/mL at 25 °C
• Refractive Index: 1.4780; n20/D 1.477; n20/D 1.478; n20/D 1.478(lit.)
• Vapor Pressure: ~2 mmHg ( 20 °C)
• Vapor Density: 4.7 (vs air)
• Optical Rotation: [α]20/D -20±2°, neat; [α]20/D -21±1°, neat; [α]20/D -21°, neat; [α]20/D -22±1°, neat; [α]20/D -30 to -15°, neat; [α]25/D -22°, neat; -21 (neat)
• Organoleptic: woody

Safety Information

• RTECS: DT5077000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 2319; UN2319
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-20/21/22-36/37/38-43-51-65; 10-20/21/22-36/37/38-43-65; 10-36/37/38; R:10
• Safety Statements: 16-26-36/37-46-61-62; 16-26-36/37-46-62; 26-37; S:9-16-29
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302 + H312 + H332-H304-H315-H317-H319-H335; H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P301 + P310-P305 + P351 + P338-P331
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2319 3/PG 3
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC; FDA 21 CFR (172.515); FDA 21 CFR (175.300); FDA 21 CFR (175.320)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥80% (sum of enantiomers, GC); ≥97%; ≥99%; ≥99.0% (sum of enantiomers, GC); 90%; 99%
• Grade: analytical standard, for terpene analysis; Halal; Kosher; NI; purum; technical
• Optical Purity: ee: 97% (GLC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H16

DETAILS

MP Biomedicals - 05223399

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W290300

Packaging
1 kg in glass bottle
8 kg in steel drum
1 sample in glass bottle
20 kg in comp drum

Sigma Aldrich - 112089

Packaging
1 L in glass bottle
5, 250 mL in glass bottle

Sigma Aldrich - 402753

Packaging
1, 10 g in glass bottle
Application
Chiral intermediate used in the preparation of natural products, such as grandisol1 and robustadial.2

Sigma Aldrich - 80608

Other Notes
Chiral building block1,2,3; Preparation of (-)-α-pinene of high enantiomeric purity4