(1S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene

• ChemBase ID: 140188
• Molecular Formular: C10H16
• Molecular Mass: 136.23404
• Monoisotopic Mass: 136.12520051
• SMILES: CC1=CC[C@@H]2[C@H](C1)C2(C)C
• Canonical SMILES: CC1=CC[C@@H]2[C@H](C1)C2(C)C
• InChI: InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m1/s1
• InChIKey: BQOFWKZOCNGFEC-BDAKNGLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene
• IUPAC Traditional name: (+)-delta(3)-carene
• Synonyms: (+)-3-Carene; (1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene; (1S)-(+)-3-Carene; (+)-3-Carene; (+)-3-蒈烯; (1S)-3,7,7-三甲基双环[4.1.0]庚-3-烯; (1S)-(+)-3-蒈烯; (1S)-3,7,7-三甲基二环[4.1.0]庚-3-烯; (+)-3-蒈烯

Database IDs

• CAS Number: 498-15-7
• EC Number: 207-856-6
• MDL Number: MFCD00066417
• Beilstein Number: 1902767
• PubChem SID: 24867688; 24853149; 162234432
• PubChem CID: 443156

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.8016615
• LogD (pH = 7.4): 2.8016615
• Log P: 2.8016615
• Molar Refractivity: 44.7223 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

• Apperance: clear very slightly yellow liquid (clear)
• Boiling Point: 170-172 °C(lit.)
• Flash Point: 131 °F; 55 °C
• Density: 0.864 g/mL at 20 °C(lit.); 0.865 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.472(lit.); n20/D 1.473
• Optical Rotation: [α]20/D +17±1°, neat; [α]20/D +17°, neat

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 2319
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-43-50/53
• Safety Statements: 36/37-60-61
• GHS Pictograms: GHS02; GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H317-H410
• GHS Precautionary statements: P273-P280-P501
• 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

Product Information

• Purity: ≥98.5% (sum of enantiomers, GC); 99%
• Grade: analytical standard, for terpene analysis
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H16

DETAILS

Sigma Aldrich - 441619

Packaging
1, 5 g in glass bottle
Application
Chiral building block for the preparation of bicyclo[3.2.0]heptenes that are useful intermediates in the synthesis of (+)-lineatin and both enantiomers of capnellene.1 Has been converted to its corresponding allenyl allylic ether2 for studies of its thermal isomerization chemistry. Precursor to di(4-isocaranyl)borane, an asymmetric hydroboration reagent for olefins.3