(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

• ChemBase ID: 145540
• Molecular Formular: C10H16
• Molecular Mass: 136.23404
• Monoisotopic Mass: 136.12520051
• SMILES: CC1=CC[C@@H]2C[C@H]1C2(C)C
• Canonical SMILES: CC1=CC[C@@H]2C[C@H]1C2(C)C
• InChI: 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
• InChIKey: GRWFGVWFFZKLTI-RKDXNWHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
• IUPAC Traditional name: (+)-α-pinene
• Synonyms: (+)-α-Pinene; (1R,5R)-2-Pinene; (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; (1R)-(+)-α-Pinene; (-)-alpha-Pinene; (+)-alpha-Pinene; (+)-α-Pinene; (±)-2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; alpha-Pinene; α-Pinene; (+)-α-蒎烯; (1R,5R)-2-蒎烯; (1R,5R)-2,6,6-三甲双环[3.1.1]庚-2-烯; (1R)-(+)-α-蒎烯; (-)-α-蒎烯; (+)-α-蒎烯; α-蒎烯

Database IDs

• CAS Number: 80-56-8; 7785-26-4; 7785-70-8
• EC Number: 201-291-9; 232-087-8; 232-077-3
• MDL Number: MFCD00064145; MFCD00001346; MFCD00001339
• Beilstein Number: 1903790; 2038653; 3648264
• Merck Index: 147445
• PubChem SID: 24901385; 162239745; 24898553; 24887563; 24848559; 24856261
• PubChem CID: 82227
• FEMA ID: 2902
• Council of Europe Number: 2113

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

• Melting Point: -62 °C(lit.); -62°C; -64°C
• Boiling Point: 154-156°C; 155-156 °C; 155-156 °C(lit.)
• Flash Point: 32 °C; 32°C(89°F); 33 °C; 89.6 °F; 91.4 °F
• Auto Ignition Point: 491 °F
• Density: 0.856; 0.857 g/mL at 25 °C; 0.858; 0.858 g/mL at 20 °C(lit.); 0.858 g/mL at 25 °C(lit.)
• Refractive Index: 1.4650; 1.4660; n20/D 1.465; n20/D 1.465(lit.); n20/D 1.4652
• Optical Rotation: [α]20/D +42°, neat; [α]20/D +47±5°, neat; [α]20/D +51±2°, neat; [α]21/D +50.7°, neat; [α]22/D +47.1°, neat; -42 (neat)

Safety Information

• RTECS: DT7000000
• European Hazard Symbols: Nature polluting (N); X; Irritant (Xi)
• UN Number: 2368; UN2368
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-20/21/22-36/38-43-51/53-65; 10-36/37/38; 10-36/37/38-43-50/53; 10-36/38-43-51/53
• Safety Statements: 24-26-37-57; 26-36; 26-36/37-60-61; 9-26-36/37-57
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H317-H319-H335-H410; H226-H315-H319-H317-H411-H401; H226-H315-H319-H335; H304-H226-H302-H312-H332-H315-H319-H317-H411-H401
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P273-P280-P305 + P351 + P338-P501; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2368 3/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC); ≥98.5% (sum of enantiomers, GC); ≥99%; 97%; 98%; 98%, cont. variable amounts of enantiomer
• Grade: analytical standard, for terpene analysis; Halal; Kosher; NI; primary reference standard; purum
• Optical Purity: ee: ≥91% (GLC); ee: 97% (GLC); enantiomeric ratio: ≥98:2 (GC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H16

DETAILS

Sigma Aldrich - P45680

Packaging
100, 500 mL in glass bottle

Sigma Aldrich - 268070

Packaging
5, 25 g in glass bottle
Application
Employed in the preparation of chiral hydroboration reagents.1,2,3

Sigma Aldrich - 147524

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

Sigma Aldrich - W290238

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

Sigma Aldrich - 80604

Other Notes
Starting material for preparing isopinocampheylborane1,2; Preparation of diisopinocampheylborane3; Preparation of isopinocampheyl-BBN4,5

REFERENCES

• Forms a chiral adduct with diborane, useful for asymmetric hydroborations with high optical yields: J. Am. Chem. Soc., 99, 5514 (1977). Recrystallization of the borane adduct can be used to obtain a pure single diastereomer: J. Org. Chem., 49, 945 (1984). For reviews of the synthesis of pure enantiomers via chiral organoboranes, see: Acc. Chem. Res., 21, 287 (1988); and of asymmetric reduction with chiral organoboranes based on ɑ-pinene: Acc. Chem. Res., 25, 16 (1992).