(1R,3S,4S)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

• ChemBase ID: 152471
• Molecular Formular: C10H15BrO
• Molecular Mass: 231.1295
• Monoisotopic Mass: 230.0306271
• SMILES: C[C@@]12CC[C@@H](C1(C)C)[C@@H](C2=O)Br
• Canonical SMILES: Br[C@@H]1C(=O)[C@]2(C([C@@H]1CC2)(C)C)C
• InChI: InChI=1S/C10H15BrO/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6-7H,4-5H2,1-3H3/t6-,7+,10+/m1/s1
• InChIKey: NJQADTYRAYFBJN-FWWHASMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,4S)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• IUPAC Traditional name: (1R,3S,4S)-3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• Synonyms: endo-(1R)-3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one; (+)-3-Bromocamphor; 内型-(1R)-3-溴-1,7,7-三甲基二环[2.2.1]庚烷-2-酮; (+)-3-溴樟脑

Database IDs

• CAS Number: 10293-06-8
• EC Number: 233-652-1
• MDL Number: MFCD00003744
• Beilstein Number: 3197237
• PubChem SID: 162246616; 24850146
• PubChem CID: 512864

CALCULATED PROPERTIES

• Acid pKa: 18.136906
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.2999606
• LogD (pH = 7.4): 3.2999606
• Log P: 3.2999606
• Molar Refractivity: 51.9417 cm^3
• Polarizability: 20.483084 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-77 °C
• Optical Rotation: [α]20/D +136±3°, c = 1% in ethanol

Safety Information

• RTECS: ED6750000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC)
• Grade: purum
• Empirical Formula (Hill Notation): C10H15BrO

DETAILS

Sigma Aldrich - 16571

Other Notes
Use as chiral building block1,2,3; Debromo-silylation and -phosphonylation4