(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride

• ChemBase ID: 137486
• Molecular Formular: C10H13ClO3
• Molecular Mass: 216.66142
• Monoisotopic Mass: 216.05532196
• SMILES: C[C@@]12CC[C@@](C1(C)C)(OC2=O)C(=O)Cl
• Canonical SMILES: ClC(=O)[C@@]12CC[C@](C2(C)C)(C(=O)O1)C
• InChI: InChI=1S/C10H13ClO3/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3/t9-,10+/m0/s1
• InChIKey: PAXWODJTHKJQDZ-VHSXEESVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride
• IUPAC Traditional name: (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride
• Synonyms: (-)-Camphanoyl chloride; (1S)-3-Oxo-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride; (1S)-(-)-Camphanic chloride; (-)-莰烷酰氯; (1S)-3-氧代-4,7,7-三甲基-2-氧杂双环[2.2.1]庚烷-1-甲酰氯; (1S)-(-)-莰烷酰氯

Database IDs

• CAS Number: 39637-74-6
• EC Number: 254-552-4
• MDL Number: MFCD00135626
• Beilstein Number: 3590860
• PubChem SID: 162231748; 24853548; 24852750
• PubChem CID: 170232

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.2617886
• LogD (pH = 7.4): 2.2617886
• Log P: 2.2617886
• Molar Refractivity: 50.7758 cm^3
• Polarizability: 20.4906 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 67-70 °C; 71-73 °C(lit.)
• Optical Rotation: [α]20/D -18±1°, c = 2% in carbon tetrachloride; [α]23/D -18°, c = 2 in carbon tetrachloride

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98%; ≥98.0%; ≥98.0% (AT); 98%
• Grade: Flukabrand™ ChiraSelect reagent; for chiral derivatization
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: C10H13O3Cl

DETAILS

Sigma Aldrich - 421820

Application
Resolving agent for racemic alcohols.1
Legal Information
Flukabrand is a trademark of Sigma-Aldrich GmbH

Sigma Aldrich - 226173

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 21287

Other Notes
Chiral derivatizing reagent used for the determination of enantiomeric purity of alcohols and amines by HPLC 1,2,3,4