(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl chloroformate

• ChemBase ID: 146349
• Molecular Formular: C11H19ClO2
• Molecular Mass: 218.72036
• Monoisotopic Mass: 218.10735753
• SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)Cl)C(C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)Cl)C(C)C
• InChI: InChI=1S/C11H19ClO2/c1-7(2)9-5-4-8(3)6-10(9)14-11(12)13/h7-10H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
• InChIKey: KIUPCUCGVCGPPA-KXUCPTDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl chloroformate
• IUPAC Traditional name: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl chloroformate
• Synonyms: Chloroformic acid (1R)-menthyl ester; L-Menthyl chloroformate; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate; (-)-Menthyl chloroformate; (1R)-(-)-Menthyl chloroformate; (1R)-(-)-薄荷基氯甲酸酯; (-)-氯甲酸薄荷酯; (1R)-(-)-氯甲酸薄荷酯

Database IDs

• CAS Number: 14602-86-9
• MDL Number: MFCD00009694
• Beilstein Number: 2414686
• PubChem SID: 24854513; 162240547
• PubChem CID: 7014897

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.1121254
• LogD (pH = 7.4): 4.1121254
• Log P: 4.1121254
• Molar Refractivity: 57.3098 cm^3
• Polarizability: 22.913548 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 108-109 °C/11 mmHg(lit.); 108-109°C/11mm
• Flash Point: 158 °F; 70 °C; 70°C(158°F)
• Density: 1.02 g/mL at 25 °C(lit.); 1.025
• Refractive Index: 1.4580; n20/D 1.458(lit.)
• Vapor Pressure: 0.01 psi ( 20 °C)
• Optical Rotation: [α]20/D -83°, c = 1 in chloroform; -82 (c=1 in chloroform)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3277; UN3277
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23-34; 23-34-51/53
• Safety Statements: 26-36/37/39-45-61; 4-9-20-26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H331; H330-H314-H318-H227
• GHS Precautionary statements: P210-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3277 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 95+%
• Optical Purity: ee: 99% (GLC)
• Empirical Formula (Hill Notation): C11H19ClO2

DETAILS

Sigma Aldrich - 245305

Packaging
25, 100 g in glass bottle
Application
Chiral derivatizing agent used for the resolution of alcohols and amines by GC, HPLC, or crystallization.1
Readily forms a chloroimidodicarbonate which asymmetrically chlorinates silyl enol ethers under mild conditions and in good yields.

REFERENCES

• Chiral derivatizing agent for alcohols and amines, allowing separation by chromatographic or crystallization techniques. For use in the resolution of 1,1'-binaphthyl derivatives, see: J. Org. Chem., 60, 6599 (1995).