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245305

Sigma-Aldrich

(1R)-(−)-Menthyl chloroformate

optical purity ee: 99% (GLC)

Synonym(s):

(−)-Menthyl chloroformate

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About This Item

Empirical Formula (Hill Notation):
C11H19ClO2
CAS Number:
14602-86-9
Molecular Weight:
218.72
Beilstein:
2414686
MDL number:
MFCD00009694
UNSPSC Code:
12352101
PubChem Substance ID:
24854513
NACRES:
NA.22

vapor pressure

0.01 psi ( 20 °C)

form

liquid

optical activity

[α]20/D −83°, c = 1 in chloroform

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.458 (lit.)

bp

108-109 °C/11 mmHg (lit.)

density

1.02 g/mL at 25 °C (lit.)

functional group

chloro

storage temp.

2-8°C

SMILES string

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(Cl)=O

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

InChI key

KIUPCUCGVCGPPA-KXUCPTDWSA-N

Application

1R)-(-)-Menthyl chloroformate may be used in the preparation of 1-O-menthoxycarbonyl myo-inositol.
Chiral derivatizing agent used for the resolution of alcohols and amines by GC, HPLC, or crystallization.
Readily forms a chloroimidodicarbonate which asymmetrically chlorinates silyl enol ethers under mild conditions and in good yields.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL5280
SHBL4552
SHBH9000
SHBG1974V
SHBF8242V

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Journal of the Chemical Society. Chemical Communications, 470-470 (1987)
Saumen Hajra et al.
The Journal of organic chemistry, 72(13), 4872-4876 (2007-06-05)
New chiral N-chloroimidodicarbonates, which function as efficient chiral chlorinating agents, were designed and synthesized. Among these, C(2)-symmetric (1R,2S,5R)-(-)-menthyl-N-chloroimidodicarbonate 2a provided moderate to good enantioselectivity (up to 40%) for the chlorination of silyl enol ethers to afford alpha-chloroketones only in the
F Li et al.
Journal of chromatography, 622(2), 187-195 (1993-12-22)
A simple and sensitive high-performance liquid chromatographic (HPLC) method using chiral derivatization was developed to screen and determine the enantiomers of moprolol and their metabolites in human urine. The recovery of (+)- and (-)-moprolol from urine was 70.8-81.1% at different
R O Hughes et al.
Journal of analytical toxicology, 15(5), 256-259 (1991-09-01)
A gas chromatography/mass spectrometry assay was developed for the detection of amphetamine and methamphetamine in urine. These drugs were detected as carbamate derivatives following reaction with (-)-menthyl chloroformate. Selected ion monitoring of the 226, 182, and 227 dalton ions for
K H Kim et al.
Archives of pharmacal research, 22(6), 608-613 (2000-01-01)
Optimum conditions of chiral derivatization reaction of beta-blockers acebutolol, arotinolol, beta-xolol, bisoprolol, celiprolol, metoprolol and pindolol) with (-)-menthyl chloroformate were investigated for the resolution by HPLC. With more than 30 times molar excess of (-)-menthyl chloroformate chiral derivatization reactions were
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