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Merck
CN

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

Key Documents

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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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E B Christensen et al.
Journal of chromatography. B, Biomedical applications, 670(2), 243-249 (1995-08-18)
A fast high-performance liquid chromatographic (HPLC) assay was developed for determination of tocainide enantiomers in plasma. Subsequent to solid-phase extraction of tocainide from plasma, homochiral derivatization with (-)-menthyl chloroformate enabled separation of the enantiomers by a conventional reversed-phase HPLC system.
Ju-Il Sung et al.
Archives of pharmacal research, 33(9), 1301-1306 (2010-10-15)
Stereoisomers of nadolol were derivatized with S-(-)-menthyl chloroformate((-)-MCF) forming their diastereomers, RSR-nadolol-(-)-MCF, SRS-nadolol-(-)-MCF, RRS-nadolol-(-)-MCF and SSRnadolol-(-)-MCF. Diastereomeric mixture were then chromatographically resolved by preparative HPLC (JAIGEL-ODS-BP-L, 500 × 25 mm column) eluted with methanol-water (84:16, v/v) at flow rate 2.5
Stereospecific liquid chromatographic analysis of racemic adrenergic drugs utilizing precolumn derivatization with (-)-menthyl chloroformate.
R Mehvar
Journal of chromatography, 493(2), 402-408 (1989-09-01)
K H Kim et al.
Archives of pharmacal research, 22(6), 614-618 (2000-01-01)
A reversed-phase high-performance liquid chromatographic method was developed to determine the optical purity of metoprolol enantiomers. The enantiomers were converted to diastereomeric derivatives using (-)-menthyl chloroformate reagent. Separation of the enantiomers as diastereomers was achieved by reversed-phase HPLC within 30
N Domergue et al.
Analytical biochemistry, 214(2), 420-425 (1993-11-01)
Amino acids dissolved in aqueous methanol (or ethanol) and treated with optically active menthyl chloroformate were converted into N-menthyloxycarbonyl methyl (or ethyl) ester derivatives within a few minutes at room temperature. The obtained diastereomeric derivatives, with the exception of arginine
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