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245305

(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
MDL number:
MFCD00009694
Beilstein/REAXYS Number:
2414686
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24854513
Form:
liquid
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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

signalword

Danger

hcodes

H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Skin Corr. 1B

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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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
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
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Global Trade Item Number

SKUGTIN
245305-25G04061825772493
245305-100G04061825772486