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Merck
CN

220566

(S)-(−)-α-Methylbenzyl isocyanate

98%

Synonym(s):

(S)-(−)-1-Phenylethyl isocyanate

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About This Item

Linear Formula:
C6H5CH(CH3)NCO
CAS Number:
14649-03-7
Molecular Weight:
147.17
UNSPSC Code:
12352118
NACRES:
NA.22
PubChem Substance ID:
24853178
EC Number:
238-698-6
Beilstein/REAXYS Number:
4230972
MDL number:
MFCD00002036
Assay:
98%
Form:
liquid

Key Documents

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InChI key

JJSCUXAFAJEQGB-QMMMGPOBSA-N

InChI

1S/C9H9NO/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3/t8-/m0/s1

SMILES string

C[C@H](N=C=O)c1ccccc1

assay

98%

form

liquid

optical activity

[α]20/D −10°, neat

optical purity

ee: 96% (GLC)

refractive index

n20/D 1.5145 (lit.)

bp

55-56 °C/2.5 mmHg (lit.)

density

1.045 g/mL at 20 °C (lit.)

functional group

amine, isocyanate, phenyl

storage temp.

2-8°C

Quality Level

100

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Application

(S)-(-)-α-Methylbenzyl isocyanate may be used as a chiral auxiliary for the resolution of racemic (±)-6aR,11aR-maackiain to give the (-)-form, which is a key intermediate for synthesizing (-)-cabenegrin A-I.

General description

(S)-(-)-α-Methylbenzyl isocyanate is a commonly used chiral derivatizing agent for the resolution of enantiomers.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Aquatic Chronic 3 - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

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

wgk

WGK 3

flash_point_f

149.0 °F - closed cup

flash_point_c

65 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7521V
WXBF4677V
WXBF3320V
WXBF1078V
WXBF1772

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Absolute configuration and total synthesis of (-)-cabenegrin AI.
Tokes AL, et al.
Tetrahedron, 55(30), 9283-9296 (1999)
Resolution of salbutamol enantiomers in human urine by reversed-phase high performance liquid chromatography after derivatization with (S)-(-)-a-methylbenzyl isocyanate.
Kim KH, et al.
Archives of Pharmacal Research, 20(5), 486-490 (1997)
Determination of the optical purity of (R)-terbutaline by 1 H-NMR and RP-LC using chiral derivatizing agent,(S)-(-)-a-methylbenzyl isocyanate.
Kim KH, et al.
Journal of Pharmaceutical and Biomedical Analysis, 25(5), 947-956 (2001)
Determination of pindolol enantiomers in human plasma and urine by simple liquid-liquid extraction and high-performance liquid chromatography.
Beal JL and Tett SE
Journal of Chromatography. B, Biomedical Applications, 715(2), 409-415 (1998)
High-performance liquid chromatographic determination of the enantiomers of beta-adrenoceptor blocking agents in biological fluids. II. Studies with atenolol.
S K Chin et al.
Journal of chromatography, 489(2), 438-445 (1989-04-14)
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