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220566

(S)-(−)-α-Methylbenzyl isocyanate

Name: (<I>S</I>)-(−)-α-Methylbenzyl isocyanate
Brand: ALDRICH

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

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Properties

Quality Level

100

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

SMILES string

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

InChI

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

InChI key

JJSCUXAFAJEQGB-QMMMGPOBSA-N

Description

General description

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

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.

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pictograms

GHS06,GHS08

signalword

Danger

hcodes

H315,H317,H319,H330,H334,H335,H412

pcodes

P260 - P273 - P280 - P302 + P352 - P304 + P340 + P310 - P305 + P351 + P338

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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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)

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.