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220566

Sigma-Aldrich

(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:
Molecular Weight:
147.17
Beilstein:
4230972
EC Number:
MDL number:
UNSPSC Code:
12352118
PubChem Substance ID:
NACRES:
NA.22

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.)

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

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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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

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 Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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