Merck
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220566

Sigma-Aldrich

(S)-(−)-α-Methylbenzyl isocyanate

98%

Synonym(s):
(S)-(−)-1-Phenylethyl isocyanate
Linear Formula:
C6H5CH(CH3)NCO
CAS Number:
Molecular Weight:
147.17
Beilstein:
4230972
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

Packaging

1, 5 g in glass bottle

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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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