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Merck
CN

220574

(R)-(+)-α-Methylbenzyl isocyanate

99%

Synonym(s):

(R)-(+)-1-Phenylethyl isocyanate

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About This Item

Linear Formula:
C6H5CH(CH3)NCO
CAS Number:
33375-06-3
Molecular Weight:
147.17
UNSPSC Code:
12352118
NACRES:
NA.22
PubChem Substance ID:
24853180
EC Number:
251-485-2
Beilstein/REAXYS Number:
3196930
MDL number:
MFCD00063015
Assay:
99%
Form:
liquid

Key Documents

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InChI key

JJSCUXAFAJEQGB-MRVPVSSYSA-N

InChI

1S/C9H9NO/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3/t8-/m1/s1

SMILES string

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

assay

99%

form

liquid

optical activity

[α]20/D +10°, neat

optical purity

ee: 96% (GLC)

refractive index

n20/D 1.513 (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

200

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Application

  • Paper Title: Stereoselective metabolism of nicotine and tobacco-specific N-nitrosamines to 4-hydroxy-4-(3-pyridyl)butanoic acid in rats. (Trushin N, Hecht SS, 1999).
  • Paper Title: Absolute configuration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol formed metabolically from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. (Hecht SS, Spratt TE, Trushin N, 1997).

General description

(R)-(+)-α-Methylbenzyl isocyanate is an organic compound that belongs to the class of isocyanates. It is used in the synthesis of chiral ligands for asymmetric catalysis. These ligands play a crucial role in enantioselective reactions, allowing to produce single enantiomer products.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - 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
0000452659
0000452659
0000435567
0000435565
0000435567

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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)
Myriam Matoga et al.
Journal of enzyme inhibition and medicinal chemistry, 17(6), 375-379 (2003-04-10)
The derivatization of racemic 5-[(2-methylphenoxy)methyl]-2-amino-2-oxazoline, developed as an imidazoline binding sites ligand, with (+)-(R)-alpha-methylbenzyl isocyanate was performed in chloroform. The reaction led to two pairs of diastereomers, which were separated by RP-HPLC. A kinetic study of the derivatization reaction was

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