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Merck
CN

77968

(R)-(+)-α-Methylbenzyl isocyanate

derivatization grade (chiral), LiChropur™, ≥99.0%

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:
23151817
NACRES:
NA.22
PubChem Substance ID:
329768059
EC Number:
251-485-2
Beilstein/REAXYS Number:
3196930
MDL number:
MFCD00063015
Assay:
≥99.0% (sum of enantiomers, GC), ≥99.0%
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

grade

derivatization grade (chiral)

assay

≥99.0% (sum of enantiomers, GC), ≥99.0%

form

liquid

optical activity

[α]20/D +10.5±0.5°, neat

optical purity

enantiomeric ratio: ≥99.5:0.5 (GC)

quality

LiChropur™

technique(s)

HPLC: suitable

refractive index

n20/D 1.513 (lit.), n20/D 1.513

bp

55-56 °C/2.5 mmHg (lit.)

density

1.045 g/mL at 20 °C (lit.), 1.046 g/mL at 20 °C

storage temp.

2-8°C

Quality Level

100

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Application

(R)-(+)-MBIC has been used in derivatization of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol to form 4-(methylnitrosamino)-1-(a-methylbenzylcarbamoyl)-1-(3-pyridyl)butane. It has also been used in isolating hydroxyl acid, converting it to Methyl-4-[(S)-a-methylbenzylcarbamoyl]-4-(3-pyridyl)- butanoate which was further analysed by LC-MS/MS.1 It reacts with hydrate hydrochloride ketoaniline to yield hemiaminal, 3-((1R)-1-Phenylethyl)-(4S)-6-chloro-4-hydroxy-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one.

General description

(R)-(+)-a-Methylbenzyl isocyanate [(R)-(+)-MBIC] is a derivatizing agent.

Other Notes

Discover LiChropur reagents ideal for HPLC or LC-MS analysis
Reagent used for the determination of the enantiomeric purity of alcohols and amines

Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

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
0000307956
0000307956
0000266990
0000256504
0000247550

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Determination of metoprolol enantiomers in plasma and urine using (S)-(-)-phenylethyl isocyanate as a chiral reagent.
G Pflugmann et al.
Journal of chromatography, 421(1), 161-164 (1987-10-09)
W. Pereira et al.
Analytical Letters, 3, 23-23 (1970)
R. Dumont et al.
The Journal of Organic Chemistry, 51, 2515-2515 (1986)
Stereoselective metabolism of nicotine and tobacco-specific N-nitrosamines to 4-hydroxy-4-(3-pyridyl)butanoic acid in rats.
Trushin N, Hecht SS.
Chemical Research in Toxicology, 12(2), 164-171 (1999)
K.C. Rice et al.
The Journal of Organic Chemistry, 45, 592-592 (1980)
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