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260827

Sigma-Aldrich

2-Methylbenzamide

98%

Synonym(s):

o-Toluamide

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About This Item

Linear Formula:
CH3C6H4CONH2
CAS Number:
527-85-5
Molecular Weight:
135.16
EC Number:
208-427-6
MDL number:
MFCD00007982
UNSPSC Code:
12352100
PubChem Substance ID:
24855772
NACRES:
NA.22

assay

98%

mp

141-142 °C (lit.)

solubility

alcohol: very soluble(lit.)
benzene: very slightly soluble(lit.)
cold water: insoluble(lit.)
hydrochloric acid: very soluble (conc.)(lit.)
water: very soluble (hot)(lit.)

functional group

amide

SMILES string

Cc1ccccc1C(N)=O

InChI

1S/C8H9NO/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H2,9,10)

InChI key

XXUNIGZDNWWYED-UHFFFAOYSA-N

Application

2-Methylbenzamide (o-Toluamide) has been used in total synthesis of phenolic protoberberine alkaloid, cerasonine[1].

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD9317
BCCB3780
BCBX1703
BCBJ9034V
BCBJ7279V

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Thanh Nguyen Le et al.
Chemical & pharmaceutical bulletin, 56(7), 1026-1029 (2008-07-02)
First total synthesis of the phenolic protoberberine, cerasonine, was accomplished through a coupling reaction between o-toluamide and benzonitrile. This key step provided the 3-arylisoquinoline which was then successfully converted to 7,8-dihydro-8-oxoprotoberberine through an intramolecular S(N)2 reaction.

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