260827
2-Methylbenzamide
98%
Synonym(s):
o-Toluamide
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About This Item
Linear Formula:
CH3C6H4CONH2
CAS Number:
Molecular Weight:
135.16
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
208-427-6
MDL number:
Assay:
98%
InChI key
XXUNIGZDNWWYED-UHFFFAOYSA-N
InChI
1S/C8H9NO/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H2,9,10)
SMILES string
Cc1ccccc1C(N)=O
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
Application
2-Methylbenzamide (o-Toluamide) has been used in total synthesis of phenolic protoberberine alkaloid, cerasonine.
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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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