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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.
Signal Word
Warning
Hazard Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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