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220515

Sigma-Aldrich

Methyl benzimidate hydrochloride

97%

Synonym(s):

Benzimidoic acid methyl ester hydrochloride, Methyl benzenecarboximidate hydrochloride

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About This Item

Linear Formula:
C6H5C(=NH)OCH3·HCl
CAS Number:
5873-90-5
Molecular Weight:
171.62
EC Number:
227-537-5
MDL number:
MFCD00012575
UNSPSC Code:
12352100
PubChem Substance ID:
24853175
NACRES:
NA.22

Assay

97%

mp

105-107 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

Cl.COC(=N)c1ccccc1

InChI

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

InChI key

HDJNHVNQRJMWSH-UHFFFAOYSA-N

Application

Methyl benzimidate hydrochloride was used:
  • in the synthesis of chiral phenyldihydroimidazole derivative
  • as imidating reagent to modify Lys residues of cyclic Lys-Gly-Asp peptide to afford acetimidate analogs
  • in the synthesis of N-benzimidoyl-(1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine)

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J Einsiedel et al.
Bioorganic & medicinal chemistry letters, 11(18), 2533-2536 (2001-09-11)
Conformationally restricted benzamide bioisosteres were investigated when the chiral phenyldihydroimidazole derivative 4e (FAUC 179) showed strong and highly selective dopamine D4 receptor binding (K(i)high=0.95nM). Mitogenesis experiments indicated partial agonist properties (42%). EPC syntheses of the target compounds of type 4
R M Scarborough et al.
The Journal of biological chemistry, 268(2), 1066-1073 (1993-01-15)
Members of the snake venon-derived, "disintegrin" peptide family containing the Arg-Gly-Asp (RGD) amino acid sequence are among the most potent inhibitors of the binding of adhesive proteins to platelet glycoprotein (GP) IIb-IIIa. However, GPIIb-IIIa antagonists containing the RGD sequence are
Tao Ji et al.
Chemical research in toxicology, 20(4), 701-708 (2007-03-27)
Thiobenzamide (TB) is hepatotoxic in rats causing centrolobular necrosis, steatosis, cholestasis, and hyperbilirubinemia. It serves as a model compound for a number of thiocarbonyl compounds that undergo oxidative bioactivation to chemically reactive metabolites. The hepatotoxicity of TB is strongly dependent

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