1H-Benzimidazole-2-carboxylicacid,methylester(9CI)

1H-Benzimidazole-2-carboxylicacid,methylester(9CI) Property

Melting point:

187.3 °C

Boiling point:

343.1±25.0 °C(Predicted)

Density 

1.324±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

10.39±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H8N2O2/c1-13-9(12)8-10-6-4-2-3-5-7(6)11-8/h2-5H,1H3,(H,10,11)

InChIKey

LKUBWDNDGBVKFK-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)NC2=CC=CC=C2N=1

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

1H-Benzimidazole-2-carboxylicacid,methylester(9CI) Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of methyl 1H-benzimidazole-2-carboxylate from methanol and 2-(trichloromethyl)-1H-benzo[d]imidazole: Sodium carbonate (Na2CO3, 0.64 g, 6.07 mmol) was added to a solution of 2-(trichloromethyl)-1H-benzo[d]imidazole (1.9 g, 6.07 mmol) in methanol (20 mL). The reaction mixture was heated to reflux for 14 h and subsequently cooled to room temperature. 1N hydrochloric acid (HCl) was added to the reaction solution and stirred for 0.5 hr. The reaction mixture was extracted with ethyl acetate (EA). The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give methyl 1H-benzimidazole-2-carboxylate (0.89 g, yield not stated). Mass spectrometry (MS) analysis showed the molecular ion peak (M+1) to be 177, which was consistent with the theoretically calculated value (C9H8N2O2, 176).

References

[1] Patent: WO2011/143365, 2011, A1. Location in patent: Page/Page column 138
[2] Patent: WO2008/33739, 2008, A2. Location in patent: Page/Page column 31