1-methyl-1H-benzo[d]imidazole-2-carboxylic acid

Base Information

• Chemical Name: 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid
• CAS No.: 20572-01-4
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40390250
• Nikkaji Number: J739.874C
• Wikidata: Q82186782
• Mol file: 20572-01-4.mol

Synonyms:20572-01-4;1-methyl-1H-benzo[d]imidazole-2-carboxylic acid;1-METHYL-1H-BENZIMIDAZOLE-2-CARBOXYLIC ACID;1-methylbenzimidazole-2-carboxylic acid;1-Methyl-1H-1,3-Benzodiazole-2-Carboxylic Acid;1H-BENZIMIDAZOLE-2-CARBOXYLIC ACID, 1-METHYL-;MFCD01836869;1-Methyl-1H-benzoimidazole-2-carboxylic acid;1-Methyl-1H-benzo[d]imidazole-2-carboxylic ac;SCHEMBL760729;DTXSID40390250;BDBM105184;HMS1700N03;AMY22939;AKOS000506112;AB09980;CS-W019148;FS-3605;SY104155;2-Cyclopenten-1-one, 2-(hydroxymethyl)-;FT-0651123;1-methyl-1H-benzo[d]imidazole-2-carboxylicacid;EN300-1707437;A814706;1H-1,3-Benzimidazole-2-carboxylic acid, 1-methyl-;1-methyl-1H-1,3-benzodiazole-2-carboxylic acid (MB32-4)

Chemical Property of 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.07E-07mmHg at 25°C
• Melting Point: 146.5 °C
• Refractive Index: 1.653
• Boiling Point: 403.6 °C at 760 mmHg
• PKA: 1.19±0.30(Predicted)
• Flash Point: 197.9 °C
• PSA: 55.12000
• Density: 1.35 g/cm³
• LogP: 1.27150
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 176.058577502
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

98%min ^*data from raw suppliers

1-Methyl-1H-benzimidazole-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2N=C1C(=O)O

Technology Process of 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid

There total 18 articles about 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 1-methyl-1H-benzo[d]imidazole-2-carboxylate (2849-92-5) → 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid (20572-01-4)

Guidance literature:

methyl 1-methyl-1H-benzo[d]imidazole-2-carboxylate; With water; sodium hydroxide; In methanol; at 50 ℃; for 1h;

With hydrogenchloride; In water; pH=2;

Reference yield: 74.0%

1-Methylbenzimidazole (1632-83-3) + carbon dioxide (124-38-9,18923-20-1) → 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid (20572-01-4)

Guidance literature:

carbon dioxide; With [Au(1,3-bis(tert-butyl)imidazol-2-ylidene)(OH)]; potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h; under 1125.11 Torr;

1-Methylbenzimidazole; In tetrahydrofuran; at 20 ℃; for 12h; under 1125.11 Torr;

With hydrogenchloride; In tetrahydrofuran; water; regioselective reaction;

DOI:10.1021/ja103429q

Reference yield: 74.0%

→ 1-methyl-1H-benzo[d]imidazole-2-carboxylic acid (20572-01-4)

Guidance literature:

With [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(OH)]; potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

With hydrogenchloride; In tetrahydrofuran; water;

upstream raw materials:

1-Methylbenzimidazole

n-butyllithium

diethyl ether

N-methyl-1,2-phenylenediamine

Downstream raw materials:

(1-methyl-1H-benzoimidazol-2-yl)-[3-(3-phenylpyrazin-2-yl)azetidin-1-yl]methanone

1-methyl-1H-benzimidazole-2-carbonyl chloride

1-Methylbenzimidazole

(S)-N,1-dimethyl-N-(1-phenyl-4-(picolinamido)butan-2-yl)-1H-benzo[d]imidazole-2-carboxamide

Refernces

• 1、 -. "CARBOXYLATION CATALYSTS". Paragraph 0093. . Retrieved 2013/04/13.
• 2、 Boogaerts, Ine I. F.,Nolan, Steven P.. "Carboxylation of C-H bonds using N -heterocyclic carbene gold(I) complexes". supporting information; experimental part. p. 8858 - 8859. Retrieved 2010/08/21.