1H-Imidazole-2-carbaldehyde

Base Information

• Chemical Name: 1H-Imidazole-2-carbaldehyde
• CAS No.: 10111-08-7
• Molecular Formula: C4H4N2O
• Molecular Weight: 96.0886
• Hs Code.: 29332900
• European Community (EC) Number: 600-165-4
• DSSTox Substance ID: DTXSID70143736
• Nikkaji Number: J100.658D
• Wikidata: Q72482280
• Mol file: 10111-08-7.mol

Synonyms:10111-08-7;Imidazole-2-carboxaldehyde;1H-Imidazole-2-carbaldehyde;2-Formylimidazole;1H-IMIDAZOLE-2-CARBOXALDEHYDE;2-Imidazolecarboxaldehyde;imidazole-2-aldehyde;Imidazole-2-carbaldehyde;1H-Imidazolecarboxaldehyde;MFCD00003544;2-Formyl-1H-imidazole;formylimidazole;Isovalericacid;imidazolealdehyde;2-formyl imidazole;2-formyl-imidazole;imidazole carbaldehyde;imidazolecarboxaldehyde;2-imidazolecarbaldehyde;2-imidazol-carbaldehyde;imidazol-2-carbaldehyde;2-imidazolcarboxaldehyde;imidazole-2-carboxaldeyde;2-imidazole carboxaldehyde;2-imidazole-carboxaldehyde;imidazole 2-carboxaldehyde;1H-2-imidazolecarbaldehyde;1H-imidazol-2-carbaldehyd;1H-imidazole-2 carbaldehyde;1H-imidazole-2-carboaldehyde;YSWG441;1-H-imidazole-2-carbaldehyde;1H-Imidazole-2-carbaldehyde #;2-Imidazolecarboxaldehyde, 97%;DTXSID70143736;BCP27080;STR04050;BBL104408;STK503765;AKOS004910734;AC-6503;CS-W007321;PB47438;PS-9350;BP-12787;SY014217;AM20070660;BB 0260450;FT-0612642;I0809;EN300-52542;W-200646;F8880-2426

Chemical Property of 1H-Imidazole-2-carbaldehyde

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: 209 °C (dec.)(lit.)
• Refractive Index: 1.62
• Boiling Point: 296.5 °C at 760 mmHg
• PKA: 11.48±0.10(Predicted)
• Flash Point: 137.5 °C
• PSA: 45.75000
• Density: 1.322 g/cm³
• LogP: 0.22220
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Sonicated)
• Water Solubility.: Soluble in water.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 96.032362755
• Heavy Atom Count: 7
• Complexity: 74.1

Purity/Quality:

98% ^*data from raw suppliers

Imidazole-2-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39-3

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(N1)C=O
• Uses: 1H-Imidazole-2-carboxaldehyde is a novel PTP1b inhibitor with potential application to treat type 2 diabetes. Used in a study of the imidazole-directed allylation of aldimines.1 Imidazole-2-carboxaldehyde is a novel protein tyrosine phosphatase 1B (PTP1B) inhibitor with an important application to treat type-2 diabetes. It is used in the preparation of tridentate Schiff-base carboxylate-containing ligands by undergoing condensation reaction with amino acids beta-alanine and 2-aminobenzoic acid. It is also involved in the study of the imidazole-directed allylation of aldimines.

Technology Process of 1H-Imidazole-2-carbaldehyde

There total 20 articles about 1H-Imidazole-2-carbaldehyde 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: 99.0%

N-(2,2-Dimethoxyethyl)dichloroacetamidine → 2-imidazolecarbaldehyde (10111-08-7)

Guidance literature:

With formic acid; at 70 - 80 ℃; for 20h;

DOI:10.1021/jo00109a052

Reference yield: 92.0%

2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride (65276-01-9) → 2-imidazolecarbaldehyde (10111-08-7)

Guidance literature:

2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride; With hydrogenchloride; water; for 22h;

With sodium hydroxide; In water; pH=9.5;

DOI:10.1021/jo902588s

Reference yield: 91.0%

2-bromo-1H-imidazole (16681-56-4,151223-74-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-imidazolecarbaldehyde (10111-08-7)

Guidance literature:

2-bromo-1H-imidazole; With isopropylmagnesium chloride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 0.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -20 ℃; for 0.5h;

DOI:10.3390/molecules22111952

upstream raw materials:

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde

Methyl formate

N-((1H-imidazol-1-yl)methyl)-N-ethylethanamine

2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride

Downstream raw materials:

pyrrolo<1,2-a>imidazol-5-one

2-(dimethoxymethyl)imidazole

8-(4-Methylphenylsulfonyl)-9H-imidazo<1,2-a>azepin

7-(1H-Imidazol-2-ylmethyl)-8-methyl-6,7,8,9-tetrahydro-2H-2,7,9a-triaza-benzo[cd]azulen-1-one

Refernces

• 1、 Feng, Liang,Wang, Kun-Yu,Lv, Xiu-Liang,Powell, Joshua A.,Yan, Tian-Hao,Willman, Jeremy,Zhou, Hong-Cai. "Imprinted Apportionment of Functional Groups in Multivariate Metal-Organic Frameworks". . p. 14524 - 14529. Retrieved 2019.
• 2、 Venkateswarulu,Mukherjee, Trinetra,Mukherjee, Subhrakanti,Koner, Rik Rani. "Turn-on trivalent cation selective chemodosimetric probe to image native cellular iron pools". . p. 5269 - 5273. Retrieved 2014.
• 3、 Tian, Qingqiang,Shang, Suqin,Wang, Huajun,Shi, Guoqiang,Li, Zhiyao,Yuan, Jianyong. "Halogen–metal exchange on bromoheterocyclics with substituents containing an acidic proton via formation of a magnesium intermediate". supporting information. . Retrieved 2017/12/05.