1H-Imidazole-4-carbaldehyde

Base Information

• Chemical Name: 1H-Imidazole-4-carbaldehyde
• CAS No.: 3034-50-2
• Molecular Formula: C4H4N2O
• Molecular Weight: 96.0886
• Hs Code.: 29332900
• European Community (EC) Number: 221-227-3
• NSC Number: 400521
• UNII: DWG32KT6XA
• DSSTox Substance ID: DTXSID70184427
• Nikkaji Number: J205.342J
• Wikidata: Q72482274
• Mol file: 3034-50-2.mol

Synonyms:imidazole-4-carboxaldehyde

Chemical Property of 1H-Imidazole-4-carbaldehyde

Chemical Property:

• Appearance/Colour: White to light yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 174-177 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 367.8 °C at 760 mmHg
• PKA: 11.05±0.10(Predicted)
• Flash Point: 179.8 °C
• PSA: 45.75000
• Density: 1.322 g/cm³
• LogP: 0.22220
• Storage Temp.: Room temperature.
• Sensitive.: Air Sensitive
• Solubility.: Soluble in DMSO, methanol.
• 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:

99% ^*data from raw suppliers

5-Imidazolecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)C=O
• Uses: 1H-Imidazole-4-carbaldehyde is a 4-formyl derivative of imidazole used in the preparation of C17,20-lyase inhibitor for the treatemnet of androgen-dependent prostate cancer. 4-Imidazolecarboxaldehyde is also used in the synthesis of other biologically active compounds such as antimalarial drugs. Imidazole-4-carboxaldehyde is a 4-formyl derivative of imidazole used in the preparation of C17,20-lyase inhibitor for the treatment of androgen-dependent prostate cancer. It is also used in the synthesis of other biologically active compounds such as antimalarial drugs, fabrication of colorimetric chemosensor.

Technology Process of 1H-Imidazole-4-carbaldehyde

There total 23 articles about 1H-Imidazole-4-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%

(1H-imidazol-4-yl)methanol (822-55-9) → 4(5)formylimidazole (3034-50-2)

Guidance literature:

With manganese(IV) oxide; In methanol;

DOI:10.1016/j.bmcl.2008.04.024

Reference yield: 98.0%

(1-tritylimidazol-4-yl)carboxaldehyde (33016-47-6) → 4(5)formylimidazole (3034-50-2)

Guidance literature:

With acetic acid; In methanol; for 7h; Heating;

Reference yield: 85.0%

4-bromo-1 H-imidazole (2302-25-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4(5)formylimidazole (3034-50-2)

Guidance literature:

4-bromo-1 H-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:

(1H-imidazol-4-yl)methanol

1H-imidazole-5-methanol

1H-imidazol-5-ylmethanol hydrochloride

tert-butyl 5-formyl-1H-imidazole-1-carboxylate

Downstream raw materials:

urocanic Acid

1-methylimidazole-5-carbaldehyde

5-methyl-3-phenyl-isoxazole-4-carboxylic acid (1⁽³⁾H-imidazol-4-ylmethylene)-hydrazide

1-benzyl-4-imidazolecarboxaldehyde

Refernces

• 1、 Mohammad,Kasper,Morrison. "Urocanic acid photobiology. Purine-assisted photooxidation to 1H- imidazole-4(5)-carboxaldehyde". . p. 4903 - 4906. Retrieved 1994.
• 2、 Brocklehurst,Griffiths. "-". . p. 2407. Retrieved 1968.
• 3、 -. "Synthesis method of 1H-imidazole-4-carboxylic acid". Paragraph 0021; 0028; 0035; 0042; 0049. . Retrieved 2018/05/16.
• 4、 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.