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
• General Description: 1H-Imidazole-4-carbaldehyde is a versatile intermediate in organic synthesis, accessible through various methods such as regioselective N-alkylation of 4-formylimidazole, photooxidative cleavage of urocanic acid, and efficient synthetic routes involving lithiation and formylation. Its reactivity and applications are highlighted by its role in selective alkylation reactions, photochemical transformations, and as a precursor for N-protected derivatives.

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

Benzyl-[1-(3H-imidazol-4-yl)-meth-(E)-ylidene]-amine