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456128

Sigma-Aldrich

4-Imidazolecarboxaldehyde

98%

Synonym(s):

5-Imidazolecarboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C4H4N2O
CAS Number:
3034-50-2
Molecular Weight:
96.09
EC Number:
221-227-3
MDL number:
MFCD00173726
UNSPSC Code:
12352005
PubChem Substance ID:
24869112
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

mp

174-177 °C (lit.)

functional group

aldehyde

SMILES string

O=Cc1c[nH]cn1

InChI

1S/C4H4N2O/c7-2-4-1-5-3-6-4/h1-3H,(H,5,6)

InChI key

ZQEXIXXJFSQPNA-UHFFFAOYSA-N

General description

4-Imidazolecarboxaldehyde undergoes reductive amination with the amine in the presence of sodium borohydride to form secondary amines.

Application

4-Imidazolecarboxaldehyde may be used in the following studies:
  • Synthesis of new donor-Π-acceptor (D-Π-A) type dye.
  • Preparation of ethyl, n-dodecyl and n-hexadecyl esters of urocanic acid (4-imidazoleacrylic acid).
  • Fabrication of colorimetric chemosensor.
  • Synthesis of chiral nickel(II) complex, [Ni(II)H3L](ClO4)2, having an achiral ligand H3L (tris{2-(4-imidazolyl)methyliminoethyl}amine).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR0544V
MKBF6359V
MKBG6298V
MKBF0670V
STBB2449

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K Honda et al.
Journal of pharmaceutical sciences, 70(1), 98-99 (1981-01-01)
Ethyl, n-dodecyl, and n-hexadecyl esters of urocanic acid (4-imidazoleacrylic acid) were prepared from 4-imidazolecarboxaldehyde in satisfactory yields via the Wittig reaction.
Spontaneous Resolution Induced by a Chiral Ni (II) Complex with an Achiral Tripodal Ligand#.
Sarkar S, et al.
Bull. Korean Chem. Soc., 36(3), 838-842 (2015)
Seon-Yeong Gwon et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 117, 810-813 (2013-10-03)
A new donor-π-acceptor (D-π-A) type dye was synthesized by the condensation reaction between 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran and 4-imidazolecarboxaldehyde. The chemical structure of the dye was characterized by (1)H NMR, EA and MS. A novel chromogenic dye based on imidazole as donor unit
Peter B Madrid et al.
Journal of combinatorial chemistry, 6(3), 437-442 (2004-05-11)
Due to growing problems with drug resistance, there is an outstanding need for new, cost-effective drugs for the treatment of malaria. The 4-aminoquinolines have provided a number of useful antimalarials, and Plasmodium falciparum, the causative organism for the most deadly
Organic Process Research & Development, 11, 206-206 (2007)
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