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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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

456128-1G:
456128-5G:
456128-VAR:
456128-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR0544V
MKBF6359V
MKBG6298V
MKBF0670V
STBB2449

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Chromene and Imidazole Based D-p-A Chemosensor Preparation and Its Anion Responsive Effects.
Son YA, et al.
Mol. Cryst. Liq. Cryst., 599(1), 16-22 (2014)
Organic Process Research & Development, 11, 206-206 (2007)
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
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.
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
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Global Trade Item Number

SKUGTIN
456128-1G4061832341163
456128-5G4061832341170

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