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Sigma-Aldrich

1-Methyl-2-imidazolecarboxaldehyde

98%

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Empirical Formula (Hill Notation):
C5H6N2O
CAS Number:
13750-81-7
Molecular Weight:
110.11
MDL number:
MFCD01321308
PubChem Substance ID:
24871082
NACRES:
NA.22

Assay

98%

bp

70-74 °C/1 mmHg (lit.)

mp

36-39 °C (lit.)

SMILES string

[H]C(=O)c1nccn1C

InChI

1S/C5H6N2O/c1-7-3-2-6-5(7)4-8/h2-4H,1H3

InChI key

UEBFLTZXUXZPJO-UHFFFAOYSA-N

Related Categories

General description

1-Methyl-2-imidazolecarboxaldehyde is a heterocyclic building block. It affords tripodal ligands on condensation reaction with tris-(2-aminoethyl)amine (tren). These tripodal ligands react with iron(III) salts in the presence of air to afford iron(II) complexes. Its vibrational spectral studies have been reported.

Application

1-Methyl-2-imidazolecarboxaldehyde may be used in the synthesis of:
  • Schiff bases
  • ligand N,N-dimethyl-N′-(1-methylimidazole-2-ylmethyl)-ethylenediamine
  • [(bis(1-methylimidazol-2-yl)methyl)(2-(pyridyl-2-yl)ethyl)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)

215.6 °F - closed cup

Flash Point(C)

102 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis and characterization of tripodal iron (II) complexes prepared from 2-pyridinecarboxaldehyde and 1-methyl-2-imidazolecarboxaldehyde: stabilization of iron (II) cations with N 6 donor sets.
Brewer G, et al.
Inorgorganica Chimica Acta, 357(8), 2390-2396 (2004)
Synthesis, crystal structure and redox properties of bis-imidazolyl-containing copper (II) complexes.
Musie GT, et al.
Inorgorganica Chimica Acta, 348, 69-74 (2003)
Structural, spectroscopic and redox studies of a new ruthenium (III) complex with an imidazole-rich tripodal ligand.
Scarpellini M, et al.
Inorgorganica Chimica Acta, 357(3), 707-715 (2004)
DFT, FT-IR and FT-Raman investigations of 1-methyl-2-imidazolecarboxaldehyde.
Polat T and Yurdakul S.
Journal of Molecular Structure, 1053, 27-37 (2013)
Iron (III) complexes of sterically hindered tetradentate monophenolate ligands as functional models for catechol 1, 2-dioxygenases: The role of ligand stereoelectronic properties.
Velusamy M, et al.
Inorganic Chemistry, 43(20), 6284-6293 (2004)
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