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392154

Sigma-Aldrich

4-Methyl-5-imidazolecarboxaldehyde

99%

Synonym(s):

4-Formyl-5-methyl-1H-imidazole, 4-Methyl-1H-imidazole-5-carboxaldehyde, 4-Methyl-5-formylimidazole, 4-Methylimidazol-5-carboxaldehyde, 4-Methylimidazole-5-carbaldehyde, 5-Methyl-1H-imidazole-4-carbaldehyde, 5-Methyl-3H-imidazole-4-carboxaldehyde, 5-Methyl-4-imidazolecarboxaldehyde, 5-Methylimidazol-4-carboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O
CAS Number:
Molecular Weight:
110.11
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

powder

mp

168-170 °C (lit.)

SMILES string

Cc1nc[nH]c1C=O

InChI

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

InChI key

KMWCSNCNHSEXIF-UHFFFAOYSA-N

General description

4-Methyl-5-imidazolecarboxaldehyde is an imidazole carboxaldehyde.

Application

4-Methyl-5-imidazolecarboxaldehyde is suitable for use in the synthesis of the following:
  • 1,3-bis[(4-methyl-5-imidazol-1-yl)ethylideneamino]-propan-2-ol (BIPO).
  • 1,3-bis[(4-methyl-5-imidazol-1-yl)ethylideneamino]propane (BIP).
  • {acetatoaqua[[(4-methylimidazol-5-yl)methylene]histamine]-copper(II)} perchlorate.
  • Schiff base condensates with tris(2-aminoethyl)amine (tren) or tris(3-aminopropyl)amine (trpn).

It may be used in the synthesis of the following:
  • Imidazolate-based metal organic framework (MOF) membrane.
  • 3,11-bis(4-imidazolylmethyl)-7-methyl-3,7,11,17-tetraazabicyclo[11.3.1]hepta-deca-1(17),13,15-triene, a 4-imidazolyl derivative of a 14-membered tetraazamacrocycle.
  • Cu(II) eight and six coordinate compounds.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Syntheses, crystal structures and properties of copper (II) complexes of 1, 3-bis [(4-methyl-5-imidazol-1-yl) ethylideneamino] propan-2-ol and 1, 3-bis [(4-methyl-5-imidazol-1-yl) ethylideneamino] propane.
Long LS, et al.
Transition Metal Chemistry, 24(4), 440-444 (1999)
Crystal and molecular structures of eight-coordinate (CuN4O4) and six-coordinate (CuN4O2) Cu (II) complexes with 4-methyl-5-imidazole-carboxaldehyde or 1-benzyl-2-hydroxymethylimidazole, respectively.
Barszcz B, et al.
Polyhedron, 18(27), 3713-3721 (1999)
Properties of a new 4-imidazolyl derivative of a 14-membered tetraazamacrocyclic chelating agent.
Nunes RM, et al.
Dalton Transactions, 40, 4536-4545 (2007)
Facile synthesis of an ultramicroporous MOF tubular membrane with selectivity towards CO2.
Aguado S, et al.
New. J. Chem., 35(1), 41-44 (2011)
Synthesis and characterization of manganese (ii) and iron (iii) d 5 tripodal imidazole complexes. Effect of oxidation state, protonation state and ligand conformation on coordination number and spin state.
Brewer C, et al.
Dalton Transactions, 8, 1009-1019 (2006)

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