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Sigma-Aldrich

2-Imidazolecarboxaldehyde

97%

Synonym(s):

1H-Imidazole-2-carbaldehyde, 2-Formylimidazole, 2-Imidazolecarbaldehyde, 2-Imidazolylformaldehyde, Imidazole-2-formaldehyde

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About This Item

Empirical Formula (Hill Notation):
C4H4N2O
CAS Number:
10111-08-7
Molecular Weight:
96.09
Beilstein:
4371302
MDL number:
MFCD00003544
UNSPSC Code:
12352005
PubChem Substance ID:
24856448
NACRES:
NA.22

Assay

97%

mp

209 °C (dec.) (lit.)

SMILES string

[H]C(=O)c1ncc[nH]1

InChI

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

InChI key

XYHKNCXZYYTLRG-UHFFFAOYSA-N

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Application

2-Imidazolecarboxaldehyde was used in the preparation of tridentate Schiff-base carboxylate-containing ligands by undergoing condensation reaction with amino acids β-alanine and 2-aminobenzoic acid. It was also used in a study of the imidazole-directed allylation of aldimines.

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

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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Tohid Taghizadeh et al.
International journal of biological macromolecules, 166, 1301-1311 (2020-11-09)
A zeolitic imidazolate framework (ZIF-90) has been synthesized through solvothermal method. The structure was characterized by means of FT-IR spectroscopy, X-ray diffraction, thermogravimetric analysis (TGA), and scanning electron microscopy (SEM)/energy dispersive X-ray spectroscopy (EDS). The synthesized ZIF-90 was applied as
Nicholas R Perl et al.
Organic letters, 9(18), 3699-3701 (2007-08-10)
A new chiral allylchlorosilane has been developed that allows the highly enantioselective allylation and crotylation of a range of 2-imidazolylaldimines and ketimines. The method may be exploited for the protecting group-free synthesis of a diverse array of imidazole-bearing chiral carbinamines
Ze-Yu Jiang et al.
Angewandte Chemie (International ed. in English), 56(17), 4767-4771 (2017-03-28)
A crack-free sub-nanometer composite structure for the study of ion transfer was constructed by in situ growth of ZIF-90 [Zn(ICA)
E Colacio et al.
Inorganic chemistry, 39(13), 2882-2890 (2001-03-10)
Tridentate Schiff-base carboxylate-containing ligands, derived from the condensation of 2-imidazolecarboxaldehyde with the amino acids beta-alanine (H2L1) and 2-aminobenzoic acid (H2L5) and the condensation of 2-pyridinecarboxaldehyde with beta-alanine (HL2), D,L-3-aminobutyric acid (HL3), and 4-aminobutyric acid (HL4), react with copper(II) perchlorate to
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