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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/REAXYS Number:
4371302
MDL number:
MFCD00003544
UNSPSC Code:
12352005
PubChem Substance ID:
24856448
NACRES:
NA.22

Quality Level

100

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Rahul Sharma et al.
Environmental toxicology and pharmacology, 80, 103454-103454 (2020-07-10)
The present armamentarium of commercially available antidotes provides limited protection against the neurological effects of organophosphate exposure. Hence, there is an urgent need to design and develop molecules that can protect and reactivate inhibited-AChE in the central nervous system. Some
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)
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
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