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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
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Quality Level

100

Assay

97%

mp

209 °C (dec.) (lit.)

functional group

aldehyde

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[1]. It was also used in a study of the imidazole-directed allylation of aldimines[2].

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000280429
0000226924
MKCS5500
MKCL1809
MKCG4159

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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
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
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
Ruirui Li et al.
Small (Weinheim an der Bergstrasse, Germany), 15(52), e1904866-e1904866 (2019-11-30)
The confinement effect in asymmetrical biological ion channels makes the state of molecules and ions differs from that in the external environment, and the mass transfer confined in the biological ion channels is in a single strand form. Herein, an
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)
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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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