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456128

Sigma-Aldrich

4-Imidazolecarboxaldehyde

98%

Synonym(s):

5-Imidazolecarboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C4H4N2O
CAS Number:
3034-50-2
Molecular Weight:
96.09
EC Number:
221-227-3
MDL number:
MFCD00173726
UNSPSC Code:
12352005
PubChem Substance ID:
24869112
NACRES:
NA.22
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Assay

98%

form

solid

mp

174-177 °C (lit.)

functional group

aldehyde

SMILES string

O=Cc1c[nH]cn1

InChI

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

InChI key

ZQEXIXXJFSQPNA-UHFFFAOYSA-N

Related Categories

General description

4-Imidazolecarboxaldehyde undergoes reductive amination with the amine in the presence of sodium borohydride to form secondary amines.

Application

4-Imidazolecarboxaldehyde may be used in the following studies:
  • Synthesis of new donor-Π-acceptor (D-Π-A) type dye.[1]
  • Preparation of ethyl, n-dodecyl and n-hexadecyl esters of urocanic acid (4-imidazoleacrylic acid).[2]
  • Fabrication of colorimetric chemosensor.[3]
  • Synthesis of chiral nickel(II) complex, [Ni(II)H3L](ClO4)2, having an achiral ligand H3L (tris{2-(4-imidazolyl)methyliminoethyl}amine).[4]

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
MKBR0544V
MKBF6359V
MKBG6298V
MKBF0670V
STBB2449

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Organic Process Research & Development, 11, 206-206 (2007)
Chromene and Imidazole Based D-p-A Chemosensor Preparation and Its Anion Responsive Effects.
Son YA, et al.
Mol. Cryst. Liq. Cryst., 599(1), 16-22 (2014)
Peter B Madrid et al.
Journal of combinatorial chemistry, 6(3), 437-442 (2004-05-11)
Due to growing problems with drug resistance, there is an outstanding need for new, cost-effective drugs for the treatment of malaria. The 4-aminoquinolines have provided a number of useful antimalarials, and Plasmodium falciparum, the causative organism for the most deadly
Spontaneous Resolution Induced by a Chiral Ni (II) Complex with an Achiral Tripodal Ligand#.
Sarkar S, et al.
Bull. Korean Chem. Soc., 36(3), 838-842 (2015)
K Honda et al.
Journal of pharmaceutical sciences, 70(1), 98-99 (1981-01-01)
Ethyl, n-dodecyl, and n-hexadecyl esters of urocanic acid (4-imidazoleacrylic acid) were prepared from 4-imidazolecarboxaldehyde in satisfactory yields via the Wittig reaction.
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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?

    1 answer

    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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