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Sigma-Aldrich

4-Chloro-3-formylcoumarin

97%

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About This Item

Empirical Formula (Hill Notation):
C10H5ClO3
CAS Number:
50329-91-4
Molecular Weight:
208.60
MDL number:
MFCD00179896
UNSPSC Code:
12352100
PubChem Substance ID:
24879107
NACRES:
NA.22

Assay

97%

mp

126-130 °C (lit.)

SMILES string

[H]C(=O)C1=C(Cl)c2ccccc2OC1=O

InChI

1S/C10H5ClO3/c11-9-6-3-1-2-4-8(6)14-10(13)7(9)5-12/h1-5H

InChI key

CLLLQUGVEQADNN-UHFFFAOYSA-N

General description

4-Chloro-3-formylcoumarin, also known as 4-chloro-2-oxo-2H-chromene-3-carbaldehyde, is a coumarin derivative.

Application

4-Chloro-3-formylcoumarin may be used as a reactant in the preparation of:
  • 2-aryl[1]benzopyrano[4,3-c]pyrazol-4(2H)-ones
  • biaryl lactones (benzo[c]chromen-6-ones)
  • N-monosubstituted 4-amino-3-formylcoumarins
  • chromeno[4,3-b]quinolin-6-one

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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Reactions of 4-Chloro-3-formylcoumarin with Arylhydrazines.
Strakova I, et al.
Chemistry of Heterocyclic Compounds, 39(12), 1608-1616 (2003)
Reactions of 4-chloro-3-formyl-coumarin with primary amines.
Strakova I, et al.
Chemistry of Heterocyclic Compounds, 42(5), 574-582 (2006)
One-Pot Synthesis of Biaryl Lactones by Sonogashira Cross-Coupling Reactions of 4-Chloro-3-formylcoumarin and Subsequent Domino [5+1] Cyclization/Deacetylation Reactions with 1, 3-Dicarbonyl Compounds.
Iaroshenko VO, et al.
Advanced Synthesis & Catalysis, 354(5), 803-806 (2012)
An efficient ultrasound promoted catalyst-free protocol for the synthesis of chromeno [4,3-b] quinolin-6-ones.
Prasad JV, et al.
Chemical Science, 123(5), Prasad JV-Prasad JV (2011)
Synthesis of 6H-benzo [c] chromen-6-ones by cyclocondensation of 1,3-dicarbonyl compounds with 4-chloro-3-formylcoumarin.
Iaroshenko, VO, et al.
Tetrahedron Letters, 52(45), 5910-5912 (2011)

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