4-Chloro-3-formylcoumarin

Name: 4-Chloro-3-formylcoumarin
Brand: ALDRICH
Price: 351.05 USD

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

Key Documents

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Quality Level

100

assay

97%

mp

126-130 °C (lit.)

functional group

aldehyde
chloro
ester

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

Related Categories

Aldehydes

Chemical Building Blocks

Halogenated Heterocycles

Heterocyclic Building Blocks

Organic Building Blocks

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This Item	550361	348074	542903
Sigma-Aldrich 550337 4-Chloro-3-formylcoumarin	Sigma-Aldrich 550361 6-Bromo-4-chloro-3-formylcoumarin	Sigma-Aldrich 348074 2-Chloro-4-fluorobenzaldehyde	Sigma-Aldrich 542903 3-Chloro-4-fluoroiodobenzene
assay 97%	assay 97%	assay 97%	assay 98%
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
mp 126-130 °C (lit.)	mp 163-167 °C (lit.)	mp 60-63 °C (lit.)	mp -
functional group aldehyde	functional group aldehyde, bromo, chloro, ester	functional group aldehyde, chloro, fluoro	functional group chloro, fluoro, iodo

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[1]
biaryl lactones (benzo[c]chromen-6-ones)[2][3]
N-monosubstituted 4-amino-3-formylcoumarins[4]
chromeno[4,3-b]quinolin-6-one[5]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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

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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)

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)

Reactions of 4-chloro-3-formyl-coumarin with primary amines.

Strakova I, et al.

Chemistry of Heterocyclic Compounds, 42(5), 574-582 (2006)

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)

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)

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