133655

Sigma-Aldrich

4′-Chloroacetoacetanilide

98%

Linear Formula:
CH3COCH2CONHC6H4Cl
CAS Number:
Molecular Weight:
211.64
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

131-134 °C (lit.)

solubility

acetone: soluble 25 mg/mL, clear, colorless to light yellow

SMILES string

CC(=O)CC(=O)Nc1ccc(Cl)cc1

InChI

1S/C10H10ClNO2/c1-7(13)6-10(14)12-9-4-2-8(11)3-5-9/h2-5H,6H2,1H3,(H,12,14)

InChI key

JMRJWEJJUKUBEA-UHFFFAOYSA-N

Related Categories

General description

4′-Chloroacetoacetanilide was trilithiated with lithium diisopropylamide and condensed with several aromatic esters, followed by neutralization, separate acid cyclization and rearrangements to yield 4-anilino-6-aryl-2H-pyran-2-ones. It undergoes three-component reaction with a mixture of aromatic aldehyde and 5-aminotetrazole to form N,7-diaryl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamide.

Application

4′-Chloroacetoacetanilide was used in recombinant androgen receptor competitive binding assay for analysis of natural, synthetic and environmental chemicals.

Packaging

100 g in poly bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Synthesis and antimicrobial activity of n, 7-diaryl-5-methyl-4, 7-dihydrotetrazolo [1, 5-a] pyrimidine-6-arboxamides.
Gein VL, et al.
Pharmaceutical Chemistry Journal, 44(7), 366-369 (2010)
Preparation of 4-anilino-6-aryl-2 H-pyran-2-ones from trilithiated acetoacetanilides and aromatic esters.
Downs JR, et al.
Canadian Journal of Chemistry, 82(5), 659-664 (2004)
Hong Fang et al.
Chemical research in toxicology, 16(10), 1338-1358 (2003-10-21)
A number of environmental and industrial chemicals are reported to possess androgenic or antiandrogenic activities. These androgenic endocrine disrupting chemicals may disrupt the endocrine system of humans and wildlife by mimicking or antagonizing the functions of natural hormones. The present...

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