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About This Item
Linear Formula:
CH3COCH2CONHC6H4Cl
CAS Number:
Molecular Weight:
211.64
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
98%
form
powder
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
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[1]. 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[2].
Application
4′-Chloroacetoacetanilide was used in recombinant androgen receptor competitive binding assay for analysis of natural, synthetic and environmental chemicals[3].
Storage Class
13 - Non Combustible Solids
wgk_germany
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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)
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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