Basic information
- CAS
101-92-8- Standard SMILES
CC(=O)CC(=O)Nc1ccc(Cl)cc1- InChIKey
JMRJWEJJUKUBEA-UHFFFAOYSA-N- Molecular formula
- C10H10ClNO2
- Average molar mass
- 211.64 g/mol
- Monoisotopic mass
- 211.04000624
Overview
P-Chloroacetoacetanilide is an anilide.
Names & identifiers
- Preferred name
- p-Chloroacetoacetanilide
- IUPAC
- N-(4-chlorophenyl)-3-oxobutanamide
- English name
- 4'-Chloroacetoacetanilide
- Molecular formula
- C10H10ClNO2
- Molecular weight
- 211.64
Names & synonyms
4'-Chloroacetoacetanilide101-92-8N-(4-Chlorophenyl)-3-oxobutanamideP-CHLOROACETOACETANILIDEButanamide, N-(4-chlorophenyl)-3-oxo-Acetoacet-p-chloroanilideAcetoacetyl-4-chloroanilideAcetoacetanilide, 4'-chloro-Acetoacetanilide, p-chloro-N-(4-Chlorophenyl)acetoacetamidep-ChlorodiacetanilideAI3-17671
Show more names
AAPCAoroacetoacetaniLTIMTEC-BB SBB0034314'-ChloroacetoacetanLABOTEST-BB LT01274571p-Chloro-N-acetanilidePARA-CHLOROACETOANILIDE4′-Chloracetoacetanilid
NSC 3544HSDB 2709EINECS 202-989-6BRN 1819161421YJ21R1JNSC-3544DTXSID30366544-12-00-01225 (Beilstein Handbook Reference)
Database identifiers
- CAS
101-92-8- PubChem CID
- 7587
- DTXSID
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 46.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 222
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Color/FormCRYSTALS FROM ETHER, ALCOHOL
SolubilityVERY SOL IN ALCOHOL, ETHER, BENZENE
Melting Point66-67 °C
Physical DescriptionSolid; [HSDB]
Collision Cross Section143.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3036654]
Physicochemical properties
- Melting point
- 131 · 131-134 °C (lit.)
- Boiling point
- 303 °C · 303°C (rough estimate)
- Density
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationChemical: Butanamide, N-(4-chlorophenyl)-3-oxo-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummaryMay cause irritation; [Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- AK4375000
- hs_code
- 29242990
- Toxicity
- ipr-mus LDLo 500 mg/kg CBCCT* 4,225,52
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
Chemistry & industry
Uses & manufacturing
Uses
Used as an intermediate for CI solubilized vat yellow 8; [HSDB]
CHEMICAL INTERMEDIATE FOR CI SOLUBILIZED VAT YELLOW 8
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1976) 5.81X10+6 GRAMS (PRINCPL CUSTMS DISTS)
(1979) No Data
U.S. Production
(1977) No Data
(1979) No Data
Methods of ManufacturingPROBABLY BY REACTION OF ANILINE AND ACETOACETIC ESTERS, FOLLOWED BY CHLORINATION IN THE PRESENCE OF ACETIC ACID
General Manufacturing Information
Butanamide, N-(4-chlorophenyl)-3-oxo-: INACTIVE
4 P-SUBSTITUTED ACETOACETANILIDES COMPARED WITH ACETOACETANILIDE AS BACTERICIDES AGAINST MICROCOCCUS, STAPHYLOCOCCUS & SARCINA. P-CHLOROACETOACETANILIDE MORE ACTIVE THAN ACETOACETANILIDE.
Applications
Uses4′-Chloroacetoacetanilide was used in recombinant androgen receptor competitive binding assay for analysis of natural, synthetic and environmental chemicals.
General Description4′-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.
Upstream & downstream products
Downstream products
Related reactions
1 records
Compound notes
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