4'-Chloroacetoacetanilide

Base Information

• Chemical Name: 4'-Chloroacetoacetanilide
• CAS No.: 101-92-8
• Deprecated CAS: 1258964-44-1
• Molecular Formula: C10H10ClNO2
• Molecular Weight: 211.648
• Hs Code.: 2924.29
• European Community (EC) Number: 202-989-6
• NSC Number: 3544
• UNII: 421YJ21R1J
• DSSTox Substance ID: DTXSID3036654
• Nikkaji Number: J4.997B
• Wikidata: Q27116409
• Mol file: 101-92-8.mol

Synonyms:4'-Chloroacetoacetanilide;101-92-8;N-(4-Chlorophenyl)-3-oxobutanamide;P-CHLOROACETOACETANILIDE;Butanamide, N-(4-chlorophenyl)-3-oxo-;Acetoacet-p-chloroanilide;Acetoacetyl-4-chloroanilide;Acetoacetanilide, 4'-chloro-;Acetoacetanilide, p-chloro-;N-(4-Chlorophenyl)acetoacetamide;p-Chlorodiacetanilide;AI3-17671;NSC 3544;MFCD00000613;HSDB 2709;EINECS 202-989-6;BRN 1819161;UNII-421YJ21R1J;421YJ21R1J;NSC-3544;4-12-00-01225 (Beilstein Handbook Reference);N-(4-Chloro-phenyl)-3-oxo-butyramide;4'-chloracetoacetanilid;Acetoacet-p-chloroamilide;Maybridge1_003854;4\'-Chloroacetoacetanilide;AA PHENACYL CHLORIDE;WLN: GR DMV1V1;4' Chloro Acetyl Acetanilide;N-Acetoacetyl-4-chloroaniline;SCHEMBL4671464;Acetoacetic acid-4-chloroanilide;DTXSID3036654;4'-Chloroacetoacetanilide, 98%;CHEBI:35090;HMS552H04;JMRJWEJJUKUBEA-UHFFFAOYSA-;N-(4-Chlorphenyl)-acetoacetamid;NSC3544;PARA-CHLOROACETOACETANILIDE;N-(4-Chlorophenyl)acetylacetamide;STL185598;AKOS000120914;N-(4-Chlorophenyl)-3-oxobutanamide #;Butanamide, 3-oxo-N-(4-chlorophenyl)-;SY051444;FT-0621790;EN300-18245;D71241;10D-066;4 inverted exclamation mark -Chloroacetoacetanilide;W-108894;Q27116409;F0001-0054

Chemical Property of 4'-Chloroacetoacetanilide

Chemical Property:

• Appearance/Colour: off-white to beige crystalline powder
• Melting Point: 131-134 °C(lit.)
• Refractive Index: 1.5388 (estimate)
• Boiling Point: 400.5 °C at 760 mmHg
• PKA: 11.00±0.46(Predicted)
• Flash Point: 196 °C
• PSA: 46.17000
• Density: 1.285 g/cm³
• LogP: 2.33060
• Storage Temp.: Store below +30°C.
• Solubility.: acetone: soluble25mg/mL, clear, colorless to light yellow
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 211.0400063
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

4'-Chloroacetoacetanilide >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CC(=O)CC(=O)NC1=CC=C(C=C1)Cl
• Uses: 4′-Chloroacetoacetanilide was used in recombinant androgen receptor competitive binding assay for analysis of natural, synthetic and environmental chemicals.

Technology Process of 4'-Chloroacetoacetanilide

There total 16 articles about 4'-Chloroacetoacetanilide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + 4-chloro-aniline (106-47-8) → 4'-Chloroacetoacetanilide (101-92-8)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; Reflux;

DOI:10.2147/DDDT.S119995

Reference yield: 89.0%

3-(4-chlorophenylamino)-2-[(4-chlorophenylimino)methyl]acrylonitrile (1352630-23-9) + 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) → 4'-Chloroacetoacetanilide (101-92-8) + 5-acetyl-1-(4-chlorophenyl)-6-oxo-1,6-dihydropyridine-3-carbonitrile (1352630-35-3)

Guidance literature:

In toluene; at 110 ℃; for 0.133333h; Inert atmosphere;

DOI:10.1002/ejoc.201100800

Reference yield: 85.0%

ethyl acetoacetate (141-97-9) + 4-chloro-aniline (106-47-8) → 4'-Chloroacetoacetanilide (101-92-8)

Guidance literature:

With silver trifluoromethanesulfonate; In nitromethane; at 80 ℃; for 8h;

DOI:10.1002/ejoc.201500224

upstream raw materials:

pyridine

tetrachloromethane

ethyl acetoacetate

4-chloro-aniline

Downstream raw materials:

2-Methyl-[1,8]naphthyridine-3-carboxylic acid (4-chloro-phenyl)-amide

C₁₆H₁₂ClN₄O₈^(1-)*C₆H₁₅N*H⁽¹⁺⁾

methyl 2-[(4-chlorophenyl)amino]-2-oxoacetate

N³,N⁵-bis(4-chlorophenyl)-4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamide

Refernces

• 1、 Moosavi, Fatemeh,Ebadi, Ahmad,Mohabbati, Maryam,Damghani, Tahereh,Mortazavi, Motahareh,Miri, Ramin,Firuzi, Omidreza. "Antiproliferative effect, alteration of cancer cell cycle progression and potential MET kinase inhibition induced by 3,4-dihydropyrimidin-2(1H)-one C5 amide derivatives". . . Retrieved 2021.
• 2、 Harries et al.. "". . p. 1609,1610. Retrieved 1972.
• 3、 Wen, Li-Rong,Wang, Ning-Ning,Du, Wu-Bo,Ma, Qiang,Zhang, Lin-Bao,Li, Ming. "Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones". . p. 2895 - 2900. Retrieved 2021.
• 4、 Daniliuc, Constantin,Glorius, Frank,Hu, Tianjiao,Lückemeier, Lukas. "Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones". supporting information. p. 23193 - 23196. Retrieved 2021/09/25.