Acetoacetanilide

Base Information

• Chemical Name: Acetoacetanilide
• CAS No.: 102-01-2
• Deprecated CAS: 1258964-41-8
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Hs Code.: 2924.29 CLASSIFICATION
• European Community (EC) Number: 202-996-4
• NSC Number: 2656
• UNII: W35JB9PY3X
• DSSTox Substance ID: DTXSID0024397
• Nikkaji Number: J4.999I
• Wikipedia: Acetoacetanilide
• Wikidata: Q15720542
• ChEMBL ID: CHEMBL1604429
• Mol file: 102-01-2.mol

Synonyms:acetoacetanilide

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Chemical Property of Acetoacetanilide

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 83-86 °C
• Refractive Index: 1.563
• Boiling Point: 373.3 °C at 760 mmHg
• PKA: 12.21±0.46(Predicted)
• Flash Point: 162 °C
• PSA: 46.17000
• Density: 1.26 g/cm³
• LogP: 1.67720
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 5 g/L (20 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CC(=O)CC(=O)NC1=CC=CC=C1
• Uses: Acetoacetanilide is used as intermediate for the manufacture of organic pigments and dyestuffs. Acetoacetanilide (AAA) flakes is used as an intermediate for the manufacture of organic pigments and dyestuffs. For further information consult the Product information sheet. Product Data Sheet Acetoacetanilide may be used to synthesize:azo pigmentsacetoacetanilido-4-aminoantipyrine (Schiff base)6-aryl-2-methyl-4-oxo-N,N′-diphenyl-2-cyclohexene-1,3-dicarboxamidesphotoluminescent lanthanide complexes

Technology Process of Acetoacetanilide

There total 61 articles about Acetoacetanilide 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: 100.0%

2-chloro-N-phenyl-3-oxobutanamide (31844-92-5,119878-78-3) → N-phenylacetoacetamide (102-01-2,98624-45-4)

Guidance literature:

With potassium carbonate; para-thiocresol; In acetonitrile; at 20 ℃; for 1h; Reagent/catalyst;

DOI:10.1080/10426507.2016.1138309

Reference yield: 98.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + aniline (62-53-3) → N-phenylacetoacetamide (102-01-2,98624-45-4)

Guidance literature:

In propan-1-ol; at 30 - 50 ℃; for 5h; Solvent; Temperature; Autoclave; Large scale;

Reference yield: 98.0%

2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) + aniline (62-53-3) → N-phenylacetoacetamide (102-01-2,98624-45-4)

Guidance literature:

With sodium acetate; In tetrahydrofuran; for 24h; Reflux;

DOI:10.1055/s-0029-1217135

upstream raw materials:

4-methyleneoxetan-2-one

aniline

ethanol

diacetylacetanilide

Downstream raw materials:

3-piperidino-crotonic acid anilide

6,11-dioxo-6,11-dihydro-benzo[f]pyrido[1,2-a]indole-12-carboxylic acid anilide

2,5-bis-(N-phenyl-carbamoylacetyl)-thiophene

Acetanilid

Refernces

• 1、 Sivaramakarthikeyan, Ramar,Iniyaval, Shunmugam,Padmavathy, Krishnaraj,Liew, Hui-Shan,Looi, Chin-King,Mai, Chun-Wai,Ramalingan, Chennan. "Phenothiazine and amide-ornamented dihydropyridines: Via a molecular hybridization approach: Design, synthesis, biological evaluation and molecular docking studies". . p. 17046 - 17057. Retrieved 2019.
• 2、 Chick,Wilsmore. "-". . . Retrieved 1910.
• 3、 Suri,Satti,Suri. "Microwave induced acetoacetylation of hetaryl and aryl amines". . p. 3709 - 3718. Retrieved 2000.
• 4、 Feng, Qian,Chen, Dajun,Feng, Danyang,Jiao, Libin,Peng, Zhigang,Pei, Lixia. "Vinyl polymerizations of norbornene catalyzed by nickel complexes with acetoacetamide ligands". . p. 32 - 37. Retrieved 2014.
• 5、 Iniyaval, Shunmugam,Karuppasamy, Ayyanar,Lim, Wei-Meng,Mai, Chun-Wai,Padmavathy, Krishnaraj,Ramalingan, Chennan,Sivaramakarthikeyan, Ramar. "Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies". . p. 4049 - 4060. Retrieved 2020.
• 6、 Witzeman, J. Stewart,Nottingham, W. Dell. "Transacetoacetylation with tert-Butyl Acetoacetate: Synthetic Apllications". . p. 1713 - 1718. Retrieved 1991.
• 7、 Coffey,Thomson,Wilson. "-". . p. 856,858. Retrieved 1936.
• 8、 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". supporting information. p. 2895 - 2900. Retrieved 2021/04/14.
• 9、 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.