Pivalamide

Base Information

• Chemical Name: Pivalamide
• CAS No.: 754-10-9
• Molecular Formula: C5H11NO
• Molecular Weight: 101.148
• Hs Code.: 29241990
• European Community (EC) Number: 212-043-4
• NSC Number: 17584
• UNII: FES86MR7ZI
• DSSTox Substance ID: DTXSID6061072
• Nikkaji Number: J100.747E
• Wikipedia: Pivalamide
• Wikidata: Q7199623
• ChEMBL ID: CHEMBL345235
• Mol file: 754-10-9.mol

Synonyms:Pivalamide;754-10-9;TRIMETHYLACETAMIDE;2,2,2-Trimethylacetamide;2,2-dimethylpropanamide;Propanamide, 2,2-dimethyl-;2,2-Dimethylpropionamide;2,2-Dimethyl-propionamide;pivalic acid amide;FES86MR7ZI;EINECS 212-043-4;MFCD00008011;NSC 17584;NSC-17584;Propanamide,2,2-dimethyl-;neopentanamide;Pivaloylamine;trimethylacetarnide;trimethyl acetamide;NSC17584;TAY;Trimethylacetamide, 98%;UNII-FES86MR7ZI;SCHEMBL2484;alpha,alpha-dimethylpropionamide;CHEMBL345235;DTXSID6061072;XIPFMBOWZXULIA-UHFFFAOYSA-;HMS1763O22;AC2528;BDBM50226158;AKOS000282747;CS-W021470;PB47992;DS-10181;SY037452;.ALPHA.,.ALPHA.-DIMETHYLPROPIONAMIDE;A9605;FT-0632896;P0819;EN300-49244;AC-907/25014088;Q-102043;Q7199623;Z56895677

Chemical Property of Pivalamide

Chemical Property:

• Appearance/Colour: white to very slightly yellow crystalline powder
• Vapor Pressure: 0.236mmHg at 25°C
• Melting Point: 154-157 °C
• Refractive Index: 1.427
• Boiling Point: 206.6 °C at 760 mmHg
• PKA: 16.60±0.50(Predicted)
• Flash Point: 78.7 °C
• PSA: 43.09000
• Density: 0.903 g/cm³
• LogP: 1.21810
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 101.084063974
• Heavy Atom Count: 7
• Complexity: 80.6

Purity/Quality:

98.0%min ^*data from raw suppliers

2,2,2-Trimethylacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)N

Technology Process of Pivalamide

There total 55 articles about Pivalamide 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: 99.0%

tert-butyl isocyanide (630-18-2) → 2,2-dimethylpropionamide (754-10-9)

Guidance literature:

With water; sodium carbonate; tricyclohexylphosphine; {Rh(OMe)(cod)}2; In isopropyl alcohol; at 25 ℃; for 24h;

DOI:10.1002/anie.200800366

Reference yield: 92.0%

pivaloyl chloride (3282-30-2) + 3,4-difluoroaniline (3863-11-4) → N-trimethylacetyl-3,4-difluoroanilide + 2,2-dimethylpropionamide (754-10-9)

Guidance literature:

With triethylamine; In dichloromethane;

Reference yield: 91.0%

pivalaldehyde (630-19-3) → 2,2-dimethylpropionamide (754-10-9)

Guidance literature:

pivalaldehyde; With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃; for 1h;

With dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 2.5h; Further stages.;

DOI:10.1021/jo026407z

upstream raw materials:

tert-butyl isocyanide

2,2-dimethyl-propanoic acid ethyl ester

2,3,4-trimethylacetophenone

pivaloyl chloride

Downstream raw materials:

3,3-dimethyl-butan-2-one

2,2-dimethyl-octan-3-one

tert-butyl isocyanide

2,2-dimethylpropiophenone

Refernces

• 1、 Li, Chengcheng,Chang, Xiao-Yong,Huo, Luqiong,Tan, Haibo,Xing, Xiangyou,Xu, Chen. "Hydration of Cyanohydrins by Highly Active Cationic Pt Catalysts: Mechanism and Scope". . p. 8716 - 8726. Retrieved 2021/07/26.
• 2、 Babón, Juan C.,Esteruelas, Miguel A.,López, Ana M.,O?ate, Enrique. "Hydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism". . p. 7284 - 7296. Retrieved 2021/05/29.