2-Phenylacetamide

Base Information

• Chemical Name: 2-Phenylacetamide
• CAS No.: 103-81-1
• Deprecated CAS: 4463-20-1
• Molecular Formula: C8H9NO
• Molecular Weight: 135.166
• Hs Code.: 29242990
• European Community (EC) Number: 203-147-0
• NSC Number: 1877
• UNII: 5R219M9TJF
• DSSTox Substance ID: DTXSID1059282
• Nikkaji Number: J55.331J
• Wikidata: Q27101974
• Metabolomics Workbench ID: 41115
• ChEMBL ID: CHEMBL347645
• Mol file: 103-81-1.mol

Synonyms:Acetamide,2-phenyl- (6CI,8CI);Benzenediacetamide (7CI);Benzeneacetamide;NSC 1877;Phenacetamide;Phenyl-b-acetylamine;Phenylacetic acid amide;a-Phenylacetamide;a-Toluamide;a-Toluimidic acid;

Chemical Property of 2-Phenylacetamide

Chemical Property:

• Appearance/Colour: White krystalline powder.
• Vapor Pressure: 0.000537mmHg at 25°C
• Melting Point: 156 °C
• Refractive Index: 1.552
• Boiling Point: 312.2 °C at 760 mmHg
• PKA: 16.21±0.40(Predicted)
• Flash Point: 142.6 °C
• PSA: 43.09000
• Density: 1.098 g/cm³
• LogP: 1.41470
• Storage Temp.: Refrigerator
• Solubility.: Soluble in methanol.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 135.068413911
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

2-Phenylacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36
• Safety Statements: 22-24/25-60-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)CC(=O)N
• Uses: 2-Phenylacetamide is used as a pharmaceutical intermediate in the production of penicillin G and phenobarbital, etc. It is also used in organic synthesis.

Technology Process of 2-Phenylacetamide

There total 184 articles about 2-Phenylacetamide 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: 10.0%

phenylacetonitrile (140-29-4) → Benzeneacetamide (103-81-1) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With dihydrogen peroxide; In sodium hydroxide; ethanol; at 50 ℃; for 6h; Product distribution; Radziszewski reaction; oxydative cleavage of nitriles to shorter acids;

DOI:10.1016/S0040-4039(00)81662-7

Reference yield: 0.23%

3,4-Dioxo-4-phenylacetylamino-2-(triphenyl-λ5-phosphanylidene)-butyric acid methyl ester (113450-10-5) → Benzeneacetamide (103-81-1) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With sodium hydroxide; for 2h; Heating;

Reference yield: 0.17%

3,4-Dioxo-4-phenylacetylamino-2-(triphenyl-λ5-phosphanylidene)-butyric acid methyl ester (113450-10-5) → Benzeneacetamide (103-81-1) + triphenylphosphine (603-35-0) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

at 240 ℃; under 0.1 Torr;

upstream raw materials:

diazomethane

benzoyl chloride

styrene

phenylacetic acid

Downstream raw materials:

phenyl-acetic acid xanthen-9-ylamide

N,N'-bis-phenylacetyl-furfurylidenediamine

5-benzyl-7-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline

N,N'-((4-nitrophenyl)methylene)bis(2-phenylacetamide)

Refernces

• 1、 Keshipour, Sajjad,Shaabani, Ahmad. "Selective aerobic hydrolysis of nitriles to amides using cobalt(II)/zinc". . p. 5071 - 5078. Retrieved 2015.
• 2、 Gulyás, Henrik,Rivilla, Ivan,Curreli, Simona,Freixa, Zoraida,Van Leeuwen, Piet W. N. M.. "Highly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides". . p. 3822 - 3828. Retrieved 2015.
• 3、 Paik, Seunguk,Lee, Jun Young. "Simple and efficient cleavage of the N-(1-phenylethyl) unit of carboxamides with methanesulfonic acid". . p. 1813 - 1815. Retrieved 2006.
• 4、 Verma, Praveen Kumar,Kumar, Neeraj,Sharma, Upendra,Bala, Manju,Kumar, Vishal,Singh, Bikram. "Transition metal-free sodium borohydride promoted controlled hydration of nitriles to amides". . p. 2867 - 2875. Retrieved 2013.
• 5、 Liu, Kwang-Ting,Shih, Mei-Hsiu,Huang, Hsiau-Wen,Hu, Chia-Juei. "Catalytic Hydration of Nitriles to Amides with Manganese Dioxide on Silica Gel". . p. 715 - 717. Retrieved 1988.
• 6、 Sun, Yajun,Jin, Weiwei,Liu, Chenjiang. "Trash to treasure: Eco-friendly and practical synthesis of amides by nitriles hydrolysis in WepPA". . . Retrieved 2019.
• 7、 Merchant, Kevin J.. "Potassium trimethylsilanolate mediated hydrolysis of nitriles to primary amides". . p. 3747 - 3749. Retrieved 2000.
• 8、 Ma, Xiaoyun,He, Ying,Lu, Ming. "Efficient Mo(VI)-catalyzed hydration of nitrile with acetaldoxime". . p. 474 - 480. Retrieved 2014.
• 9、 Li, Zhengkai,Wang, Lixia,Zhou, Xiangge. "An efficient and practical protocol for catalytic hydrolysis of nitriles by a copper(I) complex in water". . p. 584 - 588. Retrieved 2012.
• 10、 Khalafi-Nezhad, Ali,Parhami, Abolfath,Soltani Rad, Mohammad Navid,Zarea, Abdolkarim. "Efficient method for the direct preparation of amides from carboxylic acids using tosyl chloride under solvent-free conditions". . p. 6879 - 6882. Retrieved 2005.