
2-Phenylacetamide
- CasNo:103-81-1
- Molecular Formula:C<sub>8</sub>H<sub>9</sub>NO
- Purity:
- Molecular Weight:135.166
Product Details
Factory Sells Best Quality 2-Phenylacetamide 103-81-1 with USP
- Molecular Formula:C8H9NO
- Molecular Weight:135.166
- 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
2-Phenylacetamide(Cas 103-81-1) Usage
Preparation |
Synthesis of 2-phenylacetamide: Add concentrated hydrochloric acid to phenylacetonitrile, stir to dissolve, and react at 50°C for half an hour. Then slowly add water under cooling to separate out crystals, filter after cooling, wash with ice water to obtain crude product. The crude product was washed with sodium carbonate solution, then washed with ice water, and dried to obtain purer phenylacetamide. |
Synthesis Reference(s) |
Journal of the American Chemical Society, 75, p. 740, 1953 DOI: 10.1021/ja01099a504The Journal of Organic Chemistry, 43, p. 402, 1978 DOI: 10.1021/jo00397a005Organic Syntheses, Coll. Vol. 4, p. 760, 1963 |
Biological Activity |
2-Phenylacetamide, the main compound isolated from the seeds of Lepidium apetalum Willd (LA) with estrogenic activities, increases the expression of Estrogen receptorα (ERα), ERβ and GPR30 in the uterus and MCF-7 cells. |
Safety Profile |
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx. |
Purification Methods |
Crystallise the acetamide repeatedly from absolute EtOH, EtOAc (m 160-161o) or H2O (m 159-160o). Dry it in vacuo over P2O5. [Beilstein 9 H 347, 9 III 2193, 9 IV 1632.] |
Definition |
ChEBI: 2-phenylacetamide is a monocarboxylic acid amide that is acetamide substituted by a phenyl group at position 2. It has a role as a mouse metabolite. It derives from a phenylacetic acid. |
InChI:InChI=1/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
103-81-1 Relevant articles
-
Dauben et al.
, p. 121,123 (1950)
-
Selective aerobic hydrolysis of nitriles to amides using cobalt(II)/zinc
Keshipour, Sajjad,Shaabani, Ahmad
, p. 5071 - 5078 (2015)
A novel protocol has been developed for ...
-
Bennett,Yoshida
, p. 3030 (1973)
-
Highly active, chemo- and enantioselective Pt-SPO catalytic systems for the synthesis of aromatic carboxamides
Gulyás, Henrik,Rivilla, Ivan,Curreli, Simona,Freixa, Zoraida,Van Leeuwen, Piet W. N. M.
, p. 3822 - 3828 (2015)
Platinum complexes modified with a chira...
Light-induced hydrolysis of nitriles by photoproduced α-MnO 2 nanorods on polystyrene beads
Jana, Subhra,Praharaj, Snigdhamayee,Panigrahi, Sudipa,Basu, Soumen,Pande, Surojit,Chang, Chien-Hsiang,Pal, Tarasankar
, p. 2191 - 2193 (2007)
A green chemistry approach has been furn...
Simple and efficient cleavage of the N-(1-phenylethyl) unit of carboxamides with methanesulfonic acid
Paik, Seunguk,Lee, Jun Young
, p. 1813 - 1815 (2006)
Cleavage of the N-(1-phenylethyl) unit o...
Choline chloride based eutectic solvent: An efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles
Patil, Umakant B.,Singh, Abhilash S.,Nagarkar, Jayashree M.
, p. 1102 - 1106 (2014)
Choline chloride: a 2ZnCl2 based deep eu...
Transition metal-free sodium borohydride promoted controlled hydration of nitriles to amides
Verma, Praveen Kumar,Kumar, Neeraj,Sharma, Upendra,Bala, Manju,Kumar, Vishal,Singh, Bikram
, p. 2867 - 2875 (2013)
A transition metal-free process, promote...
Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions
Dighe, Shashikant U.,Batra, Sanjay
, p. 500 - 505 (2016)
The visible light-induced iodine-catalyz...
Catalytic Hydration of Nitriles to Amides with Manganese Dioxide on Silica Gel
Liu, Kwang-Ting,Shih, Mei-Hsiu,Huang, Hsiau-Wen,Hu, Chia-Juei
, p. 715 - 717 (1988)
Hydration of representative nitriles wit...
Isolation of deoxybilianic acid, phenylacetic acid and ferulic acid from normal human urine
Dirscherl,Pelzer
, p. 1151 - 1153 (1970)
-
Trash to treasure: Eco-friendly and practical synthesis of amides by nitriles hydrolysis in WepPA
Sun, Yajun,Jin, Weiwei,Liu, Chenjiang
, (2019)
The hydration of nitriles to amides in a...
Selective hydration of nitriles to amides promoted by an Os-NHC catalyst: Formation and X-ray characterization of κ2-amidate intermediates
Buil, Maria L.,Cadierno, Victorio,Esteruelas, Miguel A.,Gimeno, Jose,Herrero, Juana,Izquierdo, Susana,Onate, Enrique
, p. 6861 - 6867 (2012)
The complex [Os(η6-p-cymene)(OH)IPr]OTf ...
Potassium trimethylsilanolate mediated hydrolysis of nitriles to primary amides
Merchant, Kevin J.
, p. 3747 - 3749 (2000)
Treatment of nitriles with potassium tri...
-
Dauben et al.
, p. 2117 (1946)
-
Efficient Mo(VI)-catalyzed hydration of nitrile with acetaldoxime
Ma, Xiaoyun,He, Ying,Lu, Ming
, p. 474 - 480 (2014)
A method for the selective hydration of ...
Sodium azide as a catalyst for the hydration of nitriles to primary amides in water
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Roostaei, Mohsen
, p. 267 - 269 (2015)
The selective conversion of aromatic nit...
An efficient and practical protocol for catalytic hydrolysis of nitriles by a copper(I) complex in water
Li, Zhengkai,Wang, Lixia,Zhou, Xiangge
, p. 584 - 588 (2012)
The cuprous complex - Cu4I4(H2O) 4 - has...
Silica-supported 2,4,6-trichloro-1,3,5-triazine as an efficient reagent for direct conversion of carboxylic acids to amides under solvent-free conditions
Khalafi-Nezhad, Ali,Zare, Abdolkarim,Parhami, Abolfath,Rad, Mohammad Navid Soltani,Nejabat, Gholam Reza
, p. 657 - 666 (2007)
A very simple and efficient solvent-free...
Efficient method for the direct preparation of amides from carboxylic acids using tosyl chloride under solvent-free conditions
Khalafi-Nezhad, Ali,Parhami, Abolfath,Soltani Rad, Mohammad Navid,Zarea, Abdolkarim
, p. 6879 - 6882 (2005)
A simple, clean and highly efficient sol...
The hydration of nitriles catalyzed by water-soluble rhodium complexes
Djoman, Marie Charlotte Koffi-Bié,Ajjou, Abdelaziz Nait
, p. 4845 - 4849 (2000)
The water-soluble rhodium complex genera...
Efficient Hydration of Nitriles Promoted by Gallic Acid Derived from Renewable Bioresources
Deng, Tao,Wang, Cheng-Zhang
, p. 1349 - 1353 (2017)
An efficient gallic acid promoted nitril...
2-Diphenylphosphanyl-4-pyridyl(dimethyl)amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions
Muranaka, Makoto,Hyodo, Isao,Okumura, Wataru,Oshiki, Toshiyuki
, p. 552 - 555 (2011)
New homogeneous catalyst comprised of [R...
A heterogeneous catalytic method for the conversion of nitriles into amides using molecular sieves modified with copper(II)
Kiss, árpád,Hell, Zoltán
, p. 6021 - 6023 (2011)
A heterogenous catalytic method is devel...
-
Pattison,Carmack
, p. 2033 (1946)
-
Direct preparation of primary amides from carboxylic acids and urea using imidazole under microwave irradiation
Khalafi-Nezhad, Ali,Mokhtari, Babak,Rad, Mohammad Navid Soltani
, p. 7325 - 7328 (2003)
A very simple and efficient solvent-free...
A facile one-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica: Aqueous hydration of nitriles to amides
Baig, R. B. Nasir,Varma, Rajender S.
, p. 6220 - 6222 (2012)
One-pot synthesis of ruthenium hydroxide...
Biotransformation of isofraxetin-6-O-β-D-glucopyranoside by Angelica sinensis (Oliv.) Diels callus
Zhou, Di,Zhang, Yuhua,Jiang, Zhe,Hou, Yue,Jiao, Kun,Yan, Chunyan,Li, Ning
, p. 248 - 253 (2017)
Isofraxetin-6-O-β-D-glucopyranoside, ide...
Cu-catalyzed aerobic oxidative C-CN bond cleavage of benzyl cyanide for the synthesis of primary amides
Chen, Xiuling,Peng, Yanhong,Li, Yan,Wu, Minghu,Guo, Haibing,Wang, Jian,Sun, Shaofa
, p. 18588 - 18591 (2017)
An efficient method via copper-catalyzed...
Electronic Substituent Effects in the Nitrilase-Catalyzed Hydrolysis of Para-Substituted Benzyl Cyanides
Geresh, Shimona,Giron, Yakir,Gilboa, Ygal,Glaser, Robert
, p. 10099 - 10102 (1993)
The initial rates of the nitrilase (Novo...
Chemoselective hydration of nitriles to amides using hydrated ionic liquid (IL) tetrabutylammonium hydroxide (TBAH) as a green catalyst
Veisi, Hojat,Maleki, Behrooz,Hamelian, Mona,Ashrafi, Samaneh Sedigh
, p. 6365 - 6371 (2015)
A transition metal-free process, catalyz...
HYDROLYSIS IN THE ABSENCE OF BULK WATER 1. CHEMOSELECTIVE HYDROLYSIS OF AMIDES USING TETRAHALOPHTALIC ANHYDRIDES
Eaton, Jefferson T.,Rounds, William D.,Urbanowicz, John H.,Gribble, Gordon W.
, p. 6553 - 6556 (1988)
The reaction of primary and secondary am...
Efficient and practical transition metal-free catalytic hydration of organonitriles to amides
Tu, Tao,Wang, Zhixun,Liu, Zelong,Feng, Xike,Wang, Qingyi
, p. 921 - 924 (2012)
K2CO3 can act as an efficient catalyst f...
Ruthenium on chitosan: A recyclable heterogeneous catalyst for aqueous hydration of nitriles to amides
Baig, R. B. Nasir,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
, p. 2122 - 2127 (2014)
Ruthenium has been immobilized over chit...
Amides by microwave-assisted dehydration of ammonium salts of carboxylic acids
Peng, Yanqing,Song, Gonghua
, p. 95 - 97 (2002)
-
Solid phase synthesis of aryl amines
Willoughby, Christopher A.,Chapman, Kevin T.
, p. 7181 - 7184 (1996)
A method for the solid phase synthesis o...
Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides
Kamble, Rohit B.,Mane, Kishor D.,Rupanawar, Bapurao D.,Korekar, Pranjal,Sudalai,Suryavanshi, Gurunath
, p. 724 - 728 (2019)
A new heterogeneous catalytic system (Ti...
Facile desulfurization of thioamides and thioureas with tetrabutylammonium periodate under mild conditions
Pourali, Ali Reza
, p. 733 - 737 (2005)
Thioamides and thioureas were reacted wi...
Transition metal-free 1,3-dimethylimidazolium hydrogen carbonate catalyzed hydration of organonitriles to amides
Verma, Praveen Kumar,Sharma, Upendra,Bala, Manju,Kumar, Neeraj,Singh, Bikram
, p. 895 - 899 (2013)
An efficient hydration of organonitriles...
-
Gerry,Brown
, p. 740 (1953)
-
A facile hydration of nitriles by dimethyldioxirane
Bose, D. Subhas,Baquer, Syed M.
, p. 3119 - 3123 (1997)
A new and practical method for the conve...
-
Drevina et al.
, (1968)
-
Selective hydrolysis of nitriles to amides using NaOH-PEG under microwave irradiation
Bendale, Pravin M.,Khadilkar, Bhushan M.
, p. 1713 - 1718 (2000)
We describe here an efficient, rapid and...
A continuous-flow synthesis of primary amides from hydrolysis of nitriles using hydrogen peroxide as oxidant
Zhan, Wei,Ji, Ling,Ge, Ze-mei,Wang, Xin,Li, Run-tao
, p. 1527 - 1532 (2018)
A continuous-flow synthesis of primary a...
Direct catalytic formation of primary and tertiary amides from non-activated carboxylic acids, employing carbamates as amine source
Tinnis, Fredrik,Lundberg, Helena,Adolfsson, Hans
, p. 2531 - 2536 (2012)
The operationally simple titanium(IV)- o...
Selective Cleavage of Inert Aryl C-N Bonds in N-Aryl Amides
Zhang, Zhiguo,Zheng, Dan,Wan, Yameng,Zhang, Guisheng,Bi, Jingjing,Liu, Qingfeng,Liu, Tongxin,Shi, Lei
, p. 1369 - 1376 (2018)
A highly selective, IBX-promoted reactio...
Synthesis of and catalytic nitrile hydration by a cationic tris(μ-hydroxo)diruthenium(II) complex having PMe3ligands
Kiyota, Sayori,Kobori, Takako,Soeta, Hirofumi,Ichikawa, You-ichi,Komine, Nobuyuki,Komiya, Sanshiro,Hirano, Masafumi
, p. 3 - 10 (2016)
While phenyl vinyl ether does not react ...
Direct and facile synthesis of primary amides from carboxylic acids via acyl isocyanate intermediates using mukaiyama reagent
Azadi, Roya,Motamedpoor, Zahra
, p. 801 - 804 (2018)
A very simple and efficient procedure fo...
Hydration of nitriles to amides by a chitin-supported ruthenium catalyst
Matsuoka, Aki,Isogawa, Takahiro,Morioka, Yuna,Knappett, Benjamin R.,Wheatley, Andrew E. H.,Saito, Susumu,Naka, Hiroshi
, p. 12152 - 12160 (2015)
Chitin-supported ruthenium (Ru/chitin) p...
Efficient Bimetallic Catalysis of Nitrile Hydration to Amides with a Simple Pd(OAc)2/Lewis Acid Catalyst at Ambient Temperature
Zhang, Sicheng,Xu, Haosheng,Lou, Chenlin,Senan, Ahmed M.,Chen, Zhuqi,Yin, Guochuan
, p. 1870 - 1875 (2017)
Transition-metal-catalyzed nitrile hydra...
Nitrogen Atom Transfer Catalysis by Metallonitrene C?H Insertion: Photocatalytic Amidation of Aldehydes
Schmidt-R?ntsch, Till,Verplancke, Hendrik,Lienert, Jonas N.,Demeshko, Serhiy,Otte, Matthias,Van Trieste, Gerard P.,Reid, Kaleb A.,Reibenspies, Joseph H.,Powers, David C.,Holthausen, Max C.,Schneider, Sven
, (2022/01/20)
C?H amination and amidation by catalytic...
Method for preparing primary and secondary amide compounds
-
Paragraph 0090-0100, (2021/02/06)
The invention belongs to the field of or...
Mechanochemical Synthesis of Primary Amides
Gómez-Carpintero, Jorge,Sánchez, J. Domingo,González, J. Francisco,Menéndez, J. Carlos
, p. 14232 - 14237 (2021/10/20)
Ball milling of aromatic, heteroaromatic...
Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation
Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan
, p. 10239 - 10245 (2021/08/24)
A simple and efficient system for the hy...
103-81-1 Process route
-
-
1,3-diphenyl-acetone-(O-benzenesulfonyl oxime )

-
-
7664-41-7
ammonia

-
-
1788-31-4
1,3-diphenylpropan-2-one oxime

-
-
103-81-1
Benzeneacetamide

-
-
5504-24-5
2-phenylacetamidine
Conditions | Yield |
---|---|
Produkt 5: N-Benzyl-phenacetamidin; Produkt 6:Benzylcyanid;
|
-
-
949146-91-2
(2R)-2-(benzylamino)-2-phenylacetamide

-
-
103-81-1
Benzeneacetamide

-
-
100-46-9
benzylamine
Conditions | Yield |
---|---|
With
hydrogen;
palladium on activated charcoal;
In
diethyl ether;
Product distribution;
|
103-81-1 Upstream products
-
diazomethane
-
benzoyl chloride
-
styrene
-
phenylacetic acid
103-81-1 Downstream products
-
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)