103-81-1 | 2-Phenylacetamide

Packsize	Purity	Availability	Price	Discounted Price
1g	99%	in stock	$15.00	$10.00
5g	99%	in stock	$16.00	$11.00
25g	99%	in stock	$22.00	$15.00
100g	99%	in stock	$60.00	$42.00
500g	99%	in stock	$228.00	$159.00

Description

• Catalog Number: AB42724
• Chemical Name: 2-Phenylacetamide
• CAS Number: 103-81-1
• Molecular Formula: C8H9NO
• Molecular Weight: 135.1632
• MDL Number: MFCD18449377
• SMILES: NC(=O)Cc1ccccc1
• NSC Number: 1877

Computed Properties

• Complexity: 116
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 0.5

Upstream Synthesis Route

2-Phenylacetamide, also known as benzamide, plays a crucial role in chemical synthesis as a versatile building block. With its aromatic ring and amide functional group, this compound is widely utilized as a key intermediate in the production of various pharmaceuticals, agrochemicals, and fine chemicals. In organic synthesis, 2-Phenylacetamide serves as a precursor for synthesizing a variety of compounds due to its reactivity and structural properties. It can undergo various functional group transformations, such as acylation, alkylation, and reduction, allowing for the preparation of complex molecules with specific biological or chemical activities.Furthermore, 2-Phenylacetamide can be used in the synthesis of heterocyclic compounds, which are often found in drugs and natural products. Its ability to participate in diverse chemical reactions makes it a valuable starting material for creating new molecules with desired properties.Overall, 2-Phenylacetamide is a critical component in organic chemistry, enabling chemists to access a wide range of structurally diverse and biologically active compounds through strategic synthetic routes.

Literature

• Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes.

  PloS one 20120101

• Comparative pharmacology of cholecystokinin induced activation of cultured vagal afferent neurons from rats and mice.

  PloS one 20120101

• N,N'-Dibenzyl-N,N'-dimethyl-N''-(2-phenyl-acet-yl)phospho-ric triamide.

  Acta crystallographica. Section E, Structure reports online 20111201

• Spilanthes acmella ethanolic flower extract: LC-MS alkylamide profiling and its effects on sexual behavior in male rats.

  Phytomedicine : international journal of phytotherapy and phytopharmacology 20111015

• NRPS substrate promiscuity diversifies the xenematides.

  Organic letters 20111007

• Optimisation of the anti-Trypanosoma brucei activity of the opioid agonist U50488.

  ChemMedChem 20111004

• Phenylalanine induces Burkholderia cenocepacia phenylacetic acid catabolism through degradation to phenylacetyl-CoA in synthetic cystic fibrosis sputum medium.

  Microbial pathogenesis 20110901

• Gram-positive marine bacteria as a potential resource for the discovery of quorum sensing inhibitors.

  Marine biotechnology (New York, N.Y.) 20110801

• Structure-based design, synthesis, and antifungal activity of new triazole derivatives.

  Chemical biology & drug design 20110801

• Extracellular loop 2 of the free fatty acid receptor 2 mediates allosterism of a phenylacetamide ago-allosteric modulator.

  Molecular pharmacology 20110701

• Isolation and characterization of atropisomers of seven-membered-ring benzolactams.

  The Journal of organic chemistry 20110617

• Valine and phenylalanine as precursors in the biosynthesis of alkamides in Acmella radicans.

  Natural product communications 20110601

• Efficacy of Advanced Odomos repellent cream (N, N-diethyl-benzamide) against mosquito vectors.

  The Indian journal of medical research 20110401

• Chemical composition and antioxidant properties of extracts of fresh fruiting bodies of Pleurotus sajor-caju (Fr.) Singer.

  Journal of agricultural and food chemistry 20110323

• Synthesis of new 1,3-oxazolyl-7-chloroquinazolin-4(3H)ones and evaluation of their antimicrobial activities.

  Acta poloniae pharmaceutica 20110101

• SCFAs induce mouse neutrophil chemotaxis through the GPR43 receptor.

  PloS one 20110101

• LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol.

  Journal of pharmaceutical and biomedical analysis 20101102

• 2,3-Disubstituted acrylamides as potent glucokinase activators.

  Bioorganic & medicinal chemistry letters 20101001

• Structural characterization of the Hepatitis C Virus NS3 protease from genotype 3a: the basis of the genotype 1b vs. 3a inhibitor potency shift.

  Virology 20100930

• Antitrypanosomal and antileishmanial activities of novel N-alkyl-(1-phenylsubstituted-beta-carboline)-3-carboxamides.

  Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20100701

• Discovery of a novel selective PPARgamma modulator from (-)-Cercosporamide derivatives.

  Bioorganic & medicinal chemistry letters 20100401

• Heterologous expression of leader-less pga gene in Pichia pastoris: intracellular production of prokaryotic enzyme.

  BMC biotechnology 20100101

• 2-(4-Bromo-phen-yl)-N-(2-methoxy-phen-yl)acetamide.

  Acta crystallographica. Section E, Structure reports online 20100101

• Carbonic anhydrase inhibitors. Aromatic/heterocyclic sulfonamides incorporating phenacetyl, pyridylacetyl and thienylacetyl tails act as potent inhibitors of human mitochondrial isoforms VA and VB.

  Bioorganic & medicinal chemistry 20090715

• Carbonic anhydrase inhibitors. Phenacetyl-, pyridylacetyl- and thienylacetyl-substituted aromatic sulfonamides act as potent and selective isoform VII inhibitors.

  Bioorganic & medicinal chemistry letters 20090615

• N-(3,4-Diethoxy-phen-yl)acetamide.

  Acta crystallographica. Section E, Structure reports online 20090601

• Utility of MetaSite in improving metabolic stability of the neutral indomethacin amide derivative and selective cyclooxygenase-2 inhibitor 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-phenethyl-acetamide.

  Drug metabolism and disposition: the biological fate of chemicals 20090501

• Phenylethylamide and phenylmethylamide derivatives as new tyrosinase inhibitors.

  Biological & pharmaceutical bulletin 20090201

• Regulation of phenylacetic acid degradation genes of Burkholderia cenocepacia K56-2.

  BMC microbiology 20090101

• Novel inhibitors of the v-raf murine sarcoma viral oncogene homologue B1 (BRAF) based on a 2,6-disubstituted pyrazine scaffold.

  Journal of medicinal chemistry 20080612

• Linear and cyclic peptides from the entomopathogenic bacterium Xenorhabdus nematophilus.

  Journal of natural products 20080601

• QSAR and pharmacophore analysis on amides against drug-resistant S. aureus.

  SAR and QSAR in environmental research 20080101

• The influence of leukotriene receptors' antagonists on experimentally induced ulcer in rats.

  Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi 20080101

• 2,2-Dichloro-N-(2,3-dimethyl-phen-yl)acetamide.

  Acta crystallographica. Section E, Structure reports online 20080101

• Production of enantiomerically pure (S)-beta-phenylalanine and (R)-beta-phenylalanine by penicillin G acylase from Escherichia coli in aqueous medium.

  Biotechnology letters 20071201

• Diastereospecific photocyclization of a isopropylbenzophenone derivative in crystals and the morphological changes.

  The Journal of organic chemistry 20070831

• Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents.

  Bioorganic & medicinal chemistry 20070301

• Fluorogenic substrates for lipases, esterases, and acylases using a TIM-mechanism for signal release.

  Biotechnology journal 20070201

• Synthesis and receptor binding studies of 3-substituted piperazine derivatives.

  European journal of medicinal chemistry 20060301

• [Studies on chemical constituents of the brown alga Dictyopteris divaricata].

  Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060101

• Inhibition of cyclooxygenase with indomethacin phenethylamide reduces atherosclerosis in apoE-null mice.

  Biochemical pharmacology 20050801

• SAR and pharmacokinetic studies on phenethylamide inhibitors of the hepatitis C virus NS3/NS4A serine protease.

  Bioorganic & medicinal chemistry letters 20040906

• Thyroid receptor ligands. Part 2: Thyromimetics with improved selectivity for the thyroid hormone receptor beta.

  Bioorganic & medicinal chemistry letters 20040705

• Mandelamide hydrolase from Pseudomonas putida: characterization of a new member of the amidase signature family.

  Biochemistry 20040622

• Studies on anti-Helicobacter pylori agents. Part 3: A novel, efficacious cephem derivative, FR193879.

  Bioorganic & medicinal chemistry letters 20040517

• Design, synthesis, and biological evaluation of new 8-heterocyclic xanthine derivatives as highly potent and selective human A2B adenosine receptor antagonists.

  Journal of medicinal chemistry 20040311

• Studies on the metabolism of the novel, selective cyclooxygenase-2 inhibitor indomethacin phenethylamide in rat, mouse, and human liver microsomes: identification of active metabolites.

  Drug metabolism and disposition: the biological fate of chemicals 20040101

• Metabolism of 2-phenylethylamine to phenylacetic acid, via the intermediate phenylacetaldehyde, by freshly prepared and cryopreserved guinea pig liver slices.

  In vivo (Athens, Greece) 20040101

• Bhimamycin A to approximately E and bhimanone: isolation, structure elucidation and biological activity of novel quinone antibiotics from a terrestrial Streptomycete.

  The Journal of antibiotics 20031101

• Novel, potent phenethylamide inhibitors of the hepatitis C virus (HCV) NS3 protease: probing the role of P2 aryloxyprolines with hybrid structures.

  Bioorganic & medicinal chemistry letters 20030818

• Design of selective peptidomimetic agonists for the human orphan receptor BRS-3.

  Journal of medicinal chemistry 20030508

• The scent of age.

  Proceedings. Biological sciences 20030507

• Phenethyl amides as novel noncovalent inhibitors of hepatitis C virus NS3/4A protease: discovery, initial SAR, and molecular modeling.

  Journal of medicinal chemistry 20030130

• Role of alphaArg145 and betaArg263 in the active site of penicillin acylase of Escherichia coli.

  The Biochemical journal 20020701

• Synthesis and antimicrobial activity of some novel 2-(p-substituted-phenyl)-5-substituted-carbonylaminobenzoxazoles.

  Farmaco (Societa chimica italiana : 1989) 20020301

• Synthesis and structure-activity relationships of N-(1-benzylpiperidin-4-yl)arylacetamide analogues as potent sigma1 receptor ligands.

  Journal of medicinal chemistry 20011206

• A chemostat culture as a tool for the improvement of a recombinant E. coli strain over-producing penicillin G acylase.

  Biotechnology and bioengineering 20011005

• An enzyme-labile safety catch linker for synthesis on a soluble polymeric support.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20010302

• Substitutions of Thr-103-Ile and Trp-138-Gly in amidase from Pseudomonas aeruginosa are responsible for altered kinetic properties and enzyme instability.

  Molecular biotechnology 20010301

• Potent and use-dependent block of cardiac sodium channels by U-50,488H, a benzeneacetamide kappa opioid receptor agonist.

  Experimental and clinical cardiology 20010101

• Isolation and characterization of a bacterium possessing a novel aldoxime-dehydration activity and nitrile-degrading enzymes.

  Archives of microbiology 19980801