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108227 Aldrich

Benzanilide

98%

Synonym: N-Benzoylaniline, N-Phenylbenzamide

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Properties

Related Categories Amides, Building Blocks, C8 to C20+, Carbonyl Compounds, Chemical Synthesis,
assay   98%
bp   117 °C/10 mmHg(lit.)
mp   161-163 °C(lit.)
solubility   H2O: insoluble
  diethyl ether: slightly soluble
Gene Information   human ... EPHX2(2053)
mouse ... Ephx2(13850)

Description

Packaging

100 g in poly bottle

5 g in glass bottle

Application

Benzanilide was used to study the influence of β-cyclodextrin on photorearrangement of acetanilide, benzanilide and ethyl phenyl carbonate1. It was used as amide model compound to study the reaction between the amide and epoxy2.

General description

Benzanilide undergoes diarylation with aryl triflates or bromides in the presence of a palladium-based catalyst system to form corresponding N-(2,6-diarylbenzoyl)anilines3. It is used in manufacture of dyes and perfumes.

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Protocols & Articles

Peer-Reviewed Papers

References

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1. Photochemical rearrangement of acetanilide, benzanilide, and ethyl phenyl carbonate in the presence of ß-cyclodextrin. Chenevert R and Plante R. Can. J. Chem. 61(6), 1092-1095, (1983)

2. Variable frequency microwave curing of amide-epoxy based polymers. Tanaka K, et al. IEEE Trans. Compon. Packag. Tech. 30(3), 472-477, (2007)

3. Regioselective arylation of benzanilides with aryl triflates or bromides under palladium catalysis. Kametani Y, et al. Tetrahedron Lett. 41(15), 2655-2658, (2000)

New microtubule polymerization inhibitors comprising a nitrooxymethylphenyl group. Yasuyuki Kawaratani et al Bioorg. Med. Chem. 19, 3995-4003, (2011)

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Biological activity of 2-hydroxythiobenzanilides and related compounds. Kubicová L, Sustr M, Pravda M, et al. Cent. Eur. J. Public Health 12 Suppl, S57-9, (2004)

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Lipophilicity parameter from high-performance liquid chromatography on an immobilized artificial membrane column and its relationships to bioactivity of the group of 2,4-dihydroxythiobenzanilides. Jóźwiak K, Szumiło H, and Senczyna B Acta Pol. Pharm. 59(5), 341-6, (2002)

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Correlation of fungostatic activity with log P and sigma parameters in the group of thiobenzanilides. Jóźwiak K and Szumiło H Acta Pol. Pharm. 57 Suppl, 82-4, (2000)

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Synthesis of 2-arylbenzoxazoles by copper-catalyzed intramolecular oxidative C-O coupling of benzanilides. Ueda S and Nagasawa H Angew. Chem. Int. Ed. Engl. 47(34), 6411-3, (2008)

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Design and preparation of sterol mimetics as potential antiparasitics. Gigante F, Kaiser M, Brun R, et al. Bioorg. Med. Chem. 18(20), 7291-301, (2010)

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A sensitive LC-MS/MS method for the quantitative analysis of the Echinacea purpurea constituent undeca-2-ene-8,10-diynoic acid isobutylamide in human plasma. Goey AK, Sparidans RW, Meijerman I, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 879(1), 41-8, (2011)

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Synthesis and biological evaluation of thiobenzanilides as anticancer agents. Hu WP, Yu HS, Chen YR, et al. Bioorg. Med. Chem. 16(9), 5295-302, (2008)

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Synthesis and biological activity of novel substituted benzanilides as potassium channel activators. V. Biagi G, Giorgi I, Livi O, et al. Eur. J. Med. Chem. 39(6), 491-8, (2004)

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Benzanilides with spasmolytic activity: chemistry, pharmacology, and SAR. Gerda Brunhofer et al Bioorg. Med. Chem. 16, 5974-81, (2008)

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Inhibitors of type III secretion in Yersinia: design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides. Kauppi AM, Andersson CD, Norberg HA, et al. Bioorg. Med. Chem. 15(22), 6994-7011, (2007)

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Structural modifications of benzanilide derivatives, effective potassium channel openers. X. Calderone V, Coi A, Fiamingo FL, et al. Eur. J. Med. Chem. 41(12), 1421-9, (2006)

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A journey from benzanilides to dithiobenzanilides: Synthesis of selective spasmolytic compounds. Brunhofer G, Granig WH, Studenik CR, et al. Bioorg. Med. Chem. 19(2), 994-1001, (2011)

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Synthesis, spasmolytic activity and structure-activity relationship study of a series of polypharmacological thiobenzanilides. Brunhofer G, Studenik C, Ecker GF, et al. Eur. J. Pharm. Sci. 42(1-2), 37-44, (2011)

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Fragment-based discovery of selective inhibitors of the Mycobacterium tuberculosis protein tyrosine phosphatase PtpA. Rawls KA, Lang PT, Takeuchi J, et al. Bioorg. Med. Chem. Lett. 19(24), 6851-4, (2009)

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Unusual spectral shifts on fast violet-B and benzanilide: Effect of solvents, pH and beta-cyclodextin. Antony Muthu Prabhu A, Sankaranarayanan RK, Siva S, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 74(2), 484-97, (2009)

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On the relationship between the substitution pattern of thiobenzanilides and their antimycobacterial activity. Kunes J, Balsánek V, Pour M, et al. Il Farmaco 57(9), 777-82, (2002)

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Dual fluorescence of diphenyl carbazide and benzanilide: effect of solvents and pH on electronic spectra. Sivakumar K, Stalin T, and Rajendiran N Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 62(4-5), 991-9, (2005)

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New amido derivatives as potential BKCa potassium channel activators. XI. Calderone V, Fiamingo FL, Amato G, et al. Eur. J. Med. Chem. 43(4), 792-9, (2008)

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Joint QSAR analysis using the Free-Wilson approach and quantum chemical parameters. Wei DB, Zhang AQ, Han SK, et al. SAR QSAR Environ. Res. 12(5), 471-9, (2001)

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Determination of a benzamide histone deacetylase inhibitor, MS-275, in human plasma by liquid chromatography with mass-spectrometric detection. Danish M, Gardner ER, Chen X, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 877(3), 355-9, (2009)

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The discovery of benzanilides as c-Met receptor tyrosine kinase inhibitors by a directed screening approach Allen, J. V.; et al. Bioorg. Med. Chem. Lett. 21, 5224-5229, (2011)

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Enantioseparation of benzazoles and benzanilides on polysaccharide-based chiral columns. Kubota T, Sawada N, Zhou L, et al. Chirality 22(4), 382-8, (2010)

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N-Methylbenzanilide derivatives as a novel class of selective V(1A) receptor antagonists. Kakefuda A, Tsukada J, Kusayama T, et al. Bioorg. Med. Chem. Lett. 12(2), 229-32, (2002)

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Thermodynamic interactions of a cis and trans benzanilide with Escherichia coli bacterial membranes. Dennison SR, Snape TJ, and Phoenix DA Eur. Biophys. J. 41(8), 687-93, (2012)

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Absorption of dodeca-2E,4E,8Z,10E/Z-tetraenoic acid isobutylamides after oral application of Echinacea purpurea tincture. Dietz B, Heilmann J, and Bauer R Planta Med. 67(9), 863-4, (2001)

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Merck 14,1061

Beil. 12,IV,417

FT-IR 2 (2), 3008:C / FT-IR 1 (2), 375:C / FT-NMR 1 (2), 1402:B / IR-Spectra (3), 1081:H / IR-Spectra (2), 944:C / NMR-Reference 2 (2), 344:D / RegBook 1 (2), 2023:M / Structure Index 1, 323:B:2

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