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Cas Database

55-21-0

55-21-0

Identification

  • Product Name:Benzamide

  • CAS Number: 55-21-0

  • EINECS:200-227-7

  • Molecular Weight:121.139

  • Molecular Formula: C7H7NO

  • HS Code:29242995

  • Mol File:55-21-0.mol

Synonyms:Benzenecarboxamide;Benzoic acid amide;Benzoylamine;NSC 3114;Phenylamide;Phenylcarboxamide;

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Safety information and MSDS

  • Pictogram(s):HarmfulXn

  • Hazard Codes: Xn:Harmful;

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Relevant articles and documentsAll total 825 Articles be found

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

supporting information, (2022/01/20)

C?H amination and amidation by catalytic nitrene transfer are well-established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C?H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd?N) with a diradical nitrogen ligand that is singly bonded to PdII. Despite the subvalent nitrene character, selective C?H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N3SiMe3. Based on these results, a photocatalytic protocol for aldehyde C?H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C?H nitrogen atom transfer offers facile access to primary amides after deprotection.

AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS

-

Paragraph 0008-0009; 0063-0064, (2022/03/04)

The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.

Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex

Yadav, Suman,Reshi, Noor U Din,Pal, Saikat,Bera, Jitendra K.

, p. 7018 - 7028 (2021/11/17)

Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished by its high activity and selectivity, wide substrate scope and modest reaction conditions. A variety of primary amines, RCH2NH2 (R = aliphatic, aromatic and heteroaromatic), are converted to the corresponding amides using ambient air as an oxidant in the presence of a sub-stoichiometric amount of KOtBu in tBuOH. A set of control experiments, Hammett relationships, kinetic studies and DFT calculations are undertaken to divulge mechanistic details of the amine oxidation using 1. The catalytic reaction involves abstraction of two amine protons and two benzylic hydrogen atoms of the metal-bound primary amine by the oxo and hydroxo ligands, respectively. A β-hydride transfer step for the benzylic C-H bond cleavage is not supported by Hammett studies. The nitrile generated by the catalytic oxidation undergoes hydration to afford the amide as the final product. This journal is

Ru(ii)- And Ru(iv)-dmso complexes catalyze efficient and selective aqueous-phase nitrile hydration reactions under mild conditions

Dubey, Santosh Kumar,Kaur, Gurmeet,Rath, Nigam P.,Trivedi, Manoj

, p. 17339 - 17346 (2021/10/08)

New water-soluble ruthenium(ii)- and ruthenium(iv)-dmso complexes [RuCl2(dmso)2(NH3)(CH3CN)] (1), [RuCl2(dmso)3(CH3CN)] (2), and [RuCl2(dmso)3(NH3)]·PF6·Cl (3) have been synthesized and characterized using elemental analyses, IR, 1H and 31P NMR, and electronic absorption spectroscopy. The molecular structures of complexes 1-3 were determined crystallographically. The reactivity of complexes 1-3 has been tested for aqueous-phase nitrile hydration at 60 °C in air, and good efficiency and selectivity are shown for the corresponding amide derivatives. Best performance is achieved with complex 3. Amide conversions of 56-99% were obtained with a variety of aromatic, alkyl, and vinyl nitriles. The reaction tolerated hydroxyl, nitro, bromo, formyl, pyridyl, benzyl, alkyl, and olefinic functional groups. Amides were isolated by simple decantation from the aqueous-phase catalyst. A catalyst loading down to 0.0001 mol% was examined and turnover numbers as high as 990?000 were observed. The catalyst was stable for weeks in solution and could be reused more than seven times without significant loss in catalytic activity. The gram-scale reaction was also performed to produce the desired product in high yields. This journal is

A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride

Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.

supporting information, p. 3565 - 3589 (2021/10/12)

The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.

Process route upstream and downstream products

Process route

benzimidic acid-(4-nitro-benzyl ester); hydrochloride

benzimidic acid-(4-nitro-benzyl ester); hydrochloride

4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

Conditions
Conditions Yield
at 60 ℃; Rate constant;
p-nitrobenzanilide
3393-96-2

p-nitrobenzanilide

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With methanol; ammonia; at 120 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
N-(2,2-Dichloro-1-hydroxy-3-oxo-3-phenyl-propyl)-benzamide
184970-73-8

N-(2,2-Dichloro-1-hydroxy-3-oxo-3-phenyl-propyl)-benzamide

2,2-dichloroacetophenone
2648-61-5

2,2-dichloroacetophenone

Conditions
Conditions Yield
With sodium hydroxide; In ethanol; for 12h; Ambient temperature;
60%
<i>N</i>-[(benzenesulfonyl-methyl-amino)-methyl]-benzamide

N-[(benzenesulfonyl-methyl-amino)-methyl]-benzamide

methyl(phenylsulfonyl)amide
5183-78-8

methyl(phenylsulfonyl)amide

Conditions
Conditions Yield
In water; at 38.84 - 57.84 ℃; Further Variations:; pH-values; Kinetics;
benzonitrile
100-47-0

benzonitrile

N-benzylidene benzylamine
780-25-6

N-benzylidene benzylamine

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
With ammonium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt; at 100 ℃; for 24h; under 20686.5 Torr; chemoselective reaction; Autoclave;
With ammonia; hydrogen; cobalt(II) diacetate tetrahydrate; zinc trifluoromethanesulfonate; zinc; In methanol; water; at 120 ℃; for 15h; under 30003 Torr; Reagent/catalyst; Sealed tube; Autoclave;
benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
With ammonium hydroxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt; at 100 ℃; for 24h; under 20686.5 Torr; Reagent/catalyst; chemoselective reaction; Autoclave;
benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

dibenzylamine
103-49-1

dibenzylamine

Conditions
Conditions Yield
With ammonium hydroxide; bis(benzonitrile)palladium(II) dichloride; trisodium tris(3-sulfophenyl)phosphine; hydrogen; at 100 ℃; for 24h; under 20686.5 Torr; Reagent/catalyst; chemoselective reaction; Autoclave;
benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With ammonium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; trisodium tris(3-sulfophenyl)phosphine; hydrogen; at 100 ℃; for 24h; under 20686.5 Torr; chemoselective reaction; Autoclave;
benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

dibenzylamine
103-49-1

dibenzylamine

Conditions
Conditions Yield
With ammonium hydroxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; at 100 ℃; for 24h; under 20686.5 Torr; chemoselective reaction; Autoclave;
benzaldehyde
100-52-7

benzaldehyde

benzylidenamine
16118-22-2

benzylidenamine

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

N-benzylidene benzylamine
780-25-6

N-benzylidene benzylamine

benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
With C40H62N2OP2Ru; ammonia; In (2)H8-toluene; at 25 - 135 ℃; Glovebox; Inert atmosphere;

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  • Chemwill Asia Co., Ltd.
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