14439-71-5

Basic information

• Product Name: N-(2-Benzoylphenyl)-2-bromoacetamide
• Synonyms: 2-[(2-BROMOACETYL)AMINO]BENZOPHENONE;N1-(2-BENZOYLPHENYL)-2-BROMOACETAMIDE;N-(2-benzoylphenyl)-2-bromoacetamide;2-(2-Bromoacetamido)-benzophenone;2-[(Bromoacetyl)amino]benzophenone;N-(2-Benzoylphenyl)-2-bromoacetamide, 2-Bromo-N-[2-(phenylcarbonyl)phenyl]acetamide
• CAS NO: 14439-71-5
• Molecular Formula: C₁₅H₁₂BrNO₂
• Molecular Weight: 318.17
• EINECS: 238-415-6
• Product Categories: pharmacetical
• Mol File: 14439-71-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 94-95 °C
• Boiling Point: 514.458 °C at 760 mmHg
• Flash Point: 264.935 °C
• Appearance: COA
• Density: 1.488 g/cm³
• Vapor Pressure: 1.08E-10mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 11.94±0.70(Predicted)
• CAS DataBase Reference: N-(2-Benzoylphenyl)-2-bromoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Benzoylphenyl)-2-bromoacetamide(14439-71-5)
• EPA Substance Registry System: N-(2-Benzoylphenyl)-2-bromoacetamide(14439-71-5)

Safety Data

• Hazardous Substances Data: 14439-71-5(Hazardous Substances Data)

Usage

Chemical Properties

Pink Crystals

InChI:InChI=1/C15H12BrNO2/c16-10-14(18)17-13-9-5-4-8-12(13)15(19)11-6-2-1-3-7-11/h1-9H,10H2,(H,17,18)

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Downstream Products

• 615576-88-0 N-(2-benzoylphenyl)-2-(piperidin-1-yl)acetamide 
• 881982-66-7 N-(2-benzoyl-phenyl)-2-dimethylamino-acetamide 
• 935661-46-4 N-(2-benzoyl-phenyl)-2-[[(2-benzoyl-phenylcarbamoyl)-methyl]-(1-phenyl-ethyl)-amino]-acetamide 
• 869940-99-8 N-(2-benzoyl-phenyl)-2-{[(2-benzoyl-phenylcarbamoyl)-methyl]-benzyl-amino}-acetamide 
• 1219198-31-8 C₃₈H₃₀F₃N₃O₄ 
• 1581699-74-2 C₃₈H₃₀F₃N₃O₄ 
• 1581699-76-4 C₃₈H₂₈F₃N₃NiO₄ 
• 847654-17-5 [Ni(C₅H₁₀NCH₂C(O)NC₆H₄C(C₆H₅)NCH₂CO₂)] 
• 164336-13-4 (3-tert-butoxycarbonylamino-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-1-yl)acetic acid 
• 164336-14-5 3-(tert-butoxycarbonyl)methylamino-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one-1-acetic acid 
• 149620-85-9 tert-butyl 2-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4] diazepin-1-yl)acetate 
• 162823-37-2 3-oximino-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one-1-acetic acid 
• 164336-12-3 3-amino-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one-1-acetic acid 
• 149620-84-8 2-(2,3-dihydro-2-oxo-5-phenylbenzo[e][1,4]diazepin-1-yl) acetic acid 

Relevant articles and documents

New generation of nucleophilic glycine equivalents

A new generation of nucleophilic glycine equivalents, designed to contain a functional framework, that allows control over the physical properties as well as the reactivity, is described. The reactivity of these nucleophilic glycine equivalents have been compared to previously described examples with the application of various transformations such as alkyl halide alkylations, Michael additions, and aldol condensations.

Synthesis of trifluoromethyl substituted nucleophilic glycine equivalents and the investigation of their potential for the preparation of α-amino acids

The synthetic preparation of several Ni(II) complexed Schiff Bases of glycine will be introduced, as well as investigations into their reactivity and utility. Key to these investigations is the incorporation of electron-withdrawing trifluoromethyl groups within the framework of the conjugated system that stabilizes the enolate derived from the glycine component. Reactivity was evaluated for each of the complexes under phase transfer catalyzed alkylations with hydroxide bases, as well as the DBU catalyzed Michael Additions of optically active 3′-substituted-2-oxazoladinone amides of unsaturated carboxylic acids. It was found that the trifluoromethyl containing nucleophilic glycine equivalents were more reactive than their non-trifluoromethyl analogues in both reaction types. Therefore, the application of these modified Ni(II) complexes of glycine Schiff Bases are useful for the preparation of α-amino acids through phase transfer catalyzed alkylation as well as the preparation of optically pure β-substituted pyroglutamic acid precursors.

Structure-Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin

High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.