614-76-6

Basic information

• Product Name: 2'-BROMOACETANILIDE
• Synonyms: 2-Bromo-N-acetylaniline;Acetanilide, 2'-bromo-;o-Bromoacetanilide;2'-BROMOACETANILIDE;2-BROMOACETANILIDE;N-(2-BROMOPHENYL)ACETAMIDE;NISTC614766;2'-Bromoacetanilide, 98+%
• CAS NO: 614-76-6
• Molecular Formula: C₈H₈BrNO
• Molecular Weight: 214.06
• Product Categories: Anilines, Amides & Amines;Bromine Compounds;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 614-76-6.mol
• Article Data: 80

Chemical Properties

• Melting Point: 96.5-100.5 °C(lit.)
• Boiling Point: 346.8 °C at 760 mmHg
• Flash Point: 163.5 °C
• Appearance: White/Crystalline Powder
• Density: 1.543 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.19±0.70(Predicted)
• BRN: 2086970
• CAS DataBase Reference: 2'-BROMOACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-BROMOACETANILIDE(614-76-6)
• EPA Substance Registry System: 2'-BROMOACETANILIDE(614-76-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 614-76-6(Hazardous Substances Data)

Usage

Description

2'-BROMOACETANILIDE is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is characterized by its reactivity and ability to form derivatives, making it a versatile building block in the chemical and pharmaceutical industries.

Uses

Used in Pharmaceutical Industry:
2'-BROMOACETANILIDE is used as a reagent for the preparation of furan-2-ylmethylene thiazolidinediones, which are novel, potent, and selective inhibitors of phosphoinositide 3-kinase γ. These inhibitors play a crucial role in the development of targeted therapies for various diseases, including cancer and inflammatory disorders, by modulating cellular signaling pathways.
Additionally, 2'-BROMOACETANILIDE may be utilized in other applications within the pharmaceutical industry, such as the synthesis of other bioactive molecules, depending on its specific properties and reactivity.

Upstream product

• 108-86-1 bromobenzene 
• 75-05-8 acetonitrile 
• 19519-75-6 1-bromo-2-nitrosobenzene 
• 431-03-8 dimethylglyoxal 
• 64-19-7 acetic acid 
• 615-36-1 2-bromoaniline 
• 1073483-44-9 1-(1-azidovinyl)-2-bromobenzene 
• 127-19-5 N,N-dimethyl acetamide 
• 62-53-3 aniline 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 1039765-14-4 N-benzyl-2-bromobenzenecarboximidamide 
• 2042-37-7 o-cyanobromobenzene 
• 2142-69-0 2-bromophenyl methyl ketone 
• 64-17-5 ethanol 

Downstream Products

• 1489-23-2 N-(2-(phenylthio)phenyl)acetamide 
• 605-03-8 4-phenylquinoline 
• 229-87-8 phenanthridine 
• 302357-89-7 4-(p-tolyl)quinoline 
• 103-84-4 Acetanilid 
• 869631-33-4 N-[3’-methyl-(1,1’-biphenyl)-2-yl]acetamide 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 88963-75-1 4-acetamido-3-bromobenzene-1-sulfonyl chloride 
• 62635-46-5 N-(2-bromophenyl)ethanethioamide 
• 245115-83-7 N-(2-bromo-6-nitro-phenyl)-acetamide 
• 57045-86-0 N-(2-bromo-4-nitro-phenyl)-acetamide 
• 1769-24-0 2-methyl-4-quinazolone 
• 89-52-1 o-acetylamino-benzoic acid 
• 261177-32-6 2-[undec-1'-enyl]acetanilide 

Relevant articles and documents

Ru-Catalyzed C(sp2)?H Bond Arylation of Benzamides Bearing a Novel 4-Aminoantipyrine as a Directing Group

A novel design-based removable N,O-bidentate directing group based on cheap and commercially available 4-aminoantipyrine (AAP) is reported. Aromatic AP amides bearing 4-aminoantipyrine underwent efficient Ru-catalyzed C(sp2)?H arylation using [RuCl2(PPh3)3] as a catalyst and aryl bromides as electrophiles. The novel bidentate directing group enabled the C?H functionalization reaction with good scope, good functional group tolerance and in decent yields.

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.