99474-21-2

Basic information

• Product Name: (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine
• Synonyms: (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine
• CAS NO: 99474-21-2
• Molecular Weight: 271.114
• Mol File: 99474-21-2.mol

Chemical Properties

• CAS DataBase Reference: (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine(99474-21-2)
• EPA Substance Registry System: (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine(99474-21-2)

Safety Data

• Hazardous Substances Data: 99474-21-2(Hazardous Substances Data)

Upstream product

• 60956-26-5 4-bromo-2-nitrotoluene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 52415-29-9 6-bromo-1H-indole 
• 207792-73-2 4'-Ethoxy-2-(4''-bromo-2''-nitrophenyl)acetophenone 
• 105205-50-3 6-indolyl phenyl ketone 
• 1196-70-9 indole-6-carboxaldehyde 
• 188247-38-3 2-(4 '-Ethoxyphenyl)-6-formylindole 
• 188247-35-0 2-(4'-Ethoxyphenyl)-6-bromoindole 
• 496930-15-5 6'-bromo-N-carbobenzyloxy-L-tryptophan 
• 496930-12-2 6'-bromo-N-carbobenzyloxy-D-tryptophan 
• 496930-10-0 6'-bromo-D-tryptophan 
• 52448-17-6 (2S)-2-amino-3-(6-bromo-1H-indol-3-yl)propanoic acid 
• 59278-65-8 2-amino-4-bromobenzaldehyde 
• 883149-59-5 7-bromo-3-(2,5-dimethoxyphenyl)-1H-quinolin-2-one 
• 5551-12-2 4-bromo-2-nitrobenzaldehyde 

Relevant articles and documents

2-(4-Bromo-2-nitrophenyl)-1-(4-dimethylaminophenyl )-1-ethanone

The title compound, C16H15BrN2O3, is a key intermediate in the synthesis of indole-substituted Hoechst 33258 analogues. Interaction between the dimethylamino substituent and the ketone through the aromatic ring

Convenient modification of the Leimgruber-Batcho indole synthesis: Reduction of 2-nitro-p-pyrrolidinostyrenes by the FeCl3-activated carbon-N2H4H2O system

A new catalytic system containing ferric chloride, activated carbon, and hydrazine has been proposed for the reductive cyclization of β-dialkylamino-2-nitrostyrenes to give the corresponding indoles (Leimgruber-Batcho synthesis). Various substituted indoles may be obtained in high yield under these conditions.

8-SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS

Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in the treatment of autoimmunity, inflammation allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.

Synthesis and biological evaluation of conformationally constrained analogs of the antitumor agents XK469 and SH80. Part 5

Conformational restriction of bioactive molecules offers the possibility of generating structures of increased potency. To this end, a synthesis has been achieved of (R,S)-2-[(8-chlorobenzofurano[2,3-b]quinolinyl)oxy]propionic acid (12a), a highly rigidified, polycyclic analog of 2-{4-[(7-chloro-2-quinoxalinyl) oxy]phenoxy}propionic acid (2a, XK469). Efforts to effect the same synthesis of the corresponding 8-bromo-derivative led to a mixture of intermediate, 8-chloro (9a), and 8-bromo-2-hydroxybenzofurano[2,3-b]quinoline (9b), generated by halogen-exchange, via an aromatic SRN1(ARN1) reaction of precursor, 8b, with pyridine hydrochloride. The presumption that conformational restriction of 1b-12a might enhance the antitumor potency of the latter has not been sustained. In fact, 12a proved to be significantly less active than 1b. However, it is apparent that virtually all of the spatial and steric properties of 12a, necessary for improved activity, including the disposition of the 2-oxypropionic acid side chain remain to be identified.

Microwave assisted Leimgruber-Batcho reaction for the preparation of indoles, azaindoles and pyrroylquinolines

The development of enhanced conditions for Lewis acid catalysed Leimgruber-Batcho indole synthesis using microwave acceleration is described. This approach has permitted the preparation of a variety of heteroaromatic enamine intermediates in good yield and high purities. Subsequent catalytic hydrogenation reactions, under various conditions including the use of a solid-phase encapsulated catalyst, furnish the corresponding indole derivatives in good yields.

Convenient synthesis of 7′ and 6′-bromo-D-tryptophan and their derivatives by enzymatic optical resolution using D-aminoacylase

Compounds 7′ and 6′-bromo-D-tryptophan (1 and 2) which are important derivatives for the synthesis of the chloropeptin and kistamycin A, respectively, were conveniently synthesized by optical resolution from N-acetyl-7′ and 6′-bromo-DL-tryptophan ((RS)-5 and (RS)-14) using D-aminoacylase.

Metal-Halogen Exchange of Bromoindoles. A Route to Substituted Indoles

The 4-, 5-, 6-, and 7-bromoindoles, conveniently synthesized by the Batcho-Leimgruber process, serve as efficient precursors to regiochemically pure lithiated indoles.Metal-halogen exchange was most effective if potassium hydride was used first to remove the acidic indole NH, and tert-butyllithium was used then to effect metal-halogen exchange.The resulting indolyl organometallic reagents react with a variety of electrophiles to give regioisomerically pure acylated indoles.