139409-34-0

Basic information

• Product Name: 2-BROMO-1H-INDOLE
• Synonyms: 2-BROMO-1H-INDOLE
• CAS NO: 139409-34-0
• Molecular Formula: C₈H₆BrN
• Molecular Weight: 196.04
• Mol File: 139409-34-0.mol

Chemical Properties

• Boiling Point: 316.9°C at 760 mmHg
• Flash Point: 145.5°C
• Appearance: /
• Density: 1.660
• Vapor Pressure: 0.000738mmHg at 25°C
• Refractive Index: 1.711
• PKA: 15.34±0.30(Predicted)
• CAS DataBase Reference: 2-BROMO-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1H-INDOLE(139409-34-0)
• EPA Substance Registry System: 2-BROMO-1H-INDOLE(139409-34-0)

Safety Data

• Hazardous Substances Data: 139409-34-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2495, 1992 DOI: 10.1021/jo00034a058Tetrahedron, 54, p. 2149, 1998 DOI: 10.1016/S0040-4020(97)10423-9

InChI:InChI=1/C8H6BrN/c9-8-5-6-3-1-2-4-7(6)10-8/h1-5,10H

Upstream product

• 1072943-52-2 N-[2-(2,2-dibromovinyl)phenyl]-4-methylbenzenesulfonamide 
• 557-21-1 zinc(II) cyanide 
• 167558-54-5 2-(2,2-dibromo-vinyl)-phenylamine 
• 253684-24-1 1-(2,2-dibromovinyl)-2-nitrobenzene 
• 552-89-6 2-nitro-benzaldehyde 
• 1259576-87-8 2-bromo-N-methylsulfonylindole 
• 1401452-08-1 C₉H₈⁽²⁾HBr₂NO₂S 
• 1006060-00-9 C₈H₄⁽²⁾HBr₂NO₂ 
• 50344-83-7 2-nitrobenzaldehyde-α-d₁ 
• 606-27-9 methyl 2-nitrobenzoate 
• 1259577-20-2 N-[2-(2,2-dibromoethenyl)phenyl]methanesulfonamide 
• 880153-78-6 tert-butyl (2-((2-(2,2-dibromovinyl)phenyl)amino)-2-oxoethyl)carbamate 
• 778-82-5 ethyl 3-indoleacetate 
• 26340-49-8 2-iodo-1H-indole 

Downstream Products

• 56807-26-2 2,4-diphenyl-9H-pyrimido[4,5-b]indole 
• 1240045-37-7 2-bromo-1-phenyl-1H-indole 
• 20538-21-0 α,α-diphenylindole-2-methanol 
• 1477-50-5 Indole-2-carboxylic acid 

Relevant articles and documents

Heteroaryl radicals in synthesis: Radical cyclisation reactions of 2-bromoindoles

The synthesis and radical cyclisations of 2-bromoindoles carrying an unsaturated N-alkyl group is described.

Syntheses of polybrominated indoles from the red alga Laurencia brongniartii and the brittle star Ophiocoma erinaceus

The red alga Laurencia brongniartii and brittle star Ophiocoma erinaceus metabolites 2,3,6-tribromo-1-methylindole (1) and 2,3,5,6-tetrabromo-1-methylindole (2) are easily synthesized selectively from 2,3-dibromo-1-methylindole (5), which in turn is prepared from indole (3) in one continuous sequence in 92% yield. Moreover, 2 can be made from both 1 and 5 in 67% and 65% yields, respectively.

Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics

We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m

Method for preparing 2-bromoindole by using electrochemical micro-channel device

The invention provides a method for preparing 2-bromoindole by using an electrochemical micro-channel device, which comprises the following steps: assembling an electrochemical micro-channel reactiondevice, and dissolving indole compounds and bromine-cont

Palladium-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines

An efficient Pd(0)-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines is reported. Few methods have aimed to synthesize these scaffolds which are found in many natural products and have high bioactivity. This protocol features a robust c

Selective access to 3-cyano-1 H -indoles, 9 H -pyrimido[4,5- b ]indoles, or 9 H -Pyrido[2,3- b ]indoles through copper-catalyzed one-pot multicomponent cascade reactions

Novel and selective synthetic approaches toward indole derivatives via copper-catalyzed one-pot multicomponent cascade reactions of 1-bromo-2-(2,2-dibromovinyl)benzenes with aldehydes and aqueous ammonia are presented. Intriguingly, the concentration of a

Application of nanoparticle mediated N-arylation of amines for the synthesis of pharmaceutical entities using vit-E analogues as amphiphiles in water

The first CuI-nanoparticle catalyzed inter and intramolecular N-arylation of amines using vitamin E analogues (TPGS) as amphipiles has been developed in water. Application of this transition metal-amphiphile C-N bond formation methodology is further extended for the synthesis of substituted indoles, bioactive natural product tryptanthrin and intermediates of pharmaceutical entities such as imatinib, nilotinib, selective D3 agonist/antagonist ligands, and oxacarbazepine. This journal is

Microwave irradiated synthesis of 2-bromo(chloro)indoles via intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in the presence of TBAF under metal-free conditions

2-Bromo(chloro)indoles were readily and efficiently prepared through TBAF-promoted intramolecular cyclization of 2-(gem-dibromo(chloro)vinyl)anilines in excellent yields under metal-free and microwave irradiation conditions. This journal is the Partner Organisations 2014.

The facile synthesis of 2-bromoindoles via Cs2CO 3-promoted intramolecular cyclization of 2-(gem-dibromovinyl)anilines under transition-metal-free conditions

2-Bromoindoles were readily prepared through a facile Cs2CO 3-promoted intramolecular cyclization of 2-(gem-bromovinyl)-N- methylsulfonylanilines in excellent yields under transition-metal-free conditions. This methodology could be extended to the synthesis of corresponding 2-chloroindoles. The reaction mechanism suggested that cyclization occurs through a key intermediate, phenylethynyl bromide, followed by cyclization in one-pot. The Royal Society of Chemistry.

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid

An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.