524344

Sigma-Aldrich

6-Bromoindole

96%

Empirical Formula (Hill Notation):
C8H6BrN
CAS Number:
Molecular Weight:
196.04
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

mp

92-96 °C (lit.)

SMILES string

Brc1ccc2cc[nH]c2c1

InChI

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

InChI key

MAWGHOPSCKCTPA-UHFFFAOYSA-N

General description

6-Bromoindole is an indole derivative. It undergoes palladium-catalyzed reaction with 2-(4-fluorophenyl)ethylpiperazine to afford the carbonylation products.

Application

Essential starter in 6-substituted indole chemistry.
6-Bromoindole may be used to synthesize:
  • 6-alkylthioindole
  • 3-acetoxy-6-bromoindole
  • 6,6′-dibromoindigo (Tyrian purple)
  • 6-acylindoles
  • tert-butyl 6-bromoindole-1-carboxylate

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
James R Fuchs et al.
Journal of the American Chemical Society, 126(16), 5068-5069 (2004-04-22)
The first total synthesis of racemic perophoramidine is described. The key step features the highly stereoselective introduction of the vicinial quaternary centers via base-promoted carbon-carbon bond formation between a 3-alkylindole and a 3-bromo-3-alkylindolin-2-one. This transformation presumably proceeds through a conjugate...
A facile synthesis of Tyrian purple based on a biosynthetic pathway.
Tanoue Y, et al.
Fisheries Science (Tokyo, Japan), 67(4), 726-729 (2001)
Synthesis of N-protected Nortopsentins B and D.
Moody CJ and Roffey JRA.
ARKIVOC (Gainesville, FL, United States), 1, 393-401 (2000)
Efficient synthesis of 5-and 6-tributylstannylindoles and their reactivity with acid chlorides in the Stille coupling reaction.
Cherry K, et al.
Tetrahedron Letters, 48(33), 5751-5753 (2007)
Palladium-catalyzed carbonylation of haloindoles: No need for protecting groups.
Kumar K, et al.
Organic Letters, 6(1), 7-10 (2004)

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