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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

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
Synthesis of N-protected Nortopsentins B and D.
Moody CJ and Roffey JRA.
ARKIVOC (Gainesville, FL, United States), 1, 393-401 (2000)
Leonardo S Santos et al.
The Journal of organic chemistry, 69(4), 1283-1289 (2004-02-14)
Described are the first enantioselective total syntheses of (+)-arborescidine A ((+)-1), (-)-arborescidine B ((-)-2), and (-)-arborescidine C ((-)-3), via routes that proceeded in five steps and 50% overall yield, eight steps and 61% overall yield, and nine steps and 51%
Palladium-catalyzed carbonylation of haloindoles: No need for protecting groups.
Kumar K, et al.
Organic Letters, 6(1), 7-10 (2004)
A facile synthesis of Tyrian purple based on a biosynthetic pathway.
Tanoue Y, et al.
Fisheries Science (Tokyo, Japan), 67(4), 726-729 (2001)

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