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524336

Sigma-Aldrich

4-Bromoindole

96%

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About This Item

Empirical Formula (Hill Notation):
C8H6BrN
CAS Number:
52488-36-5
Molecular Weight:
196.04
MDL number:
MFCD00671502
UNSPSC Code:
12352100
PubChem Substance ID:
24874403
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

96%

refractive index

n20/D 1.655 (lit.)

bp

283-285 °C (lit.)

density

1.563 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

Brc1cccc2[nH]ccc12

InChI

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

InChI key

GRJZJFUBQYULKL-UHFFFAOYSA-N

Application

4-Bromoindole may be used to synthesize:
  • clavicipitic acid, an ergot alkaloid[1]
  • 4-bromodehydrotryptophan[2]
  • 3-indolylacetonitrile derivative[3]
  • marine alkaloid dictyodendrin B[4]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ8315
BCBV8218
BCBS3069V
BCBN9165V
BCBH0064V

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S Liras et al.
Journal of the American Chemical Society, 123(25), 5918-5924 (2001-06-21)
Concise syntheses of the Ergot alkaloids rugulovasine A (3a), rugulovasine B (3b), and setoclavine (2) have been completed by strategies that feature inter- and intramolecular vinylogous Mannich reactions as the key steps. Thus, the first synthesis of 3a,b commenced with
Optically active total synthesis of clavicipitic acid.
Yokoyama Y, et al.
The Journal of Organic Chemistry, 60(6), 1486-1487 (1995)
Metal-halogen exchange of bromoindoles. A route to substituted indoles.
Moyer MP, et al.
The Journal of Organic Chemistry, 51(26), 5106- 5110 (1986)
Andrew K Pitts et al.
Angewandte Chemie (International ed. in English), 54(18), 5451-5455 (2015-02-24)
A sequential CH functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural
Chaitany Jayprakash Raorane et al.
Biomolecules, 10(8) (2020-08-23)
Multi-drug resistant Acinetobacter baumannii is well-known for its rapid acclimatization in hospital environments. The ability of the bacterium to endure desiccation and starvation on dry surfaces for up to a month results in outbreaks of health care-associated infections. Previously, indole

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