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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

Quality Level

200

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

Related Categories

Application

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

524336-BULK:
524336-1ML:
524336-5ML:
524336-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV8218
BCBS3069V
BCBN9165V
BCBH0064V
BCBJ4986V

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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
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
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

Global Trade Item Number

SKUGTIN
524336-1ML4061837604805
524336-5ML4061837604812

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