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524336

4-Bromoindole

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About This Item

Empirical Formula (Hill Notation):
C8H6BrN
CAS Number:
52488-36-5
Molecular Weight:
196.04
NACRES:
NA.22
PubChem Substance ID:
24874403
UNSPSC Code:
12352100
MDL number:
MFCD00671502
Assay:
96%
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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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

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
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
Optically active total synthesis of clavicipitic acid.
Yokoyama Y, et al.
The Journal of Organic Chemistry, 60(6), 1486-1487 (1995)
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