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518107

Sigma-Aldrich

tert-Butyl 1-indolecarboxylate

97%

Synonym(s):

1-(tert-Butoxycarbonyl)indole, 1-Indolecarboxylic acid tert-butyl ester, N-tert-Butoxycarbonylindole, N-Butyloxycarbonylindole

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About This Item

Empirical Formula (Hill Notation):
C13H15NO2
CAS Number:
75400-67-8
Molecular Weight:
217.26
MDL number:
MFCD02093939
UNSPSC Code:
12352100
PubChem Substance ID:
24874000
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.543 (lit.)

bp

201 °C (lit.)

density

1.07 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)n1ccc2ccccc12

InChI

1S/C13H15NO2/c1-13(2,3)16-12(15)14-9-8-10-6-4-5-7-11(10)14/h4-9H,1-3H3

InChI key

OWPIFQXNMLDXKW-UHFFFAOYSA-N

Application

Reactant for preparation of:
  • Potent plant-growth inhibitors
  • Cannabinoid CB2 receptor ligands
  • Analogues of isomeridianin G and evaluation as GSK-3β inhibitors
  • Inhibitor of the Yersinia pestis salicylate adenylation domain YbtE
  • Cholecystokinin-2 receptor antagonists
  • Antileishmanial agents

  • Reactant for:
  • Palladium-catalyzed Suzuki-Miyaura cross coupling reactions
  • Friedel-Crafts alkylation reactions

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

160.0 °F - closed cup

flash_point_c

71.1 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

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Eva Schendera et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(1), 269-274 (2019-09-26)
A metal-free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between N-aryl glycine esters and indoles leads to tetracyclic 11H-indolo[3,2-c]quinolines under mild conditions and with high yields. The reaction can be performed by using molecular iodine along with visible light, or
Solid-Phase Dendrimer Chemistry
Aldrichimica Acta, 34(3) (3001)

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