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563838

Sigma-Aldrich

5-Iodoindole

97%

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About This Item

Empirical Formula (Hill Notation):
C8H6IN
CAS Number:
16066-91-4
Molecular Weight:
243.04
MDL number:
MFCD00220065
UNSPSC Code:
12352100
PubChem Substance ID:
24880134
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

101-104 °C (lit.)

functional group

iodo

SMILES string

Ic1ccc2[nH]ccc2c1

InChI

1S/C8H6IN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

InChI key

TVQLYTUWUQMGMP-UHFFFAOYSA-N

General description

5-Iodoindole can be synthesized via nitration of m-toluidine.

Application

5-Iodoindole (5-iodogramine) may be used in the synthesis of the following:
  • 3-dimethylaminomethyl-5-iodoindole via reaction with dimethyl amine and formaldehyde
  • 5-ethynyl-1H-indole obtained via refluxing with trimethylsilylacetylene in the presence of triethylamine, catalyzed by palladium and copper(I)iodide in acetonitrile
  • 5-(3-hydroxyprop-1-enyl)-1H-indole via reaction with allyl alcohol in the presence of triphenyl phosphine, palladium acetate and silver acetate in dimethylformamide
  • 5-(3-benzyloxyprop-1-enyl)-1H-indole via reaction with allylbenzyl ether in the presence of triphenyl phosphine, palladium acetate and silver acetate in dimethylformamide
  • 5-(2-phenylethynyl)-1H-indole via refluxing with phenylacetylene catalyzed by copper(I)iodide and palladium in the presence of triethylamine in acetonitrile

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)

Not applicable

Flash Point(C)

Not applicable

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.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

563838-BULK:
563838-25G:4548173994970
563838-VAR:
563838-5G:4548173994987

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT4421
MKCN9390
MKCK9681
MKCK9682
MKCF7538

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?The synthesis of 5-iodotryptophan and some derivatives"
Harvey GD
Journal of the Chemical Society, 3760-3762 (1958)
Satish Kumar Rajasekharan et al.
Pesticide biochemistry and physiology, 163, 76-83 (2020-01-25)
Multi-drug resistance in nematodes is a serious problem as lately several resistant phenotypes have emerged following the intermittent usage of synthetic nematicides. Contemporary research continues to focus on developing and/or repurposing small molecule inhibitors that are eco-friendly. Here, we describe
"Synthesis and biological evaluation of new dipyrrolo [3, 4-a: 3, 4-c] carbazole-1, 3, 4, 6-tetraones, substituted with various saturated and unsaturated side chains via palladium catalyzed cross-coupling reactions"
Henon H, et al.
Bioorganic & Medicinal Chemistry, 14(11), 3825-3834 (2006)
Yoshimitsu Masuda et al.
Applied and environmental microbiology, 86(16) (2020-06-07)
YafQ is an endoribonuclease toxin that degrades target gene transcripts such as that of tnaA, a gene encoding tryptophanase to synthesize indole from tryptophan. DinJ is the cognate antitoxin of YafQ, and the YafQ-DinJ system was reported to regulate persister
?Convenient synthesis of 5-iodoindole?
Hydorn.EA
The Journal of Organic Chemistry, 32(12), 4100-4101 (1967)
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