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2-IODO-1H-INDOLE, also known as 2-Iodoindole, is an organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It possesses a unique structure with an indole ring and an iodine atom, which contributes to its reactivity and potential applications in medicinal chemistry.

26340-49-8

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26340-49-8 Usage

Uses

Used in Pharmaceutical Industry:
2-IODO-1H-INDOLE is used as a synthetic intermediate for the production of arylthioindole molecules, which are a class of tubulin polymerization inhibitors. These inhibitors have potential applications in the development of anticancer drugs, as they can disrupt the normal function of tubulin, a key component of the cellular cytoskeleton, leading to the inhibition of cell division and growth.
Additionally, 2-IODO-1H-INDOLE is used as a synthetic intermediate in the synthesis of combretastatin A-4 derivatives. Combretastatin A-4 is a naturally occurring compound with anti-cancer properties, and its derivatives have been studied for their potential use in cancer therapy. The unique structure of 2-IODO-1H-INDOLE allows for the efficient synthesis of these derivatives, contributing to the development of novel cancer treatments.

Check Digit Verification of cas no

The CAS Registry Mumber 26340-49-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,3,4 and 0 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 26340-49:
(7*2)+(6*6)+(5*3)+(4*4)+(3*0)+(2*4)+(1*9)=98
98 % 10 = 8
So 26340-49-8 is a valid CAS Registry Number.

26340-49-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Iodo-1H-indole

1.2 Other means of identification

Product number -
Other names 2-iodobenzofuran

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:26340-49-8 SDS

26340-49-8Relevant articles and documents

Generation and reactions of 2,3-dilithio-N-methylindole. Synthesis of 2,3-disubstituted indoles

Liu, Yanbing,Gribble, Gordon W.

, p. 2949 - 2951 (2001)

Generation of 2,3-dilithio-N-methylindole (7) from 2,3-diiodo-N-methylindole (6) and subsequent reaction with various electrophiles (NH4Cl, DMF, ClCO2Me, CO2, phthalic anhydride) affords the corresponding 2,3-disubstituted indoles in good to excellent yields (41-99%).

Synthesis of indolocarbazoles via annulations of chromium carbene complexes

Merlic, Craig A.,McInnes, Daniel M.,You, Ying

, p. 6787 - 6790 (1997)

The synthesis of indolocarbazoles containing hydrogen bonding functionality mimicking the pharmacophore contained within bioactive indolocarbazole natural products is reported. The indolocarbazoles are prepared via palladium catalyzed cross coupling of indoles followed by photochemical and thermal annulation reactions of chromium carbene complexes.

Aerobic Oxidative C-H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin-Iodine-Coupled Organocatalysis

Tanimoto, Kazumasa,Okai, Hayaki,Oka, Marina,Ohkado, Ryoma,Iida, Hiroki

, p. 2084 - 2088 (2021/04/05)

The aerobic oxidative cross-coupling of indoles with azoles driven by flavin-iodine-coupled organocatalysis has been developed for the green synthesis of 2-(azol-1-yl)indoles. The coupled organocatalytic system enabled the one-pot three-component synthesis of 2-azolyl-3-thioindoles from indoles, azoles, and thiols in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent.

Design and synthesis of azaindole heterocycle decorated new scaffold in fluorometric sensing of F? and H2PO4?

Ghosh, Kumaresh,Ali, Sk. Sarfaraj,Joardar, Soumen

, p. 3558 - 3565 (2020/08/06)

7-Azaindole has been used in designing new molecular structure 1 on enediyne spacer for its application in anion sensing. New structure 1 has been established as efficient fluorescent sensor of H2PO4? and F? ion

Heat Versus Basic Conditions: Intramolecular Dehydro-Diels-Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles

Kudoh, Takayuki,Fujisawa, Syo,Kitamura, Megumi,Sakakura, Akira

supporting information, p. 2189 - 2193 (2017/09/26)

The intramolecular dehydro-Diels-Alder reaction of 1-indolyl-1,6-heptadiynes proceeds smoothly under rather mild heating conditions to give substituted carbazoles in moderate to good yields. The reaction of 7-aryl-1-indolyl-1,6-heptadiynes under heating gives the corresponding carbazoles chemoselectively in high yields, whereas the reaction under basic conditions gives naphthalenes as major products.

Azaindole-1,2,3-triazole conjugate as selective fluorometric sensor for dihydrogenphosphate

Ghosh, Kumaresh,Kar, Debasis,Joardar, Soumen,Sahu, Debashis,Ganguly, Bishwajit

, p. 16144 - 16151 (2013/09/12)

A new receptor 1 has been designed and synthesized. The open cavity of 1 selectively recognizes H2PO4- over a series of other anions in CH3CN containing 0.01% DMSO by exhibiting a ratiometric change in emission.

Sterically controlled iodination of arenes via iridium-catalyzed C-H borylation

Partridge, Benjamin M.,Hartwig, John F.

supporting information, p. 140 - 143 (2013/03/28)

A mild method to prepare aryl and heteroaryl iodides by sequential C-H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C-H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential tracer for SPECT imaging.

Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid

Miyamoto, Hiroshi,Hirano, Tomohiro,Okawa, Yoichiro,Nakazaki, Atsuo,Kobayashi, Susumu

supporting information, p. 9481 - 9493 (2013/10/08)

An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.

A convenient iodination of indoles and derivatives

Hamri, Salha,Rodríguez, Jose,Basset, Joan,Guillaumet, Gérald,Dolors Pujol

supporting information; experimental part, p. 6269 - 6275 (2012/08/28)

We report a direct iodination of indole and derivative compounds with iodine monochloride (ICl) in the presence of Celite. This procedure has now been extended to the iodination of substituted indoles, azaindoles and pyrroles. The scope of this procedure

NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS

-

Page/Page column 46, (2010/06/19)

The invention relates to the use of at least one compound of the formula (I), in which R and R3 are particularly a hydrogen atom, R1 is particularly a hydrogen atom or a methyl, ethyl or isobutyl mi group, R4, R5, R6 and R7 are independently a hydrogen atony, an alkoxyl group with 1 to 7 carbon atoms or a halogen atom, R2 is a hydrogen atom, an O? group or an OH group, B is an N-GP1 or NRc, group, GP1 being a Boc or Cbz group, and Rc is a hydrogen atom or a methyl or t-butyl group, for preparing a drug for treating conditions associated with bacterial infections, in particular for treating bacterial diseases.

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