16863-96-0

Basic information

• Product Name: 3-Chloroindole
• Synonyms: 2-CHLOROINDOLE;3-Chloro-1H-indole;1H-Indole,3-chloro-;1H-Indole,3-chloro-(9CI);3-CHLORO-1H-INDAZOLE;2-Chlorlindole;3-chloroindole;2-chloro-1H-indole
• CAS NO: 16863-96-0
• Molecular Formula: C₈H₆ClN
• Molecular Weight: 151.59
• Product Categories: INDOLE;Indoles and derivatives
• Mol File: 16863-96-0.mol

Chemical Properties

• Melting Point: 94-95 °C(Solv: hexane (110-54-3))
• Boiling Point: 293 °C at 760 mmHg
• Flash Point: 158.9 °C
• Appearance: /
• Density: 1.331 g/cm³
• Vapor Pressure: 0.00309mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: Sealed in dry,under -80°C
• PKA: 15.42±0.30(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 3-Chloroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloroindole(16863-96-0)
• EPA Substance Registry System: 3-Chloroindole(16863-96-0)

Safety Data

• Hazardous Substances Data: 16863-96-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6ClN/c9-8-5-6-3-1-2-4-7(6)10-8/h1-5,10H

Upstream product

• 120-72-9 indole 
• 90540-07-1 1-benzoyl-3-chloro-indole 
• 98-09-9 benzenesulfonyl chloride 
• 496-15-1 1-indoline 
• 26340-47-6 3-Iodo-1H-indole 
• 67765-96-2 phenyl (β-indolyl)iodonium trifluoroacetate 
• 66037-05-6 3-chloroindolenine 
• 53000-40-1 3-Indolylphenyliodonium betaine 

Downstream Products

• 59-48-3 2-oxoindole 
• 244148-46-7 Isogranulatimide C 
• 1073968-33-8 methyl 9-benzyl-9H-carbazole-3-carboxylate 
• 3652-91-3 2-methyl-9H-carbazole 
• 78860-34-1 2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione 
• 78708-35-7 asterriquinone B1 
• 339094-44-9 2,5-dibromo-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-6-methoxy-[1,4]benzoquinone 
• 120258-33-5 3,5-dichloroindole 

Relevant articles and documents

Regio- and stereoselective allylation and crotylation of indoles at C2 through the use of potassium organotrifluoroborate salts

A practical method for the allylation, prenylation, propargylation, and diastereoselective crotylation of indoles has been developed using air- and moisture-stable potassium organotrifluoroborate reagents (see scheme). Lewis acids such as BF3×Et2O promote addition to afford 2-allyl- and 2-crotylindolines in high yields and diastereoselectivities. Copyright

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

Rapid Oxidation Indoles into 2-Oxindoles Mediated by PIFA in Combination with n-Bu4NCl ? H2O

We report the development of a rapid approach for directly converting indoles into 2-oxindoles promoted by HOCl formed in situ from the combination of (bis(trifluoroacetoxy) iodo)benzene (PIFA) and n-Bu4NCl ? H2O. The procedure is widely functional group tolerant and provides 2-oxindoles in up to 95% yield within 5 min. The potential applications of the developed methodology are demonstrated by the gram-scale preparation of 3-methyl-2-oxindole (11 a), the one-pot two-step syntheses of spiro-oxindoles 26 a and 26 b, and the formal synthesis of (-)-folicanthine (2). (Figure presented.).

Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile

An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines

C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.

PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives

This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.

A Versatile C–H Halogenation Strategy for Indole Derivatives under Electrochemical Catalyst- and Oxidant-Free Conditions

Halogenated indoles are essential structural motifs in bioactive natural products. Reported herein is an economical and scalable electrochemical protocol for regioselective 3C–H halogenation of indole derivatives. This strategy provides access to a host of 3-iodo-, 3-bromo-, 3-chloro-, and 3-thiocyanoindole derivatives under mild conditions using inexpensive (pseudo)halide salts as the sole reagent. The optimized conditions do not require any supplementary electrolyte salts.

A flavin-dependent halogenase from metagenomic analysis prefers bromination over chlorination

Flavin-dependent halogenases catalyse halogenation of aromatic compounds. In most cases, this reaction proceeds with high regioselectivity and requires only the presence of FADH2, oxygen, and halide salts. Since marine habitats contain high concentrations of halides, organisms populating the oceans might be valuable sources of yet undiscovered halogenases. A new Hidden-Markov-Model (HMM) based on the PFAM tryptophan halogenase model was used for the analysis of marine metagenomes. Eleven metagenomes were screened leading to the identification of 254 complete or partial putative flavin-dependent halogenase genes. One predicted halogenase gene (brvH) was selected, codon optimised for E. coli, and overexpressed. Substrate screening revealed that this enzyme represents an active flavin-dependent halogenase able to convert indole to 3-bromoindole. Remarkably, bromination prevails also in a large excess of chloride. The BrvH crystal structure is very similar to that of tryptophan halogenases but reveals a substrate binding site that is open to the solvent instead of being covered by a loop.

Preparation method of 3-substituted oxidized indole and derivative

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.