16863-96-0

Basic information

• Product Name: 2-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
• Article Data: 31

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: 2-CHLOROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROINDOLE(16863-96-0)
• EPA Substance Registry System: 2-CHLOROINDOLE(16863-96-0)

Safety Data

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

Usage

Uses

2-Chloroindole is used to prepare 2-pyrrolidinone derivatives as anticonvulsants.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2495, 1992 DOI: 10.1021/jo00034a058

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 
• 53000-40-1 3-Indolylphenyliodonium betaine 
• 66037-05-6 3-chloroindolenine 

Downstream Products

• 59-48-3 2-oxoindole 
• 339094-44-9 2,5-dibromo-3-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-6-methoxy-[1,4]benzoquinone 
• 78708-35-7 asterriquinone B1 
• 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 
• 55179-53-8 neoechinulin B 
• 244148-46-7 Isogranulatimide C 
• 1073968-33-8 methyl 9-benzyl-9H-carbazole-3-carboxylate 
• 1196973-78-0 3-chloro-1-tosyl-1H-indole 
• 108665-94-7 3-chloro-1-(phenylsulfonyl)-1H-indole 
• 3652-91-3 2-methyl-9H-carbazole 

Relevant articles and documents

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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.

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.).

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.