827-01-0

Basic information

• Product Name: 5-Chloroindole-3-carboxaldehyde
• Synonyms: TIMTEC-BB SBB003756;5-CHLORO-1H-INDOLE-3-CARBALDEHYDE;5-CHLORO-1H-INDOLE-3-CARBOXALDEHYDE;5-CHLOROINDOLE-3-ALDEHYDE;5-CHLOROINDOLE-3-CARBOXALDEHYDE;5-Chloro-3-formylindole;5-Chloro-3-indolecarboxaldehyde;5-CHLOROINDOLE-3-CARBOXALDEHYDE(5ClIAld)
• CAS NO: 827-01-0
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.6
• EINECS: -0
• Product Categories: Indoles and derivatives;Indole;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks
• Mol File: 827-01-0.mol
• Article Data: 50

Chemical Properties

• Melting Point: 213-216 °C(lit.)
• Boiling Point: 373.4 ºC at 760 mmHg
• Flash Point: 179.6 ºC
• Appearance: /
• Density: 1.431 g/cm³
• Vapor Pressure: 8.99E-06mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.59±0.30(Predicted)
• Sensitive: Air Sensitive
• BRN: 123794
• CAS DataBase Reference: 5-Chloroindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloroindole-3-carboxaldehyde(827-01-0)
• EPA Substance Registry System: 5-Chloroindole-3-carboxaldehyde(827-01-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 827-01-0(Hazardous Substances Data)

Usage

Uses

5-Chloroindole-3-carboxaldehyde (5-Chloro-1H-indole-3-carboxaldehyde) may be used in the preparation of:5-chloroindole-3-carboxaldehyde isonicotinoyl hydrazine2′-[(5-chloro-1H-indol-3-yl)methyl-ene]-2-(1H-indol-3-yl)acetohydrazide5-chloro-3-(2,2-dibromovinyl)-1-(2-trimethylsilylethoxymethyl)indoleIt may also be used in the preparation of the following hydrazone derivatives: 5-chloroindole-3-carboxaldehyde 3-chlorobenzoylhydrazone5-chloroindole-3-carboxaldehyde 4-nitrobenzoylhydrazone5-chloroindole-3-carboxaldehyde 3-methylbenzoylhydrazone5-chloroindole-3-carboxaldehyde 4-methylbenzoylhydrazone

General Description

5-Chloroindole-3-carboxaldehyde, also known as 5-chloro-1H-indole-3-carboxaldehyde, is an indole derivative.

InChI:InChI=1/C9H6ClNO/c10-7-1-2-9-8(3-7)6(5-12)4-11-9/h1-5,11H

Upstream product

• 17422-32-1 5-chloro-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 10517-21-2 5-chloro-1H-Indole-2-carboxylic acid 
• 36255-90-0 (5-chloro-2-nitro-phenyl)-pyruvic acid 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 100-61-8 N-methylaniline 
• 79-37-8 oxalyl dichloride 
• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 226883-77-8 1-benzyl-5-chloro-1H-indole-3-carbaldehyde 
• 226883-78-9 1-[(4-chlorophenyl)methyl]-5-chloro-1H-indole-3-carboxaldehyde 
• 701203-80-7 5-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde 
• 314248-57-2 5-chloro-3-formyl-indole-1-carboxylic acid tert-butyl ester 
• 850895-38-4 3-[5-chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-propionic acid 
• 850895-22-6 3-[5-chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-propionic acid ethyl ester 
• 65285-58-7 vincantril 
• 859163-70-5 N-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-nitrobenzenesulfonylamide 
• 859163-72-7 6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-2,3,4,9-tetrahydro-1H-β-carboline 
• 859163-71-6 N-(1-benzyloxyallyl)-N-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-nitrobenzenesulfonylamide 
• 859163-73-8 1-[6-chloro-2-(4-nitrobenzenesulfonyl)-1-vinyl-1,2,3,4-tetrahydro-β-carbolin-9-yl]-propenone 
• 3764-94-1 5-chlorotryptamine 
• 721428-27-9 4-[5-[2-(5-chloro-1H-indol-3-yl)-vinyl]-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester 
• 172596-64-4 1-benzyl-5-chloroindole-3-carboxylic acid 

Relevant articles and documents

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Design and Synthesis of Pyrano[3,2-b]indolones Showing Antimycobacterial Activity

Latent Mycobacterium tuberculosis infection presents one of the largest challenges for tuberculosis control and novel antimycobacterial drug development. A series of pyrano[3,2-b]indolone-based compounds was designed and synthesized via an original eight-step scheme. The synthesized compounds were evaluated for their in vitro activity against M. tuberculosis strains H37Rv and streptomycin-starved 18b (SS18b), representing models for replicating and nonreplicating mycobacteria, respectively. Compound 10a exhibited good activity with MIC99 values of 0.3 and 0.4 μg/mL against H37Rv and SS18b, respectively, as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An analysis of 10a-resistant M. bovis mutants disclosed a cross-resistance with pretomanid and altered relative amounts of different forms of cofactor F420 in these strains. Complementation experiments showed that F420-dependent glucose-6-phosphate dehydrogenase and the synthesis of mature F420 were important for 10a activity. Overall these studies revealed 10a to be a prodrug that is activated by an unknown F420-dependent enzyme in mycobacteria.

KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres

The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98?:?2). The practicability of the present methodology has been validated with the synthesis of a series of substrates in good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly base (KOH) have prompted the broader application of the present methodology in organic synthesis.