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

Downstream Products

• 701203-80-7 5-chloro-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde 
• 226883-77-8 1-benzyl-5-chloro-1H-indole-3-carbaldehyde 

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.

C3-Formylation of Indoles in Continuous Flow

We have developed a continuous flow C3-formylation technique for indoles using hexamethylenetetramine (HMTA) and iodine. A mixed solvent system of DMF–H2O (1:1, vol/vol) completely dissolves reagents and prevents clogging of microchannels during fluid flow. The continuous flow technique provides maximized mixing and excellent heat transfer efficiency. Thus, flow chemistry accelerates the rate of C3-formylation of indoles in the absence of a strong acid, base, or metal catalyst. We show that high yields of C3-formylated indoles (up to 83%) can be obtained at 150°C when the residence time is as low as 8 min.

First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents

Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biological activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biological assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by compounds 21g, 21h, 21i, 21j, 21l, 22h, 22i and 23h, they possessed significant biological activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core (21h, 22h and 23h), showed effective nematicidal activity in primary screening. Compounds 21g and 21i were identified as the most promising lead structures for further study.