3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

Base Information

• Chemical Name: 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile
• CAS No.: 276863-95-7
• Molecular Formula: C13H11ClN2O
• Molecular Weight: 246.696
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID30436934
• Nikkaji Number: J3.277.780E
• Wikidata: Q72456280
• Mol file: 276863-95-7.mol

Synonyms:3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile;276863-95-7;1H-Indole-5-carbonitrile, 3-(4-chloro-1-oxobutyl)-;3-(4-chlorobutyryl)-1h-indole-5-carbonitrile;3-(4-Chloro-1-oxobutyl)indole-5-carbonitrile;MFCD09833260;SCHEMBL3738329;DTXSID30436934;DFORIOBMTPKWPE-UHFFFAOYSA-N;BCP08310;BLA86395;CS-M1861;AKOS016004243;AC-26405;CS-13029;SY024413;3-(4-chlorobutanoyl)indole-5-carbonitrile;FT-0696043;3-(4-chlorobutyryl)-1H-indol-5-carbonitrile;I11726;A851858

Chemical Property of 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

Chemical Property:

• Melting Point: 169-170 °C
• Boiling Point: 489.85 °C at 760 mmHg
• PKA: 14.07±0.30(Predicted)
• Flash Point: 250.053 °C
• PSA: 56.65000
• Density: 1.314 g/cm³
• LogP: 3.24128
• Storage Temp.: 2-8°C
• Solubility.: Dimethyl Sulfoxide, Hot Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 246.0559907
• Heavy Atom Count: 17
• Complexity: 336

Purity/Quality:

98% ^*data from raw suppliers

3-(4-Chloro-1-oxobutyl)indole-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C#N)C(=CN2)C(=O)CCCCl
• Uses: Reactant in the preparation of dual 5-HT1A receptor agonists and serotonin reuptake inhibitors.

Technology Process of 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

There total 4 articles about 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

1H-indole-5-carbonitrile (15861-24-2,142396-06-3) + 4-Chlorobutanoyl chloride (4635-59-0) → 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile (276863-95-7)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2018.04.037

Reference yield:

5-aminocarbonyl-3-(4-chlorobutyryl)indole → 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile (276863-95-7)

Guidance literature:

With trichlorophosphate; In dichloromethane; at 10 ℃; Cooling with ice; Large scale;

Reference yield:

SD-169 (1670-87-7) → 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile (276863-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aluminum (III) chloride / dichloromethane / 1 h / 5 °C / Cooling with ice; Large scale

1.2: 20 °C / Cooling with ice; Large scale

2.1: trichlorophosphate / dichloromethane / 10 °C / Cooling with ice; Large scale

With aluminum (III) chloride; trichlorophosphate; In dichloromethane;

upstream raw materials:

1H-indole-5-carbonitrile

4-Chlorobutanoyl chloride

SD-169

Downstream raw materials:

3-(4-chlorobutanoyl)-1-tosyl-1H-indole-5-carbonitrile

3-(4-hydroxybutyl)-1H-indole-5-carbonitrile

3-(4-chloro-1-hydroxy-butyl)-1H-indol-5-carbonitrile

3-(4-chloro-butyl)-2,3-dihydro-1H-indole-5-carbonitrile

Refernces

• 1、 -. "Substituted indole compound and method and use thereof". Paragraph 0371; 0373; 0374. . Retrieved 2018/11/03.
• 2、 -. "Preparation method of substituted indoles compounds". Paragraph 0015; 0016. . Retrieved 2016/10/07.