2-CHLORO-1H-INDOLE-3-CARBALDEHYDE

Base Information

• Chemical Name: 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE
• CAS No.: 5059-30-3
• Molecular Formula: C9H5ClNO
• Molecular Weight: 179.606
• Hs Code.: 2933990090
• Mol file: 5059-30-3.mol

Synonyms:Indole-3-carboxaldehyde,2-chloro- (7CI,8CI);2-Chloro-1H-indole-3-carboxaldehyde;2-Chloro-3-formylindole;2-Chloroindole-3-carbaldehyde;2-Chloroindole-3-carboxaldehyde;NSC 234522;

Chemical Property of 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE

Chemical Property:

• Vapor Pressure: 1.66E-05mmHg at 25°C
• Melting Point: ca 212℃
• Refractive Index: 1.731
• Boiling Point: 364.7 °C at 760 mmHg
• PKA: 13.90±0.30(Predicted)
• Flash Point: 174.3 °C
• PSA: 32.86000
• Density: 1.431 g/cm³
• LogP: 2.63380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloroindole-3-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is used as pharmaceutical intermediates. It is used in the synthesis of indole phytoalexin cyclobrassinon. And also in unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum.

Technology Process of 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE

There total 12 articles about 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE 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: 80.0%

2-oxoindole (59-48-3) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-chloroindole-3-carboxaldehyde (5059-30-3)

Guidance literature:

With pyridine; trichlorophosphate; In chloroform; at 20 ℃; for 48h;

DOI:10.1055/s-0030-1259298

Reference yield: 67.0%

1-tosyloxyindole (134792-58-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-chloroindole-3-carboxaldehyde (5059-30-3)

Guidance literature:

With trichlorophosphate; at 0 - 20 ℃;

DOI:10.3987/COM-07-S(U)31

Reference yield: 65.0%

2-chloro-1H-indole (7135-31-1) + trimethylamine (75-50-3) → 2-chloroindole-3-carboxaldehyde (5059-30-3)

Guidance literature:

With tetrabutyl ammonium fluoride; water; at 80 ℃; for 28h; Electrolysis; Inert atmosphere; Green chemistry;

DOI:10.1039/d1gc00661d

upstream raw materials:

1-methoxyindole

N,N-dimethyl acetamide

1-(t-butyldimethylsilyloxy)indole

1H-indol-1-yl benzoate

Downstream raw materials:

2-Imino-9H-1,3-thiazino[6,5-b]indole

2-Chloro-1-(3,4-dichloro-benzyl)-1H-indole-3-carbaldehyde

2-Chloro-1-(2,4-dichloro-benzyl)-1H-indole-3-carbaldehyde

1-(2-Chlorobenzyl)-2-chloroindole-3-carboxaldehyde

Refernces

• 1、 Majumder, Swarup,Bhuyan, Pulak J.. "Stereoselective synthesis of novel annulated thiopyrano indole derivatives from simple oxindole via intramolecular 1,3-dipolar cycloaddition reactions of nitrone and nitrile oxide". . p. 762 - 764. Retrieved 2012.
• 2、 Cheng, Didi,Li, Jingyi,Li, Yujin,Ling, Fei,Liu, Lei,Liu, Tao,Zhong, Weihui. "Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source". supporting information. p. 4107 - 4113. Retrieved 2021/06/17.
• 3、 -. "INDOLE-YNONE MEDIATED BENZOANNULATION PROCESS FOR THE PREPARATION OF CARBAZOLES- CARBAZOMYCIN A, CALOTHRIXIN B AND STAUROSPORINONE". Page/Page column 31-32. . Retrieved 2020/10/20.