5-chloro-3-methyl-1H-indole

Base Information

• Chemical Name: 5-chloro-3-methyl-1H-indole
• CAS No.: 71095-42-6
• Molecular Formula: C9H8ClN
• Molecular Weight: 165.622
• Hs Code.: 2933990090
• European Community (EC) Number: 640-457-9
• DSSTox Substance ID: DTXSID50452050
• Nikkaji Number: J380.943I
• Wikidata: Q82272411
• Mol file: 71095-42-6.mol

Synonyms:5-chloro-3-methyl-1H-indole;71095-42-6;5-CHLORO-3-METHYLINDOLE;1H-Indole, 5-chloro-3-methyl-;3-Methyl-5-chloro-1H-indole;SCHEMBL4086846;DTXSID50452050;MWEBJGCQVFUVQL-UHFFFAOYSA-N;MFCD04972055;AKOS006294178;PS-5016;SB22083;5-Chloro-3-methyl-1H-indole, AldrichCPR;CS-0050527;FT-0692700;C-5161

Chemical Property of 5-chloro-3-methyl-1H-indole

Chemical Property:

• Melting Point: 112-114 °C
• Boiling Point: 302.6±22.0 °C(Predicted)
• PKA: 16.39±0.30(Predicted)
• PSA: 15.79000
• Density: 1.273±0.06 g/cm3(Predicted)
• LogP: 3.12970
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 165.0345270
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

NLT 98% ^*data from raw suppliers

5-Chloro-3-methyl-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CNC2=C1C=C(C=C2)Cl

Technology Process of 5-chloro-3-methyl-1H-indole

There total 2 articles about 5-chloro-3-methyl-1H-indole 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:

triisopropanolamine (122-20-3) + 4-chloro-aniline (106-47-8) → 5-chloro-2-methylindole (1075-35-0) + 5-chloro-3-methyl-1H-indole (71095-42-6)

Guidance literature:

With tin(ll) chloride; ruthenium trichloride; triphenylphosphine; In 1,4-dioxane; at 180 ℃; for 20h; Yield given. Yields of byproduct given;

DOI:10.1039/a801090k

Reference yield:

4-chlorobenzonitrile (100-00-5) → 5-chloro-3-methyl-1H-indole (71095-42-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate / N,N-dimethyl-formamide / 2.5 h / -24 °C

2: potassium carbonate / dimethyl sulfoxide

3: hydrogen / 24 h / 20 °C / 760.05 Torr / Schlenk technique

With potassium tert-butylate; hydrogen; potassium carbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.6b02659

Reference yield: 96.0%

5-chloro-3-methyl-1H-indole (71095-42-6) + methyl 4-phenyl-2-oxo-3-butenoate (107969-78-8,6395-86-4) → C20H18ClNO3 (1428236-52-5)

Guidance literature:

methyl 4-phenyl-2-oxo-3-butenoate; With copper(II) bis(trifluoromethanesulfonate); [3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]; In toluene; at 0 ℃; for 0.333333h; Inert atmosphere; Schlenk technique;

5-chloro-3-methyl-1H-indole; In toluene; at 0 ℃; for 18h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201209998

upstream raw materials:

triisopropanolamine

4-chloro-aniline

4-chlorobenzonitrile

Downstream raw materials:

5-chloro-3-methyl-1-(phenylsulfonyl)-1H-indole

C₂₀H₁₈ClNO₃

C₃₀H₃₀ClNO₅

1-benzyl-5-chloro-3-methyl-1H-indole

Refernces

• 1、 Cho, Chan Sik,Lim, Hyo Kyun,Shim, Sang Chul,Kim, Tae Jeong,Choi, Heung-Jin. "Ruthenium-catalysed synthesis of indoles from anilines and trialkanolamines in the presence of tin(II) chloride dihydrate". . p. 995 - 996. Retrieved 2007/10/03.