tert-Butyl 1-(Chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

Base Information

• Chemical Name: tert-Butyl 1-(Chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate
• CAS No.: 454713-41-8
• Molecular Formula: C18H20ClNO2
• Molecular Weight: 317.8099
• DSSTox Substance ID: DTXSID20431918
• Mol file: 454713-41-8.mol

Synonyms:454713-41-8;N-Boc-1-chloromethyl-1,2-dihydro-3H-benzo[e]indole;tert-Butyl 1-(Chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate;tert-butyl 1-(chloromethyl)-1,2-dihydrobenzo[e]indole-3-carboxylate;tert-Butyl 1-(chloromethyl)-1H-benzo[e]indole-3(2H)-carboxylate;SCHEMBL2398132;DTXSID20431918;FT-0663488

Chemical Property of tert-Butyl 1-(Chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

Chemical Property:

• Melting Point: 107-108 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 432.4±24.0 °C(Predicted)
• PKA: -0.72±0.40(Predicted)
• PSA: 29.54000
• Density: 1.206±0.06 g/cm3(Predicted)
• LogP: 4.98230
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 317.1182566
• Heavy Atom Count: 22
• Complexity: 420

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-1-chloromethyl-1,2-dihydro-3H-benzo[e]indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C2=C1C=CC3=CC=CC=C32)CCl
• Uses: N-Boc-1-chloromethyl-1,2-dihydro-3H-benzo[e]indole is used for the preparation of benzindole and benzoquinoline derivatives as prodrugs for tumor treatment.

Technology Process of tert-Butyl 1-(Chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate

There total 8 articles about tert-Butyl 1-(Chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 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: 97.0%

tert-butyl N-(1-bromo-2-naphthyl)-N-(3-chloroprop-2-enyl)carbamate (454713-48-5) → tert-butyl 1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (454713-41-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 18.17h; Heating / reflux;

Reference yield:

tert-butyl (1-bromonaphthalen-2-yl)carbamate (454713-47-4) → tert-butyl 1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (454713-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 2 h / 25 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 90 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/jm4000209

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate (454713-41-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 24 h / Inert atmosphere; Reflux

2.1: trifluoroacetic acid / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

3.2: 2 h / 25 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 90 °C / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/jm4000209

upstream raw materials:

tert-butyl N-(1-bromo-2-naphthyl)-N-(3-chloroprop-2-enyl)carbamate

di-tert-butyl dicarbonate

1-bromo-2-naphthylamine

bis(tert-butyl) 1-bromo-2-naphthyldicarbamate

Downstream raw materials:

C₂HF₃O₂*C₃₅H₃₇N₅O₁₀S₂

(7-(N-(2-hydroxyethyl)sulfamoyl)-5-nitro-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

(7-(N-(2-((di-tert-butoxyphosphoryl)oxy)ethyl)sulfamoyl)-3-(5-(2-morpholinoethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

(7-(N-(2-((di-tert-butoxyphosphoryl)oxy)ethyl)sulfamoyl)-3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate

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