benzyl 1H-indole-2-carboxylate

Base Information

• Chemical Name: benzyl 1H-indole-2-carboxylate
• CAS No.: 78277-27-7
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• DSSTox Substance ID: DTXSID40428885
• Wikidata: Q82241726
• Mol file: 78277-27-7.mol

Synonyms:benzyl 1H-indole-2-carboxylate;78277-27-7;Benzyl Indole-2-carboxylate;starbld0004888;Benzyl 2-indolecarboxylate;benzyl indole-2-carboxlate;SCHEMBL3964905;DTXSID40428885;GBVAGZMJJSANDQ-UHFFFAOYSA-N;HMS1739O18;AKOS000842709;NCGC00335199-01;1H-Indole-2-carboxylic acid benzyl ester;CS-0287656;FT-0760212;AB01118923-03;Z17755628

Chemical Property of benzyl 1H-indole-2-carboxylate

Chemical Property:

• PSA: 42.09000
• LogP: 3.52490
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 251.094628657
• Heavy Atom Count: 19
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

BENZYL-1H-INDOLE-2-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C2=CC3=CC=CC=C3N2

Technology Process of benzyl 1H-indole-2-carboxylate

There total 4 articles about benzyl 1H-indole-2-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: 94.0%

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) + benzyl alcohol (100-51-6,185532-71-2) → 1H-indole-2-carboxylic acid benzyl ester (78277-27-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 2.5h; Ambient temperature;

DOI:10.1021/jo00291a060

Reference yield: 93.0%

indole-2-carboxylic acid methyl ester (1202-04-6) + benzyl alcohol (100-51-6,185532-71-2) → 1H-indole-2-carboxylic acid benzyl ester (78277-27-7)

Guidance literature:

With N-methyl-N,N,N-trioctylammonium methylcarbonate; In hexane; for 3h; Reagent/catalyst; Molecular sieve; Reflux; Green chemistry;

DOI:10.1039/c7gc03858e

Reference yield: 85.0%

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → 1H-indole-2-carboxylic acid benzyl ester (78277-27-7)

Guidance literature:

With 1,1'-carbonyldiimidazole; benzyl alcohol; In tetrahydrofuran; ethyl acetate;

upstream raw materials:

Indole-2-carboxylic acid

benzyl alcohol

benzyl 2-aminoacetate hydrochloride

ortho-bromobenzaldehyde

Downstream raw materials:

C₂₇H₂₃NO₄

benzyl 3-formindole-2-carboxylate

(ii)-1-tert-Butoxycarbonylmethyl-1H-indole-2-carboxylic acid benzyl ester

(1'S,2''S,3''R,4''S)-2-<1--2-(4-imidazolyl)ethyl>-1,2,3,4-tetrahydropyrrolo<3,4-b>indol-3-one

Refernces

• 1、 -. "AMIDATION METHOD AND ESTERIFICATION METHOD USING SULFONIC ACID HALIDE". Paragraph 0038. . Retrieved 2017/01/17.
• 2、 Zhu, Zhiqiang,Yuan, Jiangjun,Zhou, Yirong,Qin, Yang,Xu, Jingshi,Peng, Yiyuan. "Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters". supporting information. p. 511 - 514. Retrieved 2015/10/05.