Ethyl (2-ethynylphenyl)carbamate

Base Information

• Chemical Name: Ethyl (2-ethynylphenyl)carbamate
• CAS No.: 148550-52-1
• Molecular Formula: C11H11 N O2
• Molecular Weight: 189.214
• DSSTox Substance ID: DTXSID501295392
• Nikkaji Number: J1.647.503C
• Mol file: 148550-52-1.mol

Synonyms:Ethyl N-(2-ethynylphenyl)carbamate;148550-52-1;Ethyl (2-ethynylphenyl)carbamate;Carbamic acid, (2-ethynylphenyl)-, ethyl ester (9CI);DTXSID501295392;2-Ethynylphenylcarbamic acid ethyl ester

Chemical Property of Ethyl (2-ethynylphenyl)carbamate

Chemical Property:

• PSA: 38.33000
• LogP: 2.30930
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 241

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)NC1=CC=CC=C1C#C

Technology Process of Ethyl (2-ethynylphenyl)carbamate

There total 6 articles about Ethyl (2-ethynylphenyl)carbamate 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: 96.0%

ethyl N-[2-(trimethylsilylethynyl)phenyl]carbamate (104919-71-3) → ethyl N-(2-ethynylphenyl)carbamate (148550-52-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jo035528b

Reference yield: 89.0%

ethyl (2-(3-hydroxy-3-methylbut-1-yn-1-yl)phenyl)carbamate (1448422-99-8) → ethyl N-(2-ethynylphenyl)carbamate (148550-52-1)

Guidance literature:

With potassium phosphate; potassium hydroxide; In toluene; Inert atmosphere; Reflux;

DOI:10.1080/00397911.2012.744841

Reference yield: 75.0%

2-ethynylaniline (52670-38-9) + chloroformic acid ethyl ester (541-41-3) → ethyl N-(2-ethynylphenyl)carbamate (148550-52-1)

Guidance literature:

With pyridine; for 1h; Ambient temperature;

DOI:10.1080/00397919308009831

upstream raw materials:

2-ethynylaniline

chloroformic acid ethyl ester

ethyl N-[2-(trimethylsilylethynyl)phenyl]carbamate

N-ethoxycarbonyl-2-iodoaniline

Downstream raw materials:

ethyl 1H-indole-1-carboxylate

methyl 5-amino-4-{[2-(ethoxycarbonylamino)phenyl]ethynyl}-7-methyl-2-(methylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

indole

ethyl (E)-3-benzylidene-3,4-dihydro-4-oxo-2-phenylquinoline-1(2H)-carboxylate

Refernces

• 1、 Smeyanov, Alexey,Schmidt, Andreas. "K3PO4-KOH mixture as efficient reagent for the deprotection of 4-aryl-2-methyl-3-butyn-2-ols to terminal acetylenes". supporting information. p. 2809 - 2816. Retrieved 2013/08/23.
• 2、 Hiroya, Kou,Itoh, Shin,Sakamoto, Takao. "Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis". . p. 1126 - 1136. Retrieved 2007/10/03.