2-Naphthyl propiolate

Base Information

• Chemical Name: 2-Naphthyl propiolate
• CAS No.: 91805-17-3
• Molecular Formula: C₁₃H₈O₂
• Molecular Weight: 196.205
• Mol file: 91805-17-3.mol

Synonyms:naphthalen-2-yl prop-2-ynoate

Chemical Property of 2-Naphthyl propiolate

Chemical Property:

• Melting Point: 65-72°C

Purity/Quality:

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

Naphthalen-2-ylPropiolate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 51
• Safety Statements: 53-61

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Naphthyl propiolate

There total 5 articles about 2-Naphthyl propiolate 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%

β-naphthol (135-19-3) + Propiolic acid (471-25-0) → naphthalen-2-yl prop-2-ynoate (91805-17-3)

Guidance literature:

β-naphthol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃;

Propiolic acid; With dicyclohexyl-carbodiimide; In tetrahydrofuran; mineral oil; at 0 - 18 ℃; for 16h;

DOI:10.1021/acs.joc.0c02011

Reference yield: 36.0%

2-naphthyl chloroformate (7693-50-7) + sodium propargylate (920-38-7) → naphthalen-2-yl prop-2-ynoate (91805-17-3) + di(naphthalen-2-yl) carbonate (89784-86-1)

Guidance literature:

In tetrahydrofuran; at 25 - 65 ℃; for 4h;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<1022::AID-HLCA1022>3.0.CO;2-Y

Reference yield:

β-naphthol (135-19-3) → naphthalen-2-yl prop-2-ynoate (91805-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / N,N,dimethylaniline / toluene / 12 h / 0 - 20 °C

2: 36 percent / tetrahydrofuran / 4 h / 25 - 65 °C

With N,N-dimethyl-aniline; In tetrahydrofuran; toluene; 1: Acylation / 2: Substitution;

DOI:10.1002/(SICI)1522-2675(20000510)83:5<1022::AID-HLCA1022>3.0.CO;2-Y

upstream raw materials:

2-naphthyl chloroformate

sodium propargylate

β-naphthol

Propiolic acid

Downstream raw materials:

(1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate

Refernces

• 1、 -. "A synthesis method of V-type organic ligand is disclosed. Synthetic V-type organic ligand and application thereof". Paragraph 0038-0043. . Retrieved 2021/09/08.
• 2、 Okamoto, Kazuhiro,Hayashi, Tamio,Rawal, Viresh H.. "Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines". supporting information; experimental part. p. 4815 - 4817. Retrieved 2009/12/08.