TERT-BUTYL PROPIOLATE

Base Information

• Chemical Name: TERT-BUTYL PROPIOLATE
• CAS No.: 13831-03-3
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 29161995
• Mol file: 13831-03-3.mol

Synonyms:Propiolicacid, tert-butyl ester (6CI,8CI);2-Propynoic acid tert-butyl ester;Propiolicacid tert-butyl ester;tert-Butoxycarbonylacetylene;tert-Butyl propynoate;

Chemical Property of TERT-BUTYL PROPIOLATE

Chemical Property:

• Vapor Pressure: 2.48mmHg at 25°C
• Melting Point: 18-20 °C(lit.)
• Refractive Index: n20/D 1.418(lit.)
• Boiling Point: 159.597 °C at 760 mmHg
• Flash Point: 38.638 °C
• PSA: 26.30000
• Density: 0.96 g/cm³
• LogP: 0.96130
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl Propiolate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: TERT-BUTYL PROPIOLATE is used to prepare heterocycles,1,2 alkaloids,3 and unsaturated amino acids.4 tert-Butyl propiolate may be used in the preparation of heterocycles, alkaloids, and unsaturated amino acids.

Technology Process of TERT-BUTYL PROPIOLATE

There total 3 articles about TERT-BUTYL 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: 74.0%

isobutene (115-11-7,15220-85-6) + Propiolic acid (471-25-0) → tert-butyl prop-2-ynoate (13831-03-3)

Guidance literature:

With sulfuric acid; In diethyl ether; at -78 - 20 ℃;

DOI:10.1039/b407558g

Reference yield:

Propiolic acid (471-25-0) + tert-butyl alcohol (75-65-0) → tert-butyl prop-2-ynoate (13831-03-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; for 24h;

Reference yield:

acetic acid tert-butyl ester (540-88-5) + Propiolic acid (471-25-0) → tert-butyl prop-2-ynoate (13831-03-3)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c5cc04538j

upstream raw materials:

isobutene

Propiolic acid

acetic acid tert-butyl ester

tert-butyl alcohol

Downstream raw materials:

2-<(1-phenylsulfonyl)tryptophyl>-4-(tert-butoxycarbonyl)-7-keto-1,2,7,8,9,10-hexahydroisoquinoline

(E)-3-{[2-(1H-Indol-3-yl)-ethyl]-[5-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexa-1,3-dienylmethyl]-amino}-acrylic acid tert-butyl ester

benzene-1,3,5-tricarboxylic acid tri-tert-butyl ester

benzene-1,2,4-tricarboxylic acid tri-tert-butyl ester

Refernces

A novel synthetic approach to reserpine based upon amino-claisen rearrangements of zwitterionic N-vinylisoquinuclidenes

10.1021/jo00171a021

The research explores a new method for synthesizing reserpine, a complex alkaloid with significant pharmaceutical importance. The study aims to develop a general synthetic methodology for constructing the hydroisoquinoline core structure found in reserpine, using amino-Claisen rearrangements of zwitterionic N-vinylisoquinuclidenes. Key chemicals used in this research include N-(indolylethyl)isoquinuclidenes, ethyl propiolate, and tert-butyl propiolate. The researchers demonstrated that these rearrangements can efficiently produce cis-fused hydroisoquinolines, which are crucial intermediates in the synthesis of reserpine. They also showed that the resulting hydroisoquinoline derivatives can undergo Wenkert cyclization to form pentacyclic systems resembling the natural product skeleton of reserpine. The study concludes that the combination of zwitterionic amino-Claisen rearrangements and Wenkert-type cyclizations offers a promising and efficient route for constructing the complex reserpine skeleton, with potential for further optimization and application in the synthesis of other Rauwolfia alkaloids.