13831-03-3

Basic information

• Product Name: TERT-BUTYL PROPIOLATE
• Synonyms: Propynoic acid tert-butyl ester;Propargylic Acid tert-Butyl Ester Propiolic Acid tert-Butyl Ester;tert-butyl prop-2-ynoate;2-Propynoic acid,1,1-diMethylethyl ester;PROPARGYLIC ACID TERT-BUTYL ESTER;PROPIOLIC ACID TERT-BUTYL ESTER;TERT-BUTYL ACETYLENECARBOXYLATE;TERT-BUTYL PROPIOLATE
• CAS NO: 13831-03-3
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.15
• Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 13831-03-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 18-20 °C(lit.)
• Boiling Point: 52-53 °C27 mm Hg(lit.)
• Flash Point: 82 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.919 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.48mmHg at 25°C
• Refractive Index: n20/D 1.418(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Air Sensitive
• BRN: 1747175
• CAS DataBase Reference: TERT-BUTYL PROPIOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL PROPIOLATE(13831-03-3)
• EPA Substance Registry System: TERT-BUTYL PROPIOLATE(13831-03-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• F: 4.5-10-23
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 13831-03-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13831-03-3 differently. You can refer to the following data:
1. TERT-BUTYL PROPIOLATE is used to prepare heterocycles,1,2 alkaloids,3 and unsaturated amino acids.4
2. tert-Butyl propiolate may be used in the preparation of heterocycles, alkaloids, and unsaturated amino acids.

General Description

tert-Butyl propiolate is an ester. It reacts with methimazole to afford tert-butyl (E)-3-(1-methyl-1H-imidazol-2-ylthio) acrylate. Crystallographic data for the lithium enolate of tert-butyl propiolate has been described..

InChI:InChI=1/C7H10O2/c1-5-6(8)9-7(2,3)4/h1H,2-4H3

Upstream product

• 115-11-7 isobutene 
• 471-25-0 Propiolic acid 
• 540-88-5 acetic acid tert-butyl ester 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 618881-57-5 4-[(1-benzyloxymethyl-2-methylpropyl)hydroxyamino]-6-methylhept-2-ynoic acid tert-butyl ester 
• 69225-39-4 benzene-1,3,5-tricarboxylic acid tri-tert-butyl ester 
• 69225-38-3 benzene-1,2,4-tricarboxylic acid tri-tert-butyl ester 
• 170989-64-7 tert-butyl 4-hydroxy-4-(4-methoxycarbonyl-6-nitrophenyl)-2-butynoate 
• 352566-53-1 [NiBr(C(CO₂(t-Bu))CHC₆H₄CH₂PPh₂)(triethylphosphine)] 
• 352566-54-2 [NiBr(CHC(CO₂(t-Bu))C₆H₄CH₂PPh₂)(triethylphosphine)] 
• 167114-12-7 Cu₂(CCCO₂C(CH₃)3)2(P(C₆H₅)3)3 
• 1338045-59-2 C₁₆H₂₄O₃ 

Relevant articles and documents

Palladium-Catalyzed Regio- and Stereoselective Coupling-Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes

A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling-addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized (E)-vinylsulfones in satisfactory yields. Arylsulfonyl hydrazides act as both aryl and sulfonyl sources via selective cleavage of Ar(C)-S and S-N bonds, which are simultaneously incorporated onto the terminal carbon atom of an alkyne molecule.

Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives

Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.

Preparation of 3-bromopropiolic esters:methyl and tert-butyl 3-bromopropiolates

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