627-09-8

Basic information

• Product Name: PROPARGYL ACETATE
• Synonyms: 2-PROPYNYL ACETATE;PROPARGYL ACETATE;2-propyn-1-ol,acetate;3-Acetoxypropyne;aceticacidprop-2-ynylester;Propargyl alcohol acetate;propargylalcoholacetate;Acetic acid propargyl ester~2-Propyn-1-yl acetate
• CAS NO: 627-09-8
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• EINECS: -0
• Product Categories: C2 to C5;Carbonyl Compounds;Esters
• Mol File: 627-09-8.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 27-28 °C(lit.)
• Flash Point: 91 °F
• Appearance: Clear colorless/Liquid
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 14mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: Flammables area
• BRN: 1742046
• CAS DataBase Reference: PROPARGYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: PROPARGYL ACETATE(627-09-8)
• EPA Substance Registry System: PROPARGYL ACETATE(627-09-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22
• Safety Statements: 16-23-36/37
• RIDADR: UN 1992 3/PG 3
• WGK Germany: 3
• RTECS: UK5076000
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 627-09-8(Hazardous Substances Data)

Usage

Description

Propargyl acetate, also known as 3-butyn-1-ol acetate, is a clear colorless liquid with unique chemical properties. It is an organic compound that features a propargyl group (an alkyne group with a triple bond) attached to an acetate group. This combination of functional groups makes it a versatile building block in organic synthesis and a valuable intermediate in the production of various chemicals.

Uses

Used in Pharmaceutical Industry:
Propargyl acetate is used as a key intermediate for the synthesis of optically active γ-hydroxy α,β-unsaturated aldehydes, which are important in the development of pharmaceuticals with chiral centers. These aldehydes are crucial in the production of various drugs, including those used to treat chronic diseases and conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, propargyl acetate is used as a starting material for the production of homopropargyl alcohols. These alcohols are valuable building blocks in the synthesis of complex organic molecules, such as natural products and bioactive compounds, which have potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Polymer Science:
Propargyl acetate is also used in polymer science for the synthesis of poly(propargyl acetate), a specialty polymer with unique properties. This polymer has potential applications in various fields, such as coatings, adhesives, and composite materials, due to its thermal stability, mechanical strength, and chemical resistance.

InChI:InChI=1/C5H6O2/c1-3-4-7-5(2)6/h1H,4H2,2H3

Upstream product

• 108-24-7 acetic anhydride 
• 107-19-7 propargyl alcohol 
• 75-36-5 acetyl chloride 
• 74-99-7 prop-1-yne 
• 127-09-3 sodium acetate 
• 106-96-7 propargyl bromide 
• 64-19-7 acetic acid 
• 1067-60-3 triethyl-prop-2-ynyloxy-stannane 
• 26755-52-2 propargyl monobromoacetate 
• 141-78-6 ethyl acetate 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 17869-81-7 methoxy(prop-2-yn-1-yloxy)methane 

Downstream Products

• 116977-29-8 3-acetoxy-1-acetylsulfanyl-propene 
• 59051-15-9 1-acetoxy-2,3-bis-acetylsulfanyl-propane 
• 69337-36-6 acetic acid (3-phenyl-5-isoxazolyl)methyl ester 
• 91356-02-4 Dimethyl-<1-isopropyl-3-acetoxymethyl-2-propin-1-yl>-amin 
• 59192-73-3 1-Acetoxy-5-cyclohexyliden-pent-4-en-2-in 
• 37559-18-5 3-phenylprop-2-ynyl acetate 
• 137513-39-4 Acetic acid (E)-4-hydroxy-4-methyl-6-phenyl-hex-2-enyl ester 
• 84920-35-4 3-methyl-1-phenylhexa-4,5-dien-3-ol 
• 84920-36-5 3-methyl-1-phenylhex-5-yn-3-ol 
• 115261-70-6 Acetic acid 5,6-diphenyl-[1,4]dithiin-2-ylmethyl ester 
• 2327-99-3 1-phenylpropadiene 
• 10147-11-2 propargyl benzene 
• 52071-96-2 (Z)-3-phenylthio-2-propenyl acetate 
• 52071-97-3 (E)-3-phenylthio-2-propenyl acetate 

Relevant articles and documents

Cis and trans radicals generated in helical poly(propargyl acetate)s prepared using a [Rh(norbornadiene)Cl]2 catalyst

The poly(propargyl acetate) (A) having a helical cis-transoid structure was stereospecifically prepared using the Rh complex catalyst, [Rh(norbornadiene) Cl]2, in MeOH or NEt3 solvent at 0 and 40 °C in moderate yield. Electron spin resonance (ESR) analysis of the polymer revealed the formation of the cis (B) and trans (C) radicals which were produced through the thermal rotational scission of the helical cis CC bonds in the main-chain during the polymerization. The spatial and geometrical structure was successfully deduced using the two analogues' polymers in which either methyl or methylene group is deuterated, by the aide of computer simulation of the observed ESR spectra together with the calculation of spin density of the two radicals.

Simple One-Pot Preparation of 1,2-Diacetoxy-2-propene. A Convenient Precursor of 1-Acetoxy-3-chloro-2-propanone

From a neat mixture of acetic acid and propargyl alcohol, 1,2-diacetoxy-2-propene was prepared by successive treatment with an acid catalyst and a Ru catalyst in one-pot procedure.The product was a convenient precursor of 1-acetoxy-3-chloro-2-propanone.

Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles

Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).

Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition

A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).