4652-27-1

Basic information

• Product Name: 4-METHOXY-3-BUTEN-2-ONE
• Synonyms: 4-METHOXY-3-BUTEN-2-ONE;TRANS-1-METHOXY-1-BUTEN-3-ONE;TRANS-4-METHOXY-3-BUTEN-2-ONE;4-methoxybut-3-en-2-one;4-Methoxy-3-buten-2-one, tech., 90%;4-Methoxy-3-buten-2-one, 90%,tech;1-Methoxy-1-buten-3-one;2-Methoxyvinyl methyl ketone
• CAS NO: 4652-27-1
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• EINECS: 257-364-0
• Mol File: 4652-27-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 200 °C(lit.)
• Flash Point: 146 °F
• Appearance: Clear yellow/Liquid
• Density: 0.982 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.332mmHg at 25°C
• Refractive Index: n20/D 1.468(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with tetrahydrofuran, ether, acetonitrile and benzene.
• BRN: 1741053
• CAS DataBase Reference: 4-METHOXY-3-BUTEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-3-BUTEN-2-ONE(4652-27-1)
• EPA Substance Registry System: 4-METHOXY-3-BUTEN-2-ONE(4652-27-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 4652-27-1(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

4-Methoxy-3-buten-2-one is an important precursor for the synthesis of 1-methoxy-3-trimethylsilyloxy-1,3-butadiene and the Danishefsky diene and its equivalent. It is widely used as a reactant in the synthesis of hydroisoquinoline derivatives. It is employed as an intermediate for the synthesis of manzamine.

InChI:InChI=1/C5H8O2/c1-5(6)3-4-7-2/h3-4H,1-2H3/b4-3-

Upstream product

• 67-56-1 methanol 
• 999-69-9 4-methoxycarbonyloxy-but-3-en-2-one 
• 4643-20-3 (E)-4-chloro-3-buten-2-one 
• 54125-02-9 danishefsky's diene 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 593-60-2 Vinyl bromide 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 
• 77-78-1 dimethyl sulfate 
• 34713-70-7 2-Phenylpropanal 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 
• 2798-73-4 (Z)-1-methoxybut-1-en-3-yne 
• 67-64-1 acetone 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 6051-55-4 (3E)-4-morpholinyl-3-buten-2-one 
• 108-52-1 4-Methyl-pyrimidin-2-ylamin 
• 3652-91-3 2-methyl-9H-carbazole 
• 5844-71-3 3-bromo-4,4-dimethoxybutan-2-one 
• 5436-21-5 acetylacetaldehyde dimethyl acetal 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 74628-04-9 (1Z,4E)-1-Cyclohexyl-1-hydroxy-5-methoxy-penta-1,4-dien-3-one 
• 1196-67-4 3-phenyl-2-butenal 
• 779-90-8 1,3,5-triacetylbenzene 
• 698981-92-9 2,7-dimethyl-5,6,7,8-tetrahydroquinoline-5-one 
• 1468-83-3 1-(thiophen-3-yl)-ethanone 
• 13858-95-2 1-(3-phenylisoxazol-4-yl)ethan-1-one 
• 21860-07-1 methyl 3-acetylbenzoate 
• 53133-41-8 4-(benzylamino) but-3-en-2-one 

Relevant articles and documents

High Pressure Reaction of 1-Methoxy-3-trialkylsiloxybuta-1,3-diene with Aldehydes. Cycloaddition or Silicon Migration Reaction

The high pressure reaction of Danishefsky's diene with aromatic aldehydes produces the cycloadduct, while with an aliphatic aldehyde such as 2-phenylpropionaldehyde the intermolecular silicon migration from oxygen to oxygen takes place.

Identification and synthesis of elymniafuran, a new monoterpene from the butterfly elymnias thryallis

The main constituent of the scent gland secretion of the tropical butterfly Elymnias thryallis (Lepidoptera: Satyridae) could be identified as (S)-2-methyl-1-(4-methyl-2-furyl)-3-buten-2-ol (elymniafuran, 3). It is accompanied by small amounts of (E)- and (Z)-4-methyl-(2-methyl-1,3-butadienyl)-furan (4) as well as the spiro acetal 3,9-dimethyl-1,6-dioxaspiro[4.5]dec-3-ene (10). The structural assignment of these new natural products as well as the synthesis and enantiomeric separation by chiral gas chromatography are described. VCH Verlagsgesellschaft mbH, 1996.

CYCLOADDITION OF 1-METHOXY-3-TRIMETHYLSILYLOXYBUTADIENE WITH HALOGENATED CARBONYL COMPOUNDS

Cycloadditions of 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (1) with halogenated carbonyl compounds (2) yielded corresponding substituted tetrahydro- and/or dihydropyran-4-ones (3 and/or 4).Lewis acids were found to be effective as catalysts.Reactions with less reactive carbonyl compounds (2c,d) afforded p-hydroxyacetophenone (5) produced by cyclodimerization of 1.Stereochemistry of the adducts was deduced by 1H nmr spectroscopy.