18913-35-4

Basic information

• Product Name: METHYL 2 3-BUTADIENOATE
• Synonyms: METHYL 2 3-BUTADIENOATE;Methyl buta-2,3-dienoate
• CAS NO: 18913-35-4
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.09994
• Mol File: 18913-35-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 115 °C(Solv: benzene (71-43-2))
• Boiling Point: 111.3°Cat760mmHg
• Flash Point: 34.6°C
• Appearance: /
• Density: 0.905g/cm³
• Vapor Pressure: 22.8mmHg at 25°C
• Refractive Index: 1.407
• CAS DataBase Reference: METHYL 2 3-BUTADIENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2 3-BUTADIENOATE(18913-35-4)
• EPA Substance Registry System: METHYL 2 3-BUTADIENOATE(18913-35-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 26-36-45
• Hazardous Substances Data: 18913-35-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 4249, 1972 DOI: 10.1016/S0040-4039(01)94287-X

InChI:InChI=1/C5H6O2/c1-3-4-5(6)7-2/h4H,1H2,2H3

Upstream product

• 67-56-1 methanol 
• 85415-22-1 trans-2,3-dibromo-1,4-dichloro-2-butene 
• 124-41-4 sodium methylate 
• 85415-23-2 1,1,1-trimethoxy-2,3-butadiene 
• 201230-82-2 carbon monoxide 
• 106-96-7 propargyl bromide 
• 132178-16-6 Methoxyvinylketene 

Downstream Products

• 4525-28-4 methyl (E)-3-methoxybut-2-enoate 
• 19735-89-8 3-methyl-1-phenylpyrazolin-5(4H)-one 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 68870-59-7 methyl 2-(3-(4-chlorophenyl)isoxazol-5-yl)acetate 
• 68870-58-6 methyl 3-(p-chlorophenyl)-5-methylisoxazole-4-carboxylate 
• 68870-57-5 3-(4-chloro-phenyl)-4-methyl-isoxazole-5-carboxylic acid methyl ester 
• 68870-60-0 [3-(4-chloro-phenyl)-isoxazol-4-yl]-acetic acid methyl ester 
• 70758-22-4 2-Isopropenyl-3-(toluene-4-sulfonylmethyl)-but-3-enoic acid methyl ester 
• 2065-28-3 methyl 5-methyl-3-phenylisoxazole-4-carboxylate 
• 30408-26-5 methyl 4-methyl-3-phenylisoxazole-5-carboxylate 
• 30408-28-7 (3-phenyl-isoxazol-4-yl)-acetic acid methyl ester 
• 30408-27-6 methyl 2-(3-phenylisoxazol-5-yl)acetate 
• 118171-19-0 1,2,3,5-tetrahydro-2-phenyl-3-(methylcarboxyl)-4H-1-benzazepin-4-one 
• 21422-40-2 methyl 1H-indole-2-acetate 

Relevant articles and documents

Retro-Ene Reactions in Acylallene Derivatives

Allenic esters and amides 4 undergo a retro-ene reaction to vinylketene (6) and an aldehyde or imine (5) under the conditions of flash vacuum thermolysis (FVT). The same products are obtained by FVT of cyclobutenones 7 via electrocyclic ring opening to alkoxy- or aminovinylketenes 3 and 1,3-rearrangement of ketenes 3 to allenes 4. All the intermediates and products were characterized by matrix isolation IR spectroscopy, and in the case of 4c the reaction was also monitored by online mass spectrometry. A lower temperature for the retro-ene reaction of 4c, eliminating an imine, than for 4a, eliminating formaldehyde, is in agreement with a lower calculated activation barrier (167 and 181 kJ mol-1, respectively, at the G2(MP2,SVP) level of theory). The allenic amide 11 undergoes an analogous retro-ene reaction to the (unobserved) vinylketene 13, the latter isomerizing to cyclohexenylacrolein 16 in a 1,5-H shift (calculated barrier 125 kJ mol-1; G2 (MP2, SVP)).

METHANOLYSIS OF VICINALLY SUBSTITUTED TETRAHALOGENOBUTENES

The methanolysis of Z,E-1,2,3,4-tetrabromo-1-butene in the presence of strong bases leads predominantly to the formation of the ortho ester 1,1,1-trimethoxy-2,3-butadiene and the ether-acetal 1,1,4-trimethoxy-2-butyne.In the case of E-2,3-dibromo-1,4-dichloro-2-butene it leads predominantly to the ortho ester.During the reaction 10-12 linear unsaturated products containing 1-3 methoxyl groups are formed as side products.