METHYL 2 3-BUTADIENOATE
- Product Name
- METHYL 2 3-BUTADIENOATE
- CAS No.
- 18913-35-4
- Chemical Name
- METHYL 2 3-BUTADIENOATE
- Synonyms
- SKL226;METHYL 2 3-BUTADIENOATE;Methyl buta-2,3-dienoate;2,3-Butadienoic acid, methyl ester
- CBNumber
- CB5500161
- Molecular Formula
- C5H6O2
- Formula Weight
- 98.1
- MOL File
- 18913-35-4.mol
METHYL 2 3-BUTADIENOATE Property
- Melting point:
- 115 °C(Solv: benzene (71-43-2))
- Boiling point:
- 59-60 °C(Press: 52 Torr)
- Density
- 0.905±0.06 g/cm3(Predicted)
- form
- liquid
- color
- colorless
Safety
- Hazard Codes
- Xn
- Risk Statements
- 36/37/38-42/43
- Safety Statements
- 26-36-45
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
METHYL 2 3-BUTADIENOATE Chemical Properties,Usage,Production
Uses
Methyl 2,3-Butadienoate is used as an reactive electrophilic reagents for nucleophilic addition, Michael addition, [2 + 2], [2 + 3], and [2 + 4] cycloadditions, and hetero-Cope rearrangements.
Preparation
Methyl 2,3-Butadienoate is most conveniently obtained via a Wittig reaction of [E(R)CHPPh3]+X- or E(R)C=PPh3 and RR′CHCOCl (R, R′ = H, alkyl) in the presence of Triethylamine in CH2Cl2.[1]Alternatively, the Wittig reaction can be performed with the corresponding ketenes.[2]
Synthesis Reference(s)
Tetrahedron Letters, 13, p. 4249, 1972 DOI: 10.1016/S0040-4039(01)94287-X
storage
Methyl 2,3-Butadienoate can undergo polymerization and so should be stored in the presence of hydroquinone. For best results, it should be freshly distilled. Use in a fume hood.
Purification Methods
Purification of Methyl 2,3-Butadienoate: rapid distillation under reduced pressure in a short-path distillation apparatus or column chromatography on Alox N with hexane/Et2O (9:1). Hydroquinone may be added for distillation.
References
1. (a) Lang, R. W.; Hansen, H.-J. HCA 1980, 63, 438. (b) Lang, R. W.; Hansen, H.-J. OS 1984, 62, 202
2. Hamlet, Z.; Barker, W. D. S 1970, 543.
METHYL 2 3-BUTADIENOATE Preparation Products And Raw materials
Raw materials
Preparation Products
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