Methyl butadienecarboxylate
Basic information
- CAS
1515-75-9- Standard SMILES
C=CC=CC(=O)OC- InChIKey
LJDLNNZTQJVBNJ-UHFFFAOYSA-N- Molecular formula
- C6H8O2
- Average molar mass
- 112.13 g/mol
- Monoisotopic mass
- 112.05242949
Names & identifiers
- Preferred name
- Methyl butadienecarboxylate
- IUPAC
- methyl penta-2,4-dienoate
- English name
- 1,3-Butadiene-1-carboxylic acid methyl ester
- Molecular formula
- C6H8O2
- Molecular weight
- 112.13
Names & synonyms
methyl butadienecarboxylate2,4-Pentadienoic acid, methyl esterMethyl 2,4-pentadienoateSCHEMBL1408458LJDLNNZTQJVBNJ-UHFFFAOYSA-NDTXSID901294108methyl (2Z)-penta-2,4-dienoate2,4-Pentadienoic acid methyl esterpenta-2,4-dienoic acid methyl esterNS00044329F849388METHYL PENTANEDIENOATE
Show more names
methyl penta-2,4-dienoateDimethyl-2,4-pentandioate(E)-Methyl 2,4-PentadienoateVynilacrylic acid methyl esterMETHYL 1,3-BUTADIENE-1-CARBOXYLATE1,3-Butadiene-1-carboxylic acid methyl estermethyl 1,3-butadiene-1-carboxylate mixt. of cis/trans
Database identifiers
- CAS
1515-75-9- PubChem CID
- 73688
- DTXSID
DTXSID901294108
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 114
Physicochemical properties
- Boiling point
- 50 · 50-52 °C20 mm Hg(lit.)
- Density
- 0.964 g/mL · 0.964 g/mL at 20 °C
- refractive index
- 20 · n20/D 1.484
- Flash point
- 37 °C · 37 °C
- storage temp.
- -20 °C · -20°C
- solubility
- sol most organic solvents
- form
- liquid
- Appearance
- Colorless to light yellow Liquid
- BRN
- 1743332 · 1743332
- InChI
- 1S/C6H8O2/c1-3-4-5-6(7)8-2/h3-5H,1H2,2H3
- InChIKey
- LJDLNNZTQJVBNJ-UHFFFAOYSA-N
- SMILES
- COC(=O)C=CC=C
- LogP
- 1.34 · 1.340 (est)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 3272 3/PG 3
- hs_code
- 29161995
- risk_code
- 10-36/37/38-52/53
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xi
- safety_code
- 26-36-61
- hazard_class
- 3.2
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H226-H315-H319-H335-H412
- Hazard Classifications
- Aquatic Chronic 3Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P273-P305+P351+P338
Chemistry & industry
Applications
Uses1,3-BUTADIENE-1-CARBOXYLIC ACID METHYL ESTER is used as a electron-poor diene capable of cycloaddition reactions with activated dienophiles to form carbocyclic and heterocyclic compounds; metal-promoted [6 + 4] cycloadditions and metal-promoted chain extensions.
General DescriptionMethyl 2,4-pentadienoate undergoes Aza-Morita-Baylis-Hillman reaction with aldimines in DMF in the presence of 3-hydroxyquinuclidine.
Preparation methods
Preparation1,3-BUTADIENE-1-CARBOXYLIC ACID METHYL ESTER is prepared by Wittig alkenation of Acrolein with (Methoxycarbonylmethylene)triphenylphosphorane; reaction of Malonic Acid with acrolein, followed by esterification.
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Related reactions
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Compound notes
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