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Basic information
- CAS
6018-41-3- Standard SMILES
COC(=O)c1ccc(=O)oc1- InChIKey
HHWWWZQYHPFCBY-UHFFFAOYSA-N- Molecular formula
- C7H6O4
- Average molar mass
- 154.12 g/mol
- Monoisotopic mass
- 154.02660867
Names & identifiers
- Preferred name
- Methyl coumalate
- IUPAC
- methyl 6-oxopyran-3-carboxylate
- English name
- Methyl coumalate
- Molecular formula
- C7H6O4
- Molecular weight
- 154.12
Names & synonyms
Methyl coumalateMethyl 2-oxo-2H-pyran-5-carboxylateCoumalic acid, methyl ester5-(Carbomethoxy)-2-pyroneMethyl 2-pyrone-5-carboxylateCoumalic acid methyl esterUNII-1S7TMF0R8T1S7TMF0R8TEINECS 227-871-1NSC 34627NSC 137387NSC-137387
Show more names
Methyl coumaric acidTIMTEC-BB SBB000117Methyl coumalate 98%Methyl Coumalate >5-(Carbomethoxy)-2-pyroneMETHYL PYR-2-ONE-5-CARBOXYLATE
METHYL CUMALATENSC-34627CUMALIC ACID METHYL ESTERDTXSID002089235-(METHOXYCARBONYL)-2-PYRONECOUMALIC ACID METHYL ESTER [MI]Glutaconic acid, 4-(hydroxymethylene)-, .delta.-lactone, methyl ester2H-Pyran-5-carboxylic acid, 2-oxo-, methyl ester (8CI)(9CI)
Database identifiers
- CAS
6018-41-3- PubChem CID
- 80113
- DTXSID
DTXSID00208923- UNII
- 1S7TMF0R8T
- EC Number
- 227-871-1
- Nikkaji
- J223.951E
Properties
Computed structural propertiesFilling in
- XLogP
- 0.4
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 249
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Melting point
- 65 · 65-67 °C (lit.)
- Boiling point
- 178 · 178-180 °C/60 mmHg (lit.)
- Density
- 1.1993 · 1.1993 (rough estimate)
- refractive index
- 1.43 · 1.4300 (estimate)
- Flash point
- 178 · 178-180°C/60mm
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Freely soluble in dichloromethane.
- form
- powder to crystal
- color
- White to Orange to Green
- Merck
- 14 · 14,2557
- BRN
- 126301 · 126301
- InChI
- InChI=1S/C7H6O4/c1-10-7(9)5-2-3-6(8)11-4-5/h2-4H,1H3
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
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2932209090
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334-H351b
- Precautionary statements
- P201-P202-P261-P272-P280g-P302+P352-P308+P313-P363-P403-P501c
Chemistry & industry
Applications
Usesα, β-Unsaturated ketone Methyl Coumalate showed cytotoxicity against human normal gingival fibroblast cells and oral squamous cell carcinoma cell line-2.
UsesMethyl coumalate is a 2-pyrone and acts as dienophile in Diels-Alder reaction. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts. It has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives.
UsesMethyl coumalate has been used as reagent in phosphine-catalyzed [4+3] annulation of modified allylic carbonates. It was also used in the preparation of 7-carboxyquinolizinium derivatives.
General DescriptionMethyl coumalate is a 2-pyrone and acts as dienophile in Diels-Alder reaction. It reacts with 1,3-butadienes at 100°C to yield tetrahydrocoumarins and 4-methoxycarbonyltricyclo[3.2.1.02,7]octenes. It also reacts with cyclohexadiene to afford tetrahydronaphthalene-2-carboxylate. It undergoes Diels-Alder reaction with unactivated alkenes to afford para-substituted adducts.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
8 records
Compound notes
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