Dimethyl itaconate
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Basic information
- CAS
617-52-7- Standard SMILES
C=C(CC(=O)OC)C(=O)OC- InChIKey
ZWWQRMFIZFPUAA-UHFFFAOYSA-N- Molecular formula
- C7H10O4
- Average molar mass
- 158.15 g/mol
- Monoisotopic mass
- 158.0579088
Overview
structure in first source
Names & identifiers
- Preferred name
- Dimethyl itaconate
- IUPAC
- dimethyl 2-methylidenebutanedioate
- English name
- Dimethyl itaconate
- Molecular formula
- C7H10O4
- Molecular weight
- 158.15
Names & synonyms
Dimethyl itaconate617-52-7Dimethylitaconatedimethyl 2-methylidenebutanedioate11JIB0YI93Butanedioic acid, 2-methylene-, 1,4-dimethyl esterNSC-9385DTXSID80210701NSC-385RefChem:134250DTXCID70133192210-519-6
Show more names
DIMETHYL METHYLENESUCCINATEC7H10O4109533-100Gized with HQ)METHYL ITACONATEDimethylitaconatItaconate (stabiL
Dimethyl 2-methylenesuccinate1,4-dimethyl 2-methylidenebutanedioateItaconic acid dimethyl esterButanedioic acid, methylene-, dimethyl esterItaconic acid, dimethyl esterCCRIS 7232EINECS 210-519-6MFCD00008446
Database identifiers
- CAS
617-52-7- PubChem CID
- 69240
- DTXSID
DTXSID80210701- ChEMBL
CHEMBL4750162- UNII
- 11JIB0YI93
- EC Number
- 210-519-6
- Nikkaji
- J45.119C
Properties
Computed structural propertiesFilling in
- XLogP
- 0.5
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 183
Experimental & physicochemical properties
SpringerMaterials PropertiesBoiling point
Physicochemical properties
- Melting point
- 37 · 37-41 °C (lit.)
- Boiling point
- 208 °C · 208 °C (lit.)
- Density
- 1.124 g/mL · 1.124 g/mL at 25 °C (lit.)
- vapor pressure
- 4.05 Pa · 4.05Pa at 20℃
- refractive index
- 1.4457 · 1.4457 (estimate)
- Flash point
- 213 °F · 213 °F
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Crystalline Low Melting Mass or Liquid
- Specific Gravity
- 1.124 · 1.124
- color
- White
- Water Solubility
- slightly soluble
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 55.6% (5 of 9) of all reports.
Danger
H302 (22.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 9 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Status: Active Update: 17-02-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/16997
Butanedioic acid, methylene-, dimethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (22.2%)
Safety data
- F
- 3
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2917190090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationButanedioic acid, 2-methylene-, 1,4-dimethyl ester: ACTIVE
Applications
UsesDimethyl Itaconate is a chemical reagent used in the synthesis of functionalized 2-isoxazolines used in fragment-based drug discovery.
UsesDimethyl itaconate may be used in functionalization of isotactic poly(propylene). It was used in crosslinking of polyesters: poly(isosorbide itaconate)and poly(isosorbide itaconate-co-succinate).
UsesDimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.
General DescriptionDimethyl itaconate undergoes enantioselective Rh(I)-catalyzed hydrogenation which can be enhanced by appropriate choice of substituents on aromatic ring of (1,2-diarylphosphinoxy)cyclohexane.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
76 records
Compound notes
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