HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl itaconate
DIMETHYL 2-METHYLENESUCCINATE · DIMETHYL METHYLENESUCCINATE · Butanedioic acid, methylene-, dimethyl ester · C7H10O4 · 109533-100G · ized with HQ) · METHYL ITACONATE · Itaconate (stabiL
Identifiers & Physical Properties
| CAS No. | 617-52-7 |
|---|---|
| Molecular formula | C7H10O4 |
| Average molar mass | 158.15 g/mol |
| Monoisotopic mass | 158.0579088 g/mol |
| SMILES | C=C(CC(=O)OC)C(=O)OC |
| InChIKey | ZWWQRMFIZFPUAA-UHFFFAOYSA-N |
| PubChem CID | 69240 |
| ChEMBL | CHEMBL4750162 |
| EC No. | 210-519-6 |
| DTXSID | DTXSID80210701 |
Chemical & Physical Properties
| XLogP | 0.5 |
|---|---|
| Topological polar surface area | 52.6 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 5 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 183 |
| SpringerMaterials Properties | Boiling point |
| Melting point | 37-41 °C (lit.) |
| Boiling point | 208 °C (lit.) |
| Density | 1.124 g/mL at 25 °C (lit.) |
| Vapor pressure | 4.05Pa at 20℃ |
| Refractive index | 1.4457 (estimate) |
| Flash point | 213 °F |
| Storage conditions | under inert gas (nitrogen or Argon) at 2-8°C |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly)slightly soluble |
| Physical state | Crystalline Low Melting Mass or Liquid |
| Specific gravity | 1.124 |
| Color | White |
| BRN | 386674 |
| Cosmetics Ingredients Functions | HAIR CONDITIONINGSKIN PROTECTINGSKIN CONDITIONING - MISCELLANEOUSANTIOXIDANT |
| InChI | 1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3 |
| InChIKey | ZWWQRMFIZFPUAA-UHFFFAOYSA-N |
| SMILES | COC(=O)CC(=C)C(=O)OC |
| LogP (partition coefficient) | 0.86 at 25℃ |
| CAS DataBase Reference | 617-52-7(CAS DataBase Reference) |
| FDA UNII | 11JIB0YI93 |
| NIST Chemistry Reference | Butanedioic acid, methylene-, dimethyl ester(617-52-7) |
| EPA Substance Registry System | Butanedioic acid, 2-methylene-, 1,4-dimethyl ester (617-52-7) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H332-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Safety statements (S) | 24/25 |
| Water hazard class (WGK) | 3 |
| F | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29171900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Skin Irrit. 2Skin Sens. 1B |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 55.6% (5 of 9) of all reports.DangerH302 (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. |
|---|---|
| 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/16997Butanedioic 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 Categories | Acute Tox. 4 (22.2%) |
| F | 3 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29171900 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Safety statements (S) | 24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302-H315-H319-H332-H335 |
| REACH registrations | Active |
| Hazard class | Skin Irrit. 2Skin Sens. 1B |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
Applications & Uses
Uses
Dimethyl Itaconate is a chemical reagent used in the synthesis of functionalized 2-isoxazolines used in fragment-based drug discovery.
Uses
Dimethyl 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).
Uses
Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.
General Description
Dimethyl itaconate undergoes enantioselective Rh(I)-catalyzed hydrogenation which can be enhanced by appropriate choice of substituents on aromatic ring of (1,2-diarylphosphinoxy)cyclohexane.