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Acryloylchlorid
prop-2-enoyl chloride · 2-PROPENOYL CHLORIDE · oyL · acrylyl chloride · Propenoyl chloride · ACRYLIC ACID CHLORIDE · chloridkyselinyakrylove · Acryloyl chloride, 97%, for synthesis, stabilized with p-Hydroxyanisole
Identifikatoren & physikalische Daten
| CAS No. | 814-68-6 |
|---|---|
| Summenformel | C3H3ClO |
| Durchschnittliche Molmasse | 90,51 g/mol |
| Monoisotopische Masse | 89,9872424 g/mol |
| SMILES | C=CC(=O)Cl |
| InChIKey | HFBMWMNUJJDEQZ-UHFFFAOYSA-N |
| PubChem CID | 13140 |
| EC No. | 212-399-0 |
| DTXSID | DTXSID1061150 |
| Lokaler Name | Acryloylchlorid |
Chemische & physikalische Eigenschaften
| XLogP | 1,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 57,9 |
| Stoffklassen | Toxic Gases & Vapors -> Acid HalidesFlammable agents - 3rd degree |
| SpringerMaterials Properties | Schoenflies notation |
| Dichte | 1.1136 at 68 °F (EPA, 1998) - Denser than waterwill sink1.1136 g/cu cm at 20 °C1.189 @ 20°C1.114 g/mL at 25 °C (lit.) |
| Color/Form | LiquidLight yellow liquid |
| Löslichkeit | Soluble in chlorinated solventsVery soluble in chloroformChloroform (Soluble), Methanol (Slightly)Miscible with water. |
| Corrosivity | Corrosive to metals |
| Flammpunkt | 14 °C (57 °F) - closed cup61 °F |
| Siedepunkt | 167 °F at 760 mmHg (EPA, 1998)75.5 °C73 °C @760 [mm Hg]72-76 °C (lit.) |
| Decomposition | Hazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen chloride gas.When heated to decomposition it emits toxic fumes of /chloride/. |
| Schmelzpunkt | -90 °C76 °C(Solv: isopropyl ether (108-20-3)) |
| Dampfdichte | 3.63 (Air = 1)>1 (vs air) |
| Polymerization | A 500 mL bottle of the acid chloride stabilized with 0.5% of phenothiazine was shipped to a hot climate without refrigeration, and was stored on arrival in a fume cupboard for 2 days at temperatures approaching 50 °C. The material polymerized, bursting the bottle and forming a solid foam. |
| Dampfdruck | 1.93 psi ( 20 °C) |
| Brechungsindex | n20/D 1.435(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Oil |
| Farbe | Colourless to Pale Yellow |
| BRN | 635744 |
| Stabilität | Stable, but reacts violently with water. Incompatible with alcohols, oxidizing agents, strong bases. Light-sensitive. Highly flammable. |
| InChI | 1S/C3H3ClO/c1-2-3(4)5/h2H,1H2 |
| InChIKey | HFBMWMNUJJDEQZ-UHFFFAOYSA-N |
| SMILES | ClC(=O)C=C |
| CAS Datenbank | 814-68-6(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propenoyl chloride(814-68-6) |
| EPA chemische Informationen | Acrylyl chloride (814-68-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P234, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P362+P364, P363, P370+P378, P390, P391, P403+P233, P403+P235, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 158 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoyl chlorideStatus: Active Update: 06-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/21453Acryloyl chloride: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Propenoyl chloride: Human health tier I assessment |
| DOT-Kennzeichnung | Flammable Liquid Corrosive |
| Brandgefahren | When heated to decomposition, it emits toxic fumes of chlorides. Decomposes in water. (EPA, 1998) |
| Brandpotenzial | Flammable liquid. |
| Gesundheitsgefahren | Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: |
| Gefahrenübersicht | Produces acrylic acid when contacts water[HSDB] Reacts violently with water and lightA lachrymatorA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis and pulmonary edema[MSDSonline] |
| Reaktive Gruppe | Acyl Halides, Sulfonyl Halides, and Chloroformates |
Anwendungen & Verwendung
Verwenden
Acryloyl chloride is used in the production of plastics. It plays an important role in the preparation of acrylate monomers and polymers. It also acts as a substrate for cross-metathesis. Further, it is utilized in organic synthesis for the introduction of acrylic groups into other compounds.