3-Chlorpropionylchlorid
3-Chloropropanoyl chloride · Chloropropionyl chloride · oropropionyL · 3-Chloropropionyl ch · 3-Chlorpropionylchlorid · -Chloropropanoylchloride · 3-Chloropropinyl chloride · 3-chloro-propanoylchlorid
Identifikatoren & physikalische Daten
| CAS No. | 625-36-5 |
|---|---|
| Summenformel | C3H4Cl2O |
| Durchschnittliche Molmasse | 126,97 g/mol |
| Monoisotopische Masse | 125,96392011 g/mol |
| SMILES | O=C(Cl)CCCl |
| InChIKey | INUNLMUAPJVRME-UHFFFAOYSA-N |
| PubChem CID | 69364 |
| EC No. | 210-890-4 |
| DTXSID | DTXSID5060801 |
| Lokaler Name | 3-Chlorpropionylchlorid |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 52,8 |
| Stoffklassen | Toxic Gases & Vapors -> Acid Halides |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| Physical Description | Clear light yellow liquid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | -32 °C |
| Siedepunkt | 143-145 °C(lit.) |
| Dichte | 1.33 g/mL at 25 °C(lit.) |
| Dampfdruck | 10.0 hPa |
| Brechungsindex | n20/D 1.457(lit.) |
| Flammpunkt | 146 °F |
| Lagerbedingungen | Flammables area |
| Löslichkeit | Chloroform, Ethyl Acetatereacts |
| Aggregatzustand | liquid |
| Farbe | red-brown |
| pH | <7 (H2O) |
| Explosionsgrenze | 8.8-20.2%(V) |
| BRN | 635814 |
| Stabilität | Moisture Sensitive |
| InChI | 1S/C3H4Cl2O/c4-2-1-3(5)6/h1-2H2 |
| InChIKey | INUNLMUAPJVRME-UHFFFAOYSA-N |
| CAS Datenbank | 625-36-5(CAS DataBase Reference) |
| NIST chemische Informationen | Propanoyl chloride, 3-chloro-(625-36-5) |
| EPA chemische Informationen | Propanoyl chloride, 3-chloro- (625-36-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH290 (68.9%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P264, P264+P265, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 180 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Propanoyl chloride, 3-chloro-Status: Active Update: 06-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/163383-Chloropropionyl chloride: HSNO Approval: HSR004261 Approved with controls |
| Gefahrenübersicht | Reacts violently with waterCauses burns and lachrymationInhalation may cause corrosive injuries to upper respiratory tract and lungsHighly toxic by inhalationHarmful by ingestion[Sigma-Aldrich MSDS] See Chloropivaloyl chloride and Trimethylacetyl chloride. |
| Hazard Classes and Categories | Met. Corr. 1 (68.9%) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Toxicity Data | LC50 (rat) = 1,000 mg/m3/1hr |
| F | 21 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3390 6.1/PG 1 |
| Zollcode | 29159080 |
| R-Sätze (R) | 14-22-26-34-35-10 |
| Gefahrensymbole | T+ |
| Sicherheitshinweise (S) | 23-26-36/37/39-45-38-16-8 |
Anwendungen & Verwendung
Beschreibung
3-Chloropropionyl chloride is an important bifunctional reagent. It is capable of acylation and possesses a 2-chloro-ethyl fragment (CH2CH2Cl), which can be subjected to nucleophilic substitution and serves as a masked vinyl group. It can be used as a starting material in many reactions to construct a variety of (hetero)cyclic compounds.
Verwenden
3-Chloropropionyl chloride is a reagent used in the synthesis of Beclamide (B119400), which is a chlorinated benzylpropanamide used as an anticonvulsant drug. It is used in the treatment of tonic-clonic seizyres and has sedative properties.
Herstellung & Synthese
synthetische
3-Chloropropionyl chloride (1) is commercially available and can be prepared from β-propiolactone (2) and thionyl chloride.1 Other standard methods available for the preparation of acyl chlorides can also be applied: the reaction of acrylic acid (3) or 3-chloropropionic acid (4) with thionyl chloride, phosphoryl chloride, phosgene, or phosphorus trichloride.