Butyrylchlorid
N-BUTYRYL CHLORIDE · BUTANOYL CHLORIDE · butyryl · BUTYRIC ACID CHLORIDE · N-BUTYLVINYLETHER · BUTYROYL CHLORIDE · N-Butyryl · Butyrylchlorid
Identifikatoren & physikalische Daten
| CAS No. | 141-75-3 |
|---|---|
| Summenformel | C4H7ClO |
| Durchschnittliche Molmasse | 106,55 g/mol |
| Monoisotopische Masse | 106,01854252 g/mol |
| SMILES | CCCC(=O)Cl |
| InChIKey | DVECBJCOGJRVPX-UHFFFAOYSA-N |
| PubChem CID | 8855 |
| ChEMBL | CHEMBL1300263 |
| EC No. | 205-498-5 |
| DTXSID | DTXSID5024710 |
| Lokaler Name | Butyrylchlorid |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 51,5 |
| Stoffklassen | Toxic Gases & Vapors -> Other Toxic Gases & VaporsFlammable agents - 3rd degree |
| SpringerMaterials Properties | Coriolis coupling |
| Geruch | Pungent acid chloride odorSharp odor |
| Dichte | 1.0277 at 68 °F (USCG, 1999) - Denser than waterwill sink1.0263 at 20.6 °C/4 °C1.026 g/mL at 25 °C(lit.) |
| Color/Form | Colorless liquid |
| Löslichkeit | Reaction (NTP, 1992)Dissolves slowly with decomposition in waterDissolves slowly with decomposition in alcoholmiscible with etherMiscible with ether.decomposes |
| Corrosivity | Corrosive to metals |
| Flammpunkt | 71 °F (NTP, 1992)18 °C (64 °F) - closed cup |
| Siedepunkt | 216 °F at 760 mmHg (NTP, 1992)101-102 °C102 °C(lit.) |
| Decomposition | Dissolves slowly with decomposition in water, alcohol. |
| Schmelzpunkt | -128 °F (NTP, 1992)-89 °C−89 °C(lit.) |
| Dampfdichte | 3.67 (vapor specific gravity)3.7 (vs air) |
| Dampfdruck | 39 hPa (20 °C) |
| Brechungsindex | n20/D 1.412(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear slightly yellow |
| Geruch | pungent odor |
| Explosionsgrenze | 2.5-7.3%(V) |
| Merck | 14,1598 |
| BRN | 605395 |
| InChI | 1S/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3 |
| InChIKey | DVECBJCOGJRVPX-UHFFFAOYSA-N |
| SMILES | CCCC(Cl)=O |
| LogP (Verteilungskoeffizient) | 0.51 at 25℃ |
| CAS Datenbank | 141-75-3(CAS DataBase Reference) |
| NIST chemische Informationen | Butanoyl chloride(141-75-3) |
| EPA chemische Informationen | Butanoyl chloride (141-75-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P234, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P390, P403+P233, P403+P235, P405, P406, and P501 (click each P-code to see the statement) |
|---|---|
| Hazards Identification | Water-reactive material (WR) |
| Regulatorische Informationen | Chemical: Butanoyl chlorideStatus: Active Update: 02-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5853Butyryl 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 - Butanoyl chloride: Human health tier I assessment |
| DOT-Kennzeichnung | Flammable Liquid Corrosive |
| Brandgefahren | Special Hazards of Combustion Products: Emits toxic fumes of chlorine gas (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | Flammable ... . |
| Gesundheitsgefahren | Extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Inhalation may cause death as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
Anwendungen & Verwendung
Verwenden
Butyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone. It is also used as an acylation reagent. Further, it is used in the preparation of peroxides such as benzoyl peroxide, benzophenone and t-butyl perbenzoate. In addition to this, it is involved in the preparation of chromones and antiproliferative agents. Butyryl chloride has been used to esterify wood meal dissolved in the ionic liquid, 1-butyl-3-methylimidazolium chloride.
Herstellung & Synthese
synthetische
Butyryl chloride is obtained by the reaction of butyric acid with thionyl chloride. Heat the thionyl chloride to reflux, add butyric acid dropwise over approximately 4 hours, reflux for another hour, then distill. Collect the fraction at 95–115°C, redistill once, and collect the fraction at 101–105°C to obtain the final product, with a yield of over 70%. Phosphorus trichloride can also be added to the reaction, yielding a 75% yield.