Cyclopropylacetylene
ETHYNYLCYCLOPROPANE · CYCLOPROPYLACETYLENE · CPAC · Cylopropylethylnen · Cylopropyl acetylene · Cyclopropyl acetylen · Cyclopropylacethylene · Cyclopropane,ethynyl-
Identifikatoren & physikalische Daten
| CAS No. | 6746-94-7 |
|---|---|
| Summenformel | C5H6 |
| Durchschnittliche Molmasse | 66,1 g/mol |
| Monoisotopische Masse | 66,04695019 g/mol |
| SMILES | C#CC1CC1 |
| InChIKey | NPTDXPDGUHAFKC-UHFFFAOYSA-N |
| PubChem CID | 138823 |
| EC No. | 425-430-1 |
| DTXSID | DTXSID80217795 |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 69,3 |
| SpringerMaterials Properties | Coriolis coupling |
| Schmelzpunkt | 294 °C (decomp) |
| Siedepunkt | 79-80 °C |
| Dichte | 0.7801 |
| Brechungsindex | n20/D 1.4480 |
| Flammpunkt | -5 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform, Ethyl AcetateSlightly soluble in water. |
| Aggregatzustand | Liquid |
| Wichte | 0.797 |
| Farbe | Clear colorless to light yellow |
| InChI | InChI=1S/C5H6/c1-2-5-3-4-5/h1,5H,3-4H2 |
| InChIKey | NPTDXPDGUHAFKC-UHFFFAOYSA-N |
| SMILES | C1(C#C)CC1 |
| CAS Datenbank | 6746-94-7(CAS DataBase Reference) |
| NIST chemische Informationen | Cyclopropylacetylene(6746-94-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P302+P352, P303+P361+P353, P305+P354+P338, P317, P321, P332+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)H225 (96.1%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Status: Active Update: 05-09-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/1000 |
| Hazard Classes and Categories | Flam. Liq. 2 (96.1%)Flam. Liq. 2 (85.7%)Flammable liquid - category 2 |
| Wassergefährdungsklasse (WGK) | 2 |
| UN-Transportnummer | UN 1294 3/PG 2 |
| Zollcode | 29021990 |
| R-Sätze (R) | 11-36/37/38-48/20-63-65-67-52/53-41-38-4-37/38-22 |
| Gefahrensymbole | F,Xn,Xi |
| Sicherheitshinweise (S) | 26-36/37-62-37/39-16-61-33-9-36/37/39-39 |
| Gefahrenklasse | 3Aquatic Chronic 3Eye Dam. 1Flam. Liq. 2Skin Irrit. 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
Cyclopropylacetylene is used as an organic chemical synthesis intermediate.
Herstellung & Synthese
synthetische
Cyclopropylacetylene was prepared in a two-step procedure by dichlorination of cyclopropyl methyl ketone with phosphorus pentachloride (PCl5) followed by double dehydrohalogenation with a strong base. This sequence presented significant scale-up problems with low overall yields (20-25%). Similarly, cyclopropylacetylene has been prepared by base-induced dehydrohalogenation of bromovinylcyclopropane . Cyclopropylacetylene has also been prepared from the 1-trimethylsilyl derivative of cyclopropylacetylene, which was prepared by treatment of 5-chloro-1-trimethylsilyl-1-pentyne with lithium diisopropylamide at 78°C followed by warming to room temperature.