Bromcyclopropan
BROMOCYCLOPROPANE · Cyclopropyl · Cyclopropyl bromine · BromocycL · NSC 89692 · bromo-cyclopropan · 1-Bromocyclopropane · CYCLOPROPYL BROMIDE
Identifikatoren & physikalische Daten
| CAS No. | 4333-56-6 |
|---|---|
| Summenformel | C3H5Br |
| Durchschnittliche Molmasse | 120,98 g/mol |
| Monoisotopische Masse | 119,95746226 g/mol |
| SMILES | BrC1CC1 |
| InChIKey | LKXYJYDRLBPHRS-UHFFFAOYSA-N |
| PubChem CID | 78037 |
| EC No. | 224-375-7 |
| DTXSID | DTXSID8063418 |
| Lokaler Name | Bromcyclopropan |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 4 |
| Formalladung | 0 |
| Komplexität | 22,5 |
| Stoffklassen | Other Classes -> Halogenated Cyclic Hydrocarbons |
| SpringerMaterials Properties | Schoenflies notation |
| Physical Description | Colorless liquid[Alfa Aesar MSDS] |
| Siedepunkt | 69 °C (lit.) |
| Dichte | 1.51 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.458(lit.) |
| Flammpunkt | 20 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Sparingly), Methanol (Slightly)immiscible |
| Aggregatzustand | Liquid |
| Wichte | 1.510 |
| Farbe | Clear colorless |
| BRN | 1900287 |
| InChI | InChI=1S/C3H5Br/c4-3-1-2-3/h3H,1-2H2 |
| InChIKey | LKXYJYDRLBPHRS-UHFFFAOYSA-N |
| SMILES | C1(Br)CC1 |
| CAS Datenbank | 4333-56-6(CAS DataBase Reference) |
| NIST chemische Informationen | Cyclopropyl bromide(4333-56-6) |
| EPA chemische Informationen | Cyclopropane, bromo- (4333-56-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 54 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Bromocyclopropane: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A skin and strong eye irritant[Alfa Aesar MSDS] See Iodocyclohexane. See Ethyl bromide. |
| Hazard Classes and Categories | Flam. Liq. 2 (100%) |
| F | 8-19 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1993 3/PG 2 |
| Zollcode | 29035990 |
| R-Sätze (R) | 11-36/37/38 |
| Gefahrensymbole | F,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 16-26-36-37/39 |
| Gefahrenklasse | 3Flam. Liq. 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Beschreibung
Cyclopropyl bromide is also named as Bromocyclopropane. It is used in organic synthesis, for instance, for the formation of a Grignard Reagent, cyclopropyllithium. It is also used as an intermediate in the manufacture of pharmaceutical and agrochemical products.
Verwenden
Bromocyclopropane is primarily used an intermediate in the manufacture of pharmaceutical and agrochemical products. It is also used in the production of cyclopropyl boric acid. It is used as an intermediate in organic synethesis.
Herstellung & Synthese
synthetische
Bromocyclopropane has been prepared by the Hunsdiecker reaction by adding silver cyclopropanecarboxylate to bromine in dichlorodifluoromethane at 29° (53% yield) or in tetrachloroethane at 20° to 25° (15–20% yield). Decomposition of the peroxide of cyclopropanecarboxylic acid in the presence of carbon tetrabromide gave bromocyclopropane in 43% yield. An attempt to prepare the bromide via the von Braun reaction was unsuccessful. Ten percent yields are reported for the photobromination of cyclopropane and the photochemical rearrangement of allyl bromide. Treatment of 1,1,3-tribromopropane with methyllithium prepared from methyl bromide furnishes a 60–65% yield of bromocyclopropane.