Cyclopropylmethanol
CYCLOPROPYLMETHANOL · CYCLOPROPANEMETHANOL · CPMO · CP-CARBINOL · (HYDROXYMETHYL)CYCLOPROPANE · CPC-OL · Cyclopropylmethane · RARECHEM AK ML 0580
Identifikatoren & physikalische Daten
| CAS No. | 2516-33-8 |
|---|---|
| Summenformel | C4H8O |
| Durchschnittliche Molmasse | 72,11 g/mol |
| Monoisotopische Masse | 72,05751488 g/mol |
| SMILES | OCC1CC1 |
| InChIKey | GUDMZGLFZNLYEY-UHFFFAOYSA-N |
| PubChem CID | 75644 |
| EC No. | 219-735-5 |
| DTXSID | DTXSID2051922 |
| Lokaler Name | Cyclopropylmethanol |
Chemische & physikalische Eigenschaften
| XLogP | 0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 30,6 |
| Polymers | Other Classes -> Alcohols and Polyols, Other |
| SpringerMaterials Properties | Atomic environment |
| Physical Description | LiquidClear light yellow liquid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | -60 °C |
| Siedepunkt | 123-124 °C738 mm Hg(lit.) |
| Dichte | 0.89 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.431(lit.) |
| Flammpunkt | 95 °F |
| Lagerbedingungen | Flammables area |
| Löslichkeit | Chloroform, Ethyl Acetatemiscible |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 15.10±0.10(Predicted) |
| Farbe | Clear colorless |
| Wichte | 0.890 |
| BRN | 1846846 |
| InChI | 1S/C4H8O/c5-3-4-1-2-4/h4-5H,1-3H2 |
| InChIKey | GUDMZGLFZNLYEY-UHFFFAOYSA-N |
| SMILES | OCC1CC1 |
| CAS Datenbank | 2516-33-8(CAS DataBase Reference) |
| NIST chemische Informationen | Cyclopropyl carbinol(2516-33-8) |
| EPA chemische Informationen | Cyclopropanemethanol (2516-33-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226 (99.2%): Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P318, P319, P321, P330, P337+P317, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 120 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: CyclopropanemethanolCyclopropanemethanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopropanemethanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 17-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23682Cyclopropanemethanol: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Potentially neurotoxic effects observed in oral lethal-dose study of ratsCorrosive to rabbit skinHistopathological changes of the heart (myocarditis with myocardial fiber necrosis) observed in 4-week inhalation study of rats at all tested concentrations (0.003 mg/L the lowest tested concentration)[EPA - TSCATS] A strong eye irritantHarmful by ingestion[Sigma-Aldrich MSDS] See Cyclohexanol. |
| Hazard Classes and Categories | Flam. Liq. 3 (99.2%) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Toxicity Data | LC50 (rat) = 3,300 mg/m3/6hr |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1987 3/PG 3 |
| Zollcode | 29061990 |
| RTECS-Nr. | GZ2212250 |
| R-Sätze (R) | 10-22-36-34 |
| Gefahrensymbole | Xn,Xi,C,F |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 16-26-36-45-36/37/39 |
| Gefahrenklasse | 3Flam. Liq. 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
Cyclopropylmethanol used to increase selectivity of pyridyl-cinnoline phosphodiesterase 10A, inhibitors against phosphodiesterase 3 (PDE3). Also used in the synthesis of benzodiazapin-2-ones
Herstellung & Synthese
synthetische
The preparation of Cyclopropyl carbinol is as follows:A 1L three-necked flask was charged with 100 g (1mol) of methyl cyclopropanoate. 57g (1.5mol) of sodium borohydride, 500 mL of methanol, and then cooled to 2°C, 66.67g (0.5mol) of aluminum trichloride was added in batches and reacted overnight. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride, filtered, and the filtrate was concentrated and evaporated. The product was collected in a yield of 53.49g, a yield of 74.3%.