4-Chlorphenylacetonitril
Para chloro benzyl cyanide · 2-(4-Chlorophenyl)acetonitrile · (4-CHLOROPHENYL)ACETONITRILE · P-CHLOROBENZYL CYANIDE · PCCN · P-CHLOROPHENYLACETONITRILE · 4-Chlorobenzeneacetonitrile · Pyrimethamine EP Impurity C
Identifikatoren & physikalische Daten
| CAS No. | 140-53-4 |
|---|---|
| Summenformel | C8H6ClN |
| Durchschnittliche Molmasse | 151,59 g/mol |
| Monoisotopische Masse | 151,01887687 g/mol |
| SMILES | N#CCc1ccc(Cl)cc1 |
| InChIKey | IVYMIRMKXZAHRV-UHFFFAOYSA-N |
| PubChem CID | 241582 |
| ChEBI | CHEBI:17346 |
| EC No. | 205-418-9 |
| DTXSID | DTXSID8051708 |
| Lokaler Name | 4-Chlorphenylacetonitril |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 23,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 139 |
| Stoffklassen | Nitrogen Compounds -> Nitriles |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| LogP (Verteilungskoeffizient) | 2.47 |
| Dampfdruck | 0.01 [mmHg] |
| Physical Description | White to light yellow solid with a pungent odormp = 28-31 deg C[Alfa Aesar MSDS] |
| Collision Cross Section | 130.4 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID8051708] |
| Schmelzpunkt | 25-28 °C(lit.) |
| Siedepunkt | 265-267 °C(lit.) |
| Dichte | 1.19 g/mL at 20 °C(lit.) |
| Brechungsindex | n20/D 1.543 |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | 0.3g/l |
| Aggregatzustand | Liquid After Melting |
| Farbe | Clear colorless to yellow |
| BRN | 971171 |
| InChI | 1S/C8H6ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2 |
| InChIKey | IVYMIRMKXZAHRV-UHFFFAOYSA-N |
| SMILES | Clc1ccc(CC#N)cc1 |
| CAS Datenbank | 140-53-4(CAS DataBase Reference) |
| NIST chemische Informationen | Benzeneacetonitrile, 4-chloro-(140-53-4) |
| EPA chemische Informationen | Benzeneacetonitrile, 4-chloro- (140-53-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300 (20%): Fatal if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzeneacetonitrile, 4-chloro-4-Chlorobenzyl cyanide: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes convulsions and dyspnea in dermal lethal-dose studies of rabbitsCauses ataxia, dyspnea, and decreased body temperature in oral lethal-dose studies of rats[RTECS] A skin, respiratory tract, and strong eye irritantHighly toxic by ingestionToxic by inhalation and skin absorption[Alfa Aesar MSDS] See 2-Chlorobenzonitrile. |
| Hazard Classes and Categories | Acute Tox. 2 (20%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29269095 |
| RTECS-Nr. | AL8250000 |
| R-Sätze (R) | 23/24/25-36/37/38 |
| Gefahrensymbole | T,Xi |
| hazard_note | Irritant/Toxic |
| Sicherheitshinweise (S) | 26-36/37/39-45-28B |
| Gefahrenklasse | 6.1Acute Tox. 2 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe |
Anwendungen & Verwendung
Verwenden
4-Chlorobenzyl cyanide is an intermediate for the preparation of 3-methyl-2-(4-chlorophenyl)butyric acid, which can be used to prepare pyrethroid insecticides such as fenvalerate and deltamethrin, and can be used in medicine Industrial preparation of pyrimethamine.
Herstellung & Synthese
synthetische
4-Chlorobenzyl cyanide is obtained by the reaction of 4-Chlorobenzyl chloride with sodium cyanide. Add 4-Chlorobenzyl chloride and Benzyldodecyldimethylammonium bromide into the reaction pot, heat to 100°C, slowly add sodium cyanide aqueous solution, and react at 100-104°C for 5h (add sodium cyanide for 3h, keep warm for 2h). Then add water to dissolve sodium chloride, and separate the water layer to obtain the crude benzyl chloride cyanide, which is distilled under reduced pressure to collect 160 (2.66kPa) fractions to obtain the finished product of 4-Chlorobenzyl cyanide. The yield is above 81%.