Benzylchlorformiat
CBZ · Benzyl carbonochloridate · BCF · Z-CL · BENZYLOXYCARBONYL CHLORIDE · Benzyl Chlorofomate · CBZCI · Z-CHLORIDE
Identifikatoren & physikalische Daten
| CAS No. | 501-53-1 |
|---|---|
| Summenformel | C8H7ClO2 |
| Durchschnittliche Molmasse | 170,59 g/mol |
| Monoisotopische Masse | 170,01345714 g/mol |
| SMILES | O=C(Cl)OCc1ccccc1 |
| InChIKey | HSDAJNMJOMSNEV-UHFFFAOYSA-N |
| PubChem CID | 10387 |
| ChEMBL | CHEMBL1581748 |
| EC No. | 207-925-0 |
| DTXSID | DTXSID9027158 |
| Lokaler Name | Benzylchlorformiat |
Chemische & physikalische Eigenschaften
| XLogP | 3 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 130 |
| Stoffklassen | Toxic Gases & Vapors -> Acid HalidesCorrosives |
| SpringerMaterials Properties | Chemical shift |
| Geruch | ACRID ODORODOR OF PHOSGENESHARP, PENETRATING ODOR |
| Dichte | 1.22 at 68 °F (USCG, 1999) - Denser than waterwill sink1.2166 20 °C/4 °CRelative density (water = 1): 1.201.2166 @ 20°C1.212 g/mL at 20 °C |
| Viscosity | 2.57 mPa-s (cP) @ 20 °C |
| Color/Form | OILY LIQUIDCOLORLESS TO PALE YELLOW LIQUID |
| Löslichkeit | SOL IN ETHER, ACETONE, BENZENESolubility in water: reactionMiscible with ether, acetone and benzene.decomposes |
| Corrosivity | Corrosive |
| Flammpunkt | 227 °F Vigorous decomposition occurs at these temperaturesthus these values are anomalous due to the effect of the decomp. products (benzyl chloride and CO2). (USCG, 1999)[HSDB] 80 °C176 °F OC227 °F CC80.0 °C c.c.197 °F |
| Siedepunkt | 306 °F at 760 mmHg (decomposes) (USCG, 1999)152 °C AT 760 MM HG152 °C @760 [mm Hg]103 °C20 mm Hg(lit.) |
| Decomposition | EMITS HIGHLY TOXIC PHOSGENE FUMES WHEN HEATED TO 100 °C.DANGEROUSWHEN HEATED TO DECOMP ... THEY EVOLVE HIGHLY TOXIC /HYDROGEN/ CHLORIDE FUMES. /CHLORIDES/>100 °C |
| Schmelzpunkt | 0 °C-20 °C |
| Dampfdichte | 1 (vs air) |
| Dampfdruck | 1.39 psi ( 20 °C) |
| Brechungsindex | n20/D 1.519(lit.) |
| Lagerbedingungen | Store at +2°C to +8°C. |
| Aggregatzustand | Solution |
| Farbe | slightly yellow to slightly pink |
| Geruch | Irritatingsharp, penetrating. |
| Merck | 14,1801 |
| Stabilität | Stable. Incompatible with water, oxidizing agents. Combustible. |
| InChI | 1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2 |
| InChIKey | HSDAJNMJOMSNEV-UHFFFAOYSA-N |
| SMILES | ClC(=O)OCc1ccccc1 |
| CAS Datenbank | 501-53-1(CAS DataBase Reference) |
| NIST chemische Informationen | Benzyl chloroformate(501-53-1) |
| EPA chemische Informationen | Carbonochloridic acid, phenylmethyl ester (501-53-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.6% (1 of 173) of reports.H314 (99.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation] |
|---|---|
| Regulatorische Informationen | Chemical: Carbonochloridic acid, phenylmethyl esterCarbonochloridic acid, phenylmethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbonochloridic acid, phenylmethyl ester 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: 02-03-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/12078Benzyl chloroformate: 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 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Special Hazards of Combustion Products: Toxic phosgene, hydrogen chloride, and benzyl chloride vapors may form.· EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Brandpotenzial | COMBUSTIBLE |
| Gesundheitsgefahren | Inhalation causes mucous membrane irritation. Eyes are irritated by excessive exposure to vapor. Liquid causes severe irritation of eyes and irritates skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)· CORROSIVE and/or TOXIC |
Anwendungen & Verwendung
Beschreibung
Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow. It possesses a characteristic pungent odor and degrades in contact with water. The compound was first prepared by Leonidas Zervas in the early 1930s who used it for the introduction of the benzyloxycarbonyl protecting group, which became the basis of the Bergmann-Zervas carboxybenzyl method of peptide synthesis he developed with Max Bergmann. This was the first successful method of controlled peptide chemical synthesis and for twenty years it was the dominant procedure used worldwide until the 1950s. To this day, benzyl chloroformate is often used for amine group protection.
Verwenden
Benzyl chloroformate is widely used as a reactive chemical intermediate in plastic, pharmaceutical, agricultural and organic chemicals. It is useful for the introduction of carboxybenzyl (cbz) protecting group for amines such as aniline in organic synthesis. It is also involved in the synthesis of 1,2,4-oxadiazoles.
Herstellung & Synthese
synthetische
Benzyl chloroformate is prepared in the lab by treating benzyl alcohol with phosgene:PhCH2OH + COCl2→ PhCH2OC(O)Cl + HClPhosgene is used in excess to minimise the production of the carbonate (PhCH2O)2C=O.The use of phosgene gas in the lab preparation carries a very large health hazard, and has been implicated in the chronic pulmonary disease of pioneers in the usage of the compound such as Zervas.