4-Nitrophenylchlorformiat
4-NITROPHENYL CARBONOCHLORIDATE · P-NITROPHENYL CHLOROFORMATE · PNPCF · Nitrophenyl chloroforMate · PARA-NITROPHENYL CHLOROFORMATE · 4-Nitrophenyl chloridocarbonate · 4-NITROPHENYL CHLOROCARBONATE · CHLOROFORMIC ACID P-NITROPHENYL ESTER
Identifikatoren & physikalische Daten
| CAS No. | 7693-46-1 |
|---|---|
| Summenformel | C7H4ClNO4 |
| Durchschnittliche Molmasse | 201,56 g/mol |
| Monoisotopische Masse | 200,98288529 g/mol |
| SMILES | O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 |
| InChIKey | NXLNNXIXOYSCMB-UHFFFAOYSA-N |
| PubChem CID | 82129 |
| EC No. | 231-706-9 |
| DTXSID | DTXSID3064772 |
| Lokaler Name | 4-Nitrophenylchlorformiat |
Chemische & physikalische Eigenschaften
| XLogP | 2,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 72,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 207 |
| Stoffklassen | Toxic Gases & Vapors -> Acid Halides |
| Physical Description | Cream crystals with an acrid odor[Alfa Aesar MSDS] |
| Schmelzpunkt | 77-79 °C(lit.) |
| Siedepunkt | 159-162 °C19 mm Hg(lit.) |
| Dichte | 1.5719 (rough estimate) |
| Brechungsindex | 1.6000 (estimate) |
| Flammpunkt | >110°C |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in acetone, chloroform, acetone, toluene and benzene.decomposes |
| Aggregatzustand | isopropanol suspension |
| Farbe | White to yellow-beige |
| BRN | 518127 |
| Stabilität | Stable. Incompatible with strong bases, acids. Combustible. |
| Hauptanwendungen | peptide synthesis |
| InChI | 1S/C7H4ClNO4/c8-7(10)13-6-3-1-5(2-4-6)9(11)12/h1-4H |
| InChIKey | NXLNNXIXOYSCMB-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1ccc(OC(Cl)=O)cc1 |
| CAS Datenbank | 7693-46-1(CAS DataBase Reference) |
| NIST chemische Informationen | Carbonochloridic acid, 4-nitrophenyl ester(7693-46-1) |
| EPA chemische Informationen | Carbonochloridic acid, 4-nitrophenyl ester (7693-46-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH314 (96.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 09-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/245484-Nitrophenyl chloroformate: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Reacts with waterCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion and inhalation[Alfa Aesar MSDS] See CHLOROFORMATES. |
| Hazard Classes and Categories | Skin Corr. 1B (96.8%) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 19-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3261 8/PG 2 |
| Zollcode | 29159020 |
| R-Sätze (R) | 34-36/37-23/24/25-41-36/37/38-11-67-36 |
| Gefahrensymbole | C,T,Xi,F |
| hazard_note | Toxic/Corrosive/Lachrymator |
| Sicherheitshinweise (S) | 26-36/37/39-45-38-28A-36-16-27 |
| Gefahrenklasse | 8Eye Dam. 1Skin Corr. 1BSTOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
Anwendungen & Verwendung
Verwenden
4-Nitrophenyl chloroformate is used in the synthesis of poly(oxyethylene) modified dextrans. It is also used to prepare a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA. Further, it is used in the synthesis of mixed, activated carbonates, thiocarbonates and activated urethanes. In addition to this, it is used in the preparation of 4-nitrophenyl diazoacetate with diazomethane. It is an ester of chloroformic acid used in the immobilization of enzymes and other biomolecules.
Beschreibung
4-Nitrophenyl chloroformate, also known as p-nitrophenyl chloroformate, is a coupling agent used in the synthesis of ureas, carbamates, and carbonates. It is also used as a building block in solid-phase peptide synthesis (SPPS) to obtain altered side chain functionalities in peptides.