Di(tert-butyl)carbonat
BOC · (BOC)2O · DIBOC · BOC ANHYDRIDE · DI-T-BUTYL DICARBONATE · tert-Butoxycarbonyl Anhydride · tert-butyldicarbonate · DI-TERT-BUTYL PYROCARBONATE
Identifikatoren & physikalische Daten
| CAS No. | 24424-99-5 |
|---|---|
| Summenformel | C10H18O5 |
| Durchschnittliche Molmasse | 218,25 g/mol |
| Monoisotopische Masse | 218,11542368 g/mol |
| SMILES | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C |
| InChIKey | DYHSDKLCOJIUFX-UHFFFAOYSA-N |
| PubChem CID | 90495 |
| ChEBI | CHEBI:48500 |
| EC No. | 246-240-1 |
| DTXSID | DTXSID4051904 |
| Lokaler Name | Di(tert-butyl)carbonat |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 61,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 218 |
| Stoffklassen | Other Classes -> Esters, Other |
| Physical Description | White solid with a mild odormp = 22-24 deg C[Alfa Aesar MSDS] |
| Schmelzpunkt | 23 °C (lit.) |
| Siedepunkt | 56-57 °C/0.5 mmHg (lit.) |
| Dichte | 0.95 g/mL at 25 °C (lit.) |
| Dampfdruck | 3.85Pa at 25℃ |
| Brechungsindex | n20/D 1.409(lit.) |
| Flammpunkt | 99 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Sparingly), Methanol (Slightly)Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water. |
| Aggregatzustand | Low Melting Crystalline Solid |
| Farbe | White |
| Wichte | 0.950 |
| BRN | 1911173 |
| Stabilität | Acid Sensitive |
| Hauptanwendungen | peptide synthesis |
| InChI | 1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3 |
| InChIKey | DYHSDKLCOJIUFX-UHFFFAOYSA-N |
| SMILES | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C |
| LogP (Verteilungskoeffizient) | 1.87 at 25℃ |
| CAS Datenbank | 24424-99-5(CAS DataBase Reference) |
| EPA chemische Informationen | Dicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.5% (1 of 183) of reports.DangerH225 (26.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P332+P317, P333+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 183 reports by companies from 35 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Dicarbonic acid, bis(1,1-dimethylethyl) esterStatus: Active Update: 05-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/5501Di(t-butyl) carbonate: HSNO Approval: HSR004455 Approved with controls |
| Gefahrenübersicht | Causes dyspnea and weight loss in inhalation lethal-concentration studies of rats[RTECS] An irritant that may cause serious eye injuryMay cause skin sensitizationHighly toxic by inhalation[Alfa Aesar MSDS] No results in PubMed: 24424-99-5 AND (sensitizer OR sensitization OR allergic OR contact dermatitis) |
| Hazard Classes and Categories | Flam. Liq. 2 (26.8%) |
| Protective Action Criteria (PAC) | 0.067 [mg/m3]0.73 [mg/m3]4.4 [mg/m3] |
| Toxicity Data | LC50 (rat) = 100 mg/m3/4hr |
| F | 4.4-10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2929 6.1/PG 1 |
| Zollcode | 29209010 |
| RTECS-Nr. | HT0230000 |
| R-Sätze (R) | 11-19-26-36/37/38-43-10-40 |
| Toxizität | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Gefahrensymbole | T+,T,F,Xi,F+ |
| hazard_note | Flammable/Irritant/Very Toxic |
| Sicherheitshinweise (S) | 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33 |
| Gefahrenklasse | 6.1Acute Tox. 1 InhalationEye Dam. 1Flam. Liq. 3Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
| Selbstentzündungstemperatur | 460 °C |
Anwendungen & Verwendung
Verwenden
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. It plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone. It serves as a protecting group used in solid phase peptide synthesis.
Herstellung & Synthese
synthetische
The preparation of Di-tert-butyl dicarbonate is as follows:To a monoester sodium salt solution were added 2g of N, N-dimethylformamide, 1g of pyridine, 1g of triethylamine,Cooling to -5~0°C, 60g diphosgene was slowly added dropwise within 1.5h dropwise addition was complete, warmed to room temperature (25°C), incubated for 2h, the reaction was allowed to stand after filtration, washing organic solution. Dried with anhydrous magnesium sulfate, the solvent was distilled off at atmospheric pressure to give crude product 65~70g. After cooling and crystallization, 57-60g of di-tert-butyl dicarbonate were obtained in a yield of 60-63%.