Di(tert-butyl)carbonat

Bezeichnung:Di(tert-butyl)carbonat

CAS-Nr24424-99-5

Englisch Name:Di-tert-butyl dicarbonate

CBNumberCB4267614

SummenformelC10H18O5

Molgewicht218.25

MOL-Datei24424-99-5.mol

Synonyma

Di(tert-butyl)carbonat

Di(tert-butyl)carbonat physikalisch-chemischer Eigenschaften

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
storage temp.	2-8°C
Löslichkeit	Chloroform (Sparingly), Methanol (Slightly)
Aggregatzustand	Low Melting Crystalline Solid
Farbe	White
Wichte	0.950
Wasserlöslichkeit	Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
Sensitive	Moisture Sensitive
BRN	1911173
Stabilität	Acid Sensitive
InChIKey	DYHSDKLCOJIUFX-UHFFFAOYSA-N
LogP	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

Kennzeichnung gefährlicher	T+,T,F,Xi,F+
R-Sätze:	11-19-26-36/37/38-43-10-40
S-Sätze:	16-26-28-36/37-45-7/9-37/39-24-36/37/39-33
RIDADR	UN 2929 6.1/PG 1
WGK Germany	3
RTECS-Nr.	HT0230000
F	4.4-10-21
Selbstentzündungstemperatur	460 °C
Hazard Note	Flammable/Irritant/Very Toxic
TSCA	Yes
HazardClass	6.1
PackingGroup	I
HS Code	29209010
Toxizität	LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg

Gefahreninformationscode (GHS)

Di-tert-butyl dicarbonate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R19:Kann explosionsfähige Peroxide bilden.
R26:Sehr giftig beim Einatmen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R43:Sensibilisierung durch Hautkontakt möglich.
R10:Entzündlich.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S7/9:Behälter dicht geschlossen an einem gut gelüfteten Ort aufbewahren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S24:Berührung mit der Haut vermeiden.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S33:Maßnahmen gegen elektrostatische Aufladungen treffen.
Chemische Eigenschaften
Di-tert-butyl dicarbonate (BOC Anhydride, DiBOC) is a colorless to white to yellow crystals, solidified mass or clear liquid. It melts around room temperature (m.p.=23°C). It does not decompose at this or even slightly higher temperatures. For example, it is typically purified by distillation under reduced pressure at temperatures up to around 65°C. At higher temperatures it will decompose to isobutene, t-butyl alcohol and carbon dioxide.
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.
Definition
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.
Application
Di-tert-butyl dicarbonate has the following uses:
(1) As part of a series of bovine plasma amine oxidase inactivators. Aminomethylenes were prepared by the reaction of Boc propargylamine with formaldehyde, diisopropylamine and copper bromide.
(2) It can be used as a general purpose carboxylation reagent. Carbon nucleophiles generated by a non-nucleophilic base (LDA) were effectively trapped with di-tert-butyl dicarbonate (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di-tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields.
(3) Alcohols as Boc derivatives were catalytically protected by Lewis acids. Reagents for the introduction of Boc protecting groups.
(4) Reagents for the preparation of Boc-protected amines. Tri-tert-butoxycarbonyl-protected hydrazines prepare Fmoc esters in chromogenic reagents for monitoring solid-phase aldehydes.
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%.
Reaktionen
The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.
Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols
Allgemeine Beschreibung
Di-tert-butyl dicarbonate (Boc₂O) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities. It is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.
Hazard
An irritant that may cause serious eye injury; May cause skin sensitization; Highly toxic by inhalation
Flammability and Explosibility
Flammable
läuterung methode
Melt the ester by heating at ~35o, and distil it in a vacuum. If IR and NMR ( 1810m 1765 cm-1 , in CCl4 1.50 singlet) suggest very max impure, then wash with an equal volume of H2O containing citric acid to make the aqueous layer slightly acidic, collect the organic layer and dry it over anhydrous MgSO4 and distil it in a vacuum. [Pope et al. Org Synth 57 45 1977, Keller et al. Org Synth 63 160 1985, Grehn et al. Angew Chem 97 519 1985.] FLAMMABLE.

Di-tert-butyl dicarbonate Upstream-Materialien And Downstream Produkte

Di(tert-butyl)carbonat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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