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Di-tert-butyl dicarbonate

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Di-tert-butyl dicarbonate Basic information

Product Name:
Di-tert-butyl dicarbonate
CAS:
24424-99-5
MF:
C10H18O5
MW:
218.25
EINECS:
246-240-1
Mol File:
24424-99-5.mol
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Di-tert-butyl dicarbonate Chemical Properties

Melting point:
23 °C(lit.)
Boiling point:
65-67 °C
Density 
0.95 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.409(lit.)
Flash point:
99 °F
storage temp. 
2-8°C
form 
Low Melting Crystalline Solid
color 
White
Specific Gravity
0.950
Water Solubility 
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
Sensitive 
Moisture Sensitive
BRN 
1911173
InChIKey
DYHSDKLCOJIUFX-UHFFFAOYSA-N
CAS DataBase Reference
24424-99-5(CAS DataBase Reference)
EPA Substance Registry System
Dicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5)
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Safety Information

Hazard Codes 
T+,T,F,Xi,F+
Risk Statements 
11-19-26-36/37/38-43-10-40
Safety Statements 
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 
HT0230000
4.4-10-21
Autoignition Temperature
460 °C
Hazard Note 
Flammable/Irritant/Very Toxic
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
I
HS Code 
29209010
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg

MSDS

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Di-tert-butyl dicarbonate Usage And Synthesis

Chemical Properties

White to off-white microcrystalline powder

Chemical Properties

Di-tert-butyl dicarbonate (Boc2O) and di-tert-butyl tricarbonate ((BocO)2CO)  have been used as amine carbonylating reagents to obtain linear or branched aliphatic isocyanates.
most of the known methods for transforming amines into isocyanates are not mild enough and furnish undefined products as a result of uncontrolled side reactions. However, 4-dimethylaminopyridine (DMAP)-catalyzed reaction with activated carbonates as C1 building blocks constitutes a convenient laboratory method for the phosgene-free isocyanation of amines. A procedure has been described whereby alkyl- and arylamines are converted into isocyanates in high yields by reaction with activated carbonates (for example, di-tert-butyl dicarbonate, Boc2O) in the presence of a catalytic amount of a nucleophilic nitrogen base at room temperature.
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. 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.

Uses

Reagent commonly used in organic chemistry for the introduction of the BOC protecting group.

Uses

reagent for t-BOC-protected amines

Uses

Reagent for the preparation of Boc-amino acids and peptides in high yields.

Purification Methods

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 Preparation Products And Raw materials

Preparation Products

N-Boc-D-prolineBOC-L-Isoleucine 5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINETERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE1-Boc-4-cyanopiperidineTERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE6-TERT-BUTOXYCARBONYLAMINO-PYRIDINE-2-CARBOXYLIC ACID1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE(S)-N-Boc-allylglycineTERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE2-(2,2-DIMETHYL-PROPIONYLAMINO)-ISONICOTINIC ACID1-Boc-piperazineSpermidineTERT-BUTYL 3-(4-AMINO-2,6-DICHLOROPHENOXY)PROPYLCARBAMATE3-TERT-BUTOXYCARBONYLAMINO-ISONICOTINIC ACID6-BOC-HYDRAZINONICOTINIC ACID4-BOCAMINO-NICOTINIC ACID(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine(R)-PIPERAZINE-2-CARBOXYLIC ACID(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER6-(BOC-AMINO)-HEXYL BROMIDEN-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLIC ACID T-BUTYL ESTER4-ALLYL-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER1-BOC-PIPERAZINETERT-BUTYL 4-(HYDROXYMETHYL)PYRIDIN-2-YLCARBAMATE1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE(S)-(-)-1-Boc-2-pyrrolidinemethanolTERT-BUTYL 4-FORMYL-2-METHOXYPHENYL CARB ONATE, 993-[(N-(TERT-BUTYLOXYCARBONYL)AMINO)METHYL]PYRIDINEtert-Butyl N-(2-bromoethyl)carbamateN-Boc-N,N-bis(2-chloroethyl)amine4-CHLORO-(N-BOC)ANILINE 97TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE4-(BOC-AMINOMETHYL)PYRIDINEN-BOC-piperidine-4-carboxylic acid1-(4-PYRIDYLMETHYL)PIPERAZINEN,N-DIMETHYL-2-PIPERAZIN-1-YL-ACETAMIDE1-Boc-3-oxopiperazineTERT-BUTYL 4-(METHOXYCARBONYL)PYRIDIN-2-YLCARBAMATE

Raw materials

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