Di tert butyl dicarbonate is a reagent widely used in organic synthesis. Di tert butyl dicarbonate boc 2 o seemed a good candidate for the desulfurylation of the corresponding dithiocarbamate as this reagent may evolve co 2 and cos during the reaction, and residual carbon disulfide and tert butanol together with the solvent should be removed easily by evaporation. It does not decompose at this or even slightly higher temperatures. Convenient reagent for the protection of amino acids and peptides as their acidlabile tbutoxycarbonyl bocderivatives t butyl carbamates, in high yield under mild conditions. A new efficient synthesis of isothiocyanates from amines. Strong oxidizing agents, oxidizing agents, acids, bases.
Ep0256559a2 process for producing ditertiarybutyl dicarbonate. How the nature of the lewis acid catalyst may address the reaction to the synthesis of tertbutyl ethers. The term tricarbonate is sometimes used for salts that contain three carbonate anions in their stoichiometric formula, such as cerium tricarbonate. Predicted data is generated using the us environmental protection agencys episuite. Di tert butyl peroxide dtbp is widely used as modifier, crosslinking agent and polymerization initiator in industry although it is a reactive and exothermically unstable peroxide.
All mass spectra in this site plus many more are available from the nistepanih mass spectral library. These derivatives do not behave as amines, which allows certain subsequent transformations to occur that would have otherwise affected the amine functional group. Packaging 25, 100, 500 g in poly bottle application ditertbutyl dicarbonate is a reagent mainly used for the introduction of the boc protecting group. Chemeo is only indexing the data, follow the source links to retrieve the latest data. Clean and rapid introduction of the acid labile bocprotecting group in amino acids, peptides and proteins. This carbonate ester reacts with amines to give ntertbutoxycarbonyl or socalled boc derivatives. For example, it is typically purified by distillation under reduced pressure at temperatures up to around 65c. The decomposition reaction proceeds via the generation of methyl radicals. Bocprotected amino groups organic chemistry portal. Causes eye, skin, and respiratory tract irritation. Ditertbutyl dicarbonate is a reagent used for the introduction of boc protecting group.
Ditertbutyl dicarbonate is inexpensive, so it is usually purchased. Material safety data sheet di tert butyl dicarbonate msds section 1. A process for producing ditertbutyl dicarbonate which comprises reacting a. Synthesis and kinetics of decomposition of ditertbutyl. Extreme high moderate low section 1 chemical product and company identification product name ditertbutyl dicarbonate ca. As a reagent to introduce boc protecting group for the amine functionalities. It is an extremely efficient reagent to introduce the tertbutoxycarbonyl boc protecting group for the amine functionality. Sigmaaldrich offers a number of di tert butyl dicarbonate solution products.
Tert butyl carbamates are produced in high yields at low temperature by the reaction of a carboxylic acid with di tert butyl dicarbonate and sodium azide, which leads to an acyl azide intermediate. Extreme high moderate low section 1 chemical product and company identification product name di tert butyl dicarbonate ca. Wear appropriate protective eyeglasses or chemical safety goggles as described by oshas eye and face protection regulations in. Ditertbutyl dicarbonate melts around room temperature m. Tertbutyl carbamates are produced in high yields at low temperature by the reaction of a carboxylic acid with ditertbutyl dicarbonate and sodium azide, which leads to an acyl azide intermediate.
Di tert butyl dicarbonate boc 2 o is commonly used i n organic synthesis for introduct ion of the tert butox ycar bonyl boc protecting gr oup into amines. Bottles of ditertbutyl dicarbonate buildup of internal pressure in sealed containers caused by its slow decomposition to ditertbutyl carbonate and ultimately tertbutanol and co 2 in the presence of moisture. Di tert butyl dicarbonate revision date 15apr2019 eye contact rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes. The ditertbutyl dicarbonate is an intermediate and aminoprotecting agent widely used in organic synthesis. Ditertbutyl dicarbonate is a reagent widely used in organic synthesis. State righttoknow regulations component massachusettsnew jersey pennsylvania illinois rhode island ditertbutyl peroxide x x x x u. Ditertbutyl dicarbonate24424995msds melting point boiling. Skin contact wash off immediately with plenty of water for at least 15 minutes. Department of transportation reportable quantity rq.
Ditertbutyl dicarbonate is one well capable protecting agent for amino acid, utilized specially in the amino acid amino protection, widely applied in the medicine, the protein and the multipeptide synthesis, biochemistry food, the cosmetics and many kinds of product synthesis. Dmap attacks a carbonyl site on ditertbutyl dicarbonate resulting in tertbutyl carbonate leaving as a leaving group. The reaction of di tert butyl dicarbonate boc2o in the presence of the acylation catalyst 4dimethylaminopyridine dmap was examined with nboc or nacyl cyanoglycinate. This test method provides a procedure for determining the active peroxide content of commercial di tert butyl peroxide. For this reason ditertbutyl peroxide is commonly used as a radical initiator in organic synthesis and polymer chemistry. Gps safety summary 35 functional additives ditertbutyl peroxide gps 201 v0 7. Data sheet from chemical book for ditertbutyl dicarbonate.
Oct 25, 2015 di tert butyl dicarbonate is a reagent widely used in organic synthesis. The explosive instability of the lower dialkyl peroxides e. Pdf imidazole and trifluoroethanol as efficient and mild. So far, available thermal analyses were most based on dtbp in diluents. Their reactions with amines and alcohols1 the reaction of boc2o in the. Ditertbutyl dicarbonate ditertbutyl dicarbonate boc anhydride purity 99. This route is currently employed commercially by manufacturers in china and india. Central nervous system, respiratory system, eyes, skin. This boc anhydridebased foaming process can also be conducted in the. The amine attacks a carbonyl site on ditertbutyl dicarbonate resulting in tertbutyl carbonate leaving as a leaving group. Reagent for the introduction of the boc protecting group. Please see the following for information about the library and its accompanying search program. European and japanese companies use the reaction of sodium tertbutylate with carbon dioxide, catalysed by ptoluenesulfonic acid or methanesulfonic acid.
Ditertbutyldicarbonate,24424995 jinxiang chemical factory. Di tert butyl dicarbonate di tert butyl dicarbonate boc anhydride purity 99. Thermal decomposition analysis and safety study on ditert. Convenient reagent for the protection of amino acids and peptides as their acidlabile tbutoxycarbonyl bocderivatives tbutyl carbamates, in high yield under mild conditions. Ditertbutyl dicarbonate can be prepared from tertbutanol, carbon dioxide, phosgene, using dabco as a base. Ditertbutyl dicarbonate boc 2 o is commonly used i n organic synthesis for introduct ion of the tert butox ycar bonyl boc protecting gr oup into amines. It is our goal to continue to offer the broadest range of reagents in the field. Us patent for method for epoxy foam production using a liquid. For the conversion of amines to corresponding isocyanates. The boc decomposition reactions which produce gaseous co2 as a byproduct. We need to evaluate first rate constants at both temperatures. Ditertbutyl dicarbonate bocanhydride, boc2o request pdf.
Ditertbutyl dicarbonate boc 2 o seemed a good candidate for the desulfurylation of the corresponding dithiocarbamate as this reagent may evolve co 2 and cos during the reaction, and residual carbon disulfide and tertbutanol together with the solvent should be removed easily by evaporation. An important example is ditertbutyl tricarbonate h 3 c 3 cc 3 o 7 cch 3 3, a chemical reagent colorless prisms that melt at 6263 c with decomposition, soluble in pentane. The journal of organic chemistry 2006, 71 26, 95809588. This test method provides a procedure for determining the active peroxide content of commercial ditertbutyl peroxide. Synthesis and kinetics of decomposition of ditertbutyl tricarbonate. Ditertbutyl dicarbonate boc anhydride cas 24424995. As a carboxylating agent for the preparation of a variety of tert butyl carboxylates.
It serves as a protecting group used in solid phase peptide synthesis. Wear appropriate protective eyeglasses or chemical safety goggles as described by oshas eye and face protection regulations in 29 cfr 1910. Ditertbutyl dicarbonate and 4dimethylaminopyridine. At higher temperatures it will decompose to isobutene, t butyl alcohol and carbon dioxide. Di tert butyl dicarbonate can be prepared from tert butanol, carbon dioxide, phosgene, using dabco as a base. The decomposition of ditertbutyl peroxide dtbp is a first order reaction. Ditertbutyl peroxide dtbp is widely used as modifier, crosslinking agent and polymerization initiator in industry although it is a reactive and exothermically unstable peroxide. At higher temperatures it will decompose to isobutene, tbutyl alcohol and carbon dioxide. How the nature of the lewis acid catalyst may address the reaction to the synthesis of tert butyl ethers. This carbonate ester reacts with amines to give n tert butoxycarbonyl or socalled boc derivatives.
The co2 gas that forms during the reaction should be allowed to escape. Material safety data sheet ditertbutyl dicarbonate msds section 1. Find more compounds similar to ditertbutyl peroxide note. To prepare tert butyl ethers and bocalcohols in presence of lewis acid catalyst. In the case of contact with eyes, rinse immediately with plenty of water and seek medical advice. The base usually tea or diea picks up the proton from the protonated amine. Decomposition of the latter leads to an amine which reacts with 54 to afford the n boc product 5. The chart displays the number of matching substance classifications hazard class, categories and hazard statements provided by manufacturers and importers under reach and clp notifications, as well as whether the substance is defined under harmonised classification and labelling clh. Request pdf ditertbutyl dicarbonate and 4dimethylaminopyridine revisited. The amine attacks the carbonyl site on the bocpyridinium species resulting in the release of dmap catalytic. The catalytic role of the ionic liquid is envisaged as electrophilic activation of di tertbutyl dicarbonate boc2o through bifurcated hydrogen bond formation with.
As the formation of dithiocarbamate in the case of. Dmap attacks a carbonyl site on di tert butyl dicarbonate resulting in tert butyl carbonate leaving as a leaving group. Import data and price of di tert butyl dicarbonate zauba. Standard test method for assay of di tert butyl peroxide. Ditertbutyl dicarbonate bocanhydride is a widely used reagent in organic chemistry. Knowledge of the peroxide content is important in such applications.
It plays an important role in the preparation of 6acetyl1,2,3,4tetrahydropyridine by reacting with 2piperidone. The amine attacks a carbonyl site on di tert butyl dicarbonate resulting in tert butyl carbonate leaving as a leaving group. Date hs code description origin country port of discharge unit quantity value inr per unit inr nov 22 2016. Di tert butyl dicarbonate bocanhydride is a widely used reagent in organic chemistry. Di tert butyl dicarbonate melts around room temperature m. For this reason, it is usually sold and stored in plastic bottles rather than glass ones. It is an extremely efficient reagent to introduce the tert butoxycarbonyl boc protecting group for the amine functionality. Application ditertbutyl dicarbonate boc anhydride can be used. On the other hand, too high temperatures lead to a decomposition of the starting. Chemical properties of ditertbutyl peroxide cas 110054.
Subsequent curtius rearrangement in the presence of tetrabutylammonium bromide and zincii triflate and trapping of the isocyanate derivative gives. The reaction of ditertbutyl dicarbonate boc2o in the presence of the acylation catalyst 4dimethylaminopyridine dmap was examined with nboc or nacyl cyanoglycinate. The di tert butyl dicarbonate is an intermediate and aminoprotecting agent widely used in organic synthesis. The source is also providing more information like the publication year, authors and more. Chemicalbook cas database list ditertbutyl dicarbonate. Di tert butyl dicarbonate is a reagent used for the introduction of boc protecting group.