A facile method for the preparation of carbodiimides from. Predicted data is generated using the us environmental protection agencys episuite. Di tert butyl dicarbonate 70% in mtbe solution tel. Di tert butyl dicarbonate cas no 24424995 manufacturers. 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. Chromatographic conditions and sample preparation procedures have been optimized. Synthesis and kinetics of decomposition of ditertbutyl tricarbonate. The tert butyloxycarbonyl protecting group or tert butoxycarbonyl protecting group boc group is a protecting group used in organic synthesis the boc group can be added to the amine under aqueous conditions using di tert butyl dicarbonate in the presence of a base such as sodium carbonate soda ash. Hazardous combustion products carbon monoxide co, carbon dioxide co2. Ditertbutyl dicarbonate diboc lacamas laboratories. Di tert butyl dicarbonate revision date 11dec2020 flammable. A process for producing di tert butyl dicarbonate which comprises reacting a monoalkali metal monotertbutyl carbonate with phosgene or trichloromethyl.
For this reason, it is usually sold and stored in plastic bottles rather than glass ones. Ditertbutyl dicarbonate, 1m solution in thf, acrosealr di boc. For the conversion of amines to corresponding isocyanates. Reagent for the introduction of the boc protecting group. The hazard classification and labelling section shows the hazards of a substance through a standardised system of statements and pictograms, as has been established under clp classification labelling and packaging regulation. Synthesis and kinetics of decomposition of di tert butyl tricarbonate. The reaction of boc2o in the presence and absence of dmap was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. O which is the anhydride form of boc can be carried out by suspending the mixture in water at ambient temperature. Wear appropriate protective eyeglasses or chemical safety goggles as described by oshas eye and face protection regulations in 29 cfr 1910. Stability and reactivity reactive hazard none known, based on information available stability moisture sensitive. To conduct radiofluorination of catechol, boc protection was used to protect the hydroxyl function on the aromatic ring.
Sigmaaldrich offers a number of di tert butyl dicarbonate products. The preparation, characterization, and thermal decomposition. For massspec ms compatible applications the phosphoric acid needs to be replaced with formic acid. Draw the product that valine forms when it reacts with di tert butyl dicarbonate and triethylamine followed by an aqueous acid wash. How the nature of the lewis acid catalyst may address the reaction to the synthesis of tert butyl ethers. Structure, properties, spectra, suppliers and links for. By continuing on our website, you accept the use of cookies. Compound di tert butyl pyrocarbonatewith free spectra. Electrochemical nucleophilic synthesis of ditertbutyl4. 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. Di tert butyl 4 tert butyl 1,2phenylene dicarbonate 6 was synthesized and electrochemical radiofluorination of the above precursor was conducted on a specifically developed automated electrochemistry platform. Providing here the database of di tert butyl dicarbonate cas no 24424995, di tert butyl dicarbonate manufacturers, suppliers and exporters.
Draw the product in neutral form unless conditions are clearly designed to give an ionic product. Di tert butyl dicarbonate is a reagent widely used in organic synthesis. Substrate acidities and conversion times for reactions of amides with. The mechanism of addition and removal is as follows. It plays an important role in the preparation of 6acetyl1,2,3,4tetrahydropyridine by reacting with 2piperidone. Amide formation from amino acids was achieved in an easy and convenient one. Skin contact wash off immediately with plenty of water for at least 15 minutes. Synthesis and kinetics of decomposition of ditertbutyl. These manufacturing companies are delivering best quality products to the clients on time. As a reagent to introduce boc protecting group for the amine functionalities. As a carboxylating agent for the preparation of a variety of tert butyl carboxylates. The tert butyloxycarbonyl boc group is used as a protecting group for amines in organic synthesis common amine protection methods.
In reactions of aliphatic alcohols with boc2odmap, we isolated for the first time. Protection of the amine can also be accomplished in acetonitrile solution using 4. Media in category ditertbutyl dicarbonate the following 10 files are in this category, out of 10 total. A process for producing di tert butyl dicarbonate by continuously carrying out the following steps of reacting tert butyl alcohol with sodium to form sodium tert butoxide, reacting the sodium tert butoxide with carbon dioxide to form mono tert butyl sodium carbonate, and reacting the mono tert butyl sodium carbonate with an aromatic sulfonyl halide such as ptoluenesulfonyl chloride in the. Ditertbutyl dicarbonate24424995msds melting point boiling. Subsequent curtius rearrangement in the presence of tetrabutylammonium bromide and zincii triflate and trapping of the isocyanate derivative gives.
Manufacturers of di tert butyl dicarbonate and exporters. Keep product and empty container away from heat and sources of ignition. Di tert butyl dicarbonate revision date 15apr2019 viscosity not applicable molecular formula c10 h18 o5 molecular weight 218. Ditertbutyl dicarbonate and 4dimethylaminopyridine. Ep0256559a2 process for producing ditertiarybutyl dicarbonate. Di tert butyl pyrocarbonate, boc anhydride chemical form. The european chemicals agency hereinafter echa maintains this website hereinafter the echa website to enhance public access to information about its. Various aliphatic, aromatic, heterocyclic amines and aminols were protected as their corresponding monocarbamates in excellent yields and short reaction times. To prepare tert butyl ethers and bocalcohols in presence of lewis acid catalyst. Di tert butyl dicarbonate boc 2 o is commonly used i n. For precolumnar derivatization, the reagent di tert butyl dicarbonate, widely used in organic synthesis for protecting amino groups, has been used. Ybotf 3 catalyzed and di tert butyl dicarbonate mediated.
Ditertbutyl dicarbonate reagentplus, 99 % 24424995. In the case of contact with eyes, rinse immediately with plenty of water and seek medical advice. A new and general route to t butyl ethers reaction. They were unable to establish that the ether was formed via the decomposition of the carbonate.
We are experts in the manufacture, testing and logistics of diboc, and we stand ready to meet your needs with highquality di tert butyl dicarbonate. Date hs code description origin country port of discharge unit quantity value inr per unit inr nov 22 2016. Di tert butyl dicarbonate is a reagent used for the introduction of boc protecting group. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pka of alcohols, or type of amine primary or secondary. This carbonate ester reacts with amines to give n tert butoxycarbonyl or socalled b.
Since this compound can be regarded formally as the acid anhydride derived from a. Simple rapid stirring of a mixture of the amine and di tert butyl dicarbonate boc 2 o suspended in water at ambient temperature, an example of an onwater reaction. A concise method for the preparation of carbodiimides from thioureas using di tert butyl dicarbonate boc 2 o as the dehydrosulfurizative reagent has been developed. Unusual and unexpected reactivity of t butyl dicarbonate boc 2 o. Since this compound can be regarded formally as the acid anhydride derived from a tert butoxycarbonyl boc group, it is commonly referred to as boc anhydride. Ditert butyl dicarbonate bocanhydride total 200 drums total net wt 0 kgs china. The amino acid under basic conditions reacts with di tert butyl dicarbonate to give tetrahedral. This pyrocarbonate reacts with amines to give n tert butoxycarbonyl or socalled boc derivatives. Investigations of the stability of di tertiaty butyl carbonate would b of interest in connection with.
Pdf imidazole and trifluoroethanol as efficient and mild. The catalytic role of the ionic liquid is envisaged as electrophilic activation of di tert butyl dicarbonate boc2o through bifurcated hydrogen bond formation with. Boc anhydride bis1,1dimethylethyl dicarbonate boc2o di tert butyl oxydiformate di tert butyl pyrocarbonate dicarbonic acid, bis1,1dimethylethyl ester formic acid, oxydi, di. Ditertbutyl dicarbonate is a reagent widely used in organic synthesis. The tert butoxycarbonyl group is used to protect the amino group of amino acids during the merrificld solid phase peptide synthesis procedure, the group is then removed by treatment with anhydrous acid. Using dmap as the catalyst, a variety of symmetric and asymmetric 1,3diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time. Di t butyl dicarbonate a colourless to pale yellow liquid or low melting solid used in organic synthesis to protect the amine functional group. Chemicalbook provide chemical industry users with di tert butyl dicarbonate boiling point melting point, di tert butyl dicarbonate density msds formula use,if.
Keep away from open flames, hot surfaces and sources of ignition. Ditertbutyl dicarbonate can be analyzed by this reverse phase rp hplc method with simple conditions. Di tert butyl dicarbonate pyrocarbonic acid di tert butyl ester. Ditertbutyl dicarbonate is a reagent used for the introduction of boc protecting group. Tci uses cookies to personalize and improve your user experience. A process for producing ditertbutyl dicarbonate which comprises reacting a monoalkali metal monotertbutyl carbonate with phosgene or trichloromethyl.
Section 1 ditertbutyl dicarbonate 1 chemical product and company identification msds name. Application ditertbutyl dicarbonate boc anhydride can be used. It serves as a protecting group used in solid phase peptide synthesis. 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 clp regulation makes sure that the hazards presented by chemicals are clearly communicated to workers and consumers in. Ditertbutyl tricarbonate c11h18o7 cid 11780301 structure, chemical names, physical and chemical properties, classification, patents, literature, biological. The mobile phase contains an acetonitrile mecn, water, and phosphoric acid. Articles of ditertbutyl dicarbonate are included as well. You can change or update your cookiesettings at any time. An efficient rutheniumcatalyzed doublefold ch alkoxycarbonylation of arenes was developed using di tert butyl dicarbonate as the tertiary esterification reagent, which leads to a direct route to valuable 2,6dicarboxylated products. Process for producing ditertbutyl dicarbonate tokuyama.
Required temperature c for one hour and ten hours halflife. Bocprotected amino groups organic chemistry portal. Wear appropriate protective eyeglasses or chemical safety goggles as described by oshas eye and face protection regulations in. Import data and price of di tert butyl dicarbonate zauba. The conventional quick stirring of a mixture of the amine and di tert butyl dicarbonate boc. Bottles of ditertbutyl dicarbonate buildup of internal pressure in sealed containers caused by its slow decomposition to di tert butyl carbonate and ultimately tert butanol and co 2 in the presence of moisture. The journal of organic chemistry 2006, 71 26, 95809588.
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