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CAS NUMBER: 24424-99-5
EC NUMBER: 246-240-1
MOLECULAR FORMULA: [(CH3)3COCO]2O
MOLECULAR WEIGHT: 218.25
DIBOC (Di-tert-butyl carbonate) is an acyclic carboxylic anhydride.
DIBOC (Di-tert-butyl carbonate) derives from a dicarbonic acid.
DIBOC (Di-tert-butyl carbonate) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities.
DIBOC (Di-tert-butyl carbonate) is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.
DIBOC (Di-tert-butyl carbonate) is a reagent widely used in organic synthesis.
Since DIBOC (Di-tert-butyl carbonate) can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl group, DIBOC (Di-tert-butyl carbonate) is commonly referred to as Boc anhydride.
DIBOC (Di-tert-butyl carbonate) reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives.
DIBOC (Di-tert-butyl carbonate) derivatives do not behave as amines, which allows certain subsequent transformations to occur that would be incompatible with the amine functional group.
DIBOC (Di-tert-butyl carbonate) can later be removed from the amine using moderately strong acids.
DIBOC (Di-tert-butyl carbonate) serves as a protective group, for instance in solid phase peptide synthesis.
DIBOC (Di-tert-butyl carbonate)s are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an orthogonal protecting group.
DIBOC (Di-tert-butyl carbonate) is inexpensive, so it is usually purchased.
DIBOC (Di-tert-butyl carbonate) is currently employed commercially by manufacturers in China and India.
DIBOC (Di-tert-butyl carbonate) involves a distillation of the crude material yielding a very pure grade.
DIBOC (Di-tert-butyl carbonate) is also available as a 70% solution in toluene or THF.
As DIBOC (Di-tert-butyl carbonate) may melt at ambient temperatures, its storage and handling is sometimes simplified by using a solution.
DIBOC (Di-tert-butyl carbonate) can be added to the amine under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium bicarbonate.
Protection of DIBOC (Di-tert-butyl carbonate) can also be accomplished in acetonitrile solution using 4-dimethylaminopyridine (DMAP) as the base.
Removal of the DIBOC (Di-tert-butyl carbonate) in amino acids can be accomplished with strong acids such as trifluoroacetic acid neat or in dichloromethane or with HCl in methanol.
A complication may be the tendency of DIBOC (Di-tert-butyl carbonate) cation intermediate to alkylate other nucleophiles; scavengers such as anisole or thioanisole may be used.
Selective cleavage of the DIBOC (Di-tert-butyl carbonate) in the presence of other protecting groups is possible when using AlCl3.
Reaction with trimethylsilyl iodide in acetonitrile followed by methanol is a mild and versatile method of deprotecting Boc-protected amines.
The use of triethylsilane as a carbocation scavenger in the presence of trifluoroacetic acid in dichloromethane has been shown to lead to increased yields, decreased reaction times, simple work-up and improved selectivity for the deprotection of t-butyl ester and t-butoxycarbonyl sites in protected amino-acids and peptides in the presence of other acid-sensitive protecting groups such as the benzyloxycarbonyl, 9-fluorenylmethoxycarbonyl, O- and S-benzyl and t-butylthio groups.
The synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, an important bread aroma compound, starting from 2-piperidone was accomplished using DIBOC (Di-tert-butyl carbonate).
The first step in this reaction sequence is the formation of the carbamate from the reaction of the amide nitrogen with DIBOC (Di-tert-butyl carbonate) in acetonitrile using DMAP as a catalyst.
DIBOC (Di-tert-butyl carbonate) also finds applications as a polymer blowing agent due to its decomposition into gaseous products upon heating.
DIBOC (Di-tert-butyl carbonate) is a reagent used for the introduction of BOC protecting group.
DIBOC (Di-tert-butyl carbonate) plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone.
DIBOC (Di-tert-butyl carbonate) serves as a protecting group used in solid phase peptide synthesis.
The reaction of DIBOC (Di-tert-butyl carbonate) in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols.
DIBOC (Di-tert-butyl carbonate)s were observed depending on the ratio of reagents, reaction time, polarity of solvent, pKa of alcohols, or type of amine.
In reactions of aliphatic alcohols with DIBOC (Di-tert-butyl carbonate), we isolated for the first time carbonic−carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products.
DIBOC (Di-tert-butyl carbonate) is because di-tert-butyl dicarbonate has a quantitative reaction to an amino group, and the by-products in the protection reaction and the removal of the protection group are only tert-butanol and carbon dioxide gas, and the isolation of the target product.
DIBOC (Di-tert-butyl carbonate) is said to be an ideal protective agent because it does not adversely affect In order to make such characteristics of di-tert-butyl dicarbonate more effective, it is necessary to use highly purified di-tert-butyl dicarbonate.
Such DIBOC (Di-tert-butyl carbonate) is usually produced by reacting an alkali metal tert-butylate with carbon dioxide and reacting the resulting tert-butyl carbonate salt with phosgene, a carboxylic acid chloride or a sulfonic acid chloride.
The purity of the DIBOC (Di-tert-butyl carbonate) obtained by these production methods is about 90 to 98%, and such a purity is unsatisfactory when used as a protecting agent for amino groups, particularly when applied to an automatic peptide synthesizer.
Since the melting point of DIBOC (Di-tert-butyl carbonate) is about 20 ° C, it is liquid at room temperature, it has been conventionally purified by the distillation method.
DIBOC (Di-tert-butyl carbonate) crystallizes at a low temperature, but it cannot be separated from impurities by ordinary melt liquid crystal deposition, and it was difficult to purify it to a sufficiently high purity.
DIBOC (Di-tert-butyl carbonate) is preferably 0% or more, more preferably 90%, and particularly preferably 95% or more.
DIBOC (Di-tert-butyl carbonate) is used as a reaction solvent in the synthesis of di-tert-butyldicarbonate, the solvent content should be reduced.
DIBOC (Di-tert-butyl carbonate) thus obtained has a purity of 99% or more and can be advantageously used as an amino group protecting agent, particularly as an amino group protecting agent in an automatic peptide synthesizer or the like.
DIBOC (Di-tert-butyl carbonate) is preferable to use an ordinary solid-liquid separator such as a batch type centrifugal separator or a vacuum filter.
DIBOC (Di-tert-butyl carbonate) is also used in a wide range of further industrial applications, for example as a dehydrating agent in some organic reactions.
DIBOC (Di-tert-butyl carbonate) is widely used for the introduction of the acid-labile Boc-protecting group in organic synthesis.
DIBOC (Di-tert-butyl carbonate) is extensively used for the protection of amino groups in the synthesis of amino acids, alkaloids, and peptides.
DIBOC (Di-tert-butyl carbonate) reacts rapidly and cleanly with the only by-products being carbon dioxide and t-butanol.
DIBOC (Di-tert-butyl carbonate) is an efficient tert-butoxycarbonylating agent for alcohols and thiols.
DIBOC (Di-tert-butyl carbonate) is easily removed by thermolysis or under moderately acidic conditions, such as, treatment with TFA.
DIBOC (Di-tert-butyl carbonate) protecting group strategy is the preferred method of choice due to its: easy installation, removal, stability towards nucleophiles, and strong basic conditions.
In the presence of moisture, DIBOC (Di-tert-butyl carbonate) decomposes into tert-butanol and CO2.
DIBOC (Di-tert-butyl carbonate) is a reagent widely used in organic synthesis.
DIBOC (Di-tert-butyl carbonate) reacts with amines to give N-tert-butoxycarbonyl or so-called t-BOC derivatives.
DIBOC (Di-tert-butyl carbonate)s do not behave as amines, which allows certain subsequent transformations to occur that would have otherwise affected the amine functional group.
DIBOC (Di-tert-butyl carbonate) can later be removed from the amine using acids.
DIBOC (Di-tert-butyl carbonate) serves as a protective group, for instance in solid phase peptide synthesis.
DIBOC (Di-tert-butyl carbonate) is stable to most bases and nucleophiles.
DIBOC (Di-tert-butyl carbonate) group can be added to the amine under aqueous conditions using di-tert-butyl dicarbonate in the presence of a base such as sodium bicarbonate.
Protection of DIBOC (Di-tert-butyl carbonate) can also be accomplished in acetonitrile solution using 4-dimethylaminopyridine (DMAP) as the base.
Removal of DIBOC (Di-tert-butyl carbonate) in amino acids can be accomplished with strong acids such as trifluoroacetic acid neat or in dichloromethane, or with HCl in methanol.
The synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, an important bread aroma compound from 2-piperidone was accomplished using t-boc anhydride.
The first step in this reaction sequence is the formation of the carbamate from the reaction of the secondary amine with boc anhydride in acetonitrile with DMAP as a base.
DIBOC (Di-tert-butyl carbonate) is inexpensive.
DIBOC (Di-tert-butyl carbonate) is a reagent mainly used for the introduction of the Boc protecting group.
DIBOC (Di-tert-butyl carbonate) is a reagent widely used in organic synthesis.
Since DIBOC (Di-tert-butyl carbonate) can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl group, DIBOC (Di-tert-butyl carbonate) is commonly referred to as Boc anhydride.
DIBOC (Di-tert-butyl carbonate) is a colorless to white to yellow crystals, solidified mass or clear liquid.
DIBOC (Di-tert-butyl carbonate) melts around room temperature (m.p.=23°C).
DIBOC (Di-tert-butyl carbonate) does not decompose at this or even slightly higher temperatures.
DIBOC (Di-tert-butyl carbonate) is typically purified by distillation under reduced pressure at temperatures up to around 65°C.
At higher temperatures, DIBOC (Di-tert-butyl carbonate) will decompose to isobutene, t-butyl alcohol and carbon dioxide.
DIBOC (Di-tert-butyl carbonate) is a widely used reagent for introducing protecting groups in peptide synthesis.
DIBOC (Di-tert-butyl carbonate) plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone.
DIBOC (Di-tert-butyl carbonate) serves as a protecting group used in solid phase peptide synthesis.
DIBOC (Di-tert-butyl carbonate) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities.
DIBOC (Di-tert-butyl carbonate) is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.
USES:
-To introduce acid-labile DIBOC (Di-tert-butyl carbonate)-protecting group in amino acids, peptides, and proteins.
-To prepare styrene derivatives by Heck olefination of aromatic carboxylic acids in the presence of a Pd catalyst.
-To synthesize oxazolidin-2-ones and imidazolidin-2-ones by isocyanation of 1,2-aminoalcohols and 1,2-diamines using DMAP as a catalyst.
-In the preparation of N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine from MDMA.
-For the conversion of amines to corresponding isocyanates, carbamates, and urea derivatives.
-In the DIBOC (Di-tert-butyl carbonate) of amides.
-In the DIBOC (Di-tert-butyl carbonate) of sensitive compounds under non-aqueous conditions.
FEATURES:
-High Effectiveness
-Precise composition
-Safe to use
-Non-volatile
PROPERTIES:
-Quality Level: 200
-assay: ≥98.0% (GC)
-form: solid or liquid
-refractive index: n20/D 1.409 (lit.)
-bp: 56-57 °C/0.5 mmHg (lit.)
-mp: 23 °C (lit.)
-density: 0.95 g/mL at 25 °C (lit.)
-application(s): peptide synthesis
-storage temp.: 2-8°C
PHYSICAL AND CHEMICAL PROPERTIES:
-Melting Point: 23 °C(lit.)
-Boiling Point: 65-67 °C
-Flash Point: 99 °F
-Molecular Formula: C10H18O5
-Molecular Weight: 218.24700
-Density: 0.95 g/mL at 25 °C(lit.)
SPECIFICATION:
-Assay (GC, area%): ≥ 98.0 % (a/a)
-Melting range (lower value): ≥ 20 °C
-Melting range (upper value): ≤ 24 °C
-Density: 1.0200g/mL
-Color: White
-Melting Point: 22.0°C to 24.0°C
-Boiling Point: 56.0°C to 57.0°C (0.5mmHg)
-Flash Point: 37°C
-Assay Percent Range: 99%
-Infrared Spectrum: Authentic
-Linear Formula: O[CO2C(CH3)3]2
STORAGE:
Store at +2°C to +8°C.
Store in a cool place.
Keep the container tightly closed in a dry and well-ventilated place.
Moisture and light sensitive.
Incompatible with oxidizing agents, reducing agents, bases and acids.
SYNONYM:
24424-99-5
BOC anhydride
Di-tert-butyldicarbonate
BOC-anhydride
di-t-Butyl dicarbonate
Bis(tert-butoxycarbonyl)oxide
di-tert-Butyl pyrocarbonate
tert-Butoxycarbonyl anhydride
Boc2O
Di(tert-butyl) carbonate
(boc)2o
Dicarbonic acid, bis(1,1-dimethylethyl) ester
Di-t-butyl pyrocarbonate
di-tert butyl dicarbonate
di-t-butyldicarbonate
Pyrocarbonic acid di-tert-butyl ester
Diboc
di-t-butyl-dicarbonate
di-tert-butyl-dicarbonate
UNII-Z10Q236C3G
ditert-butyldicarbonate
ditertbutyl dicarbonate
tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate
di-tert.-butyldicarbonate
MFCD00008805
di(tert-butyl) dicarbonate
