6627-89-0

Usage

Uses

Used in Pharmaceutical Industry:
tert-Butyl phenyl carbonate is used as a reagent for mono-Boc protection of α,ω-diamines, which is an important step in the synthesis of various pharmaceutical compounds. The Boc protection allows for selective reactions to occur on specific functional groups, facilitating the synthesis of complex molecules.
Used in Analytical Chemistry:
tert-Butyl phenyl carbonate is used in the determination of octanol-water partition coefficients by microemulsion electrokinetic chromatography. This technique is crucial for understanding the solubility and lipophilicity of compounds, which are important factors in their biological activity and pharmacokinetics.
Used in Organic Synthesis:
tert-Butyl phenyl carbonate is used in the synthesis of 2-nitroindoles, which are key intermediates in the preparation of various indole-based compounds with potential applications in medicinal chemistry and materials science. The use of tert-butyl phenyl carbonate in this synthesis allows for mild reaction conditions and high yields.

Purification Methods

If IR is free from OH, then purify it by redistillation; otherwise dissolve it in Et2O, wash it with 5% HCl, then H2O, dry it (MgSO4), evaporate and distil it through a Claisen head under vacuum. Care should be taken as distillation of large quantities can lead to decomposition with liberation of CO2 and isobutylene; use the necessary precautions. [Carpino J Am Chem Soc 79 98 1957, Beilstein 6 IV 629.]

InChI:InChI=1/C11H14O3/c1-11(2,3)14-10(12)13-9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 1885-14-9 phenyl chloroformate 
• 75-65-0 tert-butyl alcohol 
• 865-47-4 potassium tert-butylate 
• 88345-85-1 5-bromo-1-phenoxycarbonyl-2-phenyl-1,2-dihydropyridine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 108-95-2 phenol 
• 264255-59-6 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydrophthalazine 
• 90731-83-2 3-bromo-1-(phenoxycarbonyl)pyridinium chloride 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 

Downstream Products

• 870-46-2 t-butoxycarbonylhydrazine 
• 98598-96-0 tert-butyl 2-methyl-1H-indole-1-carboxylate 
• 89378-43-8 3-methyl-indole-1-carboxylic acid tert-butyl ester 
• 82409-02-7 bis[3-(t-butoxycarbonylamino)propyl]amine 
• 51857-17-1 tert-butyl N-(6-aminohexyl)carbamate 
• 51644-96-3 5-tert-butoxycarbonylamino-1-aminopentane 
• 83392-10-3 N¹,N⁸-bis(tert-butoxycarbonyl)spermidine 
• 255735-88-7 [(2R)-2-aminopropyl]carbamic acid,1,1-dimethylethyl ester 
• 68076-36-8 1-amino-4-[(tert-butyloxycarbonyl)amino]butane 
• 95034-05-2 tert-butyl (2-amino-2-methylpropyl)carbamate 
• 108-95-2 phenol 
• 24469-50-9 t-butyl 3-benzylidenecarbazate 
• 60142-89-4 7-[(tert-butoxycarbonyl)amino]heptanoic acid 
• 88829-82-7 tert-butyl N-(8-aminooctyl)carbamate 

Relevant academic research and scientific papers

Preparation method of N-Boc-1, 2-diaminoethane

The invention relates to a preparation method of N-Boc-1, 2-diaminoethane. The preparation method comprises 1) dissolving phenol, a catalyst and a base in a first organic solvent, and adding di-tert-butyl dicarbonate into the solution with the first solvent drop by drop for a reaction to obtain tert-butyl phenyl carbonate, and 2) dissolving 1, 2-diaminoethane in the first organic solvent, and adding tert-butyl phenyl carbonate into the solution drop by drop for a reaction to obtain a final product. The preparation method has simple separation and purification processes, has a small reaction temperature range and a high reaction yield and realizes a low raw material cost.

Exploiting Peptidomimetics to Synthesize Compounds That Activate Ryanodine Receptor Calcium Release Channels

Ryanodine receptor (RyR) Ca2+-release channels are essential for contraction in skeletal and cardiac muscle and are prime targets for modification of contraction in disorders that affect either the skeletal or heart musculature. We designed and synthesized a number of compounds with structures based on a naturally occurring peptide (A peptides) that modifies the activity of RyRs. In total, 34 compounds belonging to eight different classes were prepared. The compounds were screened for their ability to enhance Ca2+ release from isolated cardiac sarcoplasmic reticulum (SR) vesicles, with 25 displaying enhanced Ca2+ release. Competition studies with the parent peptides indicated that the synthetic compounds act at a competing site. The activity of the most effective of the compounds, BIT 180, was further explored using Ca2+ release from skeletal SR vesicles and contraction in intact skeletal muscle fibers. The compounds did not alter tension in intact fibers, indicating that (as expected) they are not membrane permeable, but importantly, that they are not toxic to the intact cells. Proof in principal that the compounds would be effective in intact muscle fibers if rendered membrane permeable was obtained with a structurally related membrane-permeable scorpion toxin (imperatoxin A), which was found to enhance contraction.

Activation of Benzyl Aryl Carbonates: The Role of Cation-π Interactions

Benzyl aryl carbonates can react with a nucleophile to yield an activated electrophile and an aryloxide anion. Previously, we had utilized this in the synthesis of α-nitro esters from nitroalkanes. To further understand the process of activation of these carbonates by nucleophiles, we have performed kinetic studies on the hydrolysis of carbonates using nucleophiles. Rate constants for the hydrolysis were obtained under pseudo-first-order conditions with DABCO as the nucleophile. A comparison of rate constant for hydrolysis of isobutyl phenyl carbonate with benzyl phenyl carbonate shows that the presence of benzyl group results in a 16-fold acceleration of hydrolysis rate. This indicates that the transition state for activation of carbonate is stabilized by cation-π interactions. A comparison of the rate constant for various aromatic rings indicates that electron-donating substituents on the benzyl groups accelerate the rate of hydrolysis. Studies were also carried out with DMAP as nucleophile and the results are presented. Our studies show that stable carbonates can be activated using nucleophiles. Activated acyl groups generated from acid anhydrides have been used in several enantioselective reactions. Our studies show that carbonates can be stable alternatives to acid anhydrides.

MgBr 2 · OEt 2: A Lewis Acid Catalyst for the O - And N -Boc Protection of Phenols and Amines

MgBr2 · OEt2 efficiently catalyzes the O- and N-tert-butoxycarbonylation of functionalized phenols and amines. The presented procedure is operationally simple and done under solvent-free conditions. GRAPHICAL ABSTRACT.

General solvent-free highly selective N-tert-butyloxycarbonylation strategy using protic ionic liquid as an efficient catalyst

A simple, rapid and solvent-free protocol is described for the chemo-selective transformation of amines to tert-butyloxycarbonyl protected derivatives (NHBoc) using Boc2O and imidazolium trifluoroacetate protic ionic liquid (5-20 mol%). Unwanted side products such as isocyanate, urea or N,N-di-Boc were not detected. The scope of the protection strategy was successfully explored for substrate alcohols, phenols and thiol at elevated temperatures. Optically pure amino acids, amino acid esters and amino alcohols were efficiently converted to the corresponding N-Boc protected derivatives in excellent yields without racemization at the chiral center. The distinct advantages of this method are: operational simplicity, cleaner reaction, high selectivity, excellent yield, rapid reaction convergence, easy preparation and recyclability of the catalyst.

A new, efficient, and catalyst-free microwave-assisted approach for formation of O-tert-butoxy carbonates

A new simple, efficient, greener, and catalyst-free chemoselective protocol for the O-tert-butoxycarbonylation of various structurally diverse hydroxy compounds was carried out with (Boc)2O under microwave radiation. The corresponding O-tertbutoxy carbonates were obtained in good to excellent yields in a short reaction time without any side reactions.

Mixed metal MgO-ZrO2 nanoparticle-catalyzed O-tert-Boc protection of alcohols and phenols under solvent-free conditions

An environmentally benign method for O-tert-Boc protection of alcohols and phenols catalyzed by MgO-ZrO2 nanoparticles under solvent-free conditions is described. A variety of phenols, alcohols (aliphatic and aromatic) were converted to corresponding O-tert-Boc products in good to excellent yield (50-95%). The present protocol is expedient, simple, and efficient under solvent-free conditions. The MgO-ZrO2 Nps are easily prepared from inexpensive precursors, and are reusable, recyclable and chemoselective. Copyright 2012 John Wiley & Sons, Ltd. Copyright

An eco-sustainable erbium(iii)-catalyzed method for formation/cleavage of O-tert-butoxy carbonates

A new simple and effective method for the formation/cleavage of O-tert-butoxy carbonates of alcohols and phenols is proposed. Mesoporous silica-supported Er(iii) (ErIII-MCM-41) was used as an efficient and reusable solid catalyst in the solvent-free ultrasound-assisted synthesis of Boc-carbonate derivatives of a wide range of alcohols and phenols. The fast, selective deprotection of Boc-derivatives is achieved with a very low amount of Er(OTf)3 in ethanol under microwave irradiation. Therefore, the entire protection/de-protection process is very attractive, from the point of view of sustainability.

Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst

The chemoselective O-tert-butoxycarbonylation of phenols using low levels (5-0.1 mol %) of 6,7-dimeth-oxyisoquinoline as a reusable organocatalyst is described.