6627-89-0

Basic information

• Product Name: tert-Butyl phenyl carbonate
• Synonyms: Carbonic acid tert-butylphenyl ester;Einecs 229-601-8;Carbonicacidtert-butylesterphenylester;ert-Butyl phenyl carbonate;2-Methyl-2-propanyl phenyl carbonate;tert-Butyl phenyl carbonate Carbonic acid tert-butyl phenyl ester;tert-Butyl phenyl carbonate 98%;tert-Butyl phenyl carbonate≥ 98%(HPLC)
• CAS NO: 6627-89-0
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 229-601-8
• Product Categories: Carbonates;Carbonyl Compounds;Organic Building Blocks
• Mol File: 6627-89-0.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 83 °C0.6 mm Hg(lit.)
• Flash Point: 214 °F
• Appearance: Colorless/Liquid or Low Melting Solid
• Density: 1.05 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: n20/D 1.480
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly)
• Water Solubility: Slightly soluble in water.
• BRN: 2361602
• CAS DataBase Reference: tert-Butyl phenyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl phenyl carbonate(6627-89-0)
• EPA Substance Registry System: tert-Butyl phenyl carbonate(6627-89-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 6627-89-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear light yellow liquid

Uses

tert-Butyl phenyl carbonate is used in determination of octanol-water partition coefficients by microemulsion electrokinetic chromatography. It is also used in the synthesis of 2-nitroindoles and as a reagent for mono-Boc protection of α,ω-diamines.

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 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 
• 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 
• 24424-99-5 di-tert-butyl dicarbonate 
• 865-47-4 potassium tert-butylate 
• 88345-85-1 5-bromo-1-phenoxycarbonyl-2-phenyl-1,2-dihydropyridine 

Downstream Products

• 870-46-2 t-butoxycarbonylhydrazine 
• 82409-02-7 bis[3-(t-butoxycarbonylamino)propyl]amine 
• 51857-17-1 tert-butyl N-(6-aminohexyl)carbamate 
• 83392-10-3 N¹,N⁸-bis(tert-butoxycarbonyl)spermidine 
• 88829-82-7 tert-butyl N-(8-aminooctyl)carbamate 
• 153086-78-3 tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate 
• 333743-54-7 tert-butyl (R)-(2-aminopropyl)carbamate 
• 635-90-5 1-phenylpyrrole 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 71-43-2 benzene 
• 108-95-2 phenol 
• 959153-72-1 [bis(3-tert-butoxycarbonyl-aminopropyl)amino]acetic acid benzyl ester 
• 613-37-6 4-methoxylbiphenyl 
• 67-56-1 methanol 

Relevant articles and documents

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.

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.

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.