1659-31-0

Basic information

• Product Name: CARBONIC ACID DI-2-PYRIDYL ESTER
• Synonyms: Carbonic acid di-2-pyridyl esterCarbonic acid di-2-pyridyl ester;Dipyridin-2-yl carbonate;2-Pyridinol carbonate;DPC Carbonic acid di-2-pyridyl ester;Di-2-pyridyl carbonate≥ 98%(Titration);CARBONIC ACID DI-2-PYRIDYL ESTER;DI-2-PYRIDYL CARBONATE;Carbonicaciddipyridylester
• CAS NO: 1659-31-0
• Molecular Formula: C₁₁H₈N₂O₃
• Molecular Weight: 216.19
• EINECS: 213-988-5
• Product Categories: Synthetic Organic Chemistry;Condensation & Active Esterification
• Mol File: 1659-31-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 90 °C
• Boiling Point: 351.594 °C at 760 mmHg
• Flash Point: 166.438℃
• Appearance: /
• Density: 1.307
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Refrigerator
• PKA: 0.63±0.12(Predicted)
• CAS DataBase Reference: CARBONIC ACID DI-2-PYRIDYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CARBONIC ACID DI-2-PYRIDYL ESTER(1659-31-0)
• EPA Substance Registry System: CARBONIC ACID DI-2-PYRIDYL ESTER(1659-31-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1659-31-0(Hazardous Substances Data)

Usage

Chemical Properties

White to faint yellow crystalline powder

Uses

Di-2-pyridyl carbonate is used as a coupling agent in the esterification of carboxylic acids (e.g. 3-Cyclohexenylcarboxylic acid [C988195]). Di-2-pyridyl carbonate is also used as a reagent to synthesize active carbonates (e.g. benzyl 2-pyridyl carbonate) and carbamates (e.g. 3-Pyridyl diethylcarbamate [P992950]).

Preparation

A solution of phosgene (2.5 m in toluene, 2 mL, 5.0 mmol) was diluted with dichloromethane (8 mL) and then a solution of 2-pyridinol 853 (950 mg, 10 mmol) and triethylamine (1.214 g, 10.2 mmol) in dichloromethane (20 mL) was added at 0 ℃. The reaction mixture was stirred at 0℃ for 1 h, then washed with cold 5% NaHCO3 solution (20 mL) and cold saturated brine (20 mL), dried over MgSO4, and filtered. The filtrate was concentrated to dryness to give di-2-pyridyl carbonate, DPC, 725 (972 mg) in 90% yield. It was recrystallized from dichloromethane/petroleum ether (811 mg, 75%); mp 84–86℃. DPC has also been produced as its hydrochloride salt 877, in a more facile procedure on a larger scale, in 97% yield.

InChI:InChI=1/C11H8N2O3/c14-11(15-9-5-1-3-7-12-9)16-10-6-2-4-8-13-10/h1-8H

Upstream product

• 142-08-5 2-hydroxypyridin 
• 75-44-5 phosgene 
• 124-07-2 Octanoic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 930-70-1 2-pyridone sodium salt 

Downstream Products

• 13896-06-5 4-ethyl-2-oxazolidinone 
• 59-49-4 2-Benzoxazolinone 
• 142-08-5 2-hydroxypyridin 
• 5005-35-6 2-pyridyl benzoate 
• 93-89-0 benzoic acid ethyl ester 
• 89985-91-1 tert-butyl pyridin-2-yl carbonate 
• 2094-69-1 benzyl pivalate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 59658-05-8 2-pivaloyloxypyridine 
• 325952-80-5 cyclohexyl 2-pyridyl carbonate 
• 124-38-9 carbon dioxide 
• 1439367-20-0 1-(4-phenylphenyl)-ethyl 2-oxopyridine-1-carboxylate 
• 1439366-80-9 cyclohexyl N-[(2S,3R)-2-methyl-4-oxooxetan-3-yl]-carbamate 

Relevant articles and documents

Functional mimicry of the active site of carboxypeptidase A by a molecular imprinting strategy: Cooperativity of an amidinium and a copper ion in a transition-state imprinted cavity giving rise to high catalytic activity

A model for the natural enzyme carboxypeptidase A was prepared by molecular imprinting in synthetic polymers. An unusually high activity and efficiency for carbonate hydrolysis could be obtained by imprinting with a stable transition-state analogue template and introducing an amidinium group and a Cu2+ ion-binding site in a defined orientation to each other into the active site. With substrates having a very similar structure to the template, extraordinarily high enhancements of rates of 110000-fold were obtained of catalyzed to uncatalyzed reaction kcat/kuncat. The efficiency kcat/Km of the molecularly imprinted catalysts compared to that of the nonimprinted control polymers containing the same functional groups was 790-fold higher, a clear indication of a very efficient imprinting procedure. Copyright

Di(2-pyridyl) carbonate promoted alkoxycarbonylation of amines: A convenient synthesis of functionalized carbamates

The reaction of di(2-pyridyl) carbonate with a variety of alcohols including hindered secondary, tertiary and protected glycols afforded the corresponding mixed carbonate which was efficiently transformed into various carbamates in high yield under mild c

New Amino-protective Reagents for t-Butoxycarbonylation and Benzyloxycarbonylation of Amines and Amino Acids

New amino-protective reagents for t-butoxycarbonylation and benzyloxycarbonylation of amines and amino acids have been developed. t-Butyl 2-pyridyl carbonate and t-butyl S-(2-pyridyl) thiocarbonate react cleanly with various amines and amino acids to afford N-Boc amines and N-Boc amino acids in high yields.Benzyl 2-pyridyl carbonate and O-benzyl S-(2-pyridyl) thiocarbonate are also found to be very effective in the benzyloxycarbonylation of amino acids.