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

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

Uses

Used in Chemical Synthesis:
CARBONIC ACID DI-2-PYRIDYL ESTER is used as a coupling agent for the esterification of carboxylic acids, such as 3-Cyclohexenylcarboxylic acid [C988195]. It facilitates the formation of ester bonds, which are essential in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, CARBONIC ACID DI-2-PYRIDYL ESTER is used as a reagent to synthesize active carbonates, such as benzyl 2-pyridyl carbonate, and carbamates, such as 3-Pyridyl diethylcarbamate [P992950]. These synthesized compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Research and Development:
CARBONIC ACID DI-2-PYRIDYL ESTER is also utilized in research and development for the synthesis of novel compounds and the study of their properties. Its ability to act as a coupling agent and a reagent makes it a valuable tool in the exploration of new chemical reactions and the creation of innovative materials.

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

• 4427-92-3 4-Phenyl-1,3-dioxolan-2-one 
• 108-32-7 1,2-propylene cyclic carbonate 
• 96-49-1 [1,3]-dioxolan-2-one 
• 26654-39-7 4,4-dimethyl-1,3-oxazolidin-2-one 
• 1072-70-4 5-methyl-1,3-oxazolidin-2-one 
• 142-08-5 2-hydroxypyridin 
• 5005-35-6 2-pyridyl benzoate 
• 93-89-0 benzoic acid ethyl ester 
• 95-25-0 5-chloro-2-benzoxazolinone 
• 10276-85-4 benzyl caprylate 
• 89398-02-7 2-pyridyl caprylate 
• 2094-69-1 benzyl pivalate 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 59658-05-8 2-pivaloyloxypyridine 

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

Amino acid derivatives as paf-receptor antagonists

Compounds of general formula I: STR1 wherein W represents imidazo [4,5-c]pyridin-1-yl, imidazo [4,5-c]pyridin-3-yl and imidazo [4,5-c]pyridin-5-yl optionally substituted with one or more --C1 -C6 alkyl substituents; Z represents a) a divalent alkanediyl, alkenediyl or alkynediyl group; b) a --(CH2)q U(CH2)r -- group, optionally substituted, wherein q is an integer from 0-3, r is an integer from 0-3 and U is --O-- or --S--; Q represents a carbonyl, thiocarbonyl or sulphonyl group; B represents a) a --VR8 group wherein V is --C(=O)O-- or --CH2 O--; are antagonists of platelet activating factor (PAF).

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

2(1H)-Pyridone as Leaving Group in Acylation Reactions - Applications in Peptide Synthesis

Alkyl 2-pyridyl carbonates 3 or mixtures of 3 and the isomeric N-(alkoxycarbonyl)-2-pyridones 3' are useful for the introduction of urethane protective groups into amino acids.The N-protected amino acids 7 - 10 react with 2(1H)-pyridone (1a) using the carbodiimide method to yield 2-pyridyl active esters 11, which easily undergo coupling reactions with amino acid esters 12 with elimination of 1a to give peptides 13 in good yields as well as high optical purities.

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.

DI-2-PYRIDYL CARBONATE: A NEW EFFICIENT COUPLING AGENT FOR THE DIRECT ESTERIFICATION OF CARBOXYLIC ACIDS

Reaction of carboxylic acids with equimolar amounts of di-2-pyridyl carbonate and alcohols or thiols in the presence of 4-dimethylaminopyridine as a catalyst in methylene chloride at room temperature affords the corresponding esters in high yields under mild conditions.