Diethyl pyrocarbonate

Base Information

• Chemical Name: Diethyl pyrocarbonate
• CAS No.: 1609-47-8
• Molecular Formula: C6H10O5
• Molecular Weight: 162.142
• Hs Code.: 29209085
• European Community (EC) Number: 216-542-8
• UNII: LMR3LZG146
• DSSTox Substance ID: DTXSID2051764
• Nikkaji Number: J13.055I
• Wikipedia: Diethyl_pyrocarbonate
• Wikidata: Q421385
• Metabolomics Workbench ID: 45764
• ChEMBL ID: CHEMBL55517
• Mol file: 1609-47-8.mol

Synonyms:Anhydride, Ethoxyformic;Dicarbonate, Diethyl;Diethyl Dicarbonate;Diethyl Oxydiformate;Diethyl Pyrocarbonate;Diethylpyrocarbonate;Ethoxyformic Anhydride;Oxydiformate, Diethyl;Pyrocarbonate, Diethyl;Pyrocarbonic Acid Diethyl Ester

Chemical Property of Diethyl pyrocarbonate

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 1.31mmHg at 25°C
• Melting Point: 69℃
• Refractive Index: n20/D 1.398(lit.)
• Boiling Point: 201.3 °C at 760 mmHg
• Flash Point: 69.4 °C
• PSA: 61.83000
• Density: 1.15 g/cm³
• LogP: 1.31600
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: 95% ethanol: soluble4.5g/10 mL, clear, colorless
• Water Solubility.: slow decomposition
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

Diethyl Pyrocarbonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)OC(=O)OCC
• Uses: Modification reagent for His and Tyr residues in proteins. Robust probe for structural disruptions in dsDNA, reacting with fully or partially unstacked bases.1 Gentle esterifying agent. Preservative for wines, soft drinks, fruit juices. Diethyl pyrocarbonate may be used in the following studies:For the modification of histidyl residues in proteins.As a nuclease inhibitor, for the extraction of undegraded nucleic acids from etiolated and green plant tissues.For the modification of linear and supercoiled plasmid DNAs.As a chemical probe to investigate the secondary structure in negatively supercoiled DNA.For cabethoxylation of histidine residues of actin.

Technology Process of Diethyl pyrocarbonate

There total 9 articles about Diethyl pyrocarbonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

chloroformic acid ethyl ester (541-41-3) → diethyl dicarbonate (1609-47-8)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; at -10 ℃; for 1h;

DOI:10.1016/S0040-4020(01)81698-7

Reference yield:

sodium methacrylate (5536-61-8) + chloroformic acid ethyl ester (541-41-3) → methacryloyl anhydride (760-93-0) + diethyl dicarbonate (1609-47-8) + carboethoxymethacrylic anhydride (21982-91-2) + Diethyl carbonate (105-58-8,76619-83-5)

Guidance literature:

Reference yield:

ethanol (64-17-5) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl ethyl carbonate (27945-07-9) + Ethyl-tert-butylpyrocarbonat (19935-69-4) + diethyl dicarbonate (1609-47-8) + Diethyl carbonate (105-58-8,76619-83-5)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; Further Variations:; Solvents; reaction times; Product distribution;

DOI:10.1021/jo000257f

upstream raw materials:

chloroformic acid ethyl ester

(+-)-Emetin

chloroform

ethanol

Downstream raw materials:

N-carboethoxyaniline

ethyl (4-ethoxyphenyl)carbamate

triphenylmethyl alcohol

benzoic acid ethyl ester

Refernces

• 1、 Basel, Yochai,Hassner, Alfred. "Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols". . p. 6368 - 6380. Retrieved 2007/10/03.
• 2、 Plusquellec, Daniel,Roulleau, Fabienne,Lefeuvre, Martine,Brown, Eric. "A NEW SYNTHESIS OF CARBOXYLIC AND CARBONIC ACID ANHYDRIDES USING PHASE TRANSFER REACTIONS". . p. 2471 - 2476. Retrieved 2007/10/02.