Dibenzyl dicarbonate

Base Information

• Chemical Name: Dibenzyl dicarbonate
• CAS No.: 31139-36-3
• Molecular Formula: C16H14 O5
• Molecular Weight: 286.284
• Hs Code.: 29209090
• European Community (EC) Number: 629-545-8
• DSSTox Substance ID: DTXSID70394645
• Nikkaji Number: J615.126D
• Wikidata: Q72463595
• Mol file: 31139-36-3.mol

Synonyms:Dibenzyl dicarbonate;Dibenzyl pyrocarbonate;31139-36-3;Dibenzyldicarbonate;Benzyl Phenylmethoxycarbonyl Carbonate;Pyrocarbonic Acid Dibenzyl Ester;Dicarbonic acid, bis(phenylmethyl) ester;cbz-oxide;dibenzyl-dicarbonate;(PhCH2OCO)2O;Dibenzyl dicarbonate, 97%;SCHEMBL48133;Dicarbonic acid dibenzyl ester;DTXSID70394645;FHRRJZZGSJXPRQ-UHFFFAOYSA-N;MFCD00043124;AKOS015836853;FS-4658;CS-0204889;FT-0638952;P1281;J-018255

Chemical Property of Dibenzyl dicarbonate

Chemical Property:

• Vapor Pressure: 1.75E-07mmHg at 25°C
• Melting Point: 29-32 ºC
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 426.6°Cat760mmHg
• Flash Point: >110 ºC
• PSA: 61.83000
• Density: 1.17
• LogP: 3.67660
• Storage Temp.: −20°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 298

Purity/Quality:

98% ^*data from raw suppliers

Dibenzyl Dicarbonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)OC(=O)OCC2=CC=CC=C2
• Uses: Dibenzyl Dicarbonate is a chemical reagent used in the chemical modification of histidine residues in horseradish peroxidase.

Technology Process of Dibenzyl dicarbonate

There total 3 articles about Dibenzyl dicarbonate 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: 82.0%

benzyl chloroformate (501-53-1,94274-21-2) → dibenzyl dicarbonate (31139-36-3)

Guidance literature:

With sodium hydroxide; tetrabutyl-ammonium chloride; In diethyl ether; at -10 ℃; for 0.5h;

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

Reference yield: 53.0%

sodium benzylcarbonate (61668-49-3) + benzyl chloroformate (501-53-1,94274-21-2) → dibenzyl dicarbonate (31139-36-3)

Guidance literature:

for 8h; Ambient temperature;

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + benzyl chloroformate (501-53-1,94274-21-2) + benzyl alcohol (100-51-6,185532-71-2) → DBC (3459-92-5) + dibenzyl dicarbonate (31139-36-3)

Guidance literature:

benzyl alcohol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

carbon dioxide; In tetrahydrofuran; at 0 ℃; for 0.5h;

benzyl chloroformate; In tetrahydrofuran; at 20 ℃; for 18h; Title compound not separated from byproducts;

DOI:10.1039/b404962d

upstream raw materials:

sodium benzylcarbonate

benzyl chloroformate

carbon dioxide

benzyl alcohol

Downstream raw materials:

Benzyl N-benzyl-N-carbamate

N-(benzyloxycarbonyl)-L-serine

N-benzyloxycarbonyl-L-treonine

N-Cbz-L-Phe

Refernces

• 1、 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.