Diphenyl sulfite

Base Information

• Chemical Name: Diphenyl sulfite
• CAS No.: 4773-12-0
• Molecular Formula: C12H10O3S
• Molecular Weight: 234.276
• DSSTox Substance ID: DTXSID50464416
• Nikkaji Number: J80.898I
• Wikidata: Q82289720
• Mol file: 4773-12-0.mol

Synonyms:diphenyl sulfite;Sulfurous acid diphenyl;4773-12-0;diphenyl sulphite;diphenylsulfite;SCHEMBL775482;DTXSID50464416;AVGYVDOSBJFXFR-UHFFFAOYSA-N

Chemical Property of Diphenyl sulfite

Chemical Property:

• PSA: 54.74000
• LogP: 3.58880
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 234.03506535
• Heavy Atom Count: 16
• Complexity: 198

Purity/Quality:

99% ^*data from raw suppliers

Diphenyl sulfite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OS(=O)OC2=CC=CC=C2

Technology Process of Diphenyl sulfite

There total 15 articles about Diphenyl sulfite 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: 86.0%

phenol (108-95-2,27073-41-2) → diphenyl sulfite (4773-12-0)

Guidance literature:

With ICF₂CF₂OCF₂CF₂SO₂N=S=O; In benzene; at 25 ℃; for 3h;

DOI:10.1016/0022-1139(93)03060-Y

Reference yield:

phenyl chlorosulphinate (13165-73-6) → thionyl chloride (7719-09-7) + diphenyl sulfite (4773-12-0)

Guidance literature:

at 70 ℃; Einleiten von HCl;

DOI:10.1021/ja01188a015

Reference yield:

sodium phenoxide (139-02-6) → diphenyl sulfite (4773-12-0) + phenyl chlorosulphinate (13165-73-6)

Guidance literature:

With thionyl chloride; toluene; at -10 - -5 ℃;

upstream raw materials:

sodium phenoxide

phenyl chlorosulphinate

phenol

pyridine

Downstream raw materials:

1,1'-sulfinylbisbenzene

phenol

phenyl 4-bromobenzoate

thiophenol

Refernces

A Novel One-step Procedure for the Conversion of Thymidine into 2,3'-Anhydrothymidine

10.1039/c39890000997

T. Sudhakar Rao and Colin B. Reese describe a new method for synthesizing 2,3'-anhydrothymidine (3), a key intermediate in the production of the antiretroviral drug 3'-azido-3'-deoxythymidine (AZT). The authors discovered that heating thymidine (2) with an excess of diphenyl sulphite in dimethylacetamide solution in the presence of a catalytic amount of 1-methylimidazole at 156°C for 45 minutes yields 2,3'-anhydrothymidine (3) in approximately 65% yield. This method is advantageous over previous procedures, such as the use of 2-chloro-1-diethylamino-1,1,2-trifluoroethane, due to the greater accessibility of diphenyl sulphite. The synthesized 2,3'-anhydrothymidine (3) can then be converted into AZT by reacting with lithium azide, achieving a 71% yield of AZT. This streamlined synthesis offers a more efficient route for the production of AZT, which is crucial for the treatment of AIDS patients.