Phenyl fluorosulfate

Base Information

• Chemical Name: Phenyl fluorosulfate
• CAS No.: 330-00-7
• Molecular Formula: C6H5FO3S
• Molecular Weight: 176.168
• Hs Code.: 2915900090
• European Community (EC) Number: 852-566-0
• DSSTox Substance ID: DTXSID00186631
• Nikkaji Number: J53.766G
• Wikidata: Q83057984
• Mol file: 330-00-7.mol

Synonyms:Phenyl fluorosulfate;330-00-7;fluorosulfonyloxybenzene;Fluorosulfuric acid, phenyl ester;Phenyl fluorosulphonate;Phenoxysulphonyl fluoride;Fluoridosulfuric acid phenyl ester;Phenoxysulfonyl fluoride;BRN 1948091;Fluorosulfuric acid, phenyl ester (8CI,9CI);3-06-00-00654 (Beilstein Handbook Reference);PHENYL FLUORANESULFONATE;SCHEMBL8573406;DTXSID00186631;LS-105727;EN300-7473458

Chemical Property of Phenyl fluorosulfate

Chemical Property:

• Vapor Pressure: 0.157mmHg at 25°C
• Boiling Point: 221.6°Cat760mmHg
• Flash Point: 87.8°C
• PSA: 51.75000
• Density: 1.427g/cm³
• LogP: 2.36050
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 175.99434335
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Phenyl fluorosulfate

There total 5 articles about Phenyl fluorosulfate 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: 95.0%

phenol (108-95-2,27073-41-2) → Phenyl fluorosulfonate (330-00-7)

Guidance literature:

With fluorosulfonyl anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jo00011a010

Reference yield:

C18H24O9S (1269657-64-8) → Phenyl fluorosulfonate (330-00-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol; acetonitrile; aq. phosphate buffer / 0.5 h / 20 °C / pH 7.4

2: fluorosulfonyl fluoride; triethylamine / dichloromethane / 20 °C / Sealed tube

With fluorosulfonyl fluoride; 20% palladium hydroxide-activated charcoal; hydrogen; triethylamine; In methanol; aq. phosphate buffer; dichloromethane; acetonitrile;

DOI:10.1002/anie.202007211

Reference yield:

→ Phenyl fluorosulfonate (330-00-7)

Guidance literature:

at 110 ℃;

upstream raw materials:

phenol

C₁₈H₂₄O₉S

Downstream raw materials:

C₁₈H₂₄O₉S

isopropyl benzoate

cis-1-phenyl-1-propylene

styrene

Refernces

• 1、 Fei, Zhongbo,Hu, Jinbo,Li, Wei,Liu, Qinghe,Ni, Chuanfa,Wang, Xiu,Zhou, Min. "Deoxyfluorination of alcohols with aryl fluorosulfonates". supporting information. p. 8170 - 8173. Retrieved 2021/08/23.
• 2、 Yan, Wenjie,Zhou, Hongbo,Li, Haoyuan,Hu, Huimin,Yu, Ying,Guo, Shengmei,Cai, Hu. "NiCl 2as a Cheap and Efficient Precatalyst for the Coupling of Aryl Fluorosulfonate and Phosphite/Phosphine Oxide". supporting information. p. 1453 - 1456. Retrieved 2021/07/20.