Phenylmethylsulfonyl fluoride

Base Information

• Chemical Name: Phenylmethylsulfonyl fluoride
• CAS No.: 329-98-6
• Molecular Formula: C7H7FO2S
• Molecular Weight: 174.196
• Hs Code.: 29241990
• European Community (EC) Number: 206-350-2
• NSC Number: 88499
• UNII: 57KD15003I
• DSSTox Substance ID: DTXSID6059819
• Nikkaji Number: J150.773G
• Wikipedia: PMSF
• Wikidata: Q411575
• Metabolomics Workbench ID: 125291
• ChEMBL ID: CHEMBL190503
• Mol file: 329-98-6.mol

Synonyms:Benzenemethanesulfonyl Fluoride;Fluoride, Benzenemethanesulfonyl;Fluoride, Phenylmethanesulfonyl;Fluoride, Phenylmethylsulfonyl;Phenylmethanesulfonyl Fluoride;Phenylmethylsulfonyl Fluoride

Chemical Property of Phenylmethylsulfonyl fluoride

Chemical Property:

• Appearance/Colour: White to cream solid
• Vapor Pressure: 0.117mmHg at 25°C
• Melting Point: 92-95 °C
• Refractive Index: 1.502
• Boiling Point: 285.7 °C at 760 mmHg
• Flash Point: 126.6 °C
• PSA: 42.52000
• Density: 1.317 g/cm³
• LogP: 2.56670
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: dry solvents (ethanol, methanol, and 2-propanol): 200 mM St
• Water Solubility.: hydrolysis
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 174.01507880
• Heavy Atom Count: 11
• Complexity: 199

Purity/Quality:

99.0% ^*data from raw suppliers

Phenylmethylsulfonyl Fluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, T, C
• Hazard Codes: F,T,C
• Statements: 11-34-25-23/24/25
• Safety Statements: 7-16-45-36/37/39-28A-26-27

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1=CC=C(C=C1)CS(=O)(=O)F
• Uses: PMSF is an irreversible serine/cysteine protease inhibitor Phenylmethylsulfonyl fluoride is used as a Protease inhibitor such as Chymotrypsin, Trypsin and Thrombin as well as Acetylcholineesterase. Standard protease inhibitor in biological research; in protein purification to prevent proteolytic degradation.

Technology Process of Phenylmethylsulfonyl fluoride

There total 13 articles about Phenylmethylsulfonyl fluoride 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: 98.0%

→ phenylmethylsulphonyl fluoride (329-98-6)

Guidance literature:

With potassium hydrogen difluoride; In water; acetonitrile; at 20 ℃; for 3h;

Reference yield: 97.0%

benzenesulfonyl chloride (1939-99-7) → phenylmethylsulphonyl fluoride (329-98-6)

Guidance literature:

With potassium fluoride; triethylamine; In dichloromethane; water;

Reference yield: 95.0%

benzylsulfonylhydrazide (36331-57-4) → phenylmethylsulphonyl fluoride (329-98-6)

Guidance literature:

With Selectfluor; In water; at 60 ℃; for 14h; Schlenk technique;

DOI:10.1039/c5gc02755a

upstream raw materials:

benzenesulfonyl chloride

zephirol

dibenzyl disulphide

S-benzyl phenyl-methanethiosulfonate

Downstream raw materials:

α-Benzylsulfonyl-methylidentriphenylphosphoran

[(benzylsulfonyl)(methyl)methylene](triphenyl)phosphorane

α'-Benzylsulfonyl-α-benzylsulfonylaethylidentriphenylphosphoran

[(benzylsulfonyl)(phenyl)methylene](triphenyl)phosphorane

Refernces

Stereochemical selectivity of methanandamides for the CB1 and CB2 cannabinoid receptors and their metabolic stability

10.1016/S0968-0896(01)00088-8

The research aimed to evaluate the stereoselectivity of chiral analogues of the endogenous cannabinoid receptor ligand, arachidonylethanolamide (anandamide), in binding to CB1 and CB2 cannabinoid receptors and their metabolic stability. The study synthesized several chiral anandamide analogues with methyl groups introduced at the 2,1 and 20 positions using asymmetric synthesis. The researchers found that the introduction of a single 2-methyl group increased affinity for CB1, but only modestly improved metabolic stability. However, the 2,1-dimethyl analogues exhibited high enantio- and diastereoselectivity, with (R)-N-(1-methyl-2-hydroxyethyl)-2-(R)-methyl-arachidonamide (4) showing the highest CB1 receptor affinity. The study concluded that a partial CB1 receptor site model could be proposed, featuring two hydrophobic pockets capable of accommodating 1- and 2-methyl groups. Key chemicals used in the process included arachidonic acid, various amino alcohols, and chiral auxiliaries like 4-benzyl-2-oxazolidinone, along with reagents such as oxalyl chloride, lithium hydroxide, and phenylmethanesulfonyl fluoride (PMSF) for enzyme inhibition during binding assays.