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Phenylmethylsulfonyl fluoride

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Phenylmethylsulfonyl fluoride Basic information
Description
Product Name:Phenylmethylsulfonyl fluoride
Synonyms:α-toluenesulphonyl fluoride;Phenylmethanesulfonyl fluoride,α-Toluenesulfonyl fluoride, Benzylsulfonyl fluoride, PMSF, Phenylmethylsulfonyl fluoride;Phenylmethanesulfony;BENZYLSULFONYL FLUORIDE;A-TOLUENESULFONYL FLUORIDE;A-TOLUENESULPHONYL FLUORIDE;BENZENEMETHANESULFONYL FLUORIDE;P-TOLUENESULPHONYL FLUORIDE
CAS:329-98-6
MF:C7H7FO2S
MW:174.19
EINECS:206-350-2
Product Categories:Inhibitor;ProteaseInhibitors;329-98-6
Mol File:329-98-6.mol
Phenylmethylsulfonyl fluoride Structure
Phenylmethylsulfonyl fluoride Chemical Properties
Melting point 92-95 °C
Boiling point 112 °C16 mm Hg(lit.)
density 0.797 g/mL at 20 °C
Fp 222 °F
storage temp. 2-8°C
solubility dry solvents (ethanol, methanol, and 2-propanol): 200 mM Stock solution are stable for months at 4°C.
pka7.0
form Needles (May Agglomerate)
color White
biological sourcesynthetic
Water Solubility hydrolysis
Sensitive Moisture Sensitive
Merck 14,7542
BRN 2088311
Stability:Moisture Sensitive
Cosmetics Ingredients FunctionsSKIN CONDITIONING
InChI1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2
InChIKeyYBYRMVIVWMBXKQ-UHFFFAOYSA-N
SMILESFS(=O)(=O)Cc1ccccc1
CAS DataBase Reference329-98-6(CAS DataBase Reference)
EPA Substance Registry SystemBenzenemethanesulfonyl fluoride (329-98-6)
Safety Information
Hazard Codes F,T,C
Risk Statements 11-34-25-23/24/25
Safety Statements 7-16-45-36/37/39-28A-26-27
RIDADR UN 3261 8/PG 2
WGK Germany 3
RTECS XT8050000
3-10-21
Hazard Note Highly Toxic/Corrosive
TSCA TSCA listed
HazardClass 8
PackingGroup III
HS Code 29241990
Storage Class6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
Hazard ClassificationsAcute Tox. 3 Oral
Skin Corr. 1B
ToxicityLD50 (24 hr) in mice (mg/kg): 215 ±55 i.p. (Pinsky)
MSDS Information
ProviderLanguage
Benzenemethanesulfonyl fluoride English
SigmaAldrich English
ACROS English
ALFA English
Phenylmethylsulfonyl fluoride Usage And Synthesis
Chemical PropertiesWhite to cream solid
UsesPMSF is an irreversible serine/cysteine protease inhibitor
UsesPhenylmethylsulfonyl fluoride is used as a Protease inhibitor such as Chymotrypsin, Trypsin and Thrombin as well as Acetylcholineesterase.
UsesStandard protease inhibitor in biological research; in protein purification to prevent proteolytic degradation.
DefinitionChEBI: Phenylmethanesulfonyl fluoride is an acyl fluoride with phenylmethanesulfonyl as the acyl group. It has a role as a serine proteinase inhibitor. It derives from a phenylmethanesulfonic acid.
HazardExtremely corrosive and destructive to tissues. May cause irreversible eye damage. PMSF hydrolyzes upon exposure to water/moisture, liberating a toxic and corrosive gas (hydrogen flouride) that in contact with metal surfaces can generate flammable and/or explosive hydrogen gas.
General DescriptionIn biochemistry, Phenylmethylsulfonyl fluoride (PMSF) is a serine protease inhibitor commonly used in preparation of cell lysates. It is rapidly degraded in water and stock solutions are usually made up in anhydrous ethanol, isopropanol, corn oil, or DMSO (Dimethyl sulfoxide).    
Biological Activitypmsf (phenylmethanesulfonyl fluoride) is an irreversible inhibitor of serine proteinases, which is associated with the development of the delayed organophosphorus neuropathy. it has a role in a lot of cellular repair and regeneration processes in many kinds of tissues. pmsf is a long acting neuropathy target esterase (nte) inhibitor. nte is a protection was related to inhibition of the putative target of organophosphate-induced delayed polyneuropathy (opidp). pmsf can increase nte inhibition to more than 90%. pmsf also acts as an active site directed reagent for γ-glutamyl transpeptidase.thomas baker, herbert e. lowndes, martin k. johnson, irene c. sandborg. the effects of phenylmethanesulfonyl fluoride on delayed organophosphorus neuropathy. archives of toxicology. 1980; 46(3-4): 305 – 311.marcello lotti, stefano caroldi, eugenio capodicasa, angelo moretto. promotion of organophosphate-induced delayed polyneuropathy by phenylmethanesulfonyl fluoride. toxicology and applied pharmacology. 1991; 108(2): 234 – 241.masayasu inoue, seikoh horiuchi, yoshimasa morino. inactivation of γ-glutamyl transpeptidase by phenylmethanesulfonyl fluoride, a specific inactivator of serine enzymes. biochemical and biophysical research communications. 1978; 82(4): 1183 – 1188.
Biochem/physiol ActionsPhenylmethanesulfonyl fluoride has the ability to enhance the stability of plasma lipidome in lipidomic and metabolomic analysis. This serine protease inhibitor reduces the naloxone-precipitated withdrawal jumping behavior in morphine-dependent mice.
Synthesis
Dibenzyl disulfide

150-60-7

Phenylmethylsulfonyl fluoride

329-98-6

General procedure for the synthesis of phenylmethylsulfonyl fluoride from dibenzyl disulfide: Selectfluor? (2306.2 mg, 6.5 mmol) was added to a stirred mixed solution of dibenzyl disulfide (246.3 mg, 1.0 mmol) in acetonitrile (10.0 mL) and water (1.0 mL). The reaction mixture was heated under reflux conditions for 1.5 h and the progress of the reaction was monitored by thin layer chromatography (TLC). After the dibenzyl disulfide and the corresponding thiosulfonate disappeared on TLC, water (10 mL) was added to the reaction mixture and extracted with ethyl acetate (20 mL × 3). The organic phases were combined, washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Finally, it was purified by silica gel column chromatography to obtain phenylmethylsulfonyl fluoride (299.0 mg, 86% yield) in colorless crystal form.

storageDesiccate at RT
storagePhenylmethylsulfonyl fluoride (PMSF) is incompatible with water, acids, bases, and strong oxidizing agents. Do not store PMSF in glass or mild steel/galvanized containers. Store in a cool, dry, and well-ventilated area away from incompatible chemicals.
Purification MethodsPurify PMSF by recrystallisation from *C6H6, pet ether or CHCl3/pet ether. [Davies & Dick J Chem Soc 483 1932, cf Tullock & Coffman J Org Chem 23 2016 1960.] It is a general protease inhibitor (specific for trypsin and chymotrypsin) and is a good substitute for diisopropylphosphoro floridate [Fahrney & Gould J Am Chem Soc 85 997 1963]. [Beilstein 11 III 331.]
Description

Phenylmethanesulfonyl Fluoride (PMSF) is an inhibitor of serine proteases such as trypsin, chymotrypsin, thrombin, and papain. It is routinely added as a supplement to lysis buffers just prior to lysis, to prevent protease degradation. recommends adding PMSF at 1 mM to Cell Lysis Buffer and RIPA Buffer .

CAS
References[1] Tetrahedron Letters, 2011, vol. 52, # 24, p. 3086 - 3089
[2] Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471
[3] Tetrahedron, 2014, vol. 70, # 14, p. 2464 - 2471
Tag:Phenylmethylsulfonyl fluoride(329-98-6) Related Product Information
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