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HomeProduct name listPhenylmethylsulfonyl fluoride

Phenylmethylsulfonyl fluoride

Synonym(s):PMSF;Phenylmethylsulfonyl fluoride;Phenylmethanesulfonyl fluoride;α-Toluenesulfonyl fluoride;Benzylsulfonyl fluoride

  • CAS NO.:329-98-6
  • Empirical Formula: C7H7FO2S
  • Molecular Weight: 174.19
  • MDL number: MFCD00007424
  • EINECS: 206-350-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 08:52:35
Phenylmethylsulfonyl fluoride Structural

What is Phenylmethylsulfonyl fluoride?

Chemical properties

White to cream solid

The Uses of Phenylmethylsulfonyl fluoride

PMSF is an irreversible serine/cysteine protease inhibitor

The Uses of Phenylmethylsulfonyl fluoride

Phenylmethylsulfonyl fluoride is used as a Protease inhibitor such as Chymotrypsin, Trypsin and Thrombin as well as Acetylcholineesterase.

The Uses of Phenylmethylsulfonyl fluoride

Standard protease inhibitor in biological research; in protein purification to prevent proteolytic degradation.

What are the applications of Application

Phenylmethylsulfonyl Fluoride is an irreversible serine protease, cysteine protease, and FAAH inhibitor.

What are the applications of Application

PMSF Solution is a nonspecific, irreversible inhibitor of serine proteases and other enzymes, including arylsulfatase A and trypsin.

Definition

ChEBI: 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.

Hazard

Extremely 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 Description

In 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 Activity

pmsf (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 Actions

Phenylmethanesulfonyl 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.

storage

Phenylmethylsulfonyl 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.

storage

Desiccate at RT

Purification Methods

Purify 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.]

Properties of Phenylmethylsulfonyl fluoride

Melting point: 92-95 °C
Boiling point: 112 °C16 mm Hg(lit.)
Density  0.797 g/mL at 20 °C
Flash point: 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.
form  Needles (May Agglomerate)
color  White
Water Solubility  hydrolysis
Sensitive  Moisture Sensitive
Merck  14,7542
BRN  2088311
Stability: Moisture Sensitive
CAS DataBase Reference 329-98-6(CAS DataBase Reference)
EPA Substance Registry System Benzenemethanesulfonyl fluoride (329-98-6)

Safety information for Phenylmethylsulfonyl fluoride

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
H314:Skin corrosion/irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Phenylmethylsulfonyl fluoride

InChIKey YBYRMVIVWMBXKQ-UHFFFAOYSA-N

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