Phenylmethylsulfonyl fluoride Property

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

InChIKey

YBYRMVIVWMBXKQ-UHFFFAOYSA-N

CAS DataBase Reference

329-98-6(CAS DataBase Reference)

EPA Substance Registry System

Benzenemethanesulfonyl fluoride (329-98-6)

Safety

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

F 

3-10-21

Hazard Note 

Highly Toxic/Corrosive

TSCA 

T

HazardClass 

8

PackingGroup 

III

HS Code 

29241990

Toxicity

LD50 (24 hr) in mice (mg/kg): 215 ±55 i.p. (Pinsky)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Phenylmethylsulfonyl fluoride Chemical Properties,Usage,Production

Chemical Properties

White to cream solid

Uses

PMSF is an irreversible serine/cysteine protease inhibitor

Uses

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

Uses

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

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.

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).    

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.

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

Desiccate at RT

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.

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.]