Basic information
- Standard SMILES
O=S(=O)(F)Cc1ccccc1- InChIKey
YBYRMVIVWMBXKQ-UHFFFAOYSA-N- Molecular formula
- C7H7FO2S
- Average molar mass
- 174.19 g/mol
- Monoisotopic mass
- 174.01507868
Overview
Phenylmethanesulfonyl fluoride is an acyl fluoride with phenylmethanesulfonyl as the acyl group. It has a role as a serine proteinase inhibitor. It is functionally related to a phenylmethanesulfonic acid.
Names & identifiers
- Preferred name
- Phenylmethylsulfonyl Fluoride
- IUPAC
- phenylmethanesulfonyl fluoride
- English name
- Phenylmethylsulfonyl fluoride
- Molecular formula
- C7H7FO2S
- Molecular weight
- 174.19
Names & synonyms
Phenylmethylsulfonyl fluoridePMSF329-98-6phenylmethanesulfonyl fluorideBenzylsulfonyl fluorideBenzenemethanesulfonyl fluoridealpha-TOLUENESULFONYL FLUORIDEPhenylmethylsulfonylfluorideBenzylsulphonyl fluorideDTXSID6059819NSC-8849957KD15003I
Show more names
TOSYL FLUORIDEP-TOLUENESULFONYL FLUORIDEα-toluenesulphonyl fluoride4-METHYLBENZENESULFONYL FLUORIDEabs9146PMSF PLUSPMSF, PMs-F
CHEBI:8102Fluoride, PhenylmethylsulfonylFluoride, PhenylmethanesulfonylFluoride, BenzenemethanesulfonylRefChem:861810DTXCID2038605206-350-2alpha-Toluenesulphonyl fluoride
Database identifiers
- CAS
329-98-6- PubChem CID
- 4784
- DTXSID
DTXSID6059819- ChEMBL
CHEMBL190503- ChEBI
CHEBI:8102- UNII
- 57KD15003I
- EC Number
- 206-350-2
- Nikkaji
- J150.773G
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 42.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 199
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Biochemical Research
Physical DescriptionColorless solid; [Merck Index] White crystals; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 92 · 92-95 °C
- Boiling point
- 112 °C16 · 112 °C16 mm Hg(lit.)
- Density
- 0.797 g/mL · 0.797 g/mL at 20 °C
- Flash point
- 222 °F · 222 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 2 · dry solvents (ethanol, methanol, and 2-propanol): 200 mM Stock solution are stable for months at 4°C.
- form
- Needles (May Agglomerate)
- pka
- 7 · 7.0
- color
- White
- biological source
- synthetic
- Water Solubility
- hydrolysis
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,7542
- BRN
- 2088311 · 2088311
- Stability
- Moisture Sensitive
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2
- InChIKey
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N
- SMILES
- FS(=O)(=O)Cc1ccccc1
- CAS DataBase Reference
- 329 · 329-98-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 57 KD15003I · 57KD15003I
- EPA Substance Registry System
- Benzenemethanesulfonyl fluoride (329-98-6)
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H314
- Precautionary statements
- 260 · P260-P270-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- F,T,C
- Risk Statements
- 11 · 11-34-25-23/24/25
- Safety Statements
- 7 · 7-16-45-36/37/39-28A-26-27
- RIDADR
- 3261 · UN 3261 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 8050000 · XT8050000
- F
- 3 · 3-10-21
- Hazard Note
- Highly Toxic/Corrosive
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29241990 · 29241990
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 3 OralSkin · Acute Tox. 3 OralSkin Corr. 1B
- Toxicity
- 50 · LD50 (24 hr) in mice (mg/kg): 215 ±55 i.p. (Pinsky)
- Limited Quantities
- 100 ml · 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 103 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationPhenylmethanesulphonyl fluoride: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes convulsions and multiple enzyme effects in acute intraperitoneal studies of mice; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by ingestion; Targets the nerves, heart, blood, and eyes; [Sigma-Aldrich MSDS] See Methanesulfonyl fluoride.
Hazard Classes and CategoriesAcute Tox. 3 (99%)
Safety & protection
Exposure Control and Personal Protection
Biological Exposure Indices (BEI) [ACGIH] - Fluorides in urine = 2 mg/L prior to shift or 3 mg/L at end of shift; (Repeated measurements recommended.)
1.0 [mg/m3], inhalable fraction, as F[German Research Foundation (DFG)]
Threshold Limit Values (TLV)2.5 [mg/m3], as F
Permissible Exposure Limit (PEL)2.5 [mg/m3], as F
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 3-10-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- XT8050000
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29241990
- Toxicity
- LD50 (24 hr) in mice (mg/kg): 215 ±55 i.p. (Pinsky)
- risk_code
- 11-34-25-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- F,T,C
- hazard_note
- Highly Toxic/Corrosive
- safety_code
- 7-16-45-36/37/39-28A-26-27
- hazard_class
- 8
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- III
- Hazard statements
- H301-H314
- Limited Quantities
- 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Acute Tox. 3 OralSkin Corr. 1B
- Precautionary statements
- P260-P270-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Uses & manufacturing
UsesA serine and cysteine protease inhibitor; Used as a protease inhibitor in research and to prevent proteolytic degradation in protein purification; [Merck Index]
General Manufacturing InformationBenzenemethanesulfonyl fluoride: ACTIVE
Applications
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.
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).
DescriptionPhenylmethanesulfonyl 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
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Upstream raw materials
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Additional notes
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.
Related reactions
25 records
Linked notes
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