Phenylmethylsulfonyl fluoride supplier

Name
Phenylmethylsulfonyl fluoride
EINECS 206-350-2
CAS No. 329-98-6
Article Data23
CAS DataBase
Density 1.317 g/cm³
Solubility hydrolysis
Melting Point 92-95 °C
Formula C₇H₇FO₂S
Boiling Point 285.7 °C at 760 mmHg
Molecular Weight 174.196
Flash Point 126.6 °C
Transport Information UN 3261 8/PG 2
Appearance White to cream solid
Safety 7-16-45-36/37/39-28A-26-27
Risk Codes 11-34-25-23/24/25
Molecular Structure
Hazard Symbols F, T, C
Synonyms a-Toluenesulfonyl fluoride(7CI,8CI);Benzylsulfonyl fluoride;NSC 88499;PMSF;Phenylmethanesulfonylfluoride;alpha-Toluenesulfonyl fluoride;
PSA 42.52000
LogP 2.56670

Synthetic route

: 1939-99-7
benzenesulfonyl chloride

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With potassium fluoride; triethylamine In dichloromethane; water	97%
With Methyl methanesulfonate; hydrogen fluoride at 100℃; for 8h;	90%
With potassium fluoride; water Heating;	54%

: 36331-57-4
benzylsulfonylhydrazide

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With Selectfluor In water at 60℃; for 14h; Schlenk technique;	95%
With Selectfluor In water at 60℃; for 18h; Schlenk technique;	80%

: 150-60-7
dibenzyl disulphide

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With water; Selectfluor In acetonitrile for 1.5h; Reflux;	88%
With Selectfluor In water; acetonitrile at 20℃; for 1.5h; Reflux;	88%
Multi-step reaction with 2 steps 1: Selectfluor™ / acetonitrile; water / 0.03 h / 20 °C 2: Selectfluor™ / acetonitrile; water / 1.5 h / 20 °C / Reflux View Scheme

: 16601-40-4
S-benzyl phenyl-methanethiosulfonate

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With Selectfluor In water; acetonitrile at 20℃; for 1.5h; Reflux;	88%

: 150-60-7
dibenzyl disulphide

A: 329-98-6
phenylmethylsulphonyl fluoride

B: 16601-40-4
S-benzyl phenyl-methanethiosulfonate

Conditions

Conditions	Yield
With water; Selectfluor In acetonitrile at 20℃; for 0.0333333h;	A 10% B 82%
With Selectfluor In water; acetonitrile at 20℃; for 0.0333333h;	A 10% B 82%

: 139-07-1
zephirol

: 1939-99-7
benzenesulfonyl chloride

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With potassium fluoride In dichloromethane; water	77%

: C7H7O2S(1-)*BrMg(1+)

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at 0 - 20℃; for 3h;	64%

: 17075-10-4
phenylmethanesulfonyl bromide

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	59%

: 100-53-8
phenylmethanethiol

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
With pyridine; hydrogenchloride; potassium fluoride; water In acetonitrile at 20℃; for 40h; Electrochemical reaction; Green chemistry;	45%
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; isopropyl alcohol / dichloromethane / 1 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme

: 1589-82-8
phenylmagnesium bromide

: 329-98-6
phenylmethylsulphonyl fluoride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate / tetrahydrofuran / 0.75 h / 20 °C 2: N-fluorobis(benzenesulfon)imide / tetrahydrofuran / 3 h / 0 - 20 °C View Scheme

: 616-47-7
1-methyl-1H-imidazole

: 329-98-6
phenylmethylsulphonyl fluoride

: C11H13N2O2S(1+)*F2H(1-)

Conditions

Conditions	Yield
In toluene for 8h; Menshutkin Reaction; Inert atmosphere; Sealed tube; Reflux;	100%

: 13368-42-8
4-(trimethylsilyl)morpholine

: 329-98-6
phenylmethylsulphonyl fluoride

: 19158-31-7
4-(phenylmethane)sulfonylmorpholine

Conditions

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	97%

: 329-98-6
phenylmethylsulphonyl fluoride

: 20474-37-7
benzylsulfonyl azide

Conditions

Conditions	Yield
With dmap; trimethylsilylazide In acetonitrile at 50℃; for 2h; Reagent/catalyst; Temperature;	97%

: 329-98-6
phenylmethylsulphonyl fluoride

4-methoxybenzyltriphenylphosphonium halide: 4-methoxybenzyltriphenylphosphonium halide

: 51848-93-2
[(benzylsulfonyl)(4-methoxyphenyl)methylene](triphenyl)phosphorane

Conditions

Conditions	Yield
Stage #1: 4-methoxybenzyltriphenylphosphonium halide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: phenylmethylsulphonyl fluoride In tetrahydrofuran; hexane at 20℃;	86%

: 329-98-6
phenylmethylsulphonyl fluoride

: 145412-85-7
C7H11NOS

: 1445729-37-2
C14H17NO3S2

Conditions

Conditions	Yield
Stage #1: phenylmethylsulphonyl fluoride; C7H11NOS With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	86%

: 329-98-6
phenylmethylsulphonyl fluoride

: 99-61-6
3-nitro-benzaldehyde

: 14064-52-9
3-nitrostilbene

Conditions

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In acetonitrile for 3h; Ambient temperature;	84%

: 26583-58-4
β-(2-methylphenoxy)ethylamine

: 329-98-6
phenylmethylsulphonyl fluoride

: 341936-05-8
C16H19NO3S

Conditions

Conditions	Yield
Stage #1: β-(2-methylphenoxy)ethylamine; phenylmethylsulphonyl fluoride With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	82%

: 329-98-6
phenylmethylsulphonyl fluoride

: 32597-92-5
(3-chlorobenzyl)triphenylphosphonium chloride

: 878801-20-8
[(benzylsulfonyl)(3-chlorophenyl)methylene](triphenyl)phosphorane

Conditions

Conditions	Yield
Stage #1: (3-chlorobenzyl)triphenylphosphonium chloride With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: phenylmethylsulphonyl fluoride In tetrahydrofuran; hexane at 20℃;	80%

: 329-98-6
phenylmethylsulphonyl fluoride

: 2-(bromomethyl)benzene-1-sulfonyl fluoride

Conditions

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In acetonitrile Reflux;	80%

: 329-98-6
phenylmethylsulphonyl fluoride

: 22374-89-6
(RS)-1-methyl-3-phenylpropylamine

: 432503-13-4
N-(1-methyl-3-phenylpropyl)-C-phenylmethanesulfonamide

Conditions

Conditions	Yield
Stage #1: phenylmethylsulphonyl fluoride; (RS)-1-methyl-3-phenylpropylamine With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	79%

: 329-98-6
phenylmethylsulphonyl fluoride

: 555-16-8
4-nitrobenzaldehdye

: 1694-20-8, 4003-94-5, 6624-53-9, 101977-34-8
4-nitrostilbene

Conditions

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In acetonitrile for 3h; Ambient temperature;	78%

: 329-98-6
phenylmethylsulphonyl fluoride

benzyltriphenylphosphonium halide: benzyltriphenylphosphonium halide

: 51848-91-0
[(benzylsulfonyl)(phenyl)methylene](triphenyl)phosphorane

Conditions

Conditions	Yield
Stage #1: benzyltriphenylphosphonium halide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: phenylmethylsulphonyl fluoride In tetrahydrofuran; hexane at 20℃;	78%

: 329-98-6
phenylmethylsulphonyl fluoride

: 6668-27-5, 23844-66-8, 42070-94-0, 68906-26-3
2-methyl-1-phenyl-propylamine

: 1330605-23-6
N-(2-methyl-1-phenylpropyl)-C-phenylmethanesulfonamide

Conditions

Conditions	Yield
Stage #1: phenylmethylsulphonyl fluoride; 2-methyl-1-phenyl-propylamine With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	78%

: 329-98-6
phenylmethylsulphonyl fluoride

: 70-11-1
α-bromoacetophenone

: 614-47-1
1,3-diphenyl-propen-3-one

Conditions

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In acetonitrile for 10h; Heating;	77%
With dibenzo-18-crown-6; potassium carbonate In acetonitrile for 10h; Heating; other arylmethanesulfonyl fluorides and activated haloalkanes; competition reaction with benzaldehyde and other aldehydes;	77%
With potassium carbonate; 1,4,7,10,13,20-Hexaoxa<13.1>(1,2)benzenophan In acetonitrile

: 329-98-6
phenylmethylsulphonyl fluoride

: 3218-02-8
cyclohexylmethylamine

: 885373-76-2
N-(cyclohexylmethyl)-1-phenylmethanesulfonamide

Conditions

Conditions	Yield
Stage #1: phenylmethylsulphonyl fluoride; cyclohexylmethylamine With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	76%

: 329-98-6
phenylmethylsulphonyl fluoride

: 32704-22-6
2-allyl-phenylamine

: N-(2-allylphenyl)-1-phenylmethanesulfonamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 50℃; Inert atmosphere;	75%

: 329-98-6
phenylmethylsulphonyl fluoride

4-methylbenzyltriphenylphosphonium halide: 4-methylbenzyltriphenylphosphonium halide

: 134749-73-8
[(benzylsulfonyl)(4-methylphenyl)methylene](triphenyl)phosphorane

Conditions

Conditions	Yield
Stage #1: 4-methylbenzyltriphenylphosphonium halide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: phenylmethylsulphonyl fluoride In tetrahydrofuran; hexane at 20℃;	74%

: 329-98-6
phenylmethylsulphonyl fluoride

: 2767-70-6
(p-nitrobenzyl)triphenylphosphonium bromide

: 51848-94-3
[(benzylsulfonyl)(4-nitrophenyl)methylene](triphenyl)phosphorane

Conditions

Conditions	Yield
Stage #1: (p-nitrobenzyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: phenylmethylsulphonyl fluoride In tetrahydrofuran; hexane at 20℃; for 5h;	72%
(i) nBuLi, (ii) /BRN= 2088311/; Multistep reaction;

: 329-98-6
phenylmethylsulphonyl fluoride

: 345965-54-0
1-(4-bromophenyl)-cyclopropylamine

: 1376113-41-5
C16H16BrNO2S

Conditions

Conditions	Yield
Stage #1: phenylmethylsulphonyl fluoride; 1-(4-bromophenyl)-cyclopropylamine With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	72%

: 329-98-6
phenylmethylsulphonyl fluoride

: 99-73-0
para-bromophenacyl bromide

: 72758-69-1, 2403-27-2, 22966-23-0
(E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one

Conditions

Conditions	Yield
With dibenzo-18-crown-6; potassium carbonate In acetonitrile for 10h; Heating;	71%

: 4-(morpholinomethyl)piperidin-4-ol

: 329-98-6
phenylmethylsulphonyl fluoride

: 1445743-46-3
C17H26N2O4S

Conditions

Conditions	Yield
Stage #1: 4-(morpholinomethyl)piperidin-4-ol; phenylmethylsulphonyl fluoride With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 4h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	71%

: 329-98-6
phenylmethylsulphonyl fluoride

: 100-52-7
benzaldehyde

: 588-59-0
stilbene

Conditions

Conditions	Yield
With potassium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide for 3h; Ambient temperature;	70%
With dibenzo-18-crown-6; potassium carbonate In acetonitrile for 3h; Product distribution; Mechanism; Ambient temperature; other substituted methanesulphonyl fluorides, other aldehydes and ketones; var. times, temp. and solvents;	69%

: 329-98-6
phenylmethylsulphonyl fluoride

: 144-80-9
sulphaacetamide

: 4-phenylmethylsulfonylamido-sulfacetamide

Conditions

Conditions	Yield
With triethylamine In water; acetone at 4℃; sulfonylation;	69%

Phenylmethylsulfonyl fluoride Consensus Reports

Reported in EPA TSCA Inventory.

Phenylmethylsulfonyl fluoride Specification

1.Introduction of Phenylmethylsulfonyl fluoride

Phenylmethylsulfonyl fluoride, with the register CAS NO 329-98-6, is a kind of White to cream solid. It has synonyms of a-Toluenesulfonyl fluoride(7CI,8CI);Benzylsulfonyl fluoride;NSC 88499; PMSF; Phenylmethanesulfonylfluoride and alpha-Toluenesulfonyl fluoride. Phenylmethylsulfonyl fluoride should store in 2-8°C and can be used as inhibition of serine protease.

2.Properties of Phenylmethylsulfonyl fluoride

(1)XLogP3: 1.3 (2)H-Bond Donor: 0 (3)H-Bond Acceptor: 3 (4) EINECS: 206-350-2 (5) Appearance: White to cream solid (6)Storage temp.: 2-8 °C(7) Solubility: dry solvents (ethanol, methanol, and 2-propanol): 200 mM Stock solution are stable for months at 4 °C.(8)Water Solubility: hydrolysis (9)Sensitive: Moisture Sensitive (10)Melting Point: 92-95 °C(11) Index of Refraction: 1.521 (12) Molar Refractivity: 40.31 cm3 (13)Molar Volume: 132.2 cm3(14) Surface Tension: 42 dyne/cm (15) Density: 1.317 g/cm3 (16)Flash Point: 126.6 °C(17)Enthalpy of Vaporization: 50.37 kJ/mol (18) Boiling Point: 285.7 °C at 760 mmHg(19) Vapour Pressure: 0.00474 mmHg at 25 °C (20)Classification Code: Enzyme inhibitors; Protease inhibitors

3.Structure descriptors of Phenylmethylsulfonyl fluoride

SMILES: C1=CC=C(C=C1)CS(=O)(=O)F

InChI: InChI=1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2

InChIKey: YBYRMVIVWMBXKQ-UHFFFAOYSA-N

4.Safety profile of Phenylmethylsulfonyl fluoride

Hazard Codes: F,T,C
Risk Statements: 11-34-25-23/24/25
R11:Highly flammable.
R25 :Toxic if swallowed.
R34:Causes burns.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 7-16-45-36/37/39-28A-26-27
S7:Keep container tightly closed.
S16:Keep away from sources of ignition.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27:Take off immediately all contaminated clothing.
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

5.Toxicity of Phenylmethylsulfonyl fluoride

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	215mg/kg (215mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Life Sciences. Vol. 31, Pg. 1193, 1982.
mouse	LD50	oral	200mg/kg (200mg/kg)		Farmakologiya i Toksikologiya Vol. 39, Pg. 265, 1976.
rat	LD50	intraperitoneal	150mg/kg (150mg/kg)		Nature. Vol. 173, Pg. 33, 1954.

Product Name

Phenylmethylsulfonyl fluoride

Synthetic route

Phenylmethylsulfonyl fluoride Consensus Reports

Phenylmethylsulfonyl fluoride Specification

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