30827-99-7

Basic information

• Product Name: 4-(2-Aminoethyl)benzenesulfonylfluoride hydrochloride
• Synonyms: AEBSF;AEBSF HCL;AEBSF HYDROCHLORIDE;4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE HYDROCHLORIDE;4-(2-AMINOETHYL)BENZENESULPHONYL FLUORIDE HYDROCHLORIDE;4-(2-AMINOETHYL)-BENZENESULFONYL FLUORIDE;4-(2-AMINOETHYL)BENZENESULFONYLFLUORIDE HCL;4-(2-AMINOETYL)-BENZENESULFONYL FLUORIDE HYDROCHLORIDE
• CAS NO: 30827-99-7
• Molecular Formula: C₈H₁₀FNO₂S*ClH
• Molecular Weight: 239.69
• EINECS: 608-547-2
• Product Categories: ProteaseInhibitors;inhibitor;Inhibitors
• Mol File: 30827-99-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 175-177 °C
• Boiling Point: 292.5 °C at 760 mmHg
• Flash Point: 130.7 °C
• Appearance: White/Powder
• Vapor Pressure: 7.72E-05mmHg at 25°C
• Storage Temp.: 0-6°C
• Solubility: H2O: soluble50mg/mL (stable for up to six months if stored refri
• Water Solubility: 10 g/L (20 ºC)
• Sensitive: Moisture Sensitive
• Stability: Stable for 1 year from date of purchase as supplied. Solutions at pH <7 are stable for up to 6 months if stored in the refrigerator
• BRN: 7604627
• CAS DataBase Reference: 4-(2-Aminoethyl)benzenesulfonylfluoride hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Aminoethyl)benzenesulfonylfluoride hydrochloride(30827-99-7)
• EPA Substance Registry System: 4-(2-Aminoethyl)benzenesulfonylfluoride hydrochloride(30827-99-7)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 45-36/37/39-26-36
• RIDADR: UN 3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 30827-99-7(Hazardous Substances Data)

Usage

Description

4-(2-Aminoethyl)benzenesulfonylfluoride hydrochloride, also known as AEBSF, is a water-soluble, irreversible, broad-spectrum inhibitor of serine proteases, including trypsin, chymotrypsin, plasmin, thrombin, and kallikreins. It is a white powder that maintains stability in slightly acidic aqueous solutions and serves as a nontoxic alternative to the organophosphate inhibitors, PMSF and DFP.

Uses

Used in Cholesterol Regulatory Gene Studies:
AEBSF is used as an inhibitor for Site-1-protease (S1P) in studies aiming to describe cholesterol regulatory genes. By selectively inhibiting S1P, a serine protease located in the Golgi apparatus responsible for activating sterol regulatory element-binding proteins (SREBP), AEBSF can be used to characterize the downstream result of SREBP inhibition and its influence on cholesterol regulation.
Used in Enzyme Inhibition:
AEBSF is used as an enzyme inhibitor in various applications due to its broad-spectrum activity against serine proteases. It can prevent the activation of the ROS generator, NADPH oxidase, and attenuate airway inflammation in a mouse model of airway allergy at concentrations of 10-50 μg.
Used in Synthesis:
Pefabloc SC, a trypsin inhibitor, can be used in the synthesis of its arginine-like analogue, 4-(2-guanidinoethyl)benzenesulfonyl fluoride, which is related to AEBSF.
Recommended concentrations for use are 0.1-1 mM.

Biochem/physiol Actions

Irreversible serine protease inhibitor. Inhibition constants are similar to those of PMSF and DFP. AEBSF has been shown to inhibit trypsin, chymotrypsin, plasmin kallikrein and thrombin. As an alternative to PMSF and DFP, AEBSF offers lower toxicity, improved solubility in water and improved stability in aqueous solutions. AEBSF has been used in cell culture in concentrations of up to 0.25?mM.

References

1) Powers?et al. (2002),?Irreversible inhibitors of serine, cysteine and threonine proteases; Chem. Rev.,?102?4639 2) Diatchuk?et al.?(1997),?Inhibition of NADPH oxidase activation by 4-(2-aminoethyl)-benzenesulfonyl fluoride and related compounds; J. Biol. Chem.,?272?13292

InChI:InChI=1/C8H10FNO2S.ClH/c9-13(11,12)8-4-2-1-3-7(8)5-6-10;/h1-4H,5-6,10H2;1H

Synthetic route

2-(1-carboxymethyl-1H-quinolin-4-ylidenemethyl)-3-methyl-benzothiazol-3-ium + pefabloc SC (30827-99-7) → C28H25FN3O3S2(1+)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	47%

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) + pefabloc SC (30827-99-7) → 4-(2-N',N''-diboc-guanidinoethyl)benzenesulfonyl fluoride

Conditions	Yield
With copper(II) choride dihydrate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	40%

(1'R,2'S,4'S,5'S)-4-{2-[(hydroxycarbonyl)-1-pentynyl]-6-methylaminopurin-9-yl}-1-[(phosphato)-methyl]-2-(phosphato)-bicyclo[3.1.0]hexane + triethylammonium acetate (5204-74-0) + pefabloc SC (30827-99-7) → (x)C6H15N*C27H33FN6O11P2S

Conditions	Yield
Stage #1: (1'R,2'S,4'S,5'S)-4-{2-[(hydroxycarbonyl)-1-pentynyl]-6-methylaminopurin-9-yl}-1-[(phosphato)-methyl]-2-(phosphato)-bicyclo[3.1.0]hexane; pefabloc SC With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; Stage #2: triethylammonium acetate In acetonitrile	25%

(1'R,2'S,4'S,5'S)-4-{2-[5-(hydroxycarbonyl)-1-pentynyl]-6-methylaminopurin-9-yl}-1-[(phosphato)methyl]-2-(phosphato)bicyclo[3.1.0]hexane triethylammonium salt + triethylammonium acetate (5204-74-0) + pefabloc SC (30827-99-7) → (1'R,2'S,4'S,5'S)-4-{2-[6-(4-(fluorosulfonyl)phenethylamino)-6-oxohex-1-ynyl]-6-methylaminopurin-9-yl}-1-[(phosphato)methyl]-2-(phosphato)bicyclo[3.1.0]hexane triethylammonium salt

Conditions	Yield
Stage #1: (1'R,2'S,4'S,5'S)-4-{2-[5-(hydroxycarbonyl)-1-pentynyl]-6-methylaminopurin-9-yl}-1-[(phosphato)methyl]-2-(phosphato)bicyclo[3.1.0]hexane triethylammonium salt; pefabloc SC With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; Stage #2: triethylammonium acetate In acetonitrile	25%

1-(2-amino-6-methylaminopyrimidin-yl)-piperidine-4-carboxylic acid + pefabloc SC (30827-99-7) → 4-(2-((1-(2-amino-6-methylamino-pyrimidin-4-yl)-piperidine-4-carbonyl)amino)ethyl)benzenesulfonyl fluoride

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube;	48 mg

pefabloc SC (30827-99-7) → 4-(2-guanidinoethyl)benzenesulfonyl fluoride hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; copper(II) choride dihydrate / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 20 °C View Scheme

pefabloc SC (30827-99-7) → C9H12(2)HN3O3S*ClH

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; copper(II) choride dihydrate / dichloromethane / 1 h / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 20 °C 3: water-d2 / aq. buffer / pH 7.7 View Scheme

Ac-Lys(Me,Boc)-Gln(Trt)-OH + pefabloc SC (30827-99-7) → C46H56FN5O8S

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;

Ac-Lys(Me,Boc)-Gln(Trt)-OH + pefabloc SC (30827-99-7) → Ac-Lys(Me)-Gln-AEBSF

Conditions	Yield
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C 2: chlorotriisopropylsilane / water / 2 h / 20 °C View Scheme

MEG-Lys(Me,Boc)-Gln(Trt)-OH + pefabloc SC (30827-99-7) → C49H62FN5O10S

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;

MEG-Lys(Me,Boc)-Gln(Trt)-OH + pefabloc SC (30827-99-7) → MEG-Lys(Me)-Gln-AEBSF

Conditions	Yield
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C 2: chlorotriisopropylsilane / water / 2 h / 20 °C View Scheme

Ac-Asp-Lys(Me,Boc)-Gln(Trt)-OH + pefabloc SC (30827-99-7) → C50H61FN6O11S

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;

Ac-Asp-Lys(Me,Boc)-Gln(Trt)-OH + pefabloc SC (30827-99-7) → Ac-Asp-Lys(Me)-Gln-AEBSF

Conditions	Yield
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C 2: chlorotriisopropylsilane / water / 2 h / 20 °C View Scheme

C23H36ClNO12 + pefabloc SC (30827-99-7) → 1-(4,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-2-nitrophenyl)ethyl 4-(fluorosulfonyl)phenethylcarbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide