4263-52-9

Basic information

• Product Name: Sodium 2-bromoethanesulphonate
• Synonyms: 2-Bromoethanesulfonicacid,Sodium;2-bromo-ethanesulfonicacisodiumsalt;Ethanesulfonicacid,2-bromo-,sodiumsalt;2-BROMOETHANESULPHONIC ACID, NA SALT;2-BROMOETHANESULPHONIC ACID SODIUM SALT;2-BROMOETHANESULFONIC ACID;2-BROMOETHANESULFONIC ACID, NA, SALT;2-BROMOETHANESULFONIC ACID SODIUM SALT
• CAS NO: 4263-52-9
• Molecular Formula: C₂H₄BrNaO₃S
• Molecular Weight: 211.01
• EINECS: 224-244-4
• Product Categories: Organic acids;Miscellaneous Reagents;Sulfur & Selenium Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonic/Sulfinic Acid Salts;Sulfur Compounds;buffer
• Mol File: 4263-52-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 283 °C (dec.)(lit.)
• Appearance: White to off-white/Crystalline Powder
• Density: 2.026g/cm3
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility: water: soluble100mg/mL, clear, colorless
• Water Solubility: 500 g/L (20 ºC)
• Stability: Hygroscopic
• BRN: 4590828
• CAS DataBase Reference: Sodium 2-bromoethanesulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 2-bromoethanesulphonate(4263-52-9)
• EPA Substance Registry System: Sodium 2-bromoethanesulphonate(4263-52-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4263-52-9(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT BEIGE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 4263-52-9 differently. You can refer to the following data:
1. Sodium 2-bromoethanesulphonate is usually used to investigate the effect of BES on inhibition of bacterial growth.
2. Sodium 2-bromoethanesulfonate(BES) was used to investigate the effect of BES on inhibition of bacterial growth.

General Description

Sodium 2-bromoethanesulfonate acts as methanogenesis inhibitor during anaerobic digestion. It reacts with lithium sulfinated polysulfones(PSU) to yield sulfoethylated PSU.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C2H5BrO3S/c3-1-2-7(4,5)6/h1-2H2,(H,4,5,6)/p-1

Synthetic route

ethylene dibromide (106-93-4) → sodium 2-bromethanesulfonate (4263-52-9)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium sulfite In ethanol; water for 16h; Reflux;	56%
With sodium sulfite In ethanol; water for 6h; Reflux;	55%
With sodium sulfite In ethanol; water for 6h; Reflux;	55%
With sodium sulfite In water for 5h;
With sodium sulfite

sodium 2-hydroxyethanesulfonate (1562-00-1) → sodium 2-bromethanesulfonate (4263-52-9)

Conditions	Yield
With hydrogen bromide In water Heating / reflux;

4-hydroxy-benzaldehyde (123-08-0) + sodium 2-bromethanesulfonate (4263-52-9) → C9H9O5S(1-)*Na(1+)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Inert atmosphere; Reflux;	98%
With potassium carbonate In acetonitrile for 24h; Inert atmosphere; Reflux;	98%
With potassium carbonate In acetonitrile at 75℃; for 24h; Inert atmosphere;	98%

ethanolamine (141-43-5) + sodium 2-bromethanesulfonate (4263-52-9) → 2-(2-hydroxyethylamino) ethane sulfonic acid (29706-49-8)

Conditions	Yield
In water at 20 - 70℃; for 1h; Sealed tube;	88%

N-hydroxyphthalimide (524-38-9) + sodium 2-bromethanesulfonate (4263-52-9) → sodium 2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]ethanesulfonate

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 120℃; for 6h;	88%

pyridine (110-86-1) + sodium 2-bromethanesulfonate (4263-52-9) → pyridinebetaine B (24020-66-4)

Conditions	Yield
for 24h; Reflux;	87%

(2E,6E)-3,7,11-trimethyldodeca-2,6,10-triene-1-thiol (138077-74-4) + sodium 2-bromethanesulfonate (4263-52-9) → sodium S-farnesyl-2-thioethyl sulfonate (141198-61-0)

Conditions	Yield
In water for 48h; Heating;	85%

1,3,4-thiadiazolidine-2,5-dithione (1072-71-5) + sodium 2-bromethanesulfonate (4263-52-9) → disodium salt of S,S'-(1,3,4-thiadiazole-2,5-diyl)bis(2-mercaptoethanesulfonic acid)

Conditions	Yield
With sodium hydroxide In methanol; isopropyl alcohol at 80℃; for 3h; Substitution;	85%

1-[(-)-menthoxycarbonylmethyl]-3-methylbenzimidazolium chloride + sodium 2-bromethanesulfonate (4263-52-9) → 1-[(-)-menthoxycarbonylmethyl]-3-methylbenzimidazolium 2-bromoethylsulfonate

Conditions	Yield
In water at 20℃; for 12h;	85%

1-[(-)-borneoxycarbonylmethyl]-3-methylbenzimidazolium chloride + sodium 2-bromethanesulfonate (4263-52-9) → 1-[(-)-borneoxycarbonylmethyl]-3-methylbenzimidazolium 2-bromoethylsulfonate

Conditions	Yield
In water at 20℃; for 12h;	83%

1-methyl-1H-imidazole (616-47-7) + sodium 2-bromethanesulfonate (4263-52-9) → C6H10N2O3S*Na(1+)*Br(1-)

Conditions	Yield
In toluene at 150℃; for 48h; Autoclave;	82%

trimethyltin(IV)chloride (1066-45-1) + sodium 2-bromethanesulfonate (4263-52-9) → sodium-2-trimethylstannylethylsulfonate monohydrate

Conditions	Yield
With sodium In ammonia a mixture of Na and (CH3)3SnCl in liq. ammonia gives NaSn(CH3)3; to the mixt. is added at -60°C solid BrCH2CH2SO3Na in portions; stirring for 1 h; evapn., the residue is washed with ether and filtered; extg. with ethanol; concg. and crystg. from H2O; elem. anal.;	81%

Maleic hydrazide (123-33-1) + sodium 2-bromethanesulfonate (4263-52-9) → disodium 3,6-di(2-sulfonatoethoxy)pyridazine

Conditions	Yield
With sodium hydroxide for 4h; Heating;	80.1%

1,3-bis(methylamino)propane (111-33-1) + sodium 2-bromethanesulfonate (4263-52-9) → N,N'-dimethyl-N,N'-bis(2-sulfoethyl)-1,3-propanediamine di-inner salt (185305-85-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol; water at 20℃;	79%

sodium 2-bromethanesulfonate (4263-52-9) → 2-bromoethanesulfonyl chloride (54429-56-0)

Conditions	Yield
With phosphorus pentachloride at 70 - 130℃; for 1h;	78%
With phosphorus pentachloride at 110℃; for 2.08333h;

1-Butylimidazole (4316-42-1) + sodium 2-bromethanesulfonate (4263-52-9) → 1-butyl-3-(ethyl-2-sodiumsulfonate)imidazolium bromide

Conditions	Yield
In toluene at 150℃; for 48h; Autoclave;	75%

1H-imidazole (288-32-4) + sodium 2-bromethanesulfonate (4263-52-9) → sodium 3-sulfonatoethylimidazolium bromide

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Inert atmosphere; Schlenk technique; Reflux;	75%

N-methyldodecylamine (7311-30-0) + sodium 2-bromethanesulfonate (4263-52-9) → 2-(N-methyldodecylammonio)ethanesulfonate (2617-73-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere;	74%

dmap (1122-58-3) + sodium 2-bromethanesulfonate (4263-52-9) → 2-(4-dimethylamino-1-pyridinium)-1-ethanesulfonate

Conditions	Yield
In N,N-dimethyl-formamide	72%

triphenyltin chloride (639-58-7) + sodium 2-bromethanesulfonate (4263-52-9) → sodium-2-triphenylstannylethylsulfonate monohydrate

Conditions	Yield
With sodium In ammonia a mixture of Na and (C6H5)3SnCl in liq. ammonia gives NaSn(C6H5)3; to the mixt. is added at -60°C solid BrCH2CH2SO3Na in portions; stirring for 1 h; evapn., the residue is washed with ether and filtered; extg. with ethanol; concg. and crystg. from H2O; elem. anal.;	72%

1-Methylbenzimidazole (1632-83-3) + sodium 2-bromethanesulfonate (4263-52-9) → C10H12N2O3S*Na(1+)*Br(1-)

Conditions	Yield
In toluene at 150℃; for 48h; Autoclave;	70%

9-(aminomethyl)anthracene (2476-68-8) + sodium 2-bromethanesulfonate (4263-52-9) → 2-[(anthracen-9-ylmethyl)(2-sulfonatoethyl)amino]ethane-1-sulfonate

Conditions	Yield
With dipotassium hydrogenphosphate; potassium iodide In N,N-dimethyl-formamide at 120 - 130℃; for 72h;	70%

1-(((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis [1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methyl)-4-aza-1-azoniabicyclo[2.2.2] octane iodide + sodium 2-bromethanesulfonate (4263-52-9) → 1-(((3aS,5S,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl)methyl)-4-aza-1-azoniabicyclo[2.2.2]octane bromoethanesulfonate

Conditions	Yield
In water	69%

1-(2,6-diisopropylphenyl)-1H-imidazole (25364-47-0) + sodium 2-bromethanesulfonate (4263-52-9) → C17H24N2O3S*Na(1+)*Br(1-)

Conditions	Yield
In N,N-dimethyl-formamide; toluene at 150℃; for 72h; Autoclave;	68%

sodium 2-bromethanesulfonate (4263-52-9) → 2-bromoethane-1-sulfonyl bromide

Conditions	Yield
With phosphorus pentabromide In dichloromethane at 0℃; for 6h;	68%
With phosphorus pentabromide In dichloromethane for 6h; Reflux;	67.5%
With phosphorus pentabromide In dichloromethane for 6h; Reflux;	67.5%

(dicyclohexylphosphino)borane (108756-88-3) + sodium 2-bromethanesulfonate (4263-52-9) → Na(1+)*(C6H11)2P(BH3)C2H4SO3(1-)=(C6H11)2P(BH3)C2H4SO3Na

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane Ar-atmosphere; stirring (-78°C, to room temp., 2 h), sulfonate soln. addn. (-78°C), stirring (65°C, 12 h); evapn. (reduced pressure), extg. (CH2Cl2), pptn. on concg. and ether addn. (-50°C); elem. anal.;	67%

trans-1,2-bis(pyridin-4-yl)ethene (13362-78-2) + sodium 2-bromethanesulfonate (4263-52-9) → 2,2'-[(E)-ethene-1,2-diylbis(pyridinio-4,1-diyl)]diethanesulfonate (1290573-46-4)

Conditions	Yield
In ethanol for 50h; Reflux;	64%

N-methyltetradecylamine (29369-63-9) + sodium 2-bromethanesulfonate (4263-52-9) → 2-(N-methyltetradecylammonio)-ethanesulfonate (1415008-30-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 135℃; Inert atmosphere;	64%
With potassium carbonate In N,N-dimethyl-formamide Reflux;

4-aminopyridine (504-24-5) + sodium 2-bromethanesulfonate (4263-52-9) → 2-(4-amino-1-pyridinium)-1-ethanesulfonate

Conditions	Yield
In N,N-dimethyl-formamide	62%

C(13)CH6N(15)NO + sodium 2-bromethanesulfonate (4263-52-9) → C3(13)CH10N(15)NO4S

Conditions	Yield
With sodium hydroxide In water for 3h; pH=8 - 9; Reflux;	61%

trimetazidine dihydrochloride (13171-25-0, 127881-54-3) + sodium 2-bromethanesulfonate (4263-52-9) → 2-(1-(2,3,4-trimethoxybenzyl)piperazine-4-yl)-ethanesulfonic acid sodium salt (1383744-14-6)

Conditions	Yield
With triethylamine In water for 2h; Reflux;	60%

Upstream product

• 1562-00-1 sodium 2-hydroxyethanesulfonate 
• 106-93-4 ethylene dibromide 

Downstream Products

• 7465-57-8 2-(N,N,N-trimethylamino)ethanesulfonate 
• 111277-83-9 2-(4-Styrylpyridinio)ethanesulfonate 
• 1345982-88-8 2,2'-({[(3R,5R)-3-butyl-3-ethyl-7-(methyloxy)-1,1-dioxido-5-phenyl-2,3,4,5-tetrahydro-1,4-benzothiazepin-8-yl]methyl}imino)diethanesulfonic acid trifluoroacetate 
• 1383744-14-6 2-(1-(2,3,4-trimethoxybenzyl)piperazine-4-yl)-ethanesulfonic acid sodium salt 
• 1345982-86-6 2-({[(3R,5R)-3-butyl-3-ethyl-7-(methyloxy)-1,1-dioxido-5-phenyl-2,3,4,5-tetrahydro-1,4-benzothiazepin-8-yl]methyl}amino)ethanesulfonic acid ammonium salt 
• 1349808-74-7 C₁₅H₂₃NO₅S 
• 24020-66-4 pyridinebetaine B 

Relevant articles and documents

Synthesis of the 1-Bromotricyclo[4.1.0.02,7]heptane Adduct with 2-Bromoethanesulfonyl Bromide and Its Transformations

Abstract: The addition of 2-bromoethanesulfonyl bromide to1-bromotricyclo[4.1.0.02,7]heptane at theC1–C7 centralbicyclobutane bond follows a radical mechanism to give 1:1 adduct with abicyclo[3.1.1]heptane structure. Treatment of the adduct with triethylamineleads to the formation of vinyl sulfone as a result of 1,2-dehydrobromination,and its reaction with 2 equiv of sodium methoxide involves 1,2- and1,3-dehydrobromination to afford7-bromo-1-(ethenesulfonyl)tricyclo[4.1.0.02,7]heptane.The latter is capable of reacting with sodium methoxide and sodiummethanesulfonate to form nucleophilic addition products.

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Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside-CoA bisubstrates as mechanistic probes for aminoglycoside N-6′-acetyltransferase

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