4263-52-9

Usage

Uses

Used in Bacterial Growth Inhibition:
Sodium 2-bromoethanesulphonate is used as a growth inhibitor for bacteria, particularly to investigate the effect of BES on the inhibition of bacterial growth. This application is valuable in understanding the mechanisms of bacterial growth and developing potential treatments for bacterial infections.
Used in Anaerobic Digestion:
In the field of anaerobic digestion, Sodium 2-bromoethanesulphonate is used as a methanogenesis inhibitor. This application helps in controlling the production of methane during the digestion process, which can be beneficial for optimizing the efficiency of biogas production and reducing greenhouse gas emissions.
Used in Chemical Synthesis:
Sodium 2-bromoethanesulphonate is also used in the synthesis of various compounds, such as its reaction with lithium sulfinated polysulfones (PSU) to yield sulfoethylated PSU. This application is important in the development of new materials and chemicals with specific properties for various industries.

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

• 45127-11-5 2,2’-dithio-bis-ethane sulfonate 
• 7465-57-8 2-(N,N,N-trimethylamino)ethanesulfonate 
• 111277-83-9 2-(4-Styrylpyridinio)ethanesulfonate 
• 3039-83-6 sodium vinylsulfonate 
• 51358-15-7 sodium 2-anilinoethanesulfonate 
• 113132-77-7 L-tyrosyl-D-S³3-(2-sulfoethyl)cysteinylglycyl-L-4-nitrophenylalanyl-L-prolinamine sodium salt 
• 637-95-6 2-(dimethylamino)ethanesulfonic acid 
• 946608-01-1 2-{bis(o-methoxyphenyl)phosphino}ethanesulphonic acid 
• 19767-45-4 mesna 
• 26978-65-4 2-bromo-1-ethanesulfonic acid 
• 54429-56-0 2-bromoethanesulfonyl chloride 
• 24020-66-4 pyridinebetaine B 
• 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 
• 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 

Relevant academic research and scientific papers

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.

Reactions of Tricyclo[4.1.0.02,7]heptane and 1-Methyltricyclo[4.1.0.02,7]heptane with 2-Bromoethanesulfonyl Bromide

Abstract: 2-Bromoethanesulfonyl bromide reacts with tricyclo[4.1.0.02,7]heptane and 1-methyltricyclo[4.1.0.02,7]heptane according to a radical mechanism to give products of both anti and syn addition across the C1–C7 central bicyclobutane bond having a norpinane (bicyclo[3.1.1]heptane) structure. Treatment of the adducts with triethylamine leads to the formation of vinyl sulfones as a result of 1,2-dehydrobromination, and their reaction with sodium methoxide involves 1,2- and 1,3-dehydrobromination and nucleophilic addition, depending on the substrate structure and reactant ratio.

Naphthocyanines for Use as Contrast Agents

Cyanine dyes having optional sulfonic acid substituents on the aromatic nucleus have been developed for use as contrast agents for assisting in surgery and diagnosis, especially for simplifying the surgical removal of basal membranes of the eye, such as the internal limiting membrane (ILM), and for dyeing the lens capsule.

Cyanine dyes as optical contrast agents for ophthalmological surgery

Cyanine dyes were prepared as optical contrast media for supporting the surgery of the lamina limitans interna (LLI) of the retina and other structures of the human eye. Their absorption spectra were adapted both to the spectral sensitivity of the human eye and to standard illumination. The contrast could be further amplified by the application of the strong fluorescence of the dyes used. The binding of the dyes to various surfaces was studied. No toxic effects could be detected for the applied dyes.

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

Aminoglycoside-coenzyme A conjugates are challenging synthetic targets because of the wealth of functional groups and high polarity of the starting materials. We previously reported a one-pot synthesis of amide-linked aminoglycoside-CoA bisubstrates. These molecules are nanomolar inhibitors of aminoglycoside N-6′-acetyltransferase Ii (AAC(6′)-Ii), an important enzyme involved in bacterial resistance to aminoglycoside antibiotics. We report here the synthesis and biological activity of five new aminoglycoside-CoA bisubstrates containing sulfonamide, sulfoxide, or sulfone groups. Interestingly, the sulfonamide-linked bisubstrate, which was expected to best mimic the tetrahedral intermediate, does not show improved inhibition when compared with amide-linked bisubstrates. On the other hand, most of the sulfone- and sulfoxide-containing bisubstrates prepared are nanomolar inhibitors of AAC(6′)-Ii.

Process for synthesizing disulfides

This invention relates to a process for producing a substantially pure disulfide compound of Formula II as disclosed herein, such as disodium 2,2′-dithiobis ethane sulfonate, by an efficient procedure from available, relatively inexpensive raw materials.

The mechanism of hydrolysis of 2-hydroxyethanesulfonyl chloride: the intermediacy of 1,2-oxathietane 2,2-dioxide (β-sultone)

The hydrolysis of 2-hydroxyethanesulfonyl chloride (1) has been investigated with the aid of kinetic and product analysis studies.The results are quantitatively consistent with the mechanism of hydrolysis shown in Scheme 1, the chief features of which are (a) formation of β-sultone (2) and its rapid further reaction (the major pathway), together with (b) a minor direct hydrolysis route.The kinetics of both the β-sultone formation and the direct hydrolysis shows two terms, one first order in 1 alone, and the other first order in hydroxide as well; the rates of the first- and second-order reactions are lowered by added sodium chloride.It is suggested (a) that the unimolecular β-sultone formation involves 1 in a complex with water (as in 9) and that the water acts as a general base in the cyclization to 2, and (b) the hydroxide-promoted reaction proceeds by cyclization of the conjugate base of 1 (i.e., 10).The unimolecular direct hydrolysis is regarded as a conventional hydrolysis of a sulfonyl chloride with attack of the water with general base assistence from a second water molecule.The hydroxide-promoted direct reaction in D2O leads to no uptake of deuterium, showing taht the reaction does not go by way of the sulfene, and a reaction by way of a six-membered cyclic transition state is tentatively proposed.Evidence is presented that the chloride ion rate suppression is not primarily due to reaction of β-sultone with Cl- to give back 1; the possible origins of the effect are discussed.Key words: sulfonyl chloride, 2-hydroxyethanesulfonyl chloride, β-sultone, kinetics of sulfonyl chloride hydrolysis, mechanism of sulfonyl chloride hydrolysis