5324-84-5

Basic information

• Product Name: Sodium 1-octanesulfonate
• Synonyms: 1-0ctanesulfonicacid,sodiumsalt;1-0ctanesulfonicacidsodiumsalt,monohydrate;1-octanesulfonicacid,sodiumsalthydrate;sodium1-0ctanesulfonate;sodium-1-octane;SODIUM OCTANESULFONATE;SODIUM OCTYL SULFONATE;SODIUM 1-OCTANESULFONATE
• CAS NO: 5324-84-5
• Molecular Formula: C₈H₁₇O₃S*Na
• Molecular Weight: 216.27
• EINECS: 226-195-4
• Product Categories: Alkyl Aryl Sodium Sulfonate Series;Analytical Chemistry;HPLC Ion-Pair Reagents for Basic Samples;Ion-Pair Reagents for HPLC;Alkyl SulfonatesResearch Essentials;Detergents A to Z;DetergentsDetergents;Anionic;Core Bioreagents;Detergents
• Mol File: 5324-84-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: >300 °C(lit.)
• Appearance: White/Crystalline Powder
• Density: 1.084g/cm3
• Storage Temp.: Store at +5°C to +30°C.
• Solubility: H2O: soluble1M at 20°C, clear, colorless
• Water Solubility: Soluble in water producing a clear and colorless solution.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3574241
• CAS DataBase Reference: Sodium 1-octanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 1-octanesulfonate(5324-84-5)
• EPA Substance Registry System: Sodium 1-octanesulfonate(5324-84-5)

Safety Data

• Hazard Codes: Xi,C,F
• Statements: 36/37/38-34-11
• Safety Statements: 22-24/25-45-36/37/39-26-16-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 5324-84-5(Hazardous Substances Data)

Usage

Description

Sodium 1-octanesulfonate can be used as ion-pairing reagent for ultra-high performance liquid chromatography (UPLC) analysis with photodiode array detection, to estimate paraquat (methyl viologen) in tissue homogenate1,2. It may also be used in determination of dopamine and its metabolites in brain microdialysates using liquid chromatography combined with electrospray ionization tandem mass spectrometry (LC–ESI-MS/MS). It can also be used as a reagent for HPLC analysis of organic compounds, and more specifically, peptides and proteins. It is found to interact with human serum albumin. It is also used as an ion complexation agent for N-nitrosodiethanolamine3. Its monohydrate is used as an anionic detergent and is a surface-active reagent4.

Sources

https://www.sigmaaldrich.com/catalog/product/sial/74884?lang=en®ion=US Orentien?, Asta, et al. "UPLC a Powerful Tool for the Separation of Imidazolium Ionic Liquid Cations." Chromatographia 73.1-2(2011): 17-24. https://www.alfa.com/en/catalog/A14292/ https://www.alfa.com/en/catalog/015764/

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 5324-84-5 differently. You can refer to the following data:
1. suzuki reaction
2. 1-Octanesulfonic Acid Sodium Salt is a non-fluorinated surfactant with potential bactericidal efficacy against Escherichia coli.
3. NaOS has been used as ion-pairing reagent for ultra-high performance liquid chromatography (UPLC) analysis with photodiode array detection to estimate paraquat (methyl viologen) in tissue homogenate. It may also be used in determination of dopamine and its metabolites in brain microdialysates using liquid chromatography combined with electrospray ionization tandem mass spectrometry (LC–ESI-MS/MS).

Flammability and Explosibility

Notclassified

Purification Methods

Recrystallise it from absolute EtOH. [Beilstein 4 IV 58.]

InChI:InChI=1/C8H18.Na.H2O3S/c1-3-5-7-8-6-4-2;;1-4(2)3/h3-8H2,1-2H3;;4H,(H,1,2,3)/q;+1;/p-1

Synthetic route

1-bromo-octane (111-83-1) → sodium octylsulfonate (5324-84-5)

Conditions	Yield
With water; sodium sulfite at 180 - 200℃;
With sodium sulfite In water for 24h; Heating;

Sodium trans-1-octene-1-sulfonate (83633-61-8) → sodium octylsulfonate (5324-84-5)

Conditions	Yield
With hydrogen; palladium on activated charcoal In water under 41371.8 Torr; for 2h; Ambient temperature;

oct-1-ene (111-66-0) + nickel carbonyl → sodium octylsulfonate (5324-84-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: 49 percent / benzoyl peroxide / benzene / 20 h / Heating 2: 98 percent / NaI / acetone / 1 h / Ambient temperature 3: 88 percent / PCl5 4: 55 percent / Et3N / benzene 5: 78 percent / NaHCO3 / H2O / 1 h / Heating 6: H2 / 10percent Pd/C / H2O / 2 h / 41371.8 Torr / Ambient temperature View Scheme

trans-1-Octene-1-sulfonyl chloride (83633-59-4) → sodium octylsulfonate (5324-84-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaHCO3 / H2O / 1 h / Heating 2: H2 / 10percent Pd/C / H2O / 2 h / 41371.8 Torr / Ambient temperature View Scheme

2-Chlorooctane-1-sulfonyl chloride (83633-57-2) → sodium octylsulfonate (5324-84-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / Et3N / benzene 2: 78 percent / NaHCO3 / H2O / 1 h / Heating 3: H2 / 10percent Pd/C / H2O / 2 h / 41371.8 Torr / Ambient temperature View Scheme

Methyl 2-chlorooctane-1-sulfonate (83633-53-8) → sodium octylsulfonate (5324-84-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / NaI / acetone / 1 h / Ambient temperature 2: 88 percent / PCl5 3: 55 percent / Et3N / benzene 4: 78 percent / NaHCO3 / H2O / 1 h / Heating 5: H2 / 10percent Pd/C / H2O / 2 h / 41371.8 Torr / Ambient temperature View Scheme

Sodium 2-chlorooctane-1-sulfonate (83633-55-0) → sodium octylsulfonate (5324-84-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / PCl5 2: 55 percent / Et3N / benzene 3: 78 percent / NaHCO3 / H2O / 1 h / Heating 4: H2 / 10percent Pd/C / H2O / 2 h / 41371.8 Torr / Ambient temperature View Scheme

sodium octylsulfonate (5324-84-5) + 2-phenylbenzo<1,2>quinolyzino<3,4,5,6-def>phenanthridinium tetrafluoroborate → C8H17O3S(1-)*C29H18N(1+) (1172640-53-7)

Conditions	Yield
for 6h; Reflux;	93%

2-phenyl-9-tetradecylbenzo[8,9]quinolizino[4,5,6,7-fed]phenanthridinylium chloride + sodium octylsulfonate (5324-84-5) → 2-phenyl-9-tetradecyl-benzo[8,9]quinolizino[4,5,6,7-fed]phenanthridinylium octanesulfonate (1293990-65-4)

Conditions	Yield
In methanol for 6h; Reflux;	86%

sodium octylsulfonate (5324-84-5) + doxorubicin hydrochloride (25316-40-9) → doxorubicin octanesulfonate (114370-94-4)

Conditions	Yield
In water at 20℃; for 2.5h;	85%

1,2-dimethyl-3-[2-oxo-2-(1-piperidinyl)ethyl]-1H-imidazolium bromide (1456904-77-0) + sodium octylsulfonate (5324-84-5) → 1,2-dimethyl-3-[2-oxo-2-(1-piperidinyl)ethyl]-1H-imidazolium octylsulfate

Conditions	Yield
In water at 20℃; for 24h;	79%

sodium octylsulfonate (5324-84-5) + methylene blue (152071-32-4) → methylene blue octanesulfonate salt

Conditions	Yield
In dichloromethane; water for 24h; Reflux;	75%

6NO3(1-)*H2O*4HO(1-)*4O(2-)*6Bi(3+) + sodium octylsulfonate (5324-84-5) + dimethyl sulfoxide (67-68-5) → 45O(2-)*10NO3(1-)*38Bi(3+)*28C2H6OS*14C6H13O3S(1-)

Conditions	Yield
In neat (no solvent) at 80℃; for 4h;	64%

sodium octylsulfonate (5324-84-5) + iron(II) chloride → Fe(2+)*2CH3(CH2)7SO3(1-)*6H2O=Fe(CH3(CH2)7SO3)2*6H2O

Conditions	Yield
With ascorbic acid In water stirring iron salt and sodium salt in water containing ascorbic acid; filtration, drying in vac. over P2O5; elem. anal.;	60%

sodium octylsulfonate (5324-84-5) → dioctyl disulfide (822-27-5)

Conditions	Yield
With polyphosphoric acid ethyl ester; tetra-(n-butyl)ammonium iodide; potassium iodide In chloroform for 2h; Heating;	47%

(1-(tert-butylperoxy)-3,3,4,4,5,5,6,6,6-nonafluorohexyl)benzene + sodium octylsulfonate (5324-84-5) → 3,4-bis(octylsulfonyl)-2-(perfluoroethyl)-5-phenylfuran

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; caesium carbonate In tert-butyl alcohol at 70℃; for 24h; regioselective reaction;	37%

sodium octylsulfonate (5324-84-5) + erythromycin (114-07-8) → 6-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione; compound with octane-1-sulfonic acid

Conditions	Yield
With phosphate buffer pH=5.5; ion pair formation;

sodium octylsulfonate (5324-84-5) → octane-1-sulfonyl chloride (7795-95-1)

Conditions	Yield
With thionyl chloride In benzene for 4h; Heating;
In thionyl chloride; diethyl ether

sodium octylsulfonate (5324-84-5) + guanidine hydrochloride (50-01-1) → octane-1-sulfonic acid; compound with guanidine

Conditions	Yield
Stage #1: sodium octylsulfonate With silver nitrate In ethanol at 20℃; Stage #2: guanidine hydrochloride In ethanol at 20℃;

sodium octylsulfonate (5324-84-5) → octane-1-sulfonic acid (2-oxo-tetrahydro-furan-3-yl)-amide

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / benzene / 4 h / Heating 2: 1,8-diazabicyclo[5.4.0]-undec-7-ene; 4-dimethylaminopyridine / CH2Cl2 / 24 h / 20 °C View Scheme

trihydroxonitratodicopper(II) + sodium octylsulfonate (5324-84-5) → copper (II) hydroxide octylsulfonate

Conditions	Yield
In water 0.2 g of Cu2(OH)3NO3 and 0.1 M NaC8H17SO3 dispersed in distd. water (100ml); stirred in air-free flask for 48 h at room temp.; fintrn.; washing with distd. water and ethanol; dried in vacuum at 35°C; IR; chem.anal.;
In water Cu2(OH)3NO3 (0.2 g) and NaC8H17SO3 (0.1 mol) dispersed in H2O, stirred in air-free flask for 48 h at room temp.; filtered, washed (H2O and C2H5OH), dried in vac. at 35°C; elem.anal.;

aluminum(III) nitrate nonahydrate + copper(II) nitrate hexahydrate + sodium octylsulfonate (5324-84-5) + water (7732-18-5) + sodium hydroxide (1310-73-2) → [Cu0.69Al0.31(OH)2](0.31+)*0.31CH3(CH2)7SO3(1-)*0.97H2O=[Cu0.69Al0.31(OH)2](CH3(CH2)7SO3)031*0.97H2O

Conditions	Yield
In water decarbonated aq. soln. of Cu(NO3)2*6H2O and Al(NO3)3*9H2O added dropwiseto decarbonated aq. soln. of CH3(CH2)7SO3; mixed and co-pptd. with NaOH ; suspension stirred for 24 h under inert atm. (N2) at room temp.; washed (decarbonated H2O); dried under vac.; XRD; elem. anal.;

bis(ethylenediamine)palladium(II) dibromide + sodium octylsulfonate (5324-84-5) + bromine (7726-95-6) → [Pd(ethylenediamine)2][PdBr2(ethylenediamine)](octylsulfonate)4*2H2O

Conditions	Yield
In water Br2 gas diffused to aq. soln. contg. C8H17SO3Na and Pd complex;

gadolinium hydroxynitrate hydrate + sodium octylsulfonate (5324-84-5) + water (7732-18-5) → gadolinium hydroxy(octanesulfonate) sesquihydrate

Conditions	Yield
In water heated at 60°C for 1-10 h in air; filtered off, washed (water), dried at40°C for 1 d, elem. anal.;

ammonium pillar[5]arene + sodium octylsulfonate (5324-84-5) → 10Br(1-)*C8H17O3S(1-)*C85H150N10O10(10+)*Na(1+)

Conditions	Yield
In water-d2 at 19.84℃; Equilibrium constant; Concentration;

aluminum(III) nitrate nonahydrate + zinc(II) nitrate hexahydrate + sodium octylsulfonate (5324-84-5) + 8-hydroxy-1,3,6-pyrenetrisulfonic acid trisodium salt (6358-69-6) + sodium hydroxide (1310-73-2) → Zn0.718Al0.282(OH)2(octanesulfonate)0.166(8-hydroxypyrene-1,3,6-trisulphonate)0.0181(CO3)0.0119(NO3)0.0380*0.94H2O

Conditions	Yield
In ethanol; water High Pressure; salts dissolved in aq. EtOH; pH adjusted to 5.5 (0.5 M NaOH) under N2 atm.; mixt. aged in autoclave at 80°C for 24 h;

aluminum(III) nitrate nonahydrate + zinc(II) nitrate hexahydrate + sodium octylsulfonate (5324-84-5) + 8-hydroxy-1,3,6-pyrenetrisulfonic acid trisodium salt (6358-69-6) + sodium hydroxide (1310-73-2) → Zn0.696Al0.304(OH)2(octanesulfonate)0.201(8-hydroxypyrene-1,3,6-trisulphonate)0.0102(CO3)0.0117(NO3)0.0490*1.08H2O

Conditions	Yield
In ethanol; water High Pressure; salts dissolved in aq. EtOH; pH adjusted to 5.5 (0.5 M NaOH) under N2 atm.; mixt. aged in autoclave at 80°C for 24 h;

Upstream product

• 111-83-1 1-bromo-octane 
• 83633-55-0 Sodium 2-chlorooctane-1-sulfonate 
• 83633-53-8 Methyl 2-chlorooctane-1-sulfonate 
• 83633-57-2 2-Chlorooctane-1-sulfonyl chloride 
• 83633-59-4 trans-1-Octene-1-sulfonyl chloride 
• 111-66-0 oct-1-ene 
• 83633-61-8 Sodium trans-1-octene-1-sulfonate 

Downstream Products

• 1293990-65-4 2-phenyl-9-tetradecyl-benzo[8,9]quinolizino[4,5,6,7-fed]phenanthridinylium octanesulfonate 
• 1172640-53-7 C₈H₁₇O₃S^(1-)*C₂₉H₁₈N⁽¹⁺⁾ 
• 7795-95-1 octane-1-sulfonyl chloride 
• 822-27-5 dioctyl disulfide 

Relevant articles and documents

One-Step Synthesis of Esters of Aliphatic β-Chloro Sulfonic Acids. Their Sequential Conversion to Other Sulfonic Acid Derivatives

A one-step synthesis of methyl 2-chlorohexane-1- and 2-chlorooctane-1-sulfonate by the novel free-radical addition of methyl chlorosulfonate to 1-hexene and 1-octene, respectively, is reported.These products were converted by standard techniques into the corresponding sodium and benzylthiuronium β-chlorosulfonic acid salts and sulfonyl chlorides.Dehydrochlorination of these latter products with triethylamine affored regiospecific formation of trans-α,β-unsaturated sulfonyl chlorides, which were transformed by conventional methods into sodium and benzylthiuroniumunsaturated and saturated sulfonic acid salts.Eleven new compositions of matter are reported.