22767-50-6

Basic information

• Product Name: Sodium 1-heptanesulfonate
• Synonyms: LOW UV IPC(TM) B7, TETRABUTYLAMMONIUM PHOSPHATE;HEPTYLSULFONIC ACID SODIUM SALT;HEPTANE-1-SULFONIC ACID SODIUM SALT;HEPTANE SULFONIC ACID SODIUM SALT;IPC(TM) B7;IPC-ALKS-7;1-HEPTYLSODIUMSULFONATE;1-HEPTANESULPHONATE, SODIUM SALT
• CAS NO: 22767-50-6
• Molecular Formula: C₇H₁₅O₃S*Na
• Molecular Weight: 202.25
• EINECS: 245-210-5
• Product Categories: Alkyl Aryl Sodium Sulfonate Series;Analytical Chemistry;HPLC Ion-Pair Reagents for Basic Samples;Ion-Pair Reagents for HPLC;Ion-pair Reagents
• Mol File: 22767-50-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300 °C(lit.)
• Appearance: White/Crystalline Powder of Flakes
• Density: 1.017 g/cm
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: H2O: soluble0.5M at 20°C, clear, colorless
• Water Solubility: soluble
• Stability: Hygroscopic
• BRN: 3731762
• CAS DataBase Reference: Sodium 1-heptanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 1-heptanesulfonate(22767-50-6)
• EPA Substance Registry System: Sodium 1-heptanesulfonate(22767-50-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 37/39-26-36/37-36-24/25
• WGK Germany: 3
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 22767-50-6(Hazardous Substances Data)

Usage

Description

Sodium 1-heptanesulfonate is used as an ion-pairing reagent for HPLC, including analyses of peptides and proteins. The anionic sulfonate counterion permits the separation and resolution of positively charged analytes. It is utilized in the analysis of both organic and inorganic small molecule compounds. HPLC analysis of many pharmaceutical products or metabolites commonly incorporates sodium 1-heptanesulfonate. It is also utilized in high performance capillary electrophoresis analysis of peptides.

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 22767-50-6 differently. You can refer to the following data:
1. suzuki reaction
2. Sodium 1-Heptanesulfonate is a reactant used in the preparation of surfactants for detergents or emulsifiers. Potential use in cancer therapy through NRF2-ARE interaction.
3. Sodium 1-heptanesulfonate may be used as an ion-pairing reagent for the determination of ethambutol in pharmaceutical dosage forms by ion-pair reversed phase liquid chromatography with UV detection.

General Description

Sodium 1-heptanesulfonate belongs to the sodium alkylsulfonate group of surfactants. It has a -SO?3 head group with sodium and an alkyl chain attached to the head group. Sodium 1-heptanesulfonate has a critical micelle concentration value of 0.302 mol/dm3.

Biochem/physiol Actions

Sodium 1-heptanesulfonate serves as an ion-pairing reagent for analysis of epinephrine and norepinephrine in ion-pairing chromatography (IPC).

InChI:InChI=1/C7H16O3S.Na/c1-2-3-4-5-6-7-11(8,9)10;/h2-7H2,1H3,(H,8,9,10);

Synthetic route

1-Chloroheptane (629-06-1) → sodium heptanesulfonate (22767-50-6)

Conditions	Yield
With water; sodium sulfite at 200℃;

1-Bromoheptane (629-04-9) → sodium heptanesulfonate (22767-50-6)

Conditions	Yield
With sodium sulfite In water for 24h; Heating;

n-heptane (142-82-5) → sodium heptanesulfonate (22767-50-6)

Conditions	Yield
Stage #1: n-heptane With P25; sulfur dioxide; oxygen for 5h; Irradiation; Stage #2: With sodium hydroxide In methanol Mechanism; Reagent/catalyst; Solvent; chemoselective reaction;	600 mg

choline chloride (67-48-1) + sodium heptanesulfonate (22767-50-6) → choline heptanesulfonate

Conditions	Yield
In chloroform at 20℃; for 5h;	95%

sodium heptanesulfonate (22767-50-6) → heptanesulfonyl chloride (927-92-4)

Conditions	Yield
With thionyl chloride In benzene for 4h; Heating;
With phosphorus pentachloride at 140℃; for 0.75h; Neat (no solvent);
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
With thionyl chloride Reflux; Inert atmosphere;
With thionyl chloride for 6h; Reflux; Inert atmosphere;

sodium heptanesulfonate (22767-50-6) → heptane-1-sulfonic acid (2-oxo-tetrahydro-furan-3-yl)-amide (797059-78-0)

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

bis(ethylenediamine)palladium(II) dibromide + bromine (7726-95-6) + sodium heptanesulfonate (22767-50-6) → [Pd(ethylenediamine)2][PdBr2(ethylenediamine)](heptylsulfonate)4*2H2O

Conditions	Yield
In water Br2 gas diffused to aq. soln. contg. C7H15SO3Na and Pd complex;

sodium heptanesulfonate (22767-50-6) → N-(3-(5-(3'-O-Acetyl-2'-deoxyuridine))prop-2-ynyl)heptane-1-sulfonamide (1311414-38-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / Reflux; Inert atmosphere 2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme

sodium heptanesulfonate (22767-50-6) → N-(3-(5-(2'-deoxyuridine-5'-monophosphate))prop-2-ynyl)heptane-1-sulfonamide disodium salt

Conditions

Yield

Multi-step reaction with 5 steps 1.1: thionyl chloride / Reflux; Inert atmosphere 2.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: pyridine; pyridinium β-cyanoethyl phosphate; dicyclohexyl-carbodiimide / 48 h / 20 °C / Inert atmosphere 5.1: water; sodium hydroxide / 0.08 h / 100 °C 5.2: Dowex 50-WX8 (Na+ form) View Scheme

sodium heptanesulfonate (22767-50-6) → C21H32N3O11PS

Conditions

Yield

Multi-step reaction with 4 steps 1: thionyl chloride / Reflux; Inert atmosphere 2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4: pyridine; pyridinium β-cyanoethyl phosphate; dicyclohexyl-carbodiimide / 48 h / 20 °C / Inert atmosphere View Scheme

sodium heptanesulfonate (22767-50-6) + benzoyl isocyanate (4461-33-0) → benzoylcarbamic heptane-1-sulfonic anhydride

Conditions	Yield
In toluene Schlenk technique; Inert atmosphere; Reflux;	293 mg

Upstream product

• 629-06-1 1-Chloroheptane 
• 142-82-5 n-heptane 
• 629-04-9 1-Bromoheptane 

Downstream Products

• 927-92-4 heptanesulfonyl chloride 

Relevant articles and documents

Visible-light-induced sulfoxidation of alkanes in the presence of titania

The first catalytic photosulfoxidation of alkanes is accomplished in the presence of titanium dioxide and visible light (λ≥400 nm) under an atmosphere of SO2/O2. For n-heptane and cyclohexane the reaction is performed in the neat liquid, for adamantane in glacial acetic acid. Charge-transfer (CT) complexation of sulfur dioxide by the titania surface generates a CT band at 400-420 nm responsible for the visible-light activity of otherwise only UV light absorbing titania. The primary charges generated upon optical electron transfer produce alkyl radicals by dissociative electron transfer from the alkane and by hydrogen abstraction by OH radicals produced from oxygen reduction. Once formed, the alkyl radicals initiate a radical chain reaction as known from the classical UV-induced sulfoxidation in the absence of a catalyst. The reaction exhibits features characteristic for product inhibition by strong adsorption. Accordingly, the initial photocatalytic activity is fully restored after washing the catalyst with methanol. Time-resolved photovoltage measurements indicate that photocatalyst deactivation is connected with a change from n-type to p-type titanium dioxide. Small amounts of water and radical scavengers inhibit product formation. The reaction proceeds with high chemoselectivity because only traces of expected by-products like sulfates, ketones, and alcohols are formed. Thus, in addition to its basic role in visible-light-induced charge generation, the surface of titania enables also a chemoselective C-S bond formation.