142-31-4

Basic information

• Product Name: Sodium octyl sulfate
• Synonyms: S8 ION PAIR CONCENTRATE;1-OCTYLSODIUMSULFONATE;cyclorylos;duponol80;sipexols;sodiumcaprylsulfate;sodiumoctylsulphate;sos
• CAS NO: 142-31-4
• Molecular Formula: C₈H₁₇O₄S*Na
• Molecular Weight: 232.27
• EINECS: 205-535-5
• Mol File: 142-31-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 195 °C (dec.)(lit.)
• Flash Point: 93.3°C
• Appearance: White/Coarse Powder
• Density: 1.04
• Vapor Density: 8 (vs air)
• Vapor Pressure: 0.31Pa at 20℃
• Storage Temp.: Storage temperature: no restrictions.
• Solubility: H2O: soluble20mg/mL
• Water Solubility: soluble
• Stability: Stable. Incompatible with oxidizing agents.
• BRN: 3658635
• CAS DataBase Reference: Sodium octyl sulfate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium octyl sulfate(142-31-4)
• EPA Substance Registry System: Sodium octyl sulfate(142-31-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• RTECS: WT1175000
• TSCA: Yes
• Hazardous Substances Data: 142-31-4(Hazardous Substances Data)

Usage

Chemical Properties

white solid

Uses

Different sources of media describe the Uses of 142-31-4 differently. You can refer to the following data:
1. Wetting, dispersing, and emulsifying agent.
2. Sodium octyl sulfate has been used in a study to assess selective enrichment of albumin in biological samples. It has also been used in a study to investigate the behavior of mixed solution of a glycerin-modified cationic surfactant and an anionic surfactant.
3. Sodium octyl sulfate (SOS) may be used as an ion-pairing reagent:For the retention of catechols in reversed-phase high-performance liquid chromatography of catecholamines and their congeners.For the separation of asymmetric dimethylhydrazine (ADMH) and its decomposition products using ion-pair chromatography.

Definition

Anionic deter- gent, available commercially as a 35% solution.

General Description

Sodium octyl sulfate is an anionic detergent and ion pairing reagent that is used in HPLC

Safety Profile

Poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic vapors of SOx.

InChI:InChI=1/C8H18O4S.Na/c1-2-3-4-5-6-7-8-12-13(9,10)11;/h2-8H2,1H3,(H,9,10,11);/q;+1/p-1

Synthetic route

octanol (111-87-5) → sodium octyl sulphate (142-31-4)

Conditions	Yield
Stage #1: octanol With sodium hydride In 1,4-dioxane at 20℃; for 1h; Stage #2: With triethylamine sulfurtrioxide In 1,4-dioxane at 20℃;	96%
With chlorosulfonic acid; sodium hydroxide 1.) 30 min, 5 deg C, CH2Cl2; Multistep reaction;

β-cyclodextrin, 1:1 complex with NaSO4C8H17 → sodium octyl sulphate (142-31-4) + β-cyclodextrin

Conditions	Yield
In water at 25℃; Equilibrium constant; dissociation;

sodium octyl sulphate (142-31-4) + 3-(butoxycarbonyl)-1-methylpyridinium iodide (21032-39-3) → 3-(butoxycarbonyl)-1-methylpyridinium octyl sulfate (1048382-81-5)

Conditions	Yield
In water for 0.166667h;	100%

3-methyl-1-(propoxyethoxyethoxycarbonylmethyl)imidazolium bromide (1122146-85-3) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(propoxyethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-91-1)

Conditions	Yield
In water at 60℃; for 2h;	98%

2,3-dimethyl-1-(pyrrolidinylcarbonylmethyl)imidazolium bromide + sodium octyl sulphate (142-31-4) → 2,3-dimethyl-1-(pyrrolidinylcarbonylmethyl)imidazolium octylsulfate

Conditions	Yield
In water at 60℃; for 2h;	98%

3-methyl-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-imidazolium bromide + sodium octyl sulphate (142-31-4) → 3-methyl-1-(pyrrolidinylcarbonylmethyl)imidazolium octylsulfate

Conditions	Yield
In water at 60℃; for 2h;	97%

3-methyl-1-(ethoxyethoxycarbonylmethyl)imidazolium bromide (1122146-50-2) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(ethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-56-8)

Conditions	Yield
In water at 60℃; for 2h;	96%

1-methyl-3-(pentoxycarbonylmethyl)imidazolium bromide (808184-34-1) + sodium octyl sulphate (142-31-4) → 1-methyl-3-(pentoxycarbonylmethyl)imidazolium octylsulfate (911066-18-7)

Conditions	Yield
In water at 60℃; for 2h;	96%

3-methyl-1-(methoxyethoxycarbonylmethyl)imidazolium bromide (1122146-43-3) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(methoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-49-9)

Conditions	Yield
In water at 60℃; for 2h;	95%

2,3-dimethyl-1-(methoxyethoxyethoxycarbonylmethyl)imidazolium bromide (1122147-13-0) + sodium octyl sulphate (142-31-4) → 2,3-dimethyl-1-(methoxyethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122147-19-6)

Conditions	Yield
In water at 60℃; for 2h;	94%

1-n-butyl-3-methylpyridin-1-ium bromide (26576-85-2) + sodium octyl sulphate (142-31-4) → 1-butyl-3-methylpyridinium octyl sulfate (1173828-03-9)

Conditions	Yield
In water for 0.166667h;	93%

3-(butoxycarbonyl)-1-butylpyridinium iodide (1173828-08-4) + sodium octyl sulphate (142-31-4) → 3-(butoxycarbonyl)-1-butylpyridinium octyl sulfate (1048382-82-6)

Conditions	Yield
In water for 0.166667h;	93%

3-methyl-1-(butoxyethoxycarbonylmethyl)imidazolium bromide (1122146-64-8) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(butoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-70-6)

Conditions	Yield
In water at 60℃; for 2h;	93%

3-methyl-1-(ethoxyethoxyethoxycarbonylmethyl)imidazolium bromide (1122146-78-4) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(ethoxyethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-84-2)

Conditions	Yield
In water at 60℃; for 2h;	93%

3-{[bis(2-methoxyethyl)carbamoyl]methyl}-1-methyl-1H-imidazol-3-ium bromide (1122147-20-9) + sodium octyl sulphate (142-31-4) → 3-methyl-1-([bis-1-methoxyethyl]carbamylmethyl)imidazolium octylsulfate (1122147-22-1)

Conditions	Yield
In water at 60℃; for 2h;	92%
In water for 4h;

3-{2-[2-(2-butoxyethoxy)ethoxy]-2-oxoethyl}-1-methyl-1H-imidazol-3-ium bromide (1122146-92-2) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(butoxyethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-98-8)

Conditions	Yield
In water at 60℃; for 2h;	92%

sodium octyl sulphate (142-31-4) + 1-butylpyridinium bromide (874-80-6) → 1-butylpyridinium octyl sulfate (1005759-92-1)

Conditions	Yield
In water for 0.166667h;	90%

2-(3,4-dimethoxyphenyl)-2-(3-methylimidazolium)butyl acetate chloride (1241839-88-2) + sodium octyl sulphate (142-31-4) → 2-(3,4-dimethoxyphenyl)-2-(3-methylimidazolium)butyl acetate octylsulphate (1241839-91-7)

Conditions	Yield
In water	87.9%

1-butyl-3-(butylcarbamoyl)pyridinium iodide (1173828-09-5) + sodium octyl sulphate (142-31-4) → 1-butyl-3-(butylcarbamoyl)pyridinium octyl sulfate (1048382-85-9)

Conditions	Yield
In water for 0.166667h;	87%

2,3-dimethyl-1-(pentoxycarbonylmethyl)imidazolium bromide (911066-13-2) + sodium octyl sulphate (142-31-4) → 2,3-dimethyl-1-(pentoxycarbonylmethyl)imidazolium octylsulfate (911066-21-2)

Conditions	Yield
In water at 60℃; for 2h;	86%

3-methyl-1-(propoxyethoxycarbonylmethyl)imidazolium bromide (1122146-57-9) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(2-(n-propoxy)ethoxycarbonylmethyl)imidazolium octylsulfate (1122146-63-7)

Conditions	Yield
In water at 60℃; for 2h;	85%
In water at 60℃; for 2h;	85%
In water at 60℃; for 2h;	85%

3-methyl-1-(methoxyethoxyethoxyethoxycarbonylmethyl)imidazolium bromide (1122146-99-9) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(methoxyethoxyethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122147-05-0)

Conditions	Yield
In water at 60℃; for 2h;	84%

2,3-dimethyl-1-(butoxyethoxycarbonylmethyl)imidazolium bromide (1122147-06-1) + sodium octyl sulphate (142-31-4) → 2,3-dimethyl-1-(butoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122147-12-9)

Conditions	Yield
In water at 60℃; for 2h;	84%

N-(ethoxycarbonylmethyl)pyridinium bromide (17282-40-5) + sodium octyl sulphate (142-31-4) → 1-(ethoxycarbonylmethyl)pyridinium octyl sulfate (1048382-80-4)

Conditions	Yield
In water for 0.166667h;	83%

3-methyl-1-(methoxyethoxyethoxycarbonylmethyl)imidazolium bromide (1122146-71-7) + sodium octyl sulphate (142-31-4) → 3-methyl-1-(methoxyethoxyethoxycarbonylmethyl)imidazolium octylsulfate (1122146-77-3)

Conditions	Yield
In water at 60℃; for 2h;	82%

sodium octyl sulphate (142-31-4) + C47H66NO4(1+)*Cl(1-) → C47H66NO4(1+)*C8H17O4S(1-)

Conditions	Yield
In methanol at 60℃; for 2h;	82%

sodium octyl sulphate (142-31-4) + C71H114NO4(1+)*Cl(1-) → C71H114NO4(1+)*C8H17O4S(1-)

Conditions	Yield
In methanol at 60℃; for 2h;	74%

(RS)-3-methyl-1-(methylmandelylcarbonylmethyl)imidazolium bromide (1241839-40-6) + sodium octyl sulphate (142-31-4) → (RS)-3-methyl-1-(methylmandelylcarbonylmethyl)imidazolium octylsulfate (1241839-77-9)

Conditions	Yield
In water	71%

sodium octyl sulphate (142-31-4) + C63H98NO4(1+)*Cl(1-) → C63H98NO4(1+)*C8H17O4S(1-)

Conditions	Yield
In methanol at 60℃; for 2h;	71%

sodium octyl sulphate (142-31-4) + C79H130NO4(1+)*Cl(1-) → C79H130NO4(1+)*C8H17O4S(1-)

Conditions	Yield
In methanol at 60℃; for 2h;	68%

sodium octyl sulphate (142-31-4) + 1-butyl-3-methylimidazolium chloride (79917-90-1) → 1-n-butyl-3-methylimidazolium octyl sulfate

Conditions	Yield
In water Product distribution / selectivity; Heating / reflux;	66%
In dichloromethane; water

Upstream product

• 111-87-5 octanol 

Downstream Products

• 445473-58-5 1-n-butyl-3-methylimidazolium octyl sulfate 
• 1241840-18-5 2-(3,4-dihydroxyphenyl)-2-(3-methylimidazolium) butyl acetate octylsulfate 
• 1241840-08-3 2-(3,4-dimethoxyphenyl)-2-(pyridinium)methyl acetate octylsulphate 
• 1241839-91-7 2-(3,4-dimethoxyphenyl)-2-(3-methylimidazolium)butyl acetate octylsulphate 
• 1241839-77-9 (RS)-3-methyl-1-(methylmandelylcarbonylmethyl)imidazolium octylsulfate 
• 488711-63-3 2-methoxy-4-(phenylamino)-benzenediazonium octyl sulfate 

Relevant articles and documents

Enantioselective stereoinversion of sec-alkyl sulfates by an alkylsulfatase from Rhodococcus ruber DSM 44541

Enantioselective biohydrolysis of sec-alkyl sulfate esters using a bacterial alkylsulfatase from Rhodococcus ruber DSM 44541 proceeded in a stereoselective fashion though inversion of configuration. Thus, from racemic substrates, the corresponding (R)-enantiomers were hydrolyzed selectively to furnish the corresponding sec-alcohol and non-reacted sulfate ester, both of (S)-configuration, which represents a homochiral product mixture. The enantioselectivities were found to depend on the substrate structure and were optimal for sec-sulfate esters in the ω-1 position (up to E=21). Since the enzyme was inactive on prim-sulfate esters, it can be classified as a sec-alkylsulfatase [EC 3.1.6.X].

Influence of Chain Length on the Sphere-to-Rod Transition in Alkyl Sulfate Micelles

Using Quasielastic light scattering spectroscopy (QLS) we have deduced the mean hydrodynamic radius (Rh) of alkyl sulfate micelles as functions of chain length (number of carbons nc = 8-16), temperature (0-85 deg C), detergent concentration (0.01-4g/dL), and NaCl concentration (0.1-2 M).In the region of low chain length (nc h values (extrapolated to the cmc) increase approximately linearly with the chain length.These results combained with Huisman's aggregation numbers (nw(cmc)) are consistent with a micellar shape that is close to spherical (axial ratio less than 2).Under conditions of high NaCl concentrations of high NaCl concentration the micelles exhibit a temperature-dependent growth from small spherical aggregates into long spherocylindrical micelles at concentrations above the cmc.With increasing chain length the temperature dependence of Rh becomes stronger and the NaCl and detergent concentrations needed for micellar growth become smaller.Light scattering intensity measurements confirm a rodlike growth for these micelles at all chain lengths.From these Rh measurements, values of the thermodynamic parameter K governing the sphere-to-rod transition are determined by using an extension of our previous thermodynamic model (Missel et al., J.Phys.Chem., 84, 1044 (1980)).A quantitative analysis of the dependence of K on chain length, temperature, and NaCl concentration provides new insights into energetic factors which govern the structure and growth of micelles.