112-55-0

Basic information

• Product Name: 1-Dodecanethiol
• Synonyms: 1-Dodecyl mercaptan;1-dodecylmercaptan;Dodecane-1-thiol;Dodecanethiol-(1);dodecanethiol(non-specificname);dodecanethiolnormal;Dodecylthiol;laurylmercaptide
• CAS NO: 112-55-0
• Molecular Formula: C₁₂H₂₆S
• Molecular Weight: 202.4
• EINECS: 203-984-1
• Mol File: 112-55-0.mol

Chemical Properties

• Melting Point: -7 °C
• Boiling Point: 266-283 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 0.845 g/mL at 25 °C(lit.)
• Vapor Density: 7 (vs air)
• Vapor Pressure: 0.00861mmHg at 25°C
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: 2-8°C
• PKA: 10.49±0.10(Predicted)
• Water Solubility: IMMISCIBLE
• Sensitive: Air Sensitive
• BRN: 969337
• CAS DataBase Reference: 1-Dodecanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Dodecanethiol(112-55-0)
• EPA Substance Registry System: 1-Dodecanethiol(112-55-0)

Safety Data

• Hazard Codes: Xn,Xi,N,F,C
• Statements: 37/38-41-42/43-36/37/38-67-65-62-51/53-48/20-38-11-50/53-34
• Safety Statements: 23-26-36/37/39-45-37/39-63-62-61-36/37-33-29-16-9-60
• RIDADR: UN 1208 3/PG 2
• WGK Germany: 3
• RTECS: JR3155000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 112-55-0(Hazardous Substances Data)

Usage

Uses

Used in Polymer Industry:
1-Dodecanethiol is used as a polymerization inhibitor for polyurethane resins and neoprene adhesives, which are commonly utilized in the footwear industry. This application helps prevent unwanted polymerization reactions during the manufacturing process.
Used in Self-Assembled Monolayers (SAMs):
1-Dodecanethiol is employed in the preparation of hydrophobic or mixed self-assembled monolayers (SAMs). These monolayers are essential in various applications, such as surface modification and the creation of molecular devices.
Used as a Chain Transfer Agent:
In the field of radical polymerization, 1-Dodecanethiol serves as a chain transfer agent, which helps control the molecular weight and polydispersity of the resulting polymers.
Used in Protein Regeneration:
1-Dodecanethiol acts as a protein regenerating agent, used for the regeneration of native proteins from mercuribenzoate. This application is crucial in the field of biochemistry and molecular biology.
Used in the Synthesis of Metal Nanoparticles:
1-Dodecanethiol can be used for the synthesis of thiol-stabilized metal nanoparticles (NPs), such as gold and silver nanoparticles. These nanoparticles have a wide range of applications, including catalysis, electronic devices, fillers, sensors, and active components in composite materials.

Preparation

Preparation of 1-dodecanethiol: 1-Bromododecane, thiourea and 95% ethanol are heated to reflux reaction, then sodium hydroxide solution is added and heated. After the reaction is finished, cooled and left to stratify, the oil layer is the crude thiol. The crude product is washed with water, dried, distilled, and distilled under reduced pressure, which is 1-dodecanethiol.

Air & Water Reactions

Air and moisture sensitive. Insoluble in water. Reacts vigorously with water or steam.

Reactivity Profile

1-Dodecanethiol is incompatible with bases, oxidizing agents, reducing agents and alkali metals. Easily oxidized to disulfide.

Health Hazard

1-Dodecanethiol is irritating to skin, eyes, and mucous membranes. Ingestion may cause nausea. Repeated skin exposure can cause dermatitis and may produce a sensitizing effect. It is very toxic to aquatic life with long lasting effects.

Fire Hazard

Special Hazards of Combustion Products: Poisonous and irritating gases (e.g., sulfur dioxide) are generated in fires.

Purification Methods

Dry it with CaO for several days, then distil it from CaO. [Beilstein 1 IV 1851.]

InChI:InChI=1/C12H26S/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3

Synthetic route

didodecyl disulfide (2757-37-1) → 1-dodecylthiol (112-55-0)

Conditions	Yield
With hydrogen; rhodium hydrido (PEt3)3 complex In toluene for 0.5h; Heating;	86%
With sulfuric acid; zinc
With sodium hydrogensulfide; water
With RhCl(PPh3)3; hydrogen In toluene at 100℃; under 760 Torr; for 2h;	94 % Spectr.

thiocarbonic acid O-allyl ester S-dodecyl ester → 1-dodecylthiol (112-55-0)

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; water; diethylamine; palladium diacetate; heptakis(2,6-di-O-methyl)cyclomaltoheptaose In toluene at 20℃; for 3h; Substitution;	95%

1-chlorododecane (112-52-7) → 1-dodecylthiol (112-55-0)

Conditions	Yield
With sodium hydrogensulfide; tetrabutylammomium bromide In water; chlorobenzene at 65 - 70℃; for 12h;	244 g
With sodium disulfide; tetrabutylammomium bromide In water; chlorobenzene at 65 - 70℃; for 16h;	244 g

S-dodecyl dodecanethioate (103212-64-2) → lauric acid (143-07-7) + 1-dodecylthiol (112-55-0)

Conditions	Yield
With C18-alkylated polystyrene-supported sulfonic acid; water for 24h; Heating;	A 96% B n/a
With water; hydrophobic polystyrene-supported sulfonic acid for 72h; Heating;	A 95% B 95%
With C18-alkylated polystyrene-supported sulfonic acid; water for 24h; Heating;

Upstream product

• 2437-25-4 undecyl cyanide 
• 83962-22-5 Ethyl-dithiocarbamic acid dodecyl ester 
• 10478-23-6 S-dodecyl ethanethioate 
• 26960-77-0 sodium dodecanethiolate 
• 93413-77-5 N,N-didesmethylvenlafaxine 
• 2851-83-4 ethyl dodecyl sulfide 
• 25477-07-0 n-dodecyl thiosulfate, sodium 
• 765-15-1 1-dodecylthiocyanate 
• 112-53-8 1-dodecyl alcohol 
• 607731-47-5 1-((Z)-2-Dodecylsulfanyl-ethenesulfonyl)-4-methyl-benzene 
• 103212-64-2 S-dodecyl dodecanethioate 
• 82139-14-8 thiosulfuric acid S-dodecyl ester 
• 64-17-5 ethanol 
• 71-43-2 benzene 

Downstream Products

• 5441-35-0 6-dodecylmercapto-7(9)H-purine 
• 1462-52-8 3-(n-dodecylthio)-propanoic acid 
• 57322-72-2 2-n-dodecyl-mercaptohydroquinone 
• 5432-98-4 dodecyl (2-phenylethyl) sulfane 
• 496874-96-5 2,3-bis-dodecylmercapto-[1,4]naphthoquinone 
• 78-82-0 Isobutyronitrile 
• 5454-93-3 ω-(Laurylthio)undecansaeure 
• 1185-81-5 dibutyl tin ⁽²⁺⁾; bis-dodecane-1-thiolate 
• 2487-77-6 n-Dodecylthiopalmitat 
• 143-07-7 lauric acid 
• 1120-16-7 lauric acid amide 
• 10147-40-7 1-Dodecanesulfonyl chloride 
• 1510-16-3 dodecansulfonic acid 
• 40520-14-7 4-Dodecylmercapto-buttersaeure 

Related news

Influence of the molecular-scale structures of 1-Dodecanethiol (cas 112-55-0) and 4-methylbenzenethiol self-assembled monolayers on gold nanoparticles adsorption pattern08/27/2019

In an effort to understand the effects of the molecular structures of self-assembled monolayers on the patterns formed by immobilized Au nanoparticles (AuNPs), we characterized and compared the morphologies and properties of AuNPs adsorbed onto self-assembled monolayers formed by 1-dodecanethiol...detailed

Potential-assisted assembly of 1-Dodecanethiol (cas 112-55-0) on polycrystalline gold08/26/2019

The potential-controlled assembly of 1-dodecanethiol (DT) onto the polycrystalline gold surface from ethanolic solution was studied using in situ methods. The initial stage of DT adsorption and DT film nucleation were carried under potentiostatic control. The anodic polarization speeds up 1-dode...detailed

Morphological controlled synthesis of hierarchical copper selenide nanocrystals by Oleic acid, 1-Dodecanethiol (cas 112-55-0) and 1-Octadecene as surfactants08/25/2019

Copper selenide nanocrystals with hierarchical morphologies were prepared using solution processed colloidal method by employing cost effective environmentally benign surfactants. The hierarchical morphologies such as interconnected nanoflakes, stacked hexagonal nanoplatelets and nanoflowers lik...detailed

1-Dodecanethiol (cas 112-55-0) based highly stable self-assembled monolayers for germanium passivation08/23/2019

As a typical semiconductor material, germanium has the potential to replace silicon for future-generation microelectronics, due to its better electrical properties. However, the lack of stable surface state has limited its extensive use for several decades. In this work, we demonstrated highly s...detailed

The effect of synthesis parameters on the geometry and dimensions of mesoporous hydroxyapatite nanoparticles in the presence of 1-Dodecanethiol (cas 112-55-0) as a pore expander08/22/2019

Mesoporous hydroxyapatite with different pore diameters and pore volumes were synthesized by the self-assembly method using Cetyltrimethylammonium bromide (CTAB) as the cationic surfactant and 1-dodecanethiol as the pore expander at different micellization pHs, solvent types and surfactant conce...detailed

Gold partitioning between 1-Dodecanethiol (cas 112-55-0) and brine at elevated temperatures: Implications of Au transport in hydrocarbons for oil-brine ore systems08/21/2019

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