765-15-1

Basic information

• Product Name: N-DODECYL THIOCYANATE
• Synonyms: 1-thiocyanato-dodecan;Dodecane, 1-thiocyanato-;ENT 114;ent114;Lauryl rhodanate;Lauryl thiocyanate;laurylrhodanate;Laurylrhodanide
• CAS NO: 765-15-1
• Molecular Formula: C₁₃H₂₅NS
• Molecular Weight: 227.41
• EINECS: 212-142-2
• Mol File: 765-15-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 180°C 18mm
• Flash Point: 180°C/18mm
• Appearance: /
• Density: 0,896 g/cm3
• Vapor Pressure: 0.0009mmHg at 25°C
• Refractive Index: 1.4680
• BRN: 1770396
• CAS DataBase Reference: N-DODECYL THIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: N-DODECYL THIOCYANATE(765-15-1)
• EPA Substance Registry System: N-DODECYL THIOCYANATE(765-15-1)

Safety Data

• Statements: 22-32-36/38
• Safety Statements: 26-36/37/39
• RTECS: XK9625000
• Hazardous Substances Data: 765-15-1(Hazardous Substances Data)

Usage

General Description

N-Dodecyl thiocyanate, also known as Dodecyl rhodanide, is an organic compound with the chemical formula C12H25SCN. It is a colorless to pale yellow liquid and is commonly used as a surfactant or wetting agent in various industrial and research applications. N-Dodecyl thiocyanate is used in the production of functionalized nanoparticles, as a phase transfer catalyst, and as a reagent in organic synthesis, particularly in the preparation of thioether compounds. It is also used in the preparation of various pharmaceutical compounds and in some specialty chemical applications. Additionally, it can be used as a reagent for the analysis of metal ions and as a corrosion inhibitor in some formulation.

InChI:InChI=1/C13H25NS/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14/h2-12H2,1H3

Upstream product

• 112-55-0 1-dodecylthiol 
• 112-53-8 1-dodecyl alcohol 
• 1147550-11-5 ammonium thiocyanate 
• 18536-91-9 dodecyltriethoxysilane 
• 1701-93-5 silver thiocyanate 
• 2757-37-1 didodecyl disulfide 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 143-15-7 1-dodecylbromide 
• 4292-19-7 1-Iodododecane 
• 540-72-7 sodium thiocyanide 
• 112-52-7 1-chlorododecane 
• 143-33-9 sodium cyanide 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 2757-37-1 didodecyl disulfide 
• 102710-12-3 1-dodecylsulfanylmethylbenzene 
• 112-55-0 1-dodecylthiol 

Relevant articles and documents

Dynamic Nucleophilic Aromatic Substitution of Tetrazines

A dynamic nucleophilic aromatic substitution of tetrazines (SNTz) is presented herein. It combines all the advantages of dynamic covalent chemistry with the versatility of the tetrazine moiety. Indeed, libraries of compounds or sophisticated molecular structures can be easily obtained, which are susceptible to post-functionalization by inverse electron demand Diels–Alder (IEDDA) reaction, which also locks the exchange. Additionally, the structures obtained can be disassembled upon the application of the right stimulus, either UV irradiation or a suitable chemical reagent. Moreover, SNTz is compatible with the imine chemistry of anilines. The high potential of this methodology has been proved by building two responsive supramolecular systems: A macrocycle that displays a light-induced release of acetylcholine; and a truncated [4+6] tetrahedral shape-persistent fluorescent cage, which is disassembled by thiols unless it is post-stabilized by IEDDA.

Silver-mediated oxidative functionalization of alkylsilanes

A general approach to the functionalization of aliphatic C-Si bonds in the presence of silver salts and oxidants has been reported. This strategy encompasses a range of valuable C-Si transformations, including the direct conversions of a C-Si bond to C-OCF3, C-OBz, C-OCOCF3, C-SCF3, C-SCN, and C-N3 bonds. Among them, trifluoromethoxylation of alkylsilanes is reported for the first time. In addition, mechanistic studies indicate that this reaction may proceed through a radical mechanism.

General and practical formation of thiocyanates from thiols

A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.