18412-81-2

Basic information

• Product Name: DODECYLDIMETHYLSULFONIUM IODIDE
• Synonyms: DODECYLDIMETHYLSULFONIUM IODIDE
• CAS NO: 18412-81-2
• Molecular Formula: C₁₄H₃₁S*I
• Molecular Weight: 358.37
• Mol File: 18412-81-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 68 °C
• Appearance: /
• CAS DataBase Reference: DODECYLDIMETHYLSULFONIUM IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DODECYLDIMETHYLSULFONIUM IODIDE(18412-81-2)
• EPA Substance Registry System: DODECYLDIMETHYLSULFONIUM IODIDE(18412-81-2)

Safety Data

• Hazardous Substances Data: 18412-81-2(Hazardous Substances Data)

Upstream product

• 75-18-3 dimethylsulfide 
• 4292-19-7 1-Iodododecane 
• 3698-89-3 dodecyl methyl sulfide 
• 74-88-4 methyl iodide 

Downstream Products

• 1187-84-4 S-methyl-L-cysteine 
• 100-66-3 methoxybenzene 
• 2140-65-0 1-methylguanosine 
• 2140-69-4 3-methyluridine 
• 958-74-7 3-methylthymidine 
• 2140-73-0 1-methylinosine 

Relevant articles and documents

Three-Phase Model of Micellar Reactions. Methylation of Thymidine by (Long-chain-alkyl)dimethylsulfonium Iodides

Micellar methylation of thymidine to 3-methylthymidine was studied by using mainly n-octadecyldimethylsulfonium iodide at pH 7-12 and 60-75 deg C.The reaction exhibited the presence of an induction period as long as 1 h, a bell-shaped pH dependence of the methylation rate with an optimum pH ca. 10, and competitive inhibitory effects of added salts on the micellar reaction, etc.A three-phase model was proposed to analyze the micellar events, assuming that (i) the anions (dT-) of thymidine, the active species of the nucleoside, diffuse from the aqueous bulk phase to the Stern layer across the Gouy-Chapman layer, (ii) dT- ions concentrate in the Stern layer to obey the Langmuir adsorption isotherm theory, and (iii) the dT- ions in the layer are mediated in a bimolecular fashion with the dimethylsulfonium ions, the head groups of the micelles.The model furnished apparent kinetic constants such as binding constants of counterions (dT-, I-, OH-, etc.) to the micelle, a diffusion rate constant of dT- and Me-dT from the Stern layer.The effects of temperature on these constants were studied carefully to estimate the respective thermodynamic constants.The three-phase model was compared with other micellar models reported.The micellar methylation was discussed briefly in connection to the enzymatic methylation that utilizes S-adenosylmethionine as a cofactor.

Micellar Methylating Agents: (Long-chain-alkyl)dimethylsulphonium Iodides

Dodecyl-, hexadecyl-, and octadecyl-dimethylsulphonium iodide were found to methylate efficiently various nucleosides, hydroxy aromatic compounds, and thiols at pH 8-11 and 50 - 70 deg C.The optimum conditions and the mechanism of the reaction are discussed briefly in relation to the micellar reaction characteristics.