39741-91-8

Usage

Uses

Used in Organic Synthesis:
IODOMETHYLTRIMETHYLAMMONIUM IODIDE is used as an alkylating agent for various organic synthesis processes. Its ability to transfer alkyl groups makes it a valuable component in the creation of a wide range of chemical compounds.
Used in the Preparation of Quaternary Ammonium Salts:
In the chemical industry, IODOMETHYLTRIMETHYLAMMONIUM IODIDE is used as a key component in the synthesis of quaternary ammonium salts. These salts have diverse applications, including as surfactants, phase transfer catalysts, and antimicrobial agents.
Used in the Synthesis of Ylides:
IODOMETHYLTRIMETHYLAMMONIUM IODIDE is used as a precursor in the preparation of ylides, which are compounds with a unique structure containing a neutral molecule with a positive and negative charge on adjacent atoms. Ylides are important intermediates in various organic reactions and are used in the synthesis of complex organic molecules.

InChI:InChI=1/C4H11IN/c1-6(2,3)4-5/h4H2,1-3H3/q+1

Upstream product

• 75-11-6 diiodomethane 
• 75-50-3 trimethylamine 
• 85219-42-7 (2,2-Dihydroxy-3,3,3-trifluoropropyl)trimethylammonium iodide 
• 121-44-8 triethylamine 

Downstream Products

• 84173-74-0 [(5S,6R,8S)-6-(6-Bromo-benzo[1,3]dioxol-5-yl)-8-(2,4-dinitro-phenylamino)-6-methyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-yl]-carbamic acid tert-butyl ester 
• 33797-51-2 eschenmoser's salt 
• 74-88-4 methyl iodide 
• 39895-69-7 iodomethyl-trimethyl-ammonium 
• 75-58-1 tertamethylammonium iodide 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 

Relevant academic research and scientific papers

A Room-Temperature Hybrid Lead Iodide Perovskite Ferroelectric

Organic-inorganic hybrid perovskite, [CH3NH3]PbI3, holds a great potential for next-generation solar devices. However, whether the ferroelectricity exists in [CH3NH3]PbI3 and results in the ultrahigh performance is not at present clear. Beyond that, no hybrid lead iodide perovskite ferroelectric has yet been found. Here, using precise molecular modifications, we successfully designed a room-temperature hybrid perovskite ferroelectric, [(CH3)3NCH2I]PbI3. Because of the high-symmetry and nearly spherical shape of [(CH3)4N]+ cation, [(CH3)4N]PbI3 crystallizes in a centrosymmetric space group P63/m at room temperature and undergoes a structural phase transition at 184 K. Accompanied by the introduction of halogen atoms on the cation from F to I, the phase transition temperature gradually increases to 312 K and the space group transforms into a polar C2 at room temperature. The strongest halogen bond energy of [(CH3)3NCH2I]-I and the largest volume of [(CH3)3NCH2I]+ among these compounds might be possible reasons for the stabilization of ordered [(CH3)3NCH2I]+ cation array and further reservation of its ferroelectricity at relatively high temperature. This work provides an efficient molecular design strategy toward the targeted harvest of room-temperature organic-inorganic perovskite ferroelectrics, and should inspire further exploration of the interplay between structure and ferroelectricity. The discovery of lead iodide perovskite ferroelectric also offers a foothold to the possibility for the existence of ferroelectricity in [CH3NH3]PbI3.

Target Designing Phase Transition Materials through Halogen Substitution

Crystalline materials have received extensive attention due to their extraordinary physical and chemical properties. Among them, phase transition materials have attracted great attention in the fields of photovoltaic, switchable dielectric devices, and ferroelectric memories, etc. However, many of them suffer from low phase transition temperatures, which limits their practical application. In this work, we systematically designed crystalline materials, (TMXM)2PtCl6 (X=F, Cl, Br, I) through halogen substitution on the cations, aiming to improving phase transition temperature. The resulting phase transition of (TMXM)2PtCl6 (X=F, Cl, Br, I) get a significant enhancement, compared to the parent compound [(CH3)4N]2PtCl6 ((TM)2PtCl6). Such phase transition temperature enhancement can be attributed to the introduction of halogen atoms that increase the potential energy barrier of the cation rotation. In addition, (TMBM)2PtCl6 and (TMIM)2PtCl6 have a low symmetry and crystallize in the space group C2/c and P212121, respectively. This work highlights the halogen substitution in designing crystal materials with high phase transition temperature.

Precise Molecular Design Toward Organic-Inorganic Zinc Chloride ABX3 Ferroelectrics

Organic-inorganic ABX3 (A, B = cations, X = anion) hybrids with perovskite structure have recently attracted tremendous interest due to their structural tunability and rich functional properties, such as ferroelectricity. However, ABX3 hybrid ferroelectrics with other structures have rarely been reported. Here, we successfully designed an ABX3 hybrid ferroelectric [(CH3)3NCH2F]ZnCl3 with a spontaneous polarization of 4.8 μC/cm2 by the molecular modification of [(CH3)4N]ZnCl3 through hydrogen/halogen substitution. It is the first zinc halide ABX3 ferroelectric, which contains one-dimensional [ZnCl3]-n chains of corner-sharing ZnCl4 tetrahedra, distinct from the anionic framework of corner-sharing or face-sharing BX6 octahedra in the ABX3 perovskites. From zero dimension to one dimension, the high symmetry of ZnCl4 tetrahedra is broken, and all of them align along one direction to form a polar [ZnCl3]-n chain, beneficial to the generation of ferroelectricity. This finding provides an efficient polar anionic framework for enriching the family of hybrid ferroelectrics by assembling with various cations and should inspire further exploration of new classes of organic-inorganic ABX3 ferroelectrics.

A hybrid organic-inorganic perovskite with robust SHG switching

Owing to the diversity of structure and potential applications in the field of electrics, sensors, and light-emitting diodes, lead halide perovskites have attracted great attention in recent years. Especially those lead halide perovskites with non-centrosymmetric crystal structures usually exhibit nonlinear optical (NLO) characteristics, which may endow them photoelectricity switching functionality. In this work, a lead-based hybrid organic-inorganic perovskite (HOIP) material, trimethyliodomethylammonium lead trichloride (TMIM·PbCl3), is obtained on the basis of tetramethylammonium lead chloride through halogen substitution on the cation part. It shows dual-phase-transition behavior around 345 and 358 K, which is significantly improved. TMIM·PbCl3 crystallizes in the chiral space group, P212121, and shows a well-defined second harmonic generation (SHG) response, and good switching endurance, which makes it an excellent candidate for SHG switching material. This work highlights the importance of halogen substitution for crystal engineering and may pave way for the further exploration of the optoelectronic devices.

Kinetic evidence for a novel, Grob-like substitution/fragmentation mechanism for the reaction of nucleophiles with trialkylammoniomethyl halides

Kinetic evidence is presented in favor of a concerted, bimolecular mechanism for the unusual nucleophilic substitution/fragmentation reactions of iodide ion with (halomethyl)trimethylammonium salts. The relative reactivities of allyl, ethyl and methyl groups for this Grob-like reaction are also determined. Activation parameters are presented for the thermal reactions of 1-iodo-N,N,N-trimethylmethaniminium iodide (log A = 8.7. Ea = 19.0 kcal mol-1) and 1-iodo-N-allyl-N,N-dimethylmethaniminium iodide (log A = 14.6, Ea = 25.7 kcal mol-1) in acetonitrile, the latter reaction having an observed second order rate constant 39 times larger than the former at 70 °C. The results are compared with the classic data of Hughes, Ingold and Conant for SN2 reactions of alkyl halides.

The Quarternisation of Tertiary Amines with Dihalomethane

Whereas dichloromethane is inert towards reaction with most tertiary amines under atmospheric conditions, it readily reacts with a wide variety at high pressures to produce α-chloro quaternary ammonium and even bis-ammonium salts.The reaction of dichloromethane and dibromomethane with eleven tertiary amines and properties of the products are described.