38803-34-8

Basic information

• Product Name: 3-(methoxycarbonyl)-N,N,N-trimethylbenzenaminium iodide
• Synonyms: 3-(methoxycarbonyl)-N,N,N-trimethylbenzenaminium iodide
• CAS NO: 38803-34-8
• Molecular Weight: 321.158
• Mol File: 38803-34-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-(methoxycarbonyl)-N,N,N-trimethylbenzenaminium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(methoxycarbonyl)-N,N,N-trimethylbenzenaminium iodide(38803-34-8)
• EPA Substance Registry System: 3-(methoxycarbonyl)-N,N,N-trimethylbenzenaminium iodide(38803-34-8)

Safety Data

• Hazardous Substances Data: 38803-34-8(Hazardous Substances Data)

Upstream product

• 99-64-9 3-(dimethylamino)benzoic acid 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 4518-10-9 Methyl 3-aminobenzoate 
• 16518-64-2 3-(dimethylamino)benzoic acid methyl ester 

Downstream Products

• 23501-93-1 3-dimethylaminobenzyl alcohol 
• 93-58-3 benzoic acid methyl ester 
• 462100-90-9 O²-(3-(dimethylamino)benzyl)-1-(N,N-diethylamino)-diazen-1-ium-1,2-diolate 
• 734506-61-7 3-(bromomethyl)-N,N-dimethylaniline 

Relevant articles and documents

Structure of methyl 3-(trimethylammonium)benzoate iodide studied by X-ray diffraction, DFT calculations, NMR and FTIR spectra

The structure of methyl 3-(trimethylammonium)benzoate iodide, 3-(Me) 3N+C6H4CO2MeI -, (1a) has been determined by X-ray diffraction, DFT calculations and characterized by FTIR and NMR spectroscopy. The crystals are orthorhombic, space group Pnma and the structure is stabilized by interaction of I anion with the N, O(1) and O(2) atoms. The N?I distances vary between 4.541(3) and 7.752(3) ?. The correlation between the atomic distances and the Mulliken atomic charges is linear. Charge on the quaternary nitrogen atom depends on options used for generating electrostatic potential-derived charges. The interpretation of 1H and 13C NMR spectra in DMSO-d 6 has been based on 2D experiments and calculated GIAO/B3LYP/6-311G(d,p) magnetic isotropic shielding constants. The FTIR spectrum of the solid compound is consistent with the X-ray results. The probable assignments of the anharmonic experimental vibrational frequencies of the investigated ester (1a) based on the calculated harmonic frequencies are proposed.

Controlled photochemical release of nitric oxide from O2-benzyl-substituted diazeniumdiolates

An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2N-N(O)=NO-) has been initiated, and here the effect of meta electron-donating groups on the photochemistry of O2-benzyl-substituted diazeniumdiolates (R2N-N(O)=NOCH2Ar) is reported. Photolysis of the parent benzyl derivative (Ar = Ph) results almost exclusively in undesired photochemistry-the formation of nitrosamine and an oxynitrene intermediate with very little, if any, photorelease of the diazeniumdiolate. We have been able to use meta substitution to tune the photochemistry of these benzylic systems. The desired diazeniumdiolate photorelease has been shown to become more substantial with stronger π-donating meta substituents. This effect has been verified by direct observation of the photoreleased diazeniumdiolate with 1H NMR spectroscopy and by NO quantification measurements conducted in high- and low-ph solutions. In addition, the observed rates of NO release are consistent with that expected for normal thermal decomposition of the diazeniumdiolate in aqueous solutions and also show the same pH dependence.