92241-76-4

Upstream product

• 100-66-3 methoxybenzene 
• 92241-75-3 ⁽¹⁵⁾N-2-nitrophenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 63792-03-0 <15N>-o-anisidine 
• 92241-77-5 C₁₄H₁₄⁽¹⁵⁾N₂O₂ 

Relevant academic research and scientific papers

NITRATION OF AROMATIC COMPOUNDS

The present invention provides a process for nitrating aromatic compounds without the need for a solid catalyst and/or any organic solvents and/or any other additives. A typical process includes combining or admixing a nitric acid and an anhydride compound under conditions sufficient to produce a reactive intermediate. The aromatic compound to be nitrated is then added to this reactive intermediate to produce a nitroaromatic compound. The nitroaromatic compound can be substituted with one or more, typically, one to three, and often one or two nitrate (-NO2) groups.

Synthesis of 13C and 15N labeled 2,4-dinitroanisole

Syntheses of [13C6]-2,4-dinitroanisole (ring- 13C6) from [13C6]-anisole (ring-13C6) and [15N2]-2,4- dinitroanisole from anisole using in situ generated acetyl nitrate and [ 15N]-acetyl nitrate, respectively, are described. Treatment of [ 13C6]-anisole (ring-13C6) with acetyl nitrate generated in 100% HNO3 gave [13C 6]-2,4-dinitroanisole (ring-13C6) in 83% yield. Treatment of anisole with [15N]-acetyl nitrate generated in 10 N [15N]-HNO3 gave [15N2]-2,4- dinitroanisole in 44% yield after two cycles of nitration. Byproducts in the latter reaction included [15N]-2-nitroanisole and [ 15N]-4-nitroanisole.

Benzidine Rearrangements. 19. The Concerted Nature of the One-Proton Rearrangement of 2,2'-Dimethoxyhydrazobenzene

Kinetic isotope effects (KIE) in the acid-catalyzed, one-proton rearrangement of 2,2'-dimethoxyhydrazobenzene (1) into 3,3'-dimethoxybenzidine (2) have been measured.Nitrogen KIE were determined on the bis(trifluoroacetyl) derivative of 2 which was isolated from low and 100percent conversions of mixtures of 1 and 1 under kinetic conditions.The ratio of masses M(438)/M(436) as determined by whole-ion mass spectrometric techniques led to the result k(14N)/k(15N)=1.0289 (for two nitrogens).Similar measurements on the derivative of 2 isolated from conversions of mixtures of 1 and 1 led to the result k(12C)/k(13C)=1.0286 (for two carbons).These results show that the formation of 2 is a concerted process and, thus, that the acid-cytylyzed rearrangement of 1 is a 5,5-sigmatropic shift.Rearrangement via a ?-complex intermediate or a solvent-caged, radical/radical-ion pair is excluded.That bonding in the 4,4' positions of 1 is part of the rate-determining step in this rearrangement was confirmed by measurement of an inverse secondary deuterium KIE (kH/kD=0.929 for two deuteriums).This result was obtained from ratios of M(244)/M(242) which were measured on 2,2'-dimethoxyazobenzene (3), obtained by oxidizing the hydrazo substrate remaining after high conversions of mixtures of 1 and 1.