title: Synthesis of 13C and 15N labeled 2,4-dinitroanisole.
abstract: Syntheses of [(13)C6]-2,4-dinitroanisole (ring-(13)C6) from [(13)C6]-anisole (ring-(13)C6) and [(15)N2]-2,4-dinitroanisole from anisole using in situ generated acetyl nitrate and [(15)N]-acetyl nitrate, respectively, are described. Treatment of [(13)C6]-anisole (ring-(13)C6) with acetyl nitrate generated in 100% HNO3 gave [(13)C6]-2,4-dinitroanisole (ring-(13)C6) in 83% yield. Treatment of anisole with [(15)N]-acetyl nitrate generated in 10 N [(15)N]-HNO3 gave [(15)N2 ]-2,4-dinitroanisole in 44% yield after two cycles of nitration. Byproducts in the latter reaction included [(15)N]-2-nitroanisole and [(15)N]-4-nitroanisole.
authors.affiliation: Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ, 85721-0041, USA.
authors.forename: Bhumasamudram
authors.initials: B
authors.lastname: Jagadish
authors.forename: Jim A
authors.initials: JA
authors.lastname: Field
authors.forename: Jon
authors.initials: J
authors.lastname: Chorover
authors.forename: Reyes
authors.initials: R
authors.lastname: Sierra-Alvarez
authors.forename: Leif
authors.initials: L
authors.lastname: Abrell
authors.forename: Eugene A
authors.initials: EA
authors.lastname: Mash
mesh_terms: D000840:Anisoles / Q000138:chemical synthesis* / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D009566:Nitrates / Q000737:chemistry; D009587:Nitrogen Isotopes / Q000737:chemistry; D011854:Radiochemistry
chemical_list: D000840:Anisoles; D002247:Carbon Isotopes; D009566:Nitrates; D009587:Nitrogen Isotopes; C539360:2,4-dinitroanisole
keywords: [13C6]-2,4-dinitroanisole; [15N2]-2,4-dinitroanisole; [15N]-acetyl nitrate; insensitive munitions compounds; synthesis