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

被引：3

作者：

Jagadish, Bhumasamudram ^{[1
]}

Field, Jim A. ^{[2
]}

Chorover, Jon ^{[3
]}

Sierra-Alvarez, Reyes ^{[2
]}

Abrell, Leif ^{[1
,3
]}

Mash, Eugene A. ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

[2] Univ Arizona, Dept Chem & Environm Engn, Tucson, AZ 85721 USA

[3] Univ Arizona, Dept Soil Water & Environm Sci, Tucson, AZ 85721 USA

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2014年 / 57卷 / 06期

关键词：

C-13(6)]-2,4-dinitroanisole; N-15(2)]-2,4-dinitroanisole; N-15]-acetyl nitrate; synthesis; insensitive munitions compounds; POLYPHOSPHORIC ACID; AROMATIC NITRATION; ACETIC-ANHYDRIDE; COVALENT BINDING; SYSTEMS; NMR;

D O I：

10.1002/jlcr.3192

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

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

引用

页码：434 / 436

页数：3

共 16 条

[1] Thermal decomposition of acetic anhydride-nitric acid mixtures [J].

Andreozzi, R ;

Marotta, R ;

Sanchirico, R .

JOURNAL OF HAZARDOUS MATERIALS, 2002, 90 (02) :111-121

[2] Ethylammonium Nitrate (EAN)/Tf2O and EAN/TFAA: Ionic Liquid Based Systems for Aromatic Nitration [J].

Aridoss, Gopalakrishnan ;

Laali, Kenneth K. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :8088-8094

[3]

Davies P., 2006, WEAPONS SYSTEMS DIVI

[4] Nitration of tert-butyloxycarbonylated aniline and 1,3,5-triaminobenzene by acetyl nitrate [J].

Davis, Matthew C. ;

Groshens, Thomas J. .

TETRAHEDRON LETTERS, 2012, 53 (32) :4154-4155

[5] MILD AND SELECTIVE NITRATION BY CLAYCOP [J].

GIGANTE, B ;

PRAZERES, AO ;

MARCELOCURTO, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3445-3447

[6] USE OF HIGH-RESOLUTION C-13 NMR TO EXAMINE THE ENZYMATIC COVALENT BINDING OF C-13-LABELED 2,4-DICHLOROPHENOL TO HUMIC SUBSTANCES [J].

HATCHER, PG ;

BORTIATYNSKI, JM ;

MINARD, RD ;

DEC, J ;

BOLLAG, JM .

ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1993, 27 (10) :2098-2103

[7]

Iqbal R, 1997, J CHEM SOC PAKISTAN, V19, P141

[8] NITRATION OF 2,6-XYLENYL ACETATE WITH NITRONIUM TETRAFLUOROBORATE IN ACETIC-ANHYDRIDE [J].

IRIYE, R ;

MUKAI, T .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1976, 40 (01) :219-220

[9] Aromatic nitration with bismuth nitrate in ionic liquids and in molecular solvents: a comparative study of Bi(NO3)3•5H2O/[bmim][PF6] and Bi(NO3)3•5H2O/1,2-DCE systems [J].

Jacoway, Jonathan ;

Kumar, G. G. K. S. Narayana ;

Laali, Kenneth K. .

TETRAHEDRON LETTERS, 2012, 53 (50) :6782-6785

[10]

MAJUMDAR MP, 1976, INDIAN J CHEM B, V14, P1012

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