65399-18-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrophthalide is used as a chemical intermediate for the synthesis of pharmaceuticals, specifically in the production of 3-amino-4-methoxyacetophenone. This intermediate is essential for the synthesis of Diltiazem, a medication used to treat various cardiovascular conditions.
Used in Dye and Pigment Manufacturing:
4-Nitrophthalide is utilized as a chemical intermediate in the manufacturing of dyes and pigments, contributing to the coloration processes in various industries that require colored products.
Used in Organic Synthesis:
Beyond its applications in pharmaceuticals and dyes, 4-Nitrophthalide also serves as a versatile chemical intermediate in organic synthesis, enabling the creation of a wide range of chemical products.
It is important to handle and store 4-Nitrophthalide with care due to its potential to cause skin and eye irritation and its flammability, ensuring safety in its applications across different industries.

InChI:InChI=1/C8H5NO4/c10-8-5-2-1-3-7(9(11)12)6(5)4-13-8/h1-3H,4H2

Upstream product

• 86-57-7 1-Nitronaphthalene 
• 641-70-3 3-nitrophthalic acid anhydride 

Downstream Products

• 59434-19-4 4-Amino-1(3H)-isobenzofuranon 
• 603-11-2 3-nitrophthalic acid 
• 355133-61-8 4-(2-hydroxymethyl-3-nitrobenzoyl)imidazole-1-sulfonic acid dimethylamide 
• 13161-32-5 4-hydroxy-3H-isobenzofuran-1-one 
• 102308-43-0 4-bromoisobenzofuran-1(3H)-one 
• 105694-45-9 4-iodophthalide 
• 4792-33-0 4-methoxyphthalide 
• 705281-78-3 4-benzoylamino-phthalide 
• 197715-03-0 4-dibenzoylamino-phthalide 
• 98475-08-2 4-nitro-1,3-dihydro-isobenzofuran 
• 1207455-99-9 (8S,9R)-8-(4-fluorophenyl)-9-(1-methyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 
• 1207455-98-8 (8R,9S)-8-(4-fluorophenyl)-9-(1-methyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 
• 1207456-05-0 (8S,9R)-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 
• 1207456-04-9 (8R,9S)-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 

Relevant academic research and scientific papers

Dual fluorescent N-Aryl-2,3-naphthalimides: Applications in ratiometric DNA detection and white organic light-emitting devices

A ten element matrix of 5- and 6-substituted-(2,3)-naphthalimides was prepared for the appropriate placement of substituents necessary to promote dual fluorescence (DF). As prescribed by our balanced seesaw photophysical model this matrix yielded nine new DF dyes out of a possible ten compounds. From this set of nine DF dyes, 4-fluoronaphthalic amide (37) was selected as a probe for ratiometric detection of DNA and demonstration of panchromatic emission.

17O NUCLEAR MAGNETIC RESONANCE SPECTROSCOPIC STUDY OF SUBSTITUTED PHTHALIC ANHYDRIDES AND PHTHALIDES

17O chemical shift data (natural abundance) for 3-substituted phthalic anhydrides and 4- and 7-substituted phthalides in acetonitrile at 75 deg C are reported.Steric interactions of substituents ortho to the carbonyl groups result in deshielding effects (9-22 ppm) relative to parent compounds regardless of the electronic character of the substituents.Factors contributing to the deshielding effects are discussed.The relationship between 17O chemical shifts and regiochemistry of the phthalic anhydrides is discussed.

On the regioselectivity of metal hydride reductions of 3-substituted phthalic anhydrides

A problem of 3-methoxyphthalide reduction by metal hydrides was reinvestigated. Various effects controlling selectivity of reductions in 3-substituted phthalides were studied, and a qualitative interpretation of the results is now proposed. Methods for obtaining enhanced yields of one or the other lactonic product were developed.

Regioselective Addition of Grignard Reagents to 3-Methoxy- and 3-Nitrophthalic Anhydride

The regioselectivity in the addition of the grignard reagents 5a and 6a to the anhydrides 1 and 2 is determined by the solvent system: in a highly selective manner (3:97), the meta carbonyl group is attacked in tetrahydrofuran/tetramethylethylenediamine, while predominant, but relatively unselective (maximum 78:22) addition to the ortho carbonyl group is observed in diethyl ether.The influence of the solvent system on the regioselectivity is discussed.The LUMO-coefficients of the carbonyl carbon atoms in 1 and 2 were calculated.

Regioselectivity of metal hydride reductions of unsymmetrically substituted cyclic anhydrides. Systems where "steric hindrance along the preferred reaction path" rationalization is not applicable

Metal hydride reductions of planar cyclic anhydrides such as methylmaleic or 3-substituted phthalic anhydrides occur preferentially at the sterically more hindered carbonyl function.This regioselectivity cannot be rationalized in terms of "the most favourable pathway for non-perpendicular attack by a nucleophile" since both carbonyl groups present are equally accessible to non-perpendicular approach.A study which takes into account the alkaline cation and inductive, mesomeric, and steric effects has been conducted for the reduction of several conjugated and aromatic anhydrides.A qualitative interpretation for the regioselectivities observed in these reductions (as well as in reductions already reported in the literature) is suggested.An early transition state for the catalyzed versus late transition state for the non-catalyzed process is proposed.