65399-18-0

Basic information

• Product Name: 4-Nitrophthalide
• Synonyms: 4-Nitrophthalide;4-Nitro-1(3H)-isobenzofuranone;4-nitroisobenzofuran-1(3H)-one
• CAS NO: 65399-18-0
• Molecular Formula: C₈H₅NO₄
• Molecular Weight: 179.13
• Product Categories: Heterocycles;Heterocyclic Compound
• Mol File: 65399-18-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 151-154 °C
• Boiling Point: 414.6 °C at 760 mmHg
• Flash Point: 230.4 °C
• Appearance: /
• Density: 1.519
• Vapor Pressure: 4.39E-07mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 4-Nitrophthalide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophthalide(65399-18-0)
• EPA Substance Registry System: 4-Nitrophthalide(65399-18-0)

Safety Data

• Hazardous Substances Data: 65399-18-0(Hazardous Substances Data)

Usage

General Description

4-Nitrophthalide is a chemical compound primarily used as an intermediate for the synthesis of pharmaceuticals and dyes. It is a pale yellow solid with a strong odor, and it is insoluble in water but soluble in organic solvents. 4-Nitrophthalide is classified as a nitro compound due to the presence of a nitro group (NO2) in its molecular structure. It is known for its use in the production of 3-amino-4-methoxyacetophenone, which is an important intermediate for the synthesis of pharmaceuticals such as Diltiazem. Additionally, 4-Nitrophthalide is used in the manufacturing of dyes, pigments, and as a chemical intermediate in organic synthesis. Proper handling and storage of 4-Nitrophthalide are important due to its potential to cause skin and eye irritation and its flammability.

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

Upstream product

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

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 
• 827026-45-9 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 879126-98-4 Lenalidomide 
• 197715-03-0 4-dibenzoylamino-phthalide 
• 705281-78-3 4-benzoylamino-phthalide 
• 4792-33-0 4-methoxyphthalide 
• 105694-45-9 4-iodophthalide 
• 102308-43-0 4-bromoisobenzofuran-1(3H)-one 
• 13161-32-5 4-hydroxy-3H-isobenzofuran-1-one 
• 1207454-76-9 9-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 
• 1207454-71-4 8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,3-triazol-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 
• 1207454-69-0 8-(4-fluorophenyl)-9-(1,4,5-trimethyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one 

Relevant articles and documents

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.

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.

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.