59935-39-6

Basic information

• Product Name: 4-(Dimethylamino)-3-nitrobenzaldehyde
• Synonyms: 4-(dimethylamino)-3-nitrobenzenecarbaldehyde;A0966/0045157;NSC156545;ZINC03886038
• CAS NO: 59935-39-6
• Molecular Formula: C₉H₁₀N₂O₃
• Molecular Weight: 194.19
• Mol File: 59935-39-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 105-107°C
• Boiling Point: 335.9 °C at 760 mmHg
• Flash Point: 156.9 °C
• Appearance: /
• Density: 1.286 g/cm³
• Vapor Pressure: 0.000116mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 4-(Dimethylamino)-3-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Dimethylamino)-3-nitrobenzaldehyde(59935-39-6)
• EPA Substance Registry System: 4-(Dimethylamino)-3-nitrobenzaldehyde(59935-39-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 59935-39-6(Hazardous Substances Data)

Usage

General Description

4-(Dimethylamino)-3-nitrobenzaldehyde is an organic compound with the chemical formula C9H10N2O3. It is a yellow crystalline solid with a molecular weight of 182.19 g/mol. 4-(Dimethylamino)-3-nitrobenzaldehyde is often used as a reagent in organic synthesis, particularly in the preparation of various pharmaceuticals and dyes. Its structure consists of a benzene ring with a nitro group and an aldehyde group, as well as a dimethylamino substituent. 4-(Dimethylamino)-3-nitrobenzaldehyde is known for its strong fluorescence and is commonly used as a fluorescent probe in biological research. It has also been studied for its potential antibacterial and antifungal properties, making it a versatile and important chemical in various industries.

InChI:InChI=1/C9H10N2O3/c1-10(2)8-4-3-7(6-12)5-9(8)11(13)14/h3-6H,1-2H3

Upstream product

• 100-10-7 4-dimethylamino-benzaldehyde 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 124-40-3 dimethyl amine 
• 31680-08-7 4-methoxy-3-nitrobenzaldehyde 
• 16588-34-4 4-chloro-3-nitro-benzaldehyde 
• 96014-61-8 3-nitro-4-methoxybenzylidenemethylamine 
• 96022-30-9 3-nitro-4-chlorobenzylidenemethylamine 

Downstream Products

• 346428-87-3 2-(3-Nitro-4-dimethylamino-benzyliden)-indandion-(1,3) 
• 37401-08-4 (4-dimethylamino-3-nitro-benzylidene)-malononitrile 
• 2571-44-0 4-Cyan-4'-dimethylamino-2,3'-dinitro-trans-stilben 
• 41263-74-5 4-(methylamino)-3-nitrobenzoic acid 
• 1598417-82-3 4-(4-dimethylamino-3-nitro-benzylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 1598417-36-7 4-(2-(4-(4-(dimethylamino)-3-nitrobenzylamino)piperidin-1-yl)ethyl)-6-methoxyquinoline-3-carbonitrile 
• 19005-63-1 4-(dimethylamino)-3-nitrobenzonitrile 
• 40700-40-1 4-dimethylamino-3-nitro-benzoic acid ethyl ester 
• 71254-71-2 ethyl 4-(methylamino)-3-nitrobenzoate 
• 845624-81-9 Dimethyl-{2-nitro-4-[(Z)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenyl}-amine 
• 845625-13-0 Dimethyl-{2-nitro-4-[(E)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenyl}-amine 
• 2571-49-5 1,5-Bis-<4-dimethylamino-3-nitro-trans-styryl>-2,4-dinitro-benzol 
• 2571-40-6 4-Dimethylamino-5'-methyl-2',3,4'-trinitro-trans-stilben 

Relevant articles and documents

Exploring the nitro group reduction in low-solubility oligo-phenylenevinylene systems: Rapid synthesis of amino derivatives

A small series of amino oligo-phenylenevinylenes (OPVs) were successfully synthesized from their nitro-analogs in a rapid, simple, and highly efficient fashion employing a sodium sulfide/pyridine system as a reducing agent. In this research, classic and sustainable reduction methodologies including NH4HCO2/Zn and a choline chloride/tin (II) chloride deep eutectic solvent (DES) were also evaluated, showing degradation products, incomplete reactivity, and product isolation difficulties in all cases. The straightforward Na2S/pyridine synthetic protocol proved to maintain the E-E stereochemistry of the OPV backbone that has been previously assembled by the Mizoroki–Heck cross-coupling reaction. Also, the optoelectronic properties were determined and discussed, considering the amino group insertion in these conjugated systems as a contribution for future construction of novel materials with applications in supramolecular electronics, light harvesting, and photocatalysis.

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

ACTIVATING EFFECT OF THE IMINIUM GROUP IN AROMATIC NUCLEOPHILIC SUBSTITUTION OF AN ALKOXY GROUP AND HALOGEN ATOMS BY THE ACTION OF NITROGEN BASES

The characteristics of aromatic nucleophilic substitution with activation by the iminium group in the iminium derivatives of p-alkoxy- and p-halogenobenzaldehydes were investigated.They are determined by the concurrent addition of the nucleophilic agents at the C=N multiple bond.The activating effect of the iminium group depends on the nature of the leaving group, the solvent, the substituent in the benzene ring, and the nature and concentration of the protonating agent.The action of heat on p-methoxybenzylidenemethylamine with a tenfold excess of methylamine hydrochloride in a 30percent alcohol solution of methylamine at 150 deg C for 40 h leads to substitutioon of the methoxymethylamino group with a yield of 90percent.