73635-75-3

Usage

Uses

Used in Chemical Synthesis:
3,4-Dihydroxy-6-nitrobenzaldehyde is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its unique structure with hydroxyl and nitro groups allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in Pharmaceutical Industry:
3,4-Dihydroxy-6-nitrobenzaldehyde is used as a reagent in the synthesis of 5,6-diacetoxyindole, which is a stable eumelanin precursor. Eumelanin is a pigment found in the skin, hair, and eyes of humans and animals, and its precursors have potential applications in the treatment of pigmentation disorders and as additives in the cosmetic industry.
Additionally, 3,4-dihydroxy-6-nitrobenzaldehyde is used in the preparation of 6-aminoisoproterenol, which is an impurity of the non-selective beta-adrenergic agonist, Isoproterenol (I874200, HCl). Isoproterenol is a medication used to treat certain heart conditions and asthma, and the synthesis of its impurities is essential for the development of safer and more effective drugs.

Upstream product

• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 73635-74-2 5-(Chloromethoxy)-4-hydroxy-2-nitrobenzaldehyde 
• 500284-46-8 (6-nitro-1,3-benzodioxol-5-yl)methylene diacetate 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 331-39-5 caffeic acid 
• 120-57-0 piperonal 
• 75-34-3 1,1-dichloroethane 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 121-33-5 vanillin 
• 2454-72-0 6-nitrovanillin 

Downstream Products

• 99459-14-0 (E)-4,5-diacetoxy-2β-dinitrostyrene 
• 409314-45-0 1,2-diacetoxy-4-(1-acetoxy-2-nitro-ethyl)-5-nitro-benzene 
• 98369-55-2 (E)-4,5-dihydroxy-2,β-dinitrostyrene 
• 109300-70-1 2-(4,5-Dihydroxy-2-nitro-benzylidene)-malonic acid 
• 73635-76-4 4,5-bis(benzyloxy)-2-nitrobenzaldehyde diethyl acetal 
• 18002-41-0 4,5-bis(benzyloxy)-2-nitrobenzaldehyde 
• 73635-77-5 4,5-bis(benzyloxy)-2-nitroepoxystyrene 
• 73635-79-7 bis(benzyloxy)-6-nitroisoproterenol 
• 1442442-23-0 C₂₀H₁₉N₃O₈ 
• 874518-60-2 4,5-bis(methoxymethoxy)-2-nitrobenzaldehyde 
• 1609073-29-1 2-amino-4,5-bis((4-methoxybenzyl)oxy)benzoic acid 

Relevant academic research and scientific papers

Amphiphilic molecule containing o-nitrobenzyl ester photo-degradation group

The invention discloses a novel photodegradable amphiphilic molecule and a synthetic method thereof, and belongs to the field of surfactants. The synthetic method comprises the five steps that (1) diethylenetriamine pentaacetic acid is taken as a raw material, acetic anhydride is taken as a dehydrating agent, and pyridine catalytic dehydration is performed to produce diethylenetriamine pentaaceticdianhydride; (2) methylene of 6-nitropiperonal is removed under the action of aluminum chloride and hydrobromic acid; (3) 4,5-dihydroxy-2-nitrobenzaldehyde and bromoalkane are subjected to an etherification reaction under an alkaline condition; (4) the 4,5-dihydroxy-2-nitrobenzaldehyde is reduced to 4,5-dihydroxy-2-nitrobenzyl alcohol under the action of a reducing agent; (5) the 4,5-dihydroxy-2-nitrobenzyl alcohol and the excess diethylenetriamine pentaacetic dianhydride are subjected to an esterification reaction to obtain the o-nitrobenzyl ester amphiphilic molecule. The novel photodegradable amphiphilic molecule and the synthetic method thereof have the advantages that the reaction condition of an o-nitrobenzyl alcohol derivative and the diethylenetriamine pentaacetic dianhydride is mild, the excess diethylenetriamine pentaacetic dianhydride is used for reducing the occurrence of side reactions, and the amphiphilic molecule has good ultraviolet photodegradability.

Preparation method of near-infrared light-controlled visual medicine carrier

The invention discloses a near-infrared light-controlled medicine carrier, namely a carrier with medicine carrying ability which is formed by o-nitrobenzyl ester amphiphilic molecule vesicles encapsulating water-soluble upconversion nanoparticles (Ligand-UCNPs), and belongs to the field of surfactants. The total number of alkyl carbon atoms of a fatty chain is 6 to 36. A preparation method of thecarrier comprises the following three steps of synthesizing oil-soluble upconversion nanoparticles (OA-UCNPs); synthesizing the water-soluble upconversion nanoparticles (Ligand-UCNPs); encapsulatingthe upconversion nanoparticles by the o-nitrobenzyl ester amphiphilic molecules. The near-infrared light-controlled medicine carrier has the advantages that the o-nitrobenzyl ester amphiphilic molecules have ultraviolet light crackability; by introducing the upconversion nanoparticles (UCNPs) which have large tissue penetration depth and can convert the near-infrared light with little injury to ahuman body into the ultraviolet light, the defects of small penetration depth and large injury to the human body of the ultraviolet light are overcome, and the purpose of medicine release by photolysis is realized; the near-infrared light-controlled medicine carrier is a potential near-infrared light-controlled medicine release carrier.

Mussel-inspired healing of a strong and stiff polymer

Self-healability will greatly improve the reliability, service life and maintenance of synthetic materials. However, it remains a big challenge to realize the self-healing of a strong and stiff polymer due to its poor molecular mobility. Inspired by the h

New fluorine-18 labeled benzaldehydes as precursors in the synthesis of radiopharmaceuticals for positron emission tomography

4,5-Bis(butoxy)-2-nitrobenzaldehyde and 4,5-bis(tert-butoxycarbonyloxy)-2-nitrobenzaldehyde, as well as their fluorine-18 labeled derivatives (the half-life of F18 is T1/2 = 110 min) were synthesized for use as precursors in the synt

An approach to the asymmetric synthesis of 18F-labeled analog of l-threo-3,4-dihydroxyphenylserine (6-l-threo-[18F]FDOPS) - A new radiotracer for visualization of norepinephrine transporters by positron emission tomography

An asymmetric synthesis method has been suggested as a feasible approach for the preparation of fluorine-18-labeled (T 1/2 110 min) analog of l-threo-3,4-dihydroxyphenylserine, i.e., 6-l-threo-[18F]FDOPS ((2S,3R)-2-amino-3-(2-[1

Reaction of caffeic acid derivatives with acidic nitrite

Caffeic derivatives were reacted with acidic nitrite at controlled pH in order to mimic the gastric juice conditions. At pH 2, whereas caffeic acid reacts exclusively on the side chain, its esters are readily nitrated. Under more acidic conditions (pH 1),

Process for preparing 5,6-dihydroxyindole

5,6-Dihydroxyindole is prepared by the catalytic reductive cyclization of 4,5-dihydroxy-2,β-dinitrostyrene in a single step using hydrogen with a palladium, platinum or rhodium catalyst in a polar hydroxylic reaction system. No reaction byproducts or only a single reaction byproduct are produced. The 4,5-dihydroxy-2,β-dinitrostyrene intermediate can be prepared by the chemoselective debenzylation of 4,5-dibenzyloxy-2,β-dinitrostyrene using trifluoroacetic acid. 5,6-Dihydroxyindole is a useful component in hair dye formulations and as an intermediate in the synthesis of melanin.

SYNTHESIS OF 5,6-DIHYDROXYINDOLE: A NOVEL REDUCTIVE CYCLIZATION OF (E)-4,5-DIHYDROXY-2,β-DINITROSTYRENE

A unique catalytic reductive cyclization of (E)-4,5-dihydroxy-2,β-dinitrostyrene (1) to 5,6-dihydroxyindole (2) is reported.Compound 1 is obtained either by one-step CF3CO2H deprotection of 4,5-dibenzyloxy-2,β-dinitristyrene (7), or by an improved two-step demethylenation of 6-nitropiperonal (5), followed by condensation with CH3NO2.

Synthesis of 6-Aminoisoproterenol

A number of possible approaches to the ring-aminated isoproterenol derivative 4-ethyl>-5-amino-1,2-benzenediol have been attempted.Of these, the total synthesis using the commercially available starting material 6-nitrop