22233-52-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-2-nitrobenzaldehyde is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its unique chemical structure allows for the creation of a wide range of therapeutic agents.
Used in Dye and Pigment Production:
In the dye and pigment industry, 3-chloro-2-nitrobenzaldehyde is employed as a key component in the production of various dyes and pigments. Its chemical properties enable the creation of a diverse array of colorants used in different applications, including textiles, plastics, and printing inks.
Used in Agrochemicals:
3-Chloro-2-nitrobenzaldehyde is utilized in the agrochemical industry for the synthesis of various agrochemical products. Its role in the production of these compounds helps address agricultural needs, such as crop protection and pest control.
Used as a Reagent in Organic Synthesis:
3-CHLORO-2-NITROBENZALDEHYDE serves as a reagent in organic synthesis, facilitating various chemical reactions and contributing to the formation of a multitude of organic compounds. Its versatility in this capacity makes it a valuable asset in the field of organic chemistry.
Used in the Creation of Aromatic Compounds:
3-Chloro-2-nitrobenzaldehyde is used as a building block for the synthesis of various aromatic compounds. Its structural features make it an ideal candidate for the construction of complex aromatic molecules, which have applications in a wide range of industries, including pharmaceuticals, fragrances, and materials science.

Upstream product

• 138-89-6 p-dimethylaminonitrosobenzene 
• 77158-86-2 (3-chloro-2-nitrophenyl)methanol 
• 42087-81-0 3-chloro-2-nitro-benzoic acid methyl ester 
• 19088-99-4 3-chloro-2-nitrobenzoyl chloride 
• 587-04-2 m-Chlorobenzaldehyde 
• 160088-50-6 C₁₅H₁₄ClN₃O₃ 

Downstream Products

• 75618-34-7 5-Chloro-10-hydroxy-3-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H,10H-acridine-1,9-dione 
• 160088-52-8 N-(3-chloro-2-nitrobenzylidene)-o-phenylenediamine 
• 947513-50-0 C₈H₄NO₂Cl 
• 1224569-37-2 2-azido-3-chlorobenzaldehyde 
• 915922-73-5 8-chloroquinoline-2-carboxylic acid 
• 947513-83-9 C₂₆H₂₁NO₄ 
• 947513-65-7 C₂₀H₁₆NO₄Cl 

Relevant academic research and scientific papers

Iron promoted C3-H nitration of 2H-indazole: direct access to 3-nitro-2H-indazoles

An efficient C3-H functionalization of indazole has been demonstrated. Notably, this method involves chelation-free radical C-H nitration on 2H-indazole. The radical mechanism was confirmed by control experiments and quantum chemical calculations. The synthetic utility has been proven by the synthesis of bio-relevant benzimidazoindazoles via reductive cyclization.

Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators

The design and the synthesis of several chemical subclasses of imidazole containing γ-secretase modulators (GSMs) is described. Conformational restriction of pyridone 4 into bicyclic pyridone isosteres has led to compounds with high in vitro and in vivo p

NOVEL SUBSTITUTED INDAZOLE AND AZA-INDAZOLE DERIVATIVES AS GAMMA SECRETASE MODULATORS

The present invention is concerned with novel substituted indazole and aza-indazole derivatives of Formula (I), wherein R1, R2, R3, R4, Y, A1, A2, A3, A4, X1, X2, X3 and Het1 have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

METHOD FOR MAKING BIARYL COMPOUNDS, COMPOUNDS MADE BY THE METHOD, AND METHOD FOR THEIR USE

Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.

A Diels-Alder approach to biaryls (DAB): synthesis of the western portion of TMC-95

The rapid synthesis of the western biaryl portion of TMC-95 is disclosed via the use of a Diels-Alder reaction with o-nitrostyrene derivative and 1-silyloxy diene with excellent regiochemical control. Subsequent sequential substitutions of a p-iodo-phenol

Diels - Alder approach for the construction of halogenated, o-nitro biaryl templates and application to the total synthesis of the anti-HIV agent siamenol

(Chemical Equation Presented) A rapid Diels - Alder approach to halogenated biaryl templates is described. These biaryl templates are available in two steps from the corresponding aromatic aldehydes. The scope of subsequent Suzuki couplings on the biaryl chlorides is explored. Good tolerance for both electron-donating and electron-withdrawing groups in the coupling process can be achieved. Further functionalization of the biaryl templates is described. Hydrogenation of the nitro moiety with concomitant removal of the benzyl ether yields the o-anilino, o-phenolic polyaryls. Selective reduction of the nitro group can be accomplished. Alternatively, the benzyl ether can be selectively removed under Lewis acidic conditions. The utilization of the Diels - Alder adducts for the synthesis of a series of chlorinated carbazoles via the Cadogan cyclization is also demonstrated. Finally, application of this technology to the total synthesis of siamenol, an anti-HIV agent, is reported.

Synthesis and structure-activity relationships of thioflavone derivatives as specific inhibitors of the ERK-MAP kinase signaling pathway

Condensation of nitrobenzaldehydes 3 and α-[o-(p-methoxybenzylthio) benzoyl] sulfoxide 4 gave α-sulfinyl enones 5. Treatment of 5 with formic acid caused cyclization followed by debenzylation to afford 3-(methylsulfinyl) thioflavanones 6. Double-bond formation with elimination of methanesulfenic acid was performed by refluxing 6 in benzene, and, finally, the nitro group of 2-phenyl-4H-1-benzothiopyran-4-one (thioflavones) 7 was reduced with tin in tetrafluoroboric acid. Various 2′-aminothioflavones 8 thus prepared were evaluated for their inhibitory effects on the ERK-MAP kinase pathway. In a cell-based assay, 2-(2′-amino-3 ′-methoxyphenyl)-4H-1-benzothiopyran-4-one (8b) showed a more potent inhibitory effect than the corresponding oxygen compound (PD98059, 1) on the Raf-induced activation of the ERK-MAP kinase pathway as well as cell proliferation. Furthermore, compound 8b selectively and potently inhibited the proliferation of tumor cells in which the ERK-MAP kinase pathway is constitutively activated.

Polyaza Heterocycles. Part 2. Nucleophilic Substitution of Halogens in Halogenoquinoxalinocinnolines

10-Chloroquinoxalinocinnoline readily undergoes methoxydechlorination when treated with sodium methoxide.The 1-, 2-, 3-, 4- and 9-chloro isomers are unreactive towards this reagent, but the 9,10-dichloro derivative undergoes substitution of both chlorines (the 10-position being much the more reactive).The 9- and 10-bromo analogues are both unreactive towards sodium methoxide, but the 9- and 10-fluoro analogues are both highly reactive, to the extent that it has not been possible even to isolate the 10-fluoro compound.Routes to 9- and 10-piperidinoquinoxalinocinnolines are described.