25198-45-2

Usage

Uses

Used in Organic Synthesis:
(4-CHLORO-BENZYL)-HYDRAZINE is used as a reagent in organic synthesis for its capacity to form hydrazones, which are intermediates in various chemical reactions.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (4-CHLORO-BENZYL)-HYDRAZINE is utilized as a building block in the synthesis of certain drugs, contributing to the development of new medicinal compounds.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, (4-CHLORO-BENZYL)-HYDRAZINE is employed in the production of various agrochemicals, playing a role in the creation of substances that protect crops and enhance agricultural productivity.
Used in Material Development:
(4-CHLORO-BENZYL)-HYDRAZINE is also used in the development of new materials, capitalizing on its ability to form bonds with other molecules to create novel substances with unique properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (4-CHLORO-BENZYL)-HYDRAZINE is applied for its potential to contribute to the discovery and design of new pharmaceutical agents, thanks to its reactive nature and capacity to engage in diverse chemical processes.
It is crucial to handle (4-CHLORO-BENZYL)-HYDRAZINE with care due to its toxic nature, ensuring proper handling and storage to prevent hazards.

InChI:InChI=1/C7H9ClN2/c8-7-3-1-6(2-4-7)5-10-9/h1-4,10H,5,9H2

Upstream product

• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 622-95-7 4-chlorobenzyl bromide 
• 52372-80-2 4-Chlorobenzaldehyde monohydrazone 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 143425-80-3 N-(4-chlorobenzyl)-N-(2,4,6-trimethylbenzyl)hydrazine 
• 84827-89-4 5-amino-2-(4-chloro-benzyl)-3-methylthio-1,2,4-triazole 
• 84827-88-3 5-amino-1-(4-chloro-benzyl)-3-methylthio-1,2,4-triazole 
• 106898-36-6 5-Amino-1-(4-chlorobenzyl)-4-cyanopyrazole 
• 131717-75-4 methyl 1S-cis-2,2-dimethyl-3-<<1-(4-chlorobenzyl)-3,5-dimethylpyrazol-4-yl>methyl>cyclopropanecarboxylate 
• 137278-71-8 ethyl 5-amino-1-(4-chlorobenzyl)-1H-pyrazole-4-carboxylate 
• 65746-29-4 C₁₆H₁₈Cl₂N₄ 
• 65746-27-2 C₁₆H₁₈Cl₂N₄O 
• 143425-75-6 2,4,6-trimethyl-4'-chlorodibenzyl 
• 143425-70-1 N-4-chlorobenzyl-N-2,4,6-trimethylbenzyl-N'-methanesulfonylhydrazine 
• 137279-17-5 1-(4-Chlorobenzyl)-7,8-dihydro-6H,9H-pyrazolo<3,4-b>quinoline-4,5-dione 
• 137278-88-7 4-Amino-1-(4-chlorobenzyl)-7,8-dihydro-6H-pyrazolo<3,4-b>quinolin-5-one 
• 137278-74-1 4-Cyano-1-(4-chlorobenzyl)-5-<(3-oxo-1-cyclohexen-1-yl)amino>pyrazole 
• 137279-12-0 7-(4-Chlorobenzyl)-4,5-dihydro-3H-isoxazolo<5,4,3-de>pyrazolo<3,4-b>quinoline 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of spiropyrazolopyridone derivatives as potent dengue virus inhibitors

The effective treatment for dengue virus infection continues to be a challenge. We herein reported our continued SAR exploration on the spiropyrazolopyridone scaffold. Introducing different substituents at the 3?- or 5?-site of the pyrazolopyridone core or moving the benzyl chain to the adjacent nitrogen led to a significant loss of potency on DENV-2. While a narrow range of substitutions were tolerated at the para-position of the phenyl ring, di-substitution on the phenyl ring is beneficial for DENV-2 potency and has variable influences on DENV-3 potency depending on the exact compound. Among these molecules, compounds 22 (JMX0376) with 4-chloro-3-fluorobenzyl and 24 (JMX0395) with 2,4-bis(trifluoromethyl)benzyl showed the most potent and broadest inhibitory activities against DENV-1 to ?3 with nanomolar to low micromolar EC50 values.

Lead optimization of spiropyrazolopyridones: A new and potent class of dengue virus inhibitors

Spiropyrazolopyridone 1 was identified, as a novel dengue virus (DENV) inhibitor, from a DENV serotype 2 (DENV-2) high-throughput phenotypic screen. As a general trend within this chemical class, chiral resolution of the racemate revealed that R enantiomer was significantly more potent than the S. Cell-based lead optimization of the spiropyrazolopyridones focusing on improving the physicochemical properties is described. As a result, an optimal compound 14a, with balanced in vitro potency and pharmacokinetic profile, achieved about 1.9 log viremia reduction at 3 × 50 mg/kg (bid) or 3 × 100 mg/kg (QD) oral doses in the dengue in vivo mouse efficacy model.

SPIROPYRAZOLOPYRIDINE DERIVATIVES AND USES THEREOF FOR THE TREATMENT OF VIRAL INFECTIONS

A compound of Formula (I) is provided that has been shown to be useful for treating a disease caused by a viral infection: (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, X1, X2, X3 and X4, are as defined herein.

ADENOSINE A2A RECEPTOR ANTAGONISTS

Compounds having the structural formula I or a pharmaceutically acceptable salt thereof, wherein: X1 and X2 are 1-3 substituents independently selected from the group consisting of H, alkyl, halo, —CF3, —OCF3, alkoxy, —OH and —CN;n is 0, 1 or 2; andR and R1 are H or alkyl; also disclosed is the use of the compounds in the treatment of CNS diseases such as Parkinson's disease, alone or in combination with other agents for treating CNS diseases, pharmaceutical compositions comprising them and kits comprising the components of the combinations.

Diarylsemicarbazones: Synthesis, antineoplastic activity and topoisomerase I inhibition assay

A series of diarylsemicarbazones was synthesized and tested against human neoplastic cell lines. The more active members have a 1-naphthyl ring at the carbamidic nitrogen, and chloro, dimethylamino or nitro group substituents at the benzylidene moiety. None of these showed affinity to DNA. One of the more active compounds was tested as a topoisomerase I inhibitor and showed a potent effect. SAR studies demonstrated linear correlation between lypophilicity and activity on the most sensitive lines and a definite conformational shape for antineoplastic action. Copyright (C) 1999 Elsevier Science S.A.

Mechanisms of benzyl group transfer in the decay of (E)-arylmethanediazoates and aryldiazomethanes in aqueous solutions

Rate constants are reported for the buffer-independent decay of ten (E)-arylmethanediazoates in aqueous media at 25 °C, ionic strength 1 M (NaClO4), 4% 2-propanol, in the region of pH 4-12. The rate constants are proportional to hydrogen ion concentration at high pH and become pH independent in the low-pH region. Varying concentrations of oxyanion, amine, and hydrazine buffers over the range 0.05-0.2 M increased the pseudo-first-order rate constant for decay of the diazoates by less than 10%. The azide - water selectivities, ka/ks, for partitioning of the benzyl groups in the decay of (E)-(3,5-bis(trifluoromethyl)phenyl)methanediazoate and the (3,5-bis(trifluoromethyl)phenyl)diazomethane are determined to be 0.20 and 0.21 M-1, respectively, in phosphate buffered water and 0.27 and 0.26 M-1, respectively, in 20/80 DMSO-water. It is concluded that these two reactants decompose, in these media, via a common free diazonium ion intermediate that is formed in the case of the diazoate upon unassisted N-O bond cleavage of the diazoic acid. A common rate-limiting step is indicated for all the diazoates by the correlation line for the plot of log k1, the pH independent rate constant, against σ that has a slope q = -1.23. Product ratios for trapping of benzyl groups derived from other pairs of arylmethanediazoates and aryldiazomethanes with less electron withdrawing groups are different outside experimental error, indicating the importance of different nitrogen-separated ion pairs in these reactions. The (E)-(p-methoxy)phenyl)methane-16O-diazoate decomposes in 16O/18O water to give alcohol that has an "excess" abundance of 16O compared to solvent. Decomposition of the same compound in 50/50 trifluoroethanol-water with varying concentrations of azide indicates that azide ion appears to trap a limiting amount, ～80%, of the p-methoxybenzyl group. Quantitative analysis of the data indicates that 16% of the p-methoxybenzyl cation is trapped by solvent at the nitrogen-separated ion pair stage, in the absence of azide ion. There is a 9-fold enhancement of selectivity for trifluoroethanol at the ion pair stage that is ascribed to a proton switch initiated by the leaving hydroxide ion in the ion pair. The values of Ka/ks ～ 0.2 M-1 and kT/kH ～ 0.5-0.6 for the trifluoroethanol-water selectivity and kET/kT ～ 1 for the ethanol-trifluoroethanol selectivity are independent of substituent in the decay of arylmethanediazoates (X = H and EWG) in water, water-trifluoroethanol (50/50), and water-trifluoroethanol-ethanol (50/40/10), respectively. It is concluded from this that the productdetermining steps do not involve chemical bonding but rather rotational/translational reorientation of the nucleophiles in the first solvation sphere of the carbocation intermediates. It is concluded that the values of kH/kT = 0.5-0.6 indicate preferential solvation of the cation precursor by trifluoroethanol. It is shown that a preferential interaction for trifluoroethanol of 1 kcal/mol is required to generate the observed selectivities.

Synthesis and Photochemical Degragation of N-Arylmethyl Derivatives of the Herbicide 3-Amino-1,2,4-triazole

Reaction of an arylmethyl halide with 3-amino-1,2,4-triazole (1) allows the preparation of the three N-arylmethyl derivatives of 1 bearing the substituent on the heterocyclic nitrogen atoms.In basic medium (methoxide anion in DMF or methanol, or in benzene by phase transfer catalysis), the isomers 3 and 5 substituted at N-1 and N-2 respectively are obtained, while the isomer 4 is isolated from neutral medium (DMF).The isomers 3 and 4 may be also prepared by cyclization of appropiate formylguanidinium derivatives. 3-Arylmethylamino-1,2,4-triazoles 2 may be obtained through reaction of 3-chloro-1,2,4-triazole (6) with arylmethylamines.Photolysis of the N-aryl-3-amino-1,2,4-triazoles 2-5 in methanol or water-methanol mixture, induces homolytic a d heterolytic cleavage of the arylmethyl-C-N bond giving rise to 3-amino-1,2,4-triazole (1).Thus, compounds 2-5 with arylmethyl groups able to absorb solar light may be considered as potential photoactivatable herbicides.

NITRENES. SYNTHESIS OF UNSYMMETRICAL BIBENZYLS

A method was developed for the synthesis of unsymmetrical bibenzyls by thermolysis of the potassium salts of methanesulfonohydrazides in dimethyl sulfoxide in the presence of 1-pentanethiol.The yields of the unsymmetrical bibenzyls and their derivatives c