6299-85-0

Basic information

• Product Name: 2-(3-CHLOROPHENYL)MALONDIALDEHYDE
• Synonyms: 2-(3-CHLOROPHENYL)MALONDIALDEHYDE;NSC45044;Methyl 2,4-dichloropyrimidine-6-carboxylate 99%;Methyl2,4-dichloropyrimidine-6-carboxylate99%;2,6-DICHLORO-PYRIMIDINE-4-CARBOXYLIC ACID ETHYL ESTER;2,6-Dichloro-pyrimidine-4-carboxylic acid methyl ester;Methyl 2,6-dichloropyrimidine-4-carboxylate;4-Methyl-2-(3,4-dichlorophenyl)thiazole-5-carboxylicacid
• CAS NO: 6299-85-0
• Molecular Formula: C₆H₄Cl₂N₂O₂
• Molecular Weight: 207.02
• EINECS: 1806241-263-5
• Product Categories: pharmacetical;Heterocycle-Pyrimidine series
• Mol File: 6299-85-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 54-56
• Boiling Point: 306 ºC
• Flash Point: 139 ºC
• Appearance: /
• Density: 1.503
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -5.83±0.30(Predicted)
• CAS DataBase Reference: 2-(3-CHLOROPHENYL)MALONDIALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-CHLOROPHENYL)MALONDIALDEHYDE(6299-85-0)
• EPA Substance Registry System: 2-(3-CHLOROPHENYL)MALONDIALDEHYDE(6299-85-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 6299-85-0(Hazardous Substances Data)

Usage

General Description

2-(3-Chlorophenyl)malondialdehyde is a chemical compound with the formula C9H6Cl2O2. It is an aldehyde derivative of malondialdehyde, featuring a 3-chlorophenyl substituent at the 2-position. 2-(3-CHLOROPHENYL)MALONDIALDEHYDE is often used as a reagent in chemical reactions and synthesis, particularly in the production of pharmaceuticals and other organic compounds. Its unique structural properties make it useful for its ability to form stable complexes with various reagents, and it has been the subject of research into its potential as an antimicrobial agent and its role in biological processes. Additionally, it is a useful intermediate for the synthesis of various heterocyclic compounds.

Upstream product

• 6153-44-2 methyl orotate 
• 65-86-1 orotic acid 
• 3346-64-3 2,4-dioxo-1,2,3,4-tetrahydro-6-pyrimidinecarbonyl chloride 
• 67-56-1 methanol 
• 16492-28-7 2,6-dichloro-4-pyrimidinecarboxylic acid 
• 6153-44-2 2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid methyl ester 

Downstream Products

• 151323-67-0 6-{Butyl-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-2-chloro-pyrimidine-4-carboxylic acid methyl ester 
• 951004-06-1 2-chloro-6-(2,4-dichloro-phenoxy)-pyrimidine-4-carboxylic acid methyl ester 
• 149849-94-5 methyl 2,6-dichloropyrimidine-4-carboxylate 
• 1114592-06-1 methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate 
• 1207204-83-8 C₁₆H₁₅ClN₄O₂ 
• 1207204-84-9 C₁₇H₁₇ClN₄O₂ 
• 1207204-91-8 C₂₁H₃₀ClN₃O₃Si 
• 373691-31-7 C₁₅H₁₆ClN₃O₂ 
• 1244017-26-2 methyl 2-chloro-6-(4-(pyridin-3-ylethynyl)phenyl)pyrimidine-4-carboxylate 
• 1426336-96-0 (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-cyanophenoxy)piperidin-1-yl)pyrimidine-4-carboxamide 
• 1426336-97-1 (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(3-(4-(trifluoromethoxy)phenoxy)azetidin-1-yl)pyrimidine-4-carboxamide 
• 1426336-99-3 6-(((S)-1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-(trifluoromethyl)phenoxy)cyclohex-1-en-1-yl)pyrimidine-4-carboxamide 
• 1426337-09-8 (S)-methyl 2-((6-carbamoyl-2-(4-(4-fluorophenoxy)phenyl)pyrimidin-4-yl)amino)propanoate 
• 1426336-01-7 (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-(4-(4-(trifluoromethyl)phenoxy)phenyl)pyrimidine-4-carboxamide 

Relevant articles and documents

Design, Synthesis, and Pharmacological Evaluation of First-in-Class Multitarget N-Acylhydrazone Derivatives as Selective HDAC6/8 and PI3Kα Inhibitors

Targeting histone deacetylases (HDACs) and phosphatidylinositol 3-kinases (PI3Ks) is a very promising approach for cancer treatment. This manuscript describes the design, synthesis, in vitro pharmacological profile, and molecular modeling of a novel class of N-acylhydrazone (NAH) derivatives that act as HDAC6/8 and PI3Kα dual inhibitors. The surprising selectivity for PI3Kα may be related to differences in the conformation in the active site. Cellular studies showed that these compounds act in HDAC6 inhibition and the PI3/K/AKT/mTOR pathway. The compounds that are selective for inhibition of HDAC6/8 and inhibit PI3Kα show potential for the treatment of cancer.

A novel route to 2,4-dianilino-substituted pyrimidines

A method is described to couple sterically-hindered electron-poor anilines to the 4-position of the pyrimidine core using a pyrimidine-2,4-bis(trifluoromethanesulfonate).

Synthesis of substituted pyrimidine hydrazine acids (PHA) and their use in peptide recognition

Substituted pyrimidine-hydrazine-acids (PHA) were prepared from orotic acid in five synthetic steps and high yields. Their geometry of hydrogen bond acceptor and donor sites make them suitable for the molecular recognition of peptide β-sheets. In non-protic solvents the PHA unit emits at around 420 nm after irradiation at 281 nm. The emission intensity decreases upon peptide binding and signals the binding event. Peptides consisting of PHAs and natural amino acids or a turn structure motif were prepared. The investigation of the intramolecular binding pattern by NMR spectroscopy revealed the expected interaction of the PHA and peptide β-sheet.