736990-88-8

Basic information

• Product Name: 4-CARBOXY-2,6-DIFLUOROBENZALDEHYDE
• Synonyms: 4-CARBOXY-2,6-DIFLUOROBENZALDEHYDE;3,5-Difluoro-4-formylbenzoic acid;4-carboxy-2,6-difluobenzaldehyde
• CAS NO: 736990-88-8
• Molecular Formula: C₈H₄F₂O₃
• Molecular Weight: 186.1123664
• Mol File: 736990-88-8.mol

Chemical Properties

• Boiling Point: 319.877 °C at 760 mmHg
• Flash Point: 147.257 °C
• Appearance: /
• Density: 1.525 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-CARBOXY-2,6-DIFLUOROBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CARBOXY-2,6-DIFLUOROBENZALDEHYDE(736990-88-8)
• EPA Substance Registry System: 4-CARBOXY-2,6-DIFLUOROBENZALDEHYDE(736990-88-8)

Safety Data

• Hazardous Substances Data: 736990-88-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Carboxy-2,6-difluorobenzaldehyde is used as a key intermediate for the synthesis of halogenated analogs of bexarotene, which are retinoid X receptor-specific agonists. These analogs have potential applications in the treatment of various diseases, including cancer and metabolic disorders, due to their ability to modulate the activity of retinoid X receptors.
Used in Agrochemical Industry:
4-Carboxy-2,6-difluorobenzaldehyde can also be utilized in the development of novel agrochemicals, such as herbicides, insecticides, and fungicides. The halogenated structure of 4-Carboxy-2,6-difluorobenzaldehyde may confer enhanced biological activity and selectivity, making it a valuable building block for the design of new agrochemical agents.

Upstream product

• 455-40-3 3,5-difluorobenzoic acid 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1331832-71-3 C₂₄H₂₆F₂O₂ 
• 1403326-75-9 C₂₃H₂₄F₂O₃ 
• 1403326-86-2 4-benzyl 1-methyl-2,6-difluorobenzene-1,4-dioate 
• 1353843-48-7 4-(methoxycarbonyl)-3,5-difluorobenzoic acid 
• 1403326-87-3 C₉H₅ClF₂O₃ 
• 1403326-91-9 methyl 2,6-difluoro-4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl)benzoate 
• 1403326-71-5 methyl 2,6-difluoro-4-(1-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)vinyl)benzoate 
• 1403326-80-6 benzyl-3,5-difluoro-4-formylbenzoate 
• 1621165-26-1 tert-butyl (S)-2-((2-(2,6-difluoro-4-(methylcarbamoyl)phenyl)-7-methylimidazo[1,2-a]pyridine- 3-yl)methyl)morpholine-4-carboxylate 
• 1621164-77-9 (R)-tert-butyl 2-((2-(2,6-difluoro-4-(methylcarbamoyl)phenyl)-7-methylimidazo[1,2-a]pyridin-3-yl)methyl)morpholine-4-carboxylate 
• 1621164-74-6 methyl (S)-2-((2-(2,6-difluoro-4-(4-methylcarbamoyl)phenyl)-7-methylimidazo[1,2-a]pyridin-3-yl)methyl)morpholine-4-carboxylate 
• 1415124-73-0 methyl-3,5-difluoro-4-formyl benzoate 

Relevant articles and documents

Modeling, Synthesis and Biological Evaluation of Potential RetinoidX Receptor-Selective Agonists: Novel Halogenated Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene)

The synthesis of halogenated analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), known commonly as bexarotene, and their evaluation for retinoidX receptor (RXR)-specific agonist performance is described. Compound 1 is FDA approved to treat cutaneous T-cell lymphoma (CTCL); however, bexarotene treatment can induce hypothyroidism and elevated triglyceride levels, presumably by disrupting RXR heterodimer pathways for other nuclear receptors. The novel halogenated analogues in this study were modeled and assessed for their ability to bind to RXR and stimulate RXR homodimerization in an RXRE-mediated transcriptional assay as well as an RXR mammalian-2-hybrid assay. In an array of eight novel compounds, four analogues were discovered to promote RXR-mediated transcription with EC50 values similar to that of 1 and are selective RXR agonists. Our approach also uncovered a periodic trend of increased binding and homodimerization of RXR when substituting a halogen atom for a proton ortho to the carboxylic acid on 1.