110704-47-7

Basic information

• Product Name: 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole
• Synonyms: 5-Chloromethyl-3-(2-trifluoromethyl-phenyl)-[1,2,4]oxadiazole;1,2,4-Oxadiazole, 5-(chloromethyl)-3-[2-(trifluoromethyl)phenyl]-
• CAS NO: 110704-47-7
• Molecular Formula: C₁₀H₆ClF₃N₂O
• Molecular Weight: 262.62
• Mol File: 110704-47-7.mol

Chemical Properties

• Boiling Point: 327.8°C at 760 mmHg
• Flash Point: 152.1°C
• Appearance: /
• Density: 1.418g/cm³
• Vapor Pressure: 0.000376mmHg at 25°C
• Refractive Index: 1.495
• PKA: -3.26±0.44(Predicted)
• CAS DataBase Reference: 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole(110704-47-7)
• EPA Substance Registry System: 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole(110704-47-7)

Safety Data

• Hazardous Substances Data: 110704-47-7(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole is utilized as a key intermediate in the synthesis of pharmaceutical drugs. Its unique structure and reactivity allow for the development of new drug candidates with potential therapeutic applications.
Used in Materials Science:
In the field of materials science, 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole may be employed as a component in the design and synthesis of novel materials with specific properties, such as high thermal stability, chemical resistance, or unique electronic characteristics.
Used in Organic Synthesis:
As a building block for the synthesis of more complex organic molecules, 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole can be incorporated into various chemical reactions to form a wide range of compounds with diverse applications in research and industry.
Used in Chemical Research and Development:
Due to its unique properties and reactivity, 5-Chloromethyl-3-(2-trifluoromethylphenyl)-[1,2,4]oxadiazole serves as a valuable compound for chemical research and development. It can be used to explore new reaction pathways, investigate the effects of structural modifications on compound properties, and develop new synthetic methodologies.

InChI:InChI=1/C10H6ClF3N2O/c11-5-8-15-9(16-17-8)6-3-1-2-4-7(6)10(12,13)14/h1-4H,5H2

Upstream product

• 131337-66-1 C₁₀H₈ClF₃N₂O₂ 
• 40067-66-1 N-Hydroxy-2-trifluoromethyl-benzamidine 
• 79-04-9 chloroacetyl chloride 
• 447-60-9 2-(trifluoromethyl)benzonitrile 

Downstream Products

• 110704-54-6 Ethyl 3-[3-(2-trifluoromethylphenyl)-1,2,4-oxadiazol-5-ylmethyl]-4-oxo-3H-phthalazin-1-ylacetate 
• 110721-48-7 3-[3-(2-Trifluoromethylphenyl)-1,2,4-oxadiazol-5-ylmethyl]-4-oxo-3H-phthalazin-1-ylacetic acid 

Relevant articles and documents

Novel 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)-xanthine derivatives as high affinity and selective A2B adenosine receptor antagonists

A series of new 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)- xanthine derivatives as A2B-AdoR antagonists have been synthesized and evaluated for their binding affinities for the A2B, A 1, A2A, and A3-AdoRs. 8-(1-((3-phenyl-1,2,4- oxadiazol-5-yl)methyl)-1H-pyrazol-4-yl)-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione (4) displayed high affinity (Ki = 1 nM) and selectivity for the A2B-AdoR versus A1, A2A, and A 3-AdoRs (A1/A2B, A2A/A2B, and A3/A2B selectivity ratios of 370, 1100, and 480, respectively). The synthesis and SAR of this novel class of compounds are presented herein.

The discovery of a selective, high affinity A2B adenosine receptor antagonist for the potential treatment of asthma

Adenosine has been suggested to play a role in asthma, possibly via activation of A2B adenosine receptors on mast cells and other pulmonary cells. We describe our initial efforts to discover a xanthine based selective A2B AdoR antagonist that resulted in the discovery of CVT-5440, a high affinity A2B AdoR antagonist with good selectivity (A2B AdoR Ki = 50 nM, selectivity A1 > 200: A2A > 200: A3 > 167).

Potent, orally active aldose reductase inhibitors related to zopolrestat: Surrogates for benzothiazole side chain

A broad structure-activity program was undertaken in search of effective surrogates for the key benzothiazole side chain of the potent aldose reductase inhibitor, zopolrestat (1). A structure-driven approach was pursued, which spanned exploration of three areas: (1) 5/6 fused heterocycles such as benzoxazole, benzothiophene, benzofuran, and imidazopyridine; (2) 5- membered heterocycles, including oxadiazole, oxazole, thiazole, and thiadiazole, with pendant aryl groups, and (3) thioanilide as a formal equivalent of benzothiazole. Several benzoxazole- and 1,2,4-oxadiazole- derived analogues were found to be potent inhibitors of aldose reductase from human placenta and were orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications. 3,4-Dihydro-4- oxo-3-[(5,7-difluoro-2-benzoxazolyl)methyl]-1-phthalazineacetic acid (124) was the best of the benzoxazole series (IC50 = 3.2 x 10-9 M); it suppressed accumulation of sorbitol in rat sciatic nerve by 78% at an oral dose of 10 mg/kg. Compound 139, 3,4-dihydro-4-oxo-3-[[(2-fluorophenyl)-1,2,4- oxadiazol-5-yl]methyl]-1-phthalazineacetic acid, with IC50 -8 M, caused a 69% reduction in sorbitol accumulation in rat sciatic nerve at an oral dose of 25 mg/kg. The thioanilide side chain featured in 3-[2-[[3- (trifluoromethyl)phenyl]amino]-2-thioxoethyl]-3,4-dihydro-4-oxo-1- phthalazineacetic acid (195) proved to be an effective surrogate for benzothiazole. Compound 195 was highly potent in vitro (IC50 = 5.2 x 10-8 M) but did not show oral activity when tested at 100 mg/kg. Additional structure-activity relationships encompassing a variety of heterocyclic side chains are discussed.