76263-24-6

Basic information

• Product Name: 3-[2-(Trifluoromethyl)phenoxy]azetidine
• Synonyms: 3-[2-(Trifluoromethyl)phenoxy]azetidine
• CAS NO: 76263-24-6
• Molecular Formula: C10H10F3NO
• Molecular Weight: 217
• Mol File: 76263-24-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 263℃
• Flash Point: 113℃
• Appearance: /
• Density: 1.277
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-[2-(Trifluoromethyl)phenoxy]azetidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(Trifluoromethyl)phenoxy]azetidine(76263-24-6)
• EPA Substance Registry System: 3-[2-(Trifluoromethyl)phenoxy]azetidine(76263-24-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 76263-24-6(Hazardous Substances Data)

Usage

General Description

3-[2-(Trifluoromethyl)phenoxy]azetidine is a chemical compound with the molecular formula C10H9F3NO. It consists of a four-membered azetidine ring with a phenyl group substituted at the third carbon and a trifluoromethyl group at the second carbon. 3-[2-(Trifluoromethyl)phenoxy]azetidine is a member of the azetidine class of compounds, which are used in pharmaceutical research and drug development, particularly in the field of medicinal chemistry. The introduction of the trifluoromethyl and phenoxy groups may impart unique chemical and biological properties to this compound, potentially making it a valuable building block in the synthesis of new pharmaceutical agents. Its specific properties and potential applications would need to be further studied and elucidated.

Upstream product

• 960492-52-8 tert-butyl 3-(2-(trifluoromethyl)phenoxy)-azetidine-1-carboxylate 
• 444-30-4 2-(trifluoromethyl)phenol 

Relevant articles and documents

BISPECIFIC ANTAGONISTS OF RETINOL-BINDING PROTEIN 4 THAT STABILIZE TRANSTHYRETIN TETRAMERS, THEIR PREPARATION, AND USE IN THE TREATMENT OF COMMON AGE-RELATED COMORBIDITIES

The present invention provides a compound having the structure: Formula (I) wherein X is CR6 or N; R1, R2, R3, R4, and R6 are each independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CF3, -CF2H, -OCF3, -(alkyl), -(haloalkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), -(cycloalkyl), -(cycloalkylalkyl), -(heteroalkyl), heterocycle, heterocycloalkyl, -(alkylheteroalkyl), -(alkylaryl), -OH, -OAc, -0-(alkyl), -0-(alkenyl), -0-(alkynyl), -0-(aryl), -O- (heteroaryl), -SH, -S-(alkyl), -S-(alkenyl), -S-(alkynyl), -S- (aryl), -S-(heteroaryl), -NH2, -NH-(alkyl), -NH-(alkenyl), -NH- (alkynyl), -NH-(aryl), -NH-(heteroaryl), -C(O)R7, -S(O)R7, SO2R7, -NHSO2R7, -OC(O)R7, -SC(O)R7, -NHC(O)R8 or -NHC(S)R8, wherein R7 is, H, -(alkyl), -OH, -O(alkyl), -NH2, -NH(alkyl) or -N(alkyl)2, and wherein R6 is, -(alkyl), -O-(alkyl), -NH2, -NH(alkyl) or N(alkyl)2; Y is O, S, Ν, ΝΗ, or a bond; Z is O, S, N, NH, (CH2)O, or a bond; R5 is H, OH, halogen, alkyl, or R5 is (CH2)P and is bound to Y when Y is N to form a ring together with Z; o and p are independently 0, 1, 2, or 3; m and n are independently 0, 1, 2, 3, or 4; A, C, and D are each independently N or CR9; R9 is H, halogen, -OH, alkyl, cycloalkyl, cycloalkylalkyl, -O-(alkyl), -S-(alkyl), -NH2, -NH(alkyl), NH(alkyl)2, -CO2H, -CO(O-alkyl); B and E are N, CR9, or CFG wherein at least one of B or E is CFG; F is absent or present, and when present is Formula (II), Formula (III) G is H, substituted or unsubstituted monocycle, bicycle, heteromonocycle, heterobicycle, aryl, heteroaryl, alkyl, cycloalkyl, cycloalkylalkyl, CO2H, COOR10, OH, OR10, NH2, NHR10, NR10R11, SO2 (alkyl), SO2 (cycloalkyl), SO2(cycloalkylalkyl), CH2NHR10, CH2NR10R11, or CH2COOR10, wherein each R10 R11 are each independently H, alkyl, cycloalkyl, -C(O)-alkyl, -C(O)-cycloalkyl,-C(O)OH, -C(O)-O- alkyl, -C(O)-O-cycloalkyl, -C(O)NH2, -C(O)NH(alkyl), - C(O)NH(cycloalkyl), -C(O)N(alkyl)2, -CH2NH(alkyl), -CH2COOH, - SO2CH3, -OH, -O(alkyl), -NH2, -NH(alkyl), -N(alkyl)2, or a pharmaceutically acceptable salt thereof.

Design, synthesis, and evaluation of nonretinoid retinol binding protein 4 antagonists for the potential treatment of atrophic age-related macular degeneration and stargardt disease

Accumulation of lipofuscin in the retina is associated with pathogenesis of atrophic age-related macular degeneration and Stargardt disease. Lipofuscin bisretinoids (exemplified by N-retinylidene-N-retinylethanolamine) seem to mediate lipofuscin toxicity. Synthesis of lipofuscin bisretinoids depends on the influx of retinol from serum to the retina. Compounds antagonizing the retinol-dependent interaction of retinol-binding protein 4 (RBP4) with transthyretin in the serum would reduce serum RBP4 and retinol and inhibit bisretinoid formation. We recently showed that A1120 (3), a potent carboxylic acid based RBP4 antagonist, can significantly reduce lipofuscin bisretinoid formation in the retinas of Abca4-/-mice. As part of the NIH Blueprint Neurotherapeutics Network project we undertook the in vitro exploration to identify novel conformationally flexible and constrained RBP4 antagonists with improved potency and metabolic stability. We also demonstrate that upon acute and chronic dosing in rats, 43, a potent cyclopentyl fused pyrrolidine antagonist, reduced circulating plasma RBP4 protein levels by approximately 60%.

Process for preparing 3-phenoxy-1-azetidines and carboxamide derivatives

An improved process is disclosed for preparing 3-phenoxyazetidines which utilizes a phase transfer catalyst to add the phenoxy group to azetidine blocked in the 1-position by a diphenylmethane group and utilizes a stabilizing tertiary amine base to prevent dimerization during hydrogenolysis to remove the blocking group. The crude product containing diphenylmethane may be used without purification to prepare 3-phenoxy-1-azetidinecarboxamides.