1401878-45-2

Basic information

• Product Name: 3-(4-methoxyphenyl)oxetane
• Synonyms: 3-(4-methoxyphenyl)oxetane
• CAS NO: 1401878-45-2
• Molecular Weight: 164.204
• Mol File: 1401878-45-2.mol

Chemical Properties

• CAS DataBase Reference: 3-(4-methoxyphenyl)oxetane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methoxyphenyl)oxetane(1401878-45-2)
• EPA Substance Registry System: 3-(4-methoxyphenyl)oxetane(1401878-45-2)

Safety Data

• Hazardous Substances Data: 1401878-45-2(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 39267-79-3 3-oxetanyl bromide 
• 26272-85-5 3-iodooxetane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 26755-28-2 3-(4-methoxyphenyl)oxetan-3-ol 

Downstream Products

• 479582-18-8 β-(4-methoxyphenyl)-γ-butyrolactone 

Relevant articles and documents

Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes

A precisely designed chiral squaramide derivative is shown to promote the highly enantioselective addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and general access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective catalytic oxetane ring opening was employed as part of a three-step, gram-scale synthesis of pretomanid, a recently approved medication for the treatment of multidrug-resistant tuberculosis. Heavy-atom kinetic isotope effect (KIE) studies are consistent with enantiodetermining delivery of bromide from the H-bond-donor (HBD) catalyst to the activated oxetane. While the nucleophilicity of the bromide ion is expected to be attenuated by association to the HBD, overall rate acceleration is achieved by enhancement of Lewis acidity of the TMSBr reagent through anion abstraction.

Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use

The invention discloses compounds of Formula (I), wherein A1, R1, R2, R3, R4, and n are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.

Reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl and heteroaryl bromides

Reductive cross-coupling allows the direct C-C bond formation between two organic halides without the need for preformation of an organometallic reagent. A method has been developed for the reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl or heteroaryl bromides. The developed conditions use an air-stable Ni(II) source in the presence of a diamine ligand and a metal reductant to allow late-stage incorporation of saturated heterocyclic rings onto aryl halides in a functional-group tolerant manner.