123557-91-5

Basic information

• Product Name: rac BHFF
• Synonyms: rac BHFF;5,7-Bis(1,1-dimethylethyl)-3-hydroxy-3(trifluoromethyl)-2(3H)-benzofuranone;5,7-Bis(1,1-dimethylethyl)-3-hydroxy-3(trifluoromethyl) -2(3H)-benzofuranone, 5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one;BHFF;5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one;(R,S)-BHFF
• CAS NO: 123557-91-5
• Molecular Formula: C₁₇H₂₁F₃O₃
• Molecular Weight: 330.344
• Product Categories: GABA
• Mol File: 123557-91-5.mol
• Article Data: 7

Chemical Properties

• Appearance: white to beige/
• Storage Temp.: Store at +4°C
• Solubility: DMSO: ≥15mg/mL
• CAS DataBase Reference: rac BHFF(CAS DataBase Reference)
• NIST Chemistry Reference: rac BHFF(123557-91-5)
• EPA Substance Registry System: rac BHFF(123557-91-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 123557-91-5(Hazardous Substances Data)

Usage

Uses

rac BHFF is a positive allosteric modulator of GABAB receptors.

Biological Activity

Potent and selective GABA B receptor positive allosteric modulator that increases the potency and efficacy of GABA ( > 15-fold and > 149% respectively). Exhibits anxiolytic activity in vivo and is orally active.

Upstream product

• 13089-11-7 methyl 3,3,3-trifluoropyruvate 
• 96-76-4 2,4-di-tert-Butylphenol 

Relevant articles and documents

First asymmetric organocatalyzed domino Friedel-Crafts/lactonization reaction in the enantioselective synthesis of the GABAB receptor modulator (S)-BHFF

An asymmetric domino Friedel-Crafts/lactonization sequence between phenols and trifluoropyruvate has been accomplished for the first enantioselective synthesis of (S)-BHFF, a positive allosteric modulator (PAM) of GABAB receptor. The developed protocol leads to 3-OH-benzofuranone derivatives bearing a quaternary stereogenic center, and gives a valuable access to bioactive compounds with promising pharmaceutical applications.

Catalytic Friedel-Crafts/lactonization domino reaction: Facile access to 3-Hydroxybenzofuran-2-one scaffold

A valuable Lewis-acid-catalysed domino reaction involving a Friedel-Crafts alkylation of variously substituted phenols followed by a direct lactonization has been successfully developed (22 examples, yields up to 98 %). This protocol tolerates not only op

Efficient one-pot synthesis of the GABAB positive allosteric modulator (R,S)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2- one

The GABAB positive allosteric modulator (R,S)-5,7-di-tert-butyl- 3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (1) was synthesized in one pot from the anhydrous lithium salt of 2,4-di-tert-butylphenol and methyl trifluoropyruvate mediated by a stoichiometric amount of anhydrous gallium(III) chloride in 64% overall yield. The enantiomers of 1 were separated by chiral-phase HPLC (Chiralpak AD), and the absolute configuration was determined by X-ray crystallography. Copyright Taylor & Francis Group, LLC.