57373-81-6

Basic information

• Product Name: 1-[5-(tert-Butyl)-2-hydroxyphenyl]ethan-1-one, 2-Acetyl-4-(tert-butyl)phenol
• Synonyms: 1-[5-(tert-Butyl)-2-hydroxyphenyl]ethan-1-one, 2-Acetyl-4-(tert-butyl)phenol;5'-(tert-Butyl)-2'-hydroxyacetophenone
• CAS NO: 57373-81-6
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25424
• Mol File: 57373-81-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 26°C
• Boiling Point: 266.7°Cat760mmHg
• Flash Point: 111°C
• Appearance: /
• Density: 1.033g/cm³
• Vapor Pressure: 0.00518mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: 1-[5-(tert-Butyl)-2-hydroxyphenyl]ethan-1-one, 2-Acetyl-4-(tert-butyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[5-(tert-Butyl)-2-hydroxyphenyl]ethan-1-one, 2-Acetyl-4-(tert-butyl)phenol(57373-81-6)
• EPA Substance Registry System: 1-[5-(tert-Butyl)-2-hydroxyphenyl]ethan-1-one, 2-Acetyl-4-(tert-butyl)phenol(57373-81-6)

Safety Data

• Hazardous Substances Data: 57373-81-6(Hazardous Substances Data)

Usage

Preparation

in methylene chloride, first at 0°, then at r.t. (55%).

InChI:InChI=1/C12H16O2/c1-8(13)10-7-9(12(2,3)4)5-6-11(10)14/h5-7,14H,1-4H3

Upstream product

• 3056-64-2 4-(tert-butyl)phenyl acetate 
• 98-54-4 para-tert-butylphenol 
• 108-24-7 acetic anhydride 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 28460-09-5 N,N-diethyl-4-tert-butylphenyl carbamate 
• 698377-42-3 5-(tert-butyl)-N,N-diethyl-2-hydroxybenzamide 
• 75-77-4 chloro-trimethyl-silane 
• 75-05-8 acetonitrile 

Downstream Products

• 17874-32-7 4-methyl-6-tert-butylcoumarin 
• 75069-39-5 2-acetyl-4-tert-butyl-6-(N-chloroacetylaminomethyl)phenol 
• 100245-06-5 1-(5-tert-butyl-2-hydroxy-3-nitrophenyl)ethanone 
• 75060-62-7 2-Acetyl-4-tert-butyl-6-aminomethylphenol hydrochloride 
• 1247949-37-6 4-(tert-butyl)-2-(1-iminoethyl)phenol 
• 288399-61-1 6-tert-butyl-4-oxo-4H-chromene-3-carbaldehyde 
• 288399-59-7 6-tert-butyl-4H-chromen-4-one 

Relevant articles and documents

Photo-Fries rearrangement in flow under aqueous micellar conditions

A flow edition of photo-Fries rearrangement for the synthesis of 2-acylphenols in an aqueous micellar medium has been described. We take advantage of a narrow channel reactor and micelle-induced confinement effect to refine both the efficiency and selectivity of the parent photoreaction. This journal is

One-pot synthesis of ortho-acylphenols by palladium-catalyzed phenol C–H addition to nitriles

The regioselective one-pot synthesis of ortho-acylphenols via the palladium-catalyzed addition of phenols to nitriles and subsequent hydrolysis is reported. The acylation reaction proceeded smoothly using the Pd(OAc)2/DMSO system and TFA as the additive. This method also provides a direct strategy for the synthesis of a salicylketoxime scaffold.

Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors

Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.