14386-64-2

Basic information

• Product Name: 2-BROMO-1-[3,5-DI(TERT-BUTYL)-4-HYDROXYPHENYL]ETHAN-1-ONE
• Synonyms: 2-BROMO-1-[3,5-DI(TERT-BUTYL)-4-HYDROXYPHENYL]ETHAN-1-ONE;3,5-DI(TERT-BUTYL)-4-HYDROXYPHENACYL BROMIDE;2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one, 90+%;2-Bromo-3',5'-di-tert-butyl-4'-hydroxyacetophenone, 97%;1-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2-bromoethanone;2-Bromo-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone;3,5-Bis(tert-butyl)-4-hydroxyphenacylbromide
• CAS NO: 14386-64-2
• Molecular Formula: C₁₆H₂₃BrO₂
• Molecular Weight: 327.26
• Mol File: 14386-64-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 347℃
• Flash Point: 164℃
• Appearance: /
• Density: 1.230
• Vapor Pressure: 2.69E-05mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Keep Cold
• PKA: 8.08±0.40(Predicted)
• Sensitive: Lachrymatory
• CAS DataBase Reference: 2-BROMO-1-[3,5-DI(TERT-BUTYL)-4-HYDROXYPHENYL]ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-[3,5-DI(TERT-BUTYL)-4-HYDROXYPHENYL]ETHAN-1-ONE(14386-64-2)
• EPA Substance Registry System: 2-BROMO-1-[3,5-DI(TERT-BUTYL)-4-HYDROXYPHENYL]ETHAN-1-ONE(14386-64-2)

Safety Data

• Hazard Codes: C,T
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN1759
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14386-64-2(Hazardous Substances Data)

Usage

Preparation

Also obtained by reaction of bromine with 4-hydroxy-3,5-ditert-butylacetophenone in the presence of aluminium chloride in octane at 70° for 30 min (91%).

InChI:InChI=1/C16H23BrO2/c1-15(2,3)11-7-10(13(18)9-17)8-12(14(11)19)16(4,5)6/h7-8,19H,9H2,1-6H3

Upstream product

• 128-39-2 2,6-di-tert-butylphenol 
• 14035-33-7 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone 

Downstream Products

• 84700-62-9 p-toluenesulfonate of 3,5-di-tert-butyl-4-hydroxyphenyl piperidinomethyl ketone 
• 84700-63-0 1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2-morpholin-4-yl-ethanone; compound with toluene-4-sulfonic acid 
• 84217-81-2 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo<2,1-b>thiazole 
• 84217-83-4 6-(3,5-di-tert-butyl-4-hydroxyphenyl)imidazo<2,1-b>thiazole 
• 88973-03-9 2-(3,5-di-tert-butyl-4-hydroxyphenyl)imidazo<1,2-a>pyridine 
• 84700-59-4 1-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2-hexylsulfanyl-ethanone 
• 84217-42-5 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-mercaptothiazole 
• 143212-99-1 4-[5-[2-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-4-(4-ethoxy-phenyl)-4H-[1,2,4]triazol-3-ylamino]-benzoic acid ethyl ester 
• 143212-97-9 3-(3,5-di-tert-butyl-4-hydroxybenzoylmethylthio)-4-phenyl-1,2,4-triazole 
• 143212-98-0 3-(3,5-di-tert-butyl-4-hydroxybenzoylmethylthio)-4-phenyl-5-phenylamino-1,2,4-triazole 
• 84700-57-2 3,5-di-tert-butyl-4-hydroxyphenyl phenylthiomethyl ketone 
• 84700-58-3 2-Benzylsulfanyl-1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-ethanone 
• 88972-94-5 2,6-Di-tert-butyl-4-(1-methyl-1H-indol-2-yl)-phenol 
• 88973-01-7 2,6-di-tert-butyl-4-(1-methyl-1H-indol-3-yl)phenol 

Relevant articles and documents

Synthesis, redox properties and antibacterial activity of hindered phenols linked to heterocycles

A series of benzotriazole, cyclic amides and pyrimidine derivatives, containing 2,6-di-tert-butyl-phenol fragments, were synthesized. The redox properties of obtained compounds were studied using the cyclic voltammetry on a platinum electrode in acetonitrile. The oxidation potentials of all substances were comparable to those of BHT. The obtained compounds were tested for their antibacterial activity, and N-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)isatin (32 μg/mL) exerted good activity against Staphylococcus aureus.

Synthesis and biological activities of new heterocyclic aromatic retinoids

A series of 3-aryl-2H-1-benzopyrancarboxylic acid derivatives was synthesized and evaluated as Retinoic Acid Receptor (RAR) agonists. By modifications of the 3-aryl group, we have obtained new retinoids exhibiting potent cellular differentiating activities and high affinities for RARs. Moreover, hydrogenation of the 2H-1-benzopyran ring led to the 3-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl -naphthalen-2-yl)-3,4-dihydro-2H-1-benzopyran-7-yl carboxylic acid, characterized by a RARβ binding profile.

Imidazo- and triazolothiadiazines

Novel imidazo- and triazolothiadiazines of the general formula I STR1 in which R1 =C1 -C4 -alkyl, R2 =H or C1 -C3 -alkyl and the structural element --A--B--=--CH2 --CH2 --, --CH CH--, --CH=N--, --CH2 --CO-- or --CO--CH2 --, and the physiologically aceptable acid-addition salts thereof, are prepared by reacting 2-halo-1-phenylalkanones of the formula II STR2 (meaning of R1 and R2 as in formula I, X=halogen) with compounds of the formula III STR3 (meaning of --A--B-- as in formula I) and, if appropriate, converting the compounds of the formula I formed into the physiologically acceptable acid-addition salts thereof by means of suitable acids. The compounds of the formula I and the physiologically acceptable acid-addition salts thereof are principally suitable for the prevention and treatment of inflammatory--in particular inflammatory rheumatic--disorders. Some of the intermediates formed during the preparation of the compounds of the formula I are also novel, namely 1-amino-2-mercaptoimidazole STR4 and 1-amino-2-thioxo-5-imidazolidinone STR5