19715-19-6

Basic information

• Product Name: 3,5-Bis-tert-butylsalicylic acid
• Synonyms: 3,2-bis(1,1-Dimethylethyl)-2-hydroxybenzoicacid;3,5-bis(1,1-dimethylethyl)-2-hydroxy-benzoicaci;3,5-bis(1,1-dimethylethyl)-2-hydroxy-Benzoicacid;dibutylsalicylicacid;RARECHEM AL BE 0441;DTBS;3,5-bis-tert-butylsalicylic acid;3,5-DI-T-BUTYLSALICYLIC ACID
• CAS NO: 19715-19-6
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33
• EINECS: 243-246-6
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;C13 to C42+;Carbonyl Compounds;Carboxylic Acids
• Mol File: 19715-19-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 157-162 °C(lit.)
• Boiling Point: 335.6 °C at 760 mmHg
• Flash Point: 179 °C
• Appearance: Off-white to beige/Powder
• Density: 1.07 g/cm³
• Vapor Pressure: 4.19E-08mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 3.34±0.14(Predicted)
• CAS DataBase Reference: 3,5-Bis-tert-butylsalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis-tert-butylsalicylic acid(19715-19-6)
• EPA Substance Registry System: 3,5-Bis-tert-butylsalicylic acid(19715-19-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 19715-19-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to beige powder

Uses

3,5-Di-tert-butylsalicylic acid was used to study long wavelength fluorescence emission of 3,5-Di-tert-butylsalicylic acid in a variety of organic solvents. It was also used to catalyze the reaction between aldehydes and silyl ketene acetals.

InChI:InChI=1/C15H22O4/c1-14(2,3)9-7-8(13(18)19)11(16)10(12(9)17)15(4,5)6/h7,16-17H,1-6H3,(H,18,19)

Upstream product

• 124-38-9 carbon dioxide 
• 37408-22-3 potassium 2,4-di-tert-butylphenolate 
• 100-97-0 hexamethylenetetramine 
• 20834-61-1 2-bromo-4,6-di-tert-butylphenol 
• 173030-55-2 3,5-di-tert-butylacetylsalicylic aldehyde 
• 96-76-4 2,4-di-tert-Butylphenol 
• 119-36-8 methyl salicylate 
• 15018-03-8 methyl 3,5‐di‐tert-butyl‐2‐hydroxybenzoate 

Downstream Products

• 84352-59-0 4-carbomethoxyphenyl 3,5-di-t-butylsalicylate 
• 175650-08-5 benzyl 2-benzyloxy-3,5-di-tert-butylbenzoate 
• 372137-89-8 (S)-2,4-di-tert-butyl-6-(4-tert-butyl-4,5-dihydro-2-oxazolyl)-phenol 
• 37456-29-4 2,4-di-tert-butyl-6-acetylphenol 
• 853268-39-0 1,2-bis-(3,5-di-tert-butyl-2-hydroxybenzamido)benzene 
• 115669-55-1 diaquabis(3,5-di-t-butylsalicylato)zinc 
• 25130-86-3 phenyl 3,5-di-tert-butyl-2-hydroxybenzoate 
• 25130-85-2 3,5-di-tert-butylsalicylic acid chloride 
• 15018-03-8 methyl 3,5‐di‐tert-butyl‐2‐hydroxybenzoate 

Relevant articles and documents

On the Kolbe-Schmitt synthesis of pharmacologically useful salicylates: Carboxylation of 2,4-di-t-butylphenol and identification and reduction of the formation of 2,2'-dihydroxy-3,3',5,5'-tetra-t- butylbiphenyl in the synthesis of 3,5-di-t-butylsalicylic acid

The initial yield of 3,5-di-t-butylsalicylic acid obtained via Kolbe-Schmitt carboxylation of the potassium salt of 2,4-di-t-butylphenol was 1% and was accompanied by a 65% yield of 2,2'-dihydroxy-3,3',5,5'-tetra-t-butylbiphenyl, a dimer of the 2,4-di-t-butylphenol formed by ortho coupling of phenoxide radicals. Formation of this dimer was decreased to 8%, and the yield of 3,5-di-t-butylsalicylic acid was increased to 68% by optimizing reaction time and temperature and decreasing the amount of oxygen present during carboxylation. This modification of the Kolbe-Schmitt reaction conditions may be generally helpful in the synthesis of all pharmacologically useful salicylates.

COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC DISORDERS AND SYNTHESIS OF THE SAME

The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

Urotropin synthesis of 3,5-di-tert-butylsalicylic acid derivatives

The stability of 3,5-di-tert-butylsalicylic aldehyde against oxidation is due to autoinhibiting of the chain process. However its oxidation into 3,5-di-tert-butylsalicylic acid was performed at the use of acetyl protection of the hydroxy group. In reaction of 6-bromo-2,4-di-tert-butylphenol with urotropin the formation was discovered of 3,5-di-tert-butylsalicylic acid, its nitrile and amide.