3,5-Di-tert-butylcatechol

Base Information

• Chemical Name: 3,5-Di-tert-butylcatechol
• CAS No.: 1020-31-1
• Deprecated CAS: 122983-47-5
• Molecular Formula: C14H22O2
• Molecular Weight: 222.327
• Hs Code.: 29072900
• European Community (EC) Number: 213-816-9
• NSC Number: 59767
• UNII: 1328KN3F8B
• DSSTox Substance ID: DTXSID4061414
• Nikkaji Number: J149.833I
• Wikidata: Q27251465
• ChEMBL ID: CHEMBL1795400
• Mol file: 1020-31-1.mol

Synonyms:3,5-di-t-butyl catechol;3,5-di-tert-butylcatechol

Chemical Property of 3,5-Di-tert-butylcatechol

Chemical Property:

• Appearance/Colour: white to pale brown solid
• Vapor Pressure: 0.000344mmHg at 25°C
• Melting Point: 95-100 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 309.7 °C at 760 mmHg
• PKA: 10.04±0.15(Predicted)
• Flash Point: 136.5 °C
• PSA: 40.46000
• Density: 1.012 g/cm³
• LogP: 3.69280
• Storage Temp.: Store below +30°C.
• Water Solubility.: Insoluble in water.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 222.161979940
• Heavy Atom Count: 16
• Complexity: 234

Purity/Quality:

99%min ^*data from raw suppliers

3,5-Di-tert-butylcatechol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: CC(C)(C)C1=CC(=C(C(=C1)O)O)C(C)(C)C
• Uses: It is an important raw material and intermediate used in organic synthesis, Pharmaceuticals, agrochemicals and dyestuffs.

Technology Process of 3,5-Di-tert-butylcatechol

There total 97 articles about 3,5-Di-tert-butylcatechol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

3,5-di-tert-butyl-o-benzoquinone (3383-21-9) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 3,5-Di-tert-butylcatechol (1020-31-1,122983-47-5,881376-69-8) + C54H64O6P2 + 1,2-bis(diphenylphosphinoyl)ethane (4141-50-8)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1080/10426507.2012.702822

Reference yield: 46.0%

4,6-Di-tert-butyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.03,8]trideca-3,5,7-triene (110851-19-9) → 3,5-Di-tert-butylcatechol (1020-31-1,122983-47-5,881376-69-8) + 3,5-di-tert-butyl-o-benzoquinone (3383-21-9)

Guidance literature:

In dichloromethane; at -78 ℃; for 1h; Irradiation;

DOI:10.1021/jo00234a020

Reference yield: 42.0%

3,5-di-tert-butyl-o-benzoquinone (3383-21-9) + diethylchlorogermane (10177-53-4) → 3,5-Di-tert-butylcatechol (1020-31-1,122983-47-5,881376-69-8) + 2,2-diethyl(6,8-di-tert-butyl)-4,5-benzo-2-germa-1,3-dioxolane (78100-52-4) + diethyl germanium dichloride (13314-52-8)

Guidance literature:

In benzene; byproducts: HCl; heating in a sealed tube at 80 ° C for 12 h,; concn. (reduced pressure), anal. (IR, H-NMR, MS); 13% starting germane;

DOI:10.1016/0022-328X(88)80524-2

upstream raw materials:

3,5-di-tert-butyl-o-benzoquinone

tertiary butyl chloride

benzene-1,2-diol

tert-butyl alcohol

Downstream raw materials:

2-tert-butoxy-4,6-di-tert-butylphenol

4,6-di-tert-butyl-2-phenylbenzo[d][1,3,2]dioxaborole

2,4-Di-tert-butyl-6-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-phenol

{2,4-Di-tert-butyl-6-[2-(3,5-di-tert-butyl-2-hydroxy-phenoxy)-ethoxy]-phenoxy}-acetic acid ethyl ester

Refernces

Magnetic and catalytic properties of a new copper(II)-Schiff base 2D coordination polymer formed by connected helical chains

10.1016/j.ica.2011.06.024

The research presents the synthesis, characterization, and study of a new 2D copper(II)-Schiff base coordination polymer with magnetic and catalytic properties. The complex was prepared using the Schiff base ligand NN0-bis(salicylidene)-1,3-diaminopentane (H2L) and sodium dicyanamide (dca), resulting in a 2D hexagonal structure formed by helical chains connected through double 1,5-dca bridges. The complex exhibited strong antiferromagnetic coupling and was tested for its ability to catalyze the oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC) to 3,5-di-tert-butylquinone (3,5-DTBQ), showing catecholase-like activity. Various analyses were employed, including Fourier transform infrared spectroscopy (FTIR), UV–Vis spectroscopy, cyclic voltammetry, electrospray ionization mass spectrometry (ESI-MS), X-ray crystallography, and magnetic susceptibility measurements, to characterize the complex and monitor the catalytic oxidation reaction. The study also involved kinetic studies to determine the catalytic activity and compared the complex's performance to that of natural catechol oxidase.

Dioxygen Transfer from 4a-Hydroperoxyflavin Anion. 2. Oxygen Transfer to the 10 Position of 9-Hydroxyphenanthrene Anions and to 3,5-Di-tert-butylcatechol Anion

10.1021/ja00533a028

The research investigates the reaction mechanisms of oxygen transfer from the peroxy anion of N5-ethyl-4a-hydroperoxy-3-methyllumiflavin (4a-FlEtO2-) to various phenolate anions, aiming to understand the underlying processes and provide insights into biomimetic reactions of flavoenzyme dioxygenase. The study found that 4a-FlEtO2- can transfer both oxygen atoms to phenolate anions, leading to the formation of specific products and regeneration of reduced flavin. Key chemicals involved include 4a-FlEtO2-, phenolate anions such as 3,5-di-tert-butylcatechol (VIII), 10-methyl-9-phenanthrol (Ib), and 10-ethoxy-9-phenanthrol (Ia), and their respective products like 3,5-di-tert-butyl-o-quinone (IX), 10-hydroxy-10-methyl-9,10-dihydro-9-phenanthrone (IIIb), and 9,10-phenanthrenequinone (V). The research concludes that the oxygen-donating intermediate formed from 4a-FlEtO2- is likely a dioxetane or an oxygen molecule loosely associated with the flavin, and the reaction efficiency of 4a-FlEtO2- exceeds that of molecular oxygen by a significant margin, indicating a unique and efficient oxygen transfer mechanism.