3,5-Di-tert-butyl-4-hydroxybenzaldehyde

Base Information

• Chemical Name: 3,5-Di-tert-butyl-4-hydroxybenzaldehyde
• CAS No.: 1620-98-0
• Molecular Formula: C15H22O2
• Molecular Weight: 234.338
• Hs Code.: 29124990
• European Community (EC) Number: 216-592-0
• NSC Number: 14450
• UNII: 95VTI93VUL
• DSSTox Substance ID: DTXSID7057658
• Nikkaji Number: J148.925I
• Wikidata: Q27271830
• Metabolomics Workbench ID: 127567
• ChEMBL ID: CHEMBL225623
• Mol file: 1620-98-0.mol

Synonyms:3,5-di-tert-butyl-4-hydroxybenzaldehyde;BHT-CHO

Chemical Property of 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

Chemical Property:

• Appearance/Colour: light yellow to yellow-beige crystalline powder
• Vapor Pressure: 0.00128mmHg at 25°C
• Melting Point: 186-190 °C
• Refractive Index: 1.527
• Boiling Point: 289.2 °C at 760 mmHg
• PKA: 8.33±0.40(Predicted)
• Flash Point: 121.6 °C
• PSA: 37.30000
• Density: 1.006 g/cm³
• LogP: 3.79970
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Soluble in hot methanol.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

99.9% ^*data from raw suppliers

3-[5- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-36-25
• Safety Statements: 24/25-45-26-36/37

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=O
• Uses: 3,5-Di-tert-butyl-4-hydroxybenzaldehyde is employed as an OLED materials. It is also used as a pharmaceutical intermediate. The derivatives of this compound possess equipotent anti-inflammatory activities to indomethacin.

Technology Process of 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

There total 68 articles about 3,5-Di-tert-butyl-4-hydroxybenzaldehyde 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: 50.0%

2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3,74978-25-9) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Guidance literature:

With methanol; manganese triacetate; at 20 ℃; for 3h; other reagent: potassium dichromate, acetic acid;

DOI:10.1007/BF00954096

Reference yield: 43.2%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (88-26-6) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Guidance literature:

With bromine; In tert-butyl alcohol; at 40 ℃; for 1.5h;

DOI:10.1080/00304948.2015.1025632

Reference yield: 39.0%

(E)-2,6-di-tert-butyl-4-styrylphenol (21449-69-4) → 4,4'-(2,3-diphenylbutane-1,4-diylidene)bis(2,6-di-tert-butylcyclohexa-2,5-dien-1-one) (19594-77-5) + benzaldehyde (100-52-7) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Guidance literature:

With oxygen; CoSMDPT; In 1,2-dichloro-ethane; at 25 ℃; for 5h;

DOI:10.1016/S0040-4039(00)82415-6

upstream raw materials:

2,6-di-tert-butyl-4-methoxymethylene-phenol

2,6-di-tert-butyl-4-methyl-phenol

ethanol

tert-butyl vinyl ether

Downstream raw materials:

3,5-di-tert-butyl-4-hydroxycinnamic acid

2-cyano-3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-acrylic acid ethyl ester

malonoben

diethyl 2-(3,5-di-tert-butyl-4-hydroxybenzylidene)malonate

Refernces

LEUCKART REACTION OF CARBONYL DERIVATIVES OF 2,6-DI-TERT-BUTYLPHENOL

10.1007/BF00956104

The research investigates the Leuckart reaction for synthesizing sterically hindered aminophenols from carbonyl derivatives of 2,6-di-tert-butylphenol. The key chemicals involved include 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 3,5-di-tert-butyl-4-hydroxyacetophenone, and 3,5-di-tert-butyl-4-hydroxypropiophenone as starting materials. Formamide or ammonium formate is used as the reaction medium, and hydrochloric acid is employed in the acid hydrolysis step to obtain the final amines. Additionally, methylenequinone reacts with ammonia to produce aminophenol derivatives. The study demonstrates that these aminophenols and their analogs can be prepared in high yields through the Leuckart reaction, highlighting the efficiency and potential applications of this synthetic approach.