3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-

Base Information

• Chemical Name: 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-
• CAS No.: 22014-01-3
• Molecular Formula: C17H24 O3
• Molecular Weight: 276.376
• Hs Code.: 2918290000
• DSSTox Substance ID: DTXSID20241897
• Mol file: 22014-01-3.mol

Synonyms:3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-;3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid;CBDivE_006353;DTXSID20241897;CTYWXRDQWMRIIM-UHFFFAOYSA-N;AM85670;NSC 226266;3,5-di-tert.-butyl-4-hydroxycinnamic acid;FT-0614735;FT-0614736;3,5-bis(1,1-dimethylethyl)-4-hydroxycinnamic acid;3-(3,5-di-t-butyl-4-hydroxyphenyl)prop-2-enoic acid

Chemical Property of 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-

Chemical Property:

• Vapor Pressure: 2.66E-06mmHg at 25°C
• Melting Point: 193-196°C
• Boiling Point: 375.4°Cat760mmHg
• PKA: 4.71±0.10(Predicted)
• Flash Point: 195°C
• PSA: 57.53000
• Density: 1.076g/cm³
• LogP: 4.08500
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water.
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 276.17254462
• Heavy Atom Count: 20
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

3,5-Di-tert-butyl-4-hydroxycinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=CC(=O)O
• Uses: 3,5-Di-tert-butyl-4-hydroxycinnamic acid, predominantly trans,

Technology Process of 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)-

There total 5 articles about 3,5-Di-tert-butyl-4-hydroxycinnamic acid, (E)- 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: 71.0%

malonic acid (141-82-2) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-enoic acid (22014-01-3)

Guidance literature:

With piperidine; In pyridine; for 1.5h; Heating;

DOI:10.1134/S1070428008060043

Reference yield: 65.1%

acetic acid (64-19-7,77671-22-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-enoic acid (22014-01-3)

Guidance literature:

With piperidine; In ethanol; at 50 - 60 ℃; for 4h;

Reference yield: 48.0%

acetic anhydride (108-24-7) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-enoic acid (22014-01-3)

Guidance literature:

With sodium acetate; In pyridine; at 180 - 190 ℃; for 3h;

DOI:10.1134/S1070428008060043

upstream raw materials:

acetic acid

3,5-di-t-butyl-4-hydroxybenzaldehyde

3-(1-Amino-3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-propionic acid

malonic acid

Downstream raw materials:

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

C₃₄H₄₄Cl₂N₂O₅

1.4-Bis-<4-hydroxy-3.5-di-tert.-butyl-phenyl>-butan-dicarbonsaeure-dimethylester-(2.3)

dimethyl 2,3-bis[[3,5-bis(tert-butyl)-4-oxo-2,5-cyclohexadien-1-ylidene]methyl]butanedionate

Refernces

• 1、 Vol'eva,Belostotskaya,Komissarova,Kurkovskaya. "Anionic condensations of 3,5-di-tert-butyl-4(2)-hydroxybenzaldehydes in the presence of weak bases". experimental part. p. 803 - 806. Retrieved 2009/06/28.
• 2、 Volod'kin, A. A.,Ershov, V. V.,Malysheva, R. D.. "REACTION OF 6,8-DI-TERT-BUTYL-1-OXASPIRODECA-5,8-DIENE-2,7-DIONE WITH AMINES". . p. 1086 - 1088. Retrieved 2007/10/02.