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2-tert-Butyl-4-hydroxyanisole

Base Information Edit
  • Chemical Name:2-tert-Butyl-4-hydroxyanisole
  • CAS No.:88-32-4
  • Deprecated CAS:344312-06-7
  • Molecular Formula:C11H16 O2
  • Molecular Weight:180.247
  • Hs Code.:2909500000
  • European Community (EC) Number:201-820-3
  • UNII:A03IJ8ROOP
  • DSSTox Substance ID:DTXSID7058963
  • Nikkaji Number:J175.231F
  • Wikidata:Q81988615
  • NCI Thesaurus Code:C77383
  • Mol file:88-32-4.mol
2-tert-Butyl-4-hydroxyanisole

Synonyms:2-BHA;2-tert-butyl-4-hydroxyanisole

Suppliers and Price of 2-tert-Butyl-4-hydroxyanisole
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • 2-tert-Butyl-4-hydroxyanisole
  • 5g
  • $ 1695.00
  • TRC
  • 2-tert-Butyl-4-hydroxyanisole
  • 100mg
  • $ 135.00
  • Sigma-Aldrich
  • 2-tert-Butyl-4-hydroxyanisole
  • 500MG
  • $ 179.00
  • Sigma-Aldrich
  • 2-tert-Butyl-4-hydroxyanisole
  • 200mg
  • $ 399.00
  • Medical Isotopes, Inc.
  • 2-tert-BUTYL-4-HYDROXYANISOLE 99%
  • 100 mg
  • $ 600.00
  • Crysdot
  • 3-(tert-Butyl)-4-methoxyphenol 95+%
  • 10g
  • $ 1307.00
  • Crysdot
  • 3-(tert-Butyl)-4-methoxyphenol 95+%
  • 1g
  • $ 277.00
  • Crysdot
  • 3-(tert-Butyl)-4-methoxyphenol 95+%
  • 5g
  • $ 832.00
  • ChemScene
  • 3-tert-Butyl-4-methoxyphenol 99.52%
  • 5g
  • $ 310.00
  • ChemScene
  • 3-tert-Butyl-4-methoxyphenol 99.52%
  • 1g
  • $ 76.00
Total 50 raw suppliers
Chemical Property of 2-tert-Butyl-4-hydroxyanisole Edit
Chemical Property:
  • Vapor Pressure:0.000991mmHg at 25°C 
  • Melting Point:64℃ 
  • Refractive Index:1.4708 (estimate) 
  • Boiling Point:293.3 °C at 760 mmHg 
  • PKA:10.58±0.18(Predicted) 
  • Flash Point:136 °C 
  • PSA:29.46000 
  • Density:1.009 g/cm3 
  • LogP:2.69830 
  • Storage Temp.:Inert atmosphere,Room Temperature 
  • Solubility.:Chloroform (Slightly), Methanol (Slightly) 
  • XLogP3:3.2
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:2
  • Exact Mass:180.115029749
  • Heavy Atom Count:13
  • Complexity:160
Purity/Quality:

99%, *data from raw suppliers

2-tert-Butyl-4-hydroxyanisole *data from reagent suppliers

Safty Information:
  • Pictogram(s): Xn 
  • Hazard Codes:Xn 
  • Statements: 22-36 
  • Safety Statements: 26 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CC(C)(C)C1=C(C=CC(=C1)O)OC
  • Uses Labelled Phencyclidine analog as anticholinergic agent. 2-tert-Butyl-4-hydroxyanisole shows insecticidal activity.
Technology Process of 2-tert-Butyl-4-hydroxyanisole

There total 12 articles about 2-tert-Butyl-4-hydroxyanisole 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:
Guidance literature:
With palladium 10% on activated carbon; hydrogen; In dichloromethane; for 18.3h;
DOI:10.1002/anie.201406393
Guidance literature:
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline; In diethyl ether; xylene; at 120 ℃; for 17h;
DOI:10.1055/s-1980-29150
Guidance literature:
Multi-step reaction with 3 steps
1: imidazole / dimethylformamide
2: K2CO3 / acetone / Heating
3: aq. HCl / tetrahydrofuran
With 1H-imidazole; hydrogenchloride; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00191a020
Refernces Edit

Renin inhibitors for the treatment of hypertension: Design and optimization of a novel series of spirocyclic piperidines

10.1016/j.bmcl.2011.10.013

The research focuses on the discovery and structure-activity relationship (SAR) of a novel series of spirocyclic renin inhibitors for the treatment of hypertension. The study aimed to enhance renin potency and reduce hERG affinity and CYP3A4 inhibition through spirocyclization, which restricts the molecule to its bioactive conformation. Experiments involved the synthesis of various spirocyclic compounds, with compound 31 identified as an optimized renin inhibitor. Reactants used in the synthesis included 2-bromo-4,5-difluorobenzoic acid, TBSCl, imidazole, DMF, Pd(dppf)Cl2, Na2CO3, and other reagents for Suzuki coupling and cyclization reactions. Analytical methods employed in the study included buffer and plasma renin inhibition assays, hERG channel affinity measurements, and CYP3A4 inhibition assessments, which were used to evaluate the potency, safety, and metabolic profile of the synthesized compounds.

Structure-simplified and highly efficient deep blue organic light-emitting diodes with reduced efficiency roll-off at extremely high luminance

10.1039/c6cc08501f

The research focuses on the development of structure-simplified, highly efficient deep blue organic light-emitting diodes (OLEDs) that exhibit reduced efficiency roll-off at extremely high luminance. The study involves the synthesis of new fluorescent emitters, NI-1-DPhTPA, NI-2-DPhTPA, BIDPhTPA, and PhIDPhTPA, based on a triphenylamine (TPA) core with electron-poor imidazole derivative groups. These emitters were characterized using 1H, 13C NMR spectrometry, mass spectrometry, and density functional theory (DFT) calculations to evaluate their molecular orbitals and energy band gaps. The thermal stability was assessed through differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA), while cyclic voltammograms (CV) were used to estimate HOMO levels. The photophysical properties, including absorption and photoluminescence (PL) spectra, were studied in various solvents to understand solvatochromic shifts and intramolecular charge transfer (ICT) characteristics. The electroluminescent properties of these materials were probed by fabricating non-doped multilayer OLEDs and simplified single-layer OLEDs, with the devices' performance evaluated through current density-voltage-luminance (J-V-L), external quantum efficiency (EQE), and power efficiency (PE) measurements. The research demonstrated record-breaking EQEs exceeding 5.10% at 10,000 cd m-2 for the multilayer devices and an unprecedented 4.22% EQE at 10,000 cd m-2 for the simplified single-layer devices, showcasing the potential for cost-effective, high-luminosity OLED applications.

New platinum(II) and palladium(II) quinoline-imine-pyridine, quinoline-imine-thiazole and quinoline-imine-imidazole complexes by metal-assisted condensation reactions

10.1016/j.jorganchem.2011.03.046

The research focuses on the synthesis and reactivity of platinum(II) and palladium(II) complexes with tridentate N-donor ligands containing different heterocycles, such as pyridine, thiazole, and imidazole. The metal-assisted condensation reactions between 8-aminoquinoline and various aldehydes or ketones were utilized to prepare these complexes, which were then subjected to preliminary reactivity studies involving the coordinated tridentate N-donors, the chloro-ligand, and the M-CH3 bond. Reactants included 8-aminoquinoline, ortho-substituted aldehydo- or keto- N-heterocycles, and metal precursors like PtClMe(COD) and PdClMe(COD). The analyses used to characterize the complexes were elemental analysis, conductivity measurements, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and theoretical calculations using density functional theory (DFT). These techniques provided comprehensive insights into the structure, electronic properties, and reactivity of the synthesized complexes.

UNEXPECTED REACTIONS OF 1,4-DIAZA-1,3-DIENES UNDER ACYLATING CONDITIONS. A NEW CYCLIZATION TO NON-ACYLATED IMIDAZOLE DERIVATIVES

10.1016/S0040-4039(00)96577-8

The study investigates the unexpected reactions of 1,4-diaza-1,3-dienes under acylating conditions, leading to the formation of non-acylated imidazole derivatives. The researchers used 1,2-bisimines as starting materials, which were converted into anions. These anions reacted with acid chlorides, such as acetyl chloride, to produce imidazole derivatives. The key chemicals involved include 1,2-bisimines (3), which are derived from benzil and serve as the starting compounds. The anions of these bisimines are generated under specific conditions and then react with acid chlorides to yield the desired imidazole products. The study highlights the unusual reactivity of these anions, which is attributed to the cyclization of a radical generated by electron transfer from the anion to the acid chloride. The results provide a new synthetic route to imidazole derivatives and offer insights into the underlying reaction mechanisms.

N-Arylation of nitrogen heterocycles with 2,4-difluoroiodobenzene

10.1016/j.tet.2008.11.036

The research primarily focuses on the arylation reactions of NH-heterocycles, such as pyrazole, 3-(trifluoromethyl)pyrazole, imidazole, and pyrrole, with 2,4-difluoroiodobenzene, facilitated by both copper catalysis and SNAr reactions. The study aims to explore the regioselective reactions and multiple substitutions to synthesize a range of new N-arylated heterocycle derivatives. The reactants include various NH-heterocycles and 2,4-difluoroiodobenzene, with copper catalysts like Cu2O and ligands such as salicylaldoxime utilized in some reactions. The analyses involved the use of 1H, 13C, and 19F NMR spectroscopy, IR spectroscopy, and mass spectrometry to determine the structures and purities of the synthesized compounds, along with X-ray crystallography for certain products to confirm their regiochemistry. The research also includes a Suzuki–Miyaura reaction to extend the utility of the synthesized arylation products.

Ruthenium(II) complexes bearing pyridine-functionalized N-heterocyclic carbene ligands: Synthesis, structure and catalytic application over amide synthesis

10.1007/s12039-016-1169-y

The study focuses on the synthesis, structure, and catalytic application of ruthenium(II) complexes bearing pyridine-functionalized N-heterocyclic carbene (NHC) ligands. The researchers synthesized a series of imidazolium salts by reacting 2-bromopyridine with 1-substituted imidazoles, which were then used as ligand precursors for the formation of new ruthenium(II) complexes. These complexes, characterized by various spectroscopic techniques, were found to have an octahedral geometry and were effective catalysts for the one-pot conversion of aldehydes to primary amides using NH2OH.HCl and NaHCO3. The study investigated the effects of different factors such as solvent, base, temperature, time, and catalyst loading on the catalytic performance. The purpose of these chemicals was to create a catalytic system that could efficiently convert aldehydes to amides, which are important compounds in chemistry and biology, and to optimize the reaction conditions for this conversion.

Highly efficient and eco-friendly protocol to functionalized imidazoles via ring-opening of α-nitro epoxides

10.1039/c5ra07770b

The study presents a highly efficient and eco-friendly protocol for synthesizing functionalized imidazoles from α-nitro-epoxides and amidines. Imidazoles are important N-containing heteroaromatic compounds with various biological effects and applications in fields like fluorescence, agriculture, and chemsensing. The researchers optimized reaction conditions, finding that using 2.0 equivalents of NaOMe in MeOH at 25 °C provided the best results. They tested a range of nitroepoxides and amidines, discovering that both aryl and alkyl substitutions at different positions were compatible, though yields varied depending on the specific substituents. The proposed mechanism involves ring-opening of nitroepoxides followed by intramolecular nucleophilic addition and water elimination. This mild, metal-catalyst-free method offers operational simplicity and substituent variation, making it a practical approach for medicinal chemistry.

N-(tert-butyldimethylsilyl)imidazole and related heterocycles: 13C nuclear magnetic resonance study and reaction with dimethylsulfoxide

10.1139/v80-010

The study investigates the preparation, characterization, and reactions of N-tert-butyldimethylsilyl derivatives of various heterocyclic compounds, including imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, 1,2,4-triazole, and benzotriazole. These derivatives were synthesized using tert-butyldimethylsilyl chloride and the corresponding heterocyclic compounds. The products were identified and characterized using carbon and proton nuclear magnetic resonance (NMR), mass spectrometry, and elemental analysis. The study confirmed the absence of intermolecular silyl exchange at ambient temperature through carbon NMR spectra, but noted that such exchange occurred at elevated temperatures (130-160°C). The study also explored the reaction of these silyl derivatives with dimethylsulfoxide (DMSO), resulting in the formation of N-(methylthio)methyl derivatives of the heterocycles. The mechanism for this reaction involves a Pummerer rearrangement, and the products were characterized using various analytical techniques, providing insights into the stability and reactivity of these compounds under different conditions.

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