tert-Amyl alcohol

Base Information

• Chemical Name: tert-Amyl alcohol
• CAS No.: 75-85-4
• Molecular Formula: C5H12O
• Molecular Weight: 88.1497
• Hs Code.: 2905199090
• European Community (EC) Number: 200-908-9
• NSC Number: 760354,25498
• UN Number: 1105
• UNII: 69C393R11Z
• DSSTox Substance ID: DTXSID0041436
• Nikkaji Number: J4.164E
• Wikipedia: Tert-Amyl_alcohol
• Wikidata: Q209428
• Metabolomics Workbench ID: 46201
• ChEMBL ID: CHEMBL44658
• Mol file: 75-85-4.mol

Synonyms:tert-Pentylalcohol (8CI);1,1-Dimethyl-1-propanol;2-Ethyl-2-propanol;2-Hydroxy-2-methylbutane;2-Methyl-2-hydroxybutane;Amylenehydrate;Dimethylethylcarbinol;Ethyldimethylcarbinol;NSC 25498;tert-Amylalcohol;tert-Pentanol;

Chemical Property of tert-Amyl alcohol

Chemical Property:

• Appearance/Colour: colourless liquid with a camphor-like odour
• Vapor Pressure: 19.2mmHg at 25°C
• Melting Point: -12 °C
• Refractive Index: n20/D 1.405(lit.)
• Boiling Point: 102 °C at 760 mmHg
• PKA: 15.38±0.29(Predicted)
• Flash Point: 21.1 °C
• PSA: 20.23000
• Density: 0.811 g/cm³
• LogP: 1.16730
• Water Solubility.: 120 g/L (20℃)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 88.088815002
• Heavy Atom Count: 6
• Complexity: 39.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.0% min. ^*data from raw suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F:Flammable;;
• Statements: R11:; R20:; R37/38:
• Safety Statements: S46:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Alcohols (
• Canonical SMILES: CCC(C)(C)O
• General Description: Tert-Amyl alcohol (also known as tert-pentanol or 2-methyl-2-butanol) is a solvent used in organic synthesis, particularly in catalytic reactions such as Suzuki-Miyaura coupling and direct amination of bio-alcohols. It has been identified as an effective solvent for optimizing reaction conditions, especially when paired with specific phosphine ligands (e.g., DPPPent or DPPF) in palladium-catalyzed cross-coupling reactions. Additionally, it serves as a suitable medium for ruthenium-catalyzed amination processes, demonstrating compatibility with ammonia and high catalyst stability. Its role in these reactions highlights its utility in facilitating high-yield transformations in both pharmaceutical and sustainable chemistry applications.

Technology Process of tert-Amyl alcohol

There total 137 articles about tert-Amyl alcohol 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: 70.0%

methylbutane (78-78-4) → 3-methyl-butan-2-one (563-80-4) + tert-Amyl alcohol (75-85-4) + 2-Methylbutyraldehyde (96-17-3,57456-98-1) + 3-methyl-2-butanol (598-75-4)

Guidance literature:

With [2,2]bipyridinyl; Ba; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.0333333h;

DOI:10.1039/c39950000943

Reference yield:

2-iodo-2-methylbutane (594-38-7) + water (7732-18-5) → tert-Amyl alcohol (75-85-4) + hydrogen iodide (10034-85-2)

Guidance literature:

Reference yield:

benzaldehyde di-t-pentyl acetal → tert-Amyl alcohol (75-85-4) + benzaldehyde (100-52-7)

Guidance literature:

With acetate buffer; potassium chloride; In acetonitrile; at 25 ℃; pH=4.60 - 5.00; Further Variations:; Reagents; pH-values; Kinetics;

DOI:10.1021/jo0202987

upstream raw materials:

2-methyl-1,2-epoxypropane

dimethylmagnesium

2,3-epoxybutane

methylmagnesium bromide

Downstream raw materials:

2-tert-pentyloxy-ethanol

tert-Amyl methyl ether

2-methyl-2-butyl benzoate

iso-butanol

Refernces

Suzuki-miyaura coupling of diarylmethyl carbonates with arylboronic acids: A new access to triarylmethanes

10.1021/ol800078j

The research focuses on the Suzuki-Miyaura coupling reaction of diarylmethyl carbonates with arylboronic acids, which is a novel approach to synthesize triarylmethanes. These compounds are significant due to their presence in various biologically active molecules and materials science applications. The experiments involved using a [Pd(η3-C3H5)Cl]2-DPPPent catalyst in different solvents to optimize the reaction conditions. Key reactants included diarylmethyl carbonates and arylboronic acids, with the choice of solvent and phosphine ligand being crucial for the reaction's success. The study found that tert-amyl alcohol as a solvent and DPPPent or DPPF as ligands yielded the highest product formation. The analysis of the reaction's efficiency was done through GC yield and isolated yield measurements, with the conditions also being sensitive to the electronic and steric properties of the substrates. The research was supported by various foundations and grants, and the results have potential applications in constructing diverse triarylmethane frameworks in organic synthesis.

Direct amination of bio-alcohols using ammonia

10.1002/cctc.201300407

The research aims to develop a robust catalytic system for converting bio-alcohols and diols into primary amines using ammonia as the amine source. The study focuses on optimizing parameters such as ammonia concentration and the Ru/P ratio to achieve high selectivity and activity. Key chemicals used include [Ru3(CO)12] as the catalyst precursor and various phosphine ligands, with L9 (an acridine-based diphosphine) showing particularly excellent results. The solvent tert-amyl alcohol was used, and ammonia was dosed using a mass flow meter/controller. The research concludes that the optimal Ru/P ratio is 1:1, and the amount of ammonia is crucial, especially for larger batch reactions. The catalyst demonstrated high thermostability and reusability, maintaining activity and selectivity over at least six consecutive runs. This system enables efficient conversion of bio-based substrates into valuable amines, with potential applications in sustainable chemistry and polymer synthesis.