5162-48-1

Basic information

• Product Name: 2,2,4-TRIMETHYL-3-PENTANOL
• Synonyms: 2,2,4-trimethylpentan-3-ol;Einecs 225-939-5;3-Pentanol, 2,2,4-trimethyl-;2,2,4-TRIMETHYL-3-PENTANOL;2,2,4-TRIMETHYLPENTANOL-3
• CAS NO: 5162-48-1
• Molecular Formula: C₈H₁₈O
• Molecular Weight: 130.23
• EINECS: 225-939-5
• Mol File: 5162-48-1.mol

Chemical Properties

• Melting Point: -11.3°C
• Boiling Point: 148.85°C
• Flash Point: 50°C
• Appearance: /
• Density: 0.8280
• Vapor Pressure: 4.28E-06mmHg at 25°C
• Refractive Index: 1.4270
• PKA: 15.17±0.20(Predicted)
• CAS DataBase Reference: 2,2,4-TRIMETHYL-3-PENTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,4-TRIMETHYL-3-PENTANOL(5162-48-1)
• EPA Substance Registry System: 2,2,4-TRIMETHYL-3-PENTANOL(5162-48-1)

Safety Data

• Hazardous Substances Data: 5162-48-1(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
2,2,4-Trimethyl-3-pentanol is used as a fragrance ingredient for its distinctive scent. It is commonly utilized in the creation of perfumes, colognes, and other scented products due to its pleasant aroma.
Used in Flavor Industry:
In addition to its use in the fragrance industry, 2,2,4-trimethyl-3-pentanol is also employed as a flavoring agent. It is used to add a unique taste and aroma to various food and beverage products, enhancing their overall flavor profile.
Used in Chemical Synthesis:
2,2,4-Trimethyl-3-pentanol serves as a valuable building block in the synthesis of various chemicals and compounds. Its versatile structure allows it to be used in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties, 2,2,4-trimethyl-3-pentanol is often used in research and development for studying various chemical reactions and processes. It can be employed as a reference compound or as a starting material for the synthesis of novel compounds with potential applications in various industries.

InChI:InChI=1/C13H16N2O2/c1-13(2,3)15-11-8-6-4-5-7-9(8)17-12(16)10(11)14/h4-7,15H,14H2,1-3H3

Upstream product

• 598-98-1 Methyl pivalate 
• 926-62-5 isobutylmagnesium bromide 
• 920-39-8 isopropylmagnesium bromide 
• 7432-48-6 2,5,5-trimethyl-1-penten-3-ol 
• 60-29-7 diethyl ether 
• 78-84-2 isobutyraldehyde 
• 677-22-5 tert-butylmagnesium chloride 
• 96-06-0 2,3-epoxy-2,4,4-trimethylpentane 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 3938-95-2 2,2-dimethyl-propanoic acid ethyl ester 
• 1068-55-9 isopropylmagnesium chloride 
• 540-84-1 2,2,4-trimethylpentane 
• 5857-36-3 2,2,4-trimethylpentanone 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 5162-48-1 (S)-2,2,4-trimethyl-pentan-3-ol 
• 101100-53-2 benzoic acid-((R)-1-isopropyl-2,2-dimethyl-propyl ester) 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 565-77-5 2,3,4-trimethyl-2-pentene 
• 565-76-4 2,3,4-trimethyl-pent-1-ene 

Relevant articles and documents

PROCESS FOR THE ISOMERIZATION OF 2,2,4,4-TETRAALKYLCYCLOBUTANE-1,3-DIOLS

Disclosed is a process for the isomerization of 2,2,4,4-tetraalkylcyclobutane-1,3-diols, such as 2,2,4,4-tetramethylcyclobutane-1,3-diol, by contacting the diol with a supported ruthenium catalyst in the presence of hydrogen at elevated pressures and temperatures. The process is carried under conditions in which there is no net production of 2,2,4,4-tetraalkylcyclobutane-1,3-diol. The process may be carried out in the presence or absence of a solvent and in the liquid or vapor phase.

Alkane oxidation by the system 'tert-butyl hydroperoxide-[Mn 2L2O3][PF6]2 (L = 1,4,7trimethyl-1,4,7-triazacyclononane)-carboxylic acid'

The kinetics of cyclohexane (CyH) oxygenation with terf-butyl hydroperoxide (TBHP) in acetonitrile at 50°C catalysed by a dinuclear manganese(IV) complex 1 containing 1,4,7-trimethyl-1,4,7-triazacyclononane and co-catalysed by oxalic acid have been studied. It has been shown that an active form of the catalyst (mixed-valent dimeric species 'MnIIIMnIV,) is generated only in the interaction between complex 1 and TBHP and oxalic acid in the presence of water. The formation of this active form is assumed to be due to the hydrolysis of the Mn - O - Mn bonds in starting compound 1 and reduction of one MnIV to MnIII. A species which induces the CyH oxidation is radical tert-BuO generated by the decomposition of a monoperoxo derivative of the active form. The constants of the equilibrium formation and the decomposition of the intermediate adduct between TBHP and 1 have been measured: k = 7.4mol-1dm3 and k = 8.4 × 10 -2s-1, respectively, at [H2O] = 1.5 mol dm -3 and [oxalic acid] = 10-2 mol dm-3. The constant ratio for reactions of the monomolecular decomposition of tert-butoxy radical (tert-BuO → CH3COCH3+ CH3) and its interaction with the CyH (terf-BuO + CyH → fert-BuOH + Cy) was calculated: 0.26 mol dm-3. One of the reasons why oxalic acid accelerates the oxidation is due to the formation of an adduct between oxalic acid and 1 (K ≈ 103 mol-1 dm3). Copyright

Hydroperoxidation of alkanes with hydrogen peroxide catalyzed by aluminium nitrate in acetonitrile

The first example of alkane oxygenation with hydrogen peroxide catalyzed by a non-transition metal derivative (aluminium) is reported. Heating (70 °C) a solution of an alkane, RH, hydrogen peroxide (70% aqueous) and a catalytic amount of Al(NO3)3·9H2O in air for a few hours afforded the corresponding alkyl hydroperoxide, ROOH. With cyclooctane, the hydroperoxide yield attained 31% and the maximum turnover number was 150. It is proposed on the basis of measurements of the selectivity parameters for the oxidation of linear and branched alkanes and a kinetic study that the oxidation occurs with the participation of hydroxyl radicals.

Oxidations catalyzed by osmium compounds. Part 1: Efficient alkane oxidation with peroxides catalyzed by an olefin carbonyl osmium(0) complex

A carbonyl osmium(0) complex with π-coordinated olefin, (2,3-η-1,4-diphenylbut-2-en-1,4-dione)undecacarbonyl triangulotriosmium (1), efficiently catalyzes oxygenation of alkanes (cyclohexane, cyclooctane, n-heptane, isooctane, etc.) with hydrogen peroxide, as well as with tert-butyl hydroperoxide and meta-chloroperoxybenzoic acid in acetonitrile solution. Alkanes are oxidized to corresponding alcohols, ketones (aldehydes) and alkyl hydroperoxides. Thus, heating cyclooctane with the 1-H2O2 combination at 70 °C gave products with turnover number as high as 2400 after 6 h. The maximum obtained yield of all products was equal to 20% based on cyclohexane and 30% based on H2O2. The oxidation of linear and branched alkanes exhibits very low regio- and bond-selectivity parameters and this testifies that the reaction proceeds via attack of hydroxyl radicals on C-H bonds of the alkane. The oxygenation products were not formed when the reaction was carried out under argon atmosphere and it can be thus concluded that the oxygenation occurs via the reaction between alkyl radicals and atmospheric oxygen. In summary, the Os(0) complex is much more powerful generator of hydroxyl radicals than any soluble derivative of iron (which is an analogue of osmium in the Periodic System).

Alkane oxygenation with H2O2 catalysed by FeCl 3 and 2,2′-bipyridine

The H2O2-FeCl3-bipy system in acetonitrile efficiently oxidises alkanes predominantly to alkyl hydroperoxides. Turnover numbers attain 400 after 1 h at 60°C. It has been assumed that bipy facilitates proton abstraction from a H2O2 molecule coordinated to the iron ion (these reactions are stages in the catalytic cycle generating hydroxyl radicals from the hydrogen peroxide). Hydroxyl radicals then attack alkane molecules finally yielding the alkyl hydroperoxide.

Alkane oxygenation catalysed by gold complexes

Gold(III) and gold(I) complexes, NaAuCl4 and ClAuPPh3, efficiently catalyse the oxidation of alkanes by H2O2 in acetonitrile solution at 75°C. Turnover numbers (TONs) attain 520 after 144 h. Alkyl hydroperoxides are the main products, whereas ketones (aldehydes) and alcohols are formed in smaller concentrations. It is suggested on the basis of the bond selectivity study that at least one of the pathways in Au-catalysed alkane hydroperoxidation does not involve the participation of free hydroxyl radicals. Possibly, the oxidation begins from the alkane hydrogen atom abstraction by a gold oxo species. The oxidation of cyclooctane by air at room temperature catalysed by NaAuCl4 in the presence of Zn/CH3COOH as a reducing agent and methylviologen as an electron-transfer agent gave cyclooctanol (TON=10).

Reactions of Carbonyl Compounds with Grignard Reagents in the Presence of Cerium Chloride

The addition of Grignard reagents to ketones is significantly enhanced by cerium chloride with remarkable supression of side reactions, particularly enolization.Some esters, which are prone to side reactions, also react readily with Grignard reagents in the presence of cerium chloride to give normal reaction products in reasonable to high yields.

A Study of Solvent Effects on the Rates of Solvolyses of Pinacolyl Derivatives

The solvolysis rates of RCH(O3SAr)C(CH3)3 (4a, R = Et, Ar = p-BrPh; 4b, R = i-Pr, Ar = p-BrPh; 4c, R = t-Bu, Ar = p-Tol) and CF3CH(O3SR)C(CH3)3 (6-OBs, R = p-BrPh; 6-OTf, R = CF3) have been determined in mixtures of ethanol and water (the E-W solvent series) and acetic acid and formic acid (the A-F solvent series).Correlations of the rate data by eq 1 neophyl-OTs + c> showed that 4a,b responded similarly to pinacolyl brosylate (1) to the examined solvent effect, yielding separate E-W, A-F regression lines, but with decreased dispersion with increased steric bulk of R.For compound 4c a linear correlation with eq 1 was obtained.These results are interpreted in terms of steric hindrance to electrostatic solvation of the incipient carbocation.The reactivity of the CF3-substituted sulfonate 6-OBs is greatly depressed.The substrate failed to react in the E-W solvent series.Added salt produced enhanced rates of solvolysis of 6-OBs in 25percent AcOH-75percent HCOOH.These results suggest an SN2-like mechanism with very strong electrophilic solvent assistance in the transition state.However, since the solvolysis reactions of 6-OBs are attended with kinetic complexities, the data do not allow a detailed mechanistic interpretation.The solvolytic behavior of 6-OTf stands in sharp contrast to that of 6-OBs.For example, added nucleophilic salts cause only small increases in the rates of solvolysis of 6-OTf in both 70percent EtOH-30percent H2O and 25percent AcOH-75percent HCOOH.Furthemore, the solvolysis rate constants of 6-OTf in all solvents examined correlate with those of 2-adamantyl triflate.These data support a kΔ mechanism for 6-OTf and are discussed in terms of the decreased importance of electrostatic solvation of the forming carbocation from 6-OTf than from pinacolyl brosylate.

ORGANOBORANES FOR SYNTHESIS. 2. OXIDATION OF ORGANOBORANES WITH ALKALINE HYDROGEN PEROXIDE AS A CONVENIENT ROUTE FOR THE cis-HYDRATION OF ALKENES via HYDROBORATION

Aqueous hydrogen peroxide in the presence of dilute alkali effects the oxidation of organoboranes.The conditions necessary for a clean and quantitative transformation of organoboranes into the corresponding alcohols have been established.Thus, one mole of trialkylborane reacts with three moles of hydrogen peroxide in the presence of one mole of sodium hydroxide to provide three moles of the corresponding alcohol.The concentrations of these reagents or the reaction temperature can be varied widely without affecting the yield significantly.Oxidation proceeds well in water-miscible solvents, such as diglyme and THF.However, the reaction is slow and incomplete in diethyl ether.The addition of ethanol as a cosolvent circumvents this difficulty.Wide variations in the structure of organoboranes do not affect the reaction greatly.A variety of common organic functional groups, such as alkenes, alkynes, esters, ketones, nitriles, etc., are unaffected under the normal oxidation conditions.However, aldehydes are somewhat unstable under these conditions, although they do not interfere with the oxidation of organoboranes