1653-30-1

Basic information

• Product Name: 2-UNDECANOL
• Synonyms: (±)-undecan-2-ol;sec-Undecyl Alcohol;Undecan-2-ol;Methyl n-nonyl carbinol;2-UNDECANOL, 98+%;2-UNDECANOL 99+%;2-hendecanol;See A14441
• CAS NO: 1653-30-1
• Molecular Formula: C₁₁H₂₄O
• Molecular Weight: 172.31
• EINECS: 216-722-6
• Mol File: 1653-30-1.mol

Chemical Properties

• Melting Point: 2-3 °C
• Boiling Point: 130-131 °C28 mm Hg(lit.)
• Flash Point: 226 °F
• Appearance: /
• Density: 0.828 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0147mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 15.28±0.20(Predicted)
• Water Solubility: Not miscible or difficult to mix in water. Soluble in alcohol and ethyl ether.
• BRN: 1719795
• CAS DataBase Reference: 2-UNDECANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-UNDECANOL(1653-30-1)
• EPA Substance Registry System: 2-UNDECANOL(1653-30-1)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 26-36-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 1653-30-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Undecanol is used as a flavor component for its fruity note and aroma, adding a distinct taste and scent to various products. It is particularly useful in the creation of artificial fruit flavors and fragrances, where its aroma threshold values of 8.6 to 41 ppb allow for effective detection and application.
Used in Chemical Synthesis:
In the chemical industry, 2-Undecanol serves as a valuable reagent that can be converted into aldehyde or ketone under mild conditions with a copper-based catalyst. This property makes it a versatile building block for the synthesis of various organic compounds and intermediates.
Used in Research and Development:
Due to its natural occurrence in a wide range of plants and food items, 2-Undecanol is also utilized in research and development for studying its properties, potential applications, and effects on different organisms. This can lead to the discovery of new uses and applications in various industries, such as pharmaceuticals or cosmetics.

Preparation

By reduction of methyl nonyl ketone with sodium metal in alcohol; the d-form is isolated from the optically inactive material via the corresponding phthalate and in its salt with strychnine and brucine.

InChI:InChI=1/C11H24O/c1-3-4-5-6-7-8-9-10-11(2)12/h11-12H,3-10H2,1-2H3/t11-/m0/s1

Upstream product

• 112-12-9 methyl nonyl ketone 
• 111-11-5 methyl octanate 
• 83803-54-7 2,3-epoxy-3-methyl-dodecanoic acid ethyl ester 
• 64-17-5 ethanol 
• 67-64-1 acetone 
• 67-63-0 isopropyl alcohol 
• 555-31-7 aluminum isopropoxide 
• 107-21-1 ethylene glycol 
• 1120-21-4 n-Undecane 
• 10596-05-1 undecane-1,10-diol 
• 33893-85-5 4-(hydroxymethyl)cyclohexan-1-ol 
• 334-48-5 1-decanoic acid 
• 36219-73-5 undec-10-en-2-one 
• 26561-31-9 2-acetyl-deca-4t,9-dienoic acid ethyl ester 

Downstream Products

• 821-95-4 1-undecene 
• 2244-02-2 2-undecene 
• 112-12-9 methyl nonyl ketone 
• 14936-67-5 2-undecanol 2-acetate 
• 85617-06-7 (R)-(-)-2-undecanol 
• 1289644-74-1 N-(undecan-2-yl)benzenamine 
• 936716-85-7 C₂₉H₂₆O₃ 
• 1346758-14-2 1-methyldecyl 3,5-dibromobenzoate 
• 30714-90-0 C₁₃H₂₇O₅S^(1-)*Na⁽¹⁺⁾ 
• 123-91-1 1,4-dioxane 
• 6345-92-2 (1-methyl-decyl)-malonic acid diethyl ester 
• 2243-98-3 1-undecyne 
• 13490-36-3 3-methyldodecanoic acid 
• 85617-05-6 (S)-undecan-2-ol 

Relevant articles and documents

Phosphine-NHC Manganese Hydrogenation Catalyst Exhibiting a Non-Classical Metal-Ligand Cooperative H2 Activation Mode

Deprotonation of the MnI NHC-phosphine complex fac-[MnBr(CO)3(κ2P,C-Ph2PCH2NHC)] (2) under a H2 atmosphere readily gives the hydride fac-[MnH(CO)3(κ2P,C-Ph2PCH2NHC)] (3) via the intermediacy of the highly reactive 18-e NHC-phosphinomethanide complex fac-[Mn(CO)3(κ3P,C,C-Ph2PCHNHC)] (6 a). DFT calculations revealed that the preferred reaction mechanism involves the unsaturated 16-e mangana-substituted phosphonium ylide complex fac-[Mn(CO)3(κ2P,C-Ph2P=CHNHC)] (6 b) as key intermediate able to activate H2 via a non-classical mode of metal-ligand cooperation implying a formal λ5-P–λ3-P phosphorus valence change. Complex 2 is shown to be one of the most efficient pre-catalysts for ketone hydrogenation in the MnI series reported to date (TON up to 6200).

Hydrogenation of Carbonyl Derivatives Catalysed by Manganese Complexes Bearing Bidentate Pyridinyl-Phosphine Ligands

Manganese(I) catalysts incorporating readily available bidentate 2-aminopyridinyl-phosphine ligands achieve a high efficiency in the hydrogenation of carbonyl compounds, significantly better than parent ones based on more elaborated and expensive tridentate 2,6-(diaminopyridinyl)-diphosphine ligands. The reaction proceeds with low catalyst loading (0.5 mol%) under mild conditions (50 °C) with yields up to 96%. (Figure presented.).

Rhenium and manganese complexes bearing amino-bis(phosphinite) ligands: Synthesis, characterization, and catalytic activity in hydrogenation of ketones

A series of rhenium and manganese complexes supported by easily accessible and easily tunable amino-bisphosphinite ligands was prepared and characterized by NMR and IR spectroscopy, HR mass spectrometry, elemental analysis, and X-ray diffraction studies. These complexes have been tested in the hydrogenation of ketones. Notably, one of the rhenium complexes, bearing an NH moiety, proved significantly more active than the rest of the series. The reaction proceeds well at 120 °C, under 50 bar of H2, in the presence of 0.5 mol % of catalyst and 1 mol % of tBuOK. Interestingly, activation of the precatalyst could be followed stepwise by NMR and a rhenium hydride was characterized by X-ray diffraction studies.

Hydrogenation of Carbonyl Derivatives with a Well-Defined Rhenium Precatalyst

The first efficient and general rhenium-catalyzed hydrogenation of carbonyl derivatives was developed. The key to the success of the reaction was the use of a well-defined rhenium complex bearing a tridentate diphosphinoamino ligand as the catalyst (0.5 mol %) at 70 °C in the presence of H2 (30 bar). The mechanism of the reaction was investigated by DFT(PBE0-D3) calculations.

Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst

A very simple and inexpensive catalytic system based on abundant manganese as transition metal and on an inexpensive phosphine-free bidendate ligand, 2-(aminomethyl)pyridine, has been developed for the reduction of a large variety of carbonyl derivatives with 2-propanol as hydrogen donor. Remarkably, the reaction proceeds at room temperature with low catalyst loading (down to 0.1 mol %) and exhibits a good tolerance toward functional groups. High TON (2000) and TOF (3600 h-1) were obtained.

Hydrogenation of ketones with a manganese PN3P pincer pre-catalyst

A catalytic hydrogenation of carbonyl derivatives with a manganese pre-catalyst has been developed. The key feature is the use of an air stable cationic manganese pre-catalyst bearing a tridendate ligand with a 2,6-(diaminopyridinyl)diphosphine scaffold. Under 50?bar of H2, at 130?°C, various ketones were reduced to the corresponding alcohols with moderate to good yield.

Selective synthesis of primary amines by reductive amination of ketones with ammonia over supported Pt catalysts

Supported platinum catalysts are studied for the reductive amination of ketones under ammonia and hydrogen. For a model reaction with 2-adamantanone, Pt-loaded MoOx/TiO2 (Pt-MoOx/TiO2) shows the highest yield of primary amine. The catalyst is effective for the selective transformation of various aliphatic and aromatic ketones to the corresponding primary amines, which demonstrates the first example of the selective synthesis of primary amines by this reaction. The yield of the amine increases with increase in the negative shift of the C￡O stretching band in the infrared spectra of adsorbed acetone on the catalysts, suggesting that Lewis acid sites on the support material play an important role in this catalytic system.

Hydrosilylation of aldehydes and ketones catalyzed by half-sandwich manganese(I) N-heterocyclic carbene complexes

Easily available manganese(I) N-heterocyclic carbene (NHC) complexes, Cp(CO)2Mn(NHC), obtained in one step from industrially produced cymantrene, were evaluated as pre-catalysts in the hydrosilylation of carbonyl compounds under UV irradiation. Complexes with NHC ligands incorporating at least one mesityl group led to the most active and selective catalytic systems. A variety of aldehydes (13 examples) and ketones (11 examples) were efficiently reduced under mild conditions [Cp(CO)2Mn(IMes) (1 mol%), Ph 2SiH2 (1.5 equiv.), hν (350 nm), toluene, 25 °C, 1-24 h] with good functional group tolerance.

A convenient nickel-catalysed hydrosilylation of carbonyl derivatives

Hydrosilylation of aldehydes and ketones catalysed by nickel acetate and tricyclohexylphosphine as the catalytic system was demonstrated using polymethylhydrosiloxane as a cheap reducing reagent. The Royal Society of Chemistry 2013.

Hydrosilylation of aldehydes and ketones catalyzed by an n-heterocyclic carbene-nickel hydride complex under mild onditions

Half-sandwich N-heterocyclic carbene (NHC)-nickel complexes of the general formula [NiACHTUNGTRENUNG(NHC)ClCp?] (Cp?= Cp, Cp*) efficiently catalyze the hydrosilylation of aldehydes and ketones at room temperature in the presence of a catalytic amount of sodium triethylborohydride and thus join the fairly exclusive club of well-defined nickel(II) catalyst precursors for the hydrosilylation of carbonyl functionalities. Of notable interest is the isolation of an intermediate nickel hydride complex that proved to be the real catalyst precursor.