628-99-9

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Nonanol is used as a flavoring agent for its waxy, soapy, musty taste with green, fruity, and dairy nuances at 5 ppm. Its aroma threshold values make it suitable for enhancing the taste and aroma of various food and beverage products.
Used in Perfumery:
2-Nonanol is used as a fragrance ingredient due to its powerful fruity-green odor. It can be incorporated into perfumes and other scented products to provide a unique and pleasant scent.
Used in the Chemical Industry:
2-Nonanol can be utilized as a building block for the synthesis of other organic compounds, such as esters, ethers, and other derivatives. Its chemical properties make it a versatile intermediate in the chemical industry for various applications.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-Nonanol's properties may also make it a candidate for use in the pharmaceutical industry, potentially as a solvent or in the synthesis of pharmaceutical compounds.

Preparation

From nonene

InChI:InChI=1/C9H20O/c1-3-4-5-6-7-8-9(2)10/h9-10H,3-8H2,1-2H3

Upstream product

• 821-55-6 2-Nonanone 
• 124-13-0 Octanal 
• 75-16-1 methylmagnesium bromide 
• 13125-66-1 n-heptylmagnesium bromide 
• 75-07-0 acetaldehyde 
• 96-47-9 2-methyltetrahydrofuran 
• 109-72-8 n-butyllithium 
• 2216-35-5 2-bromononane 
• 629-04-9 1-Bromoheptane 
• 4282-40-0 1-Iodoheptane 
• 50517-74-3 dimesitylethylborane 
• 103687-21-4 ((CH₃)3C₆H₂)2BCHLiCH₃ 
• 68696-09-3 Tributyl-methyl-plumbane 
• 54583-22-1 1-hydroxy-2-bromooctane 

Downstream Products

• 2216-35-5 2-bromononane 
• 6434-78-2 2-nonene 
• 821-55-6 2-Nonanone 
• 14936-66-4 2-nonanyl acetate 
• 55193-09-4 2-nonyl pentanoate 
• 85558-02-7 2-(1-Methyl-octyloxy)-1,3-diphenyl-[1,3,2]diazaphospholidine 
• 111-65-9 octane 
• 628-99-9 (R)-2-nonanol 
• 69727-42-0 2-nonyl butanoate 
• 70419-06-6 (S)-nonan-2-ol 
• 13205-58-8 2-nonanamine 
• 213979-93-2 C₁₈H₃₇N 
• 117636-68-7 (R)-2-nonyl octanoate 
• 117636-58-5 (R)-2-nonyl hexanoate 

Relevant academic research and scientific papers

Catalytic deoxygenation of bio-based 3-hydroxydecanoic acid to secondary alcohols and alkanes

This work comprises the selective deoxygenation of bio-derivable 3-hydroxydecanoic acid to either linear alkanes or secondary alcohols in aqueous phase and H2-atmosphere over supported metal catalysts. Among the screened catalysts, Ru-based systems were identified to be most active. By tailoring the catalyst, the product selectivity could be directed to either secondary alcohols or linear alkanes. In the absence of a Br?nsted acidic additive, 2-nonanol and 3-decanol were accessible with a yield of 79% and 6% respectively, both of which can be used in food and perfume industries as flavoring agents and fragrances. To produce alkanes, we successfully synthesized a bifunctional Ru/HZSM-5 catalyst. The acidic zeolite support facilitated the dehydration of the intermediary formed alcohols to alkenes, while the following hydrogenation occurred at the Ru centers. Thus, full 3-hydroxydecanoic acid deoxygenation to nonane and decane, which are both well-established as diesel and jet fuels, was achieved with up to 72% and 12% yield, respectively.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Dinuclear Di(N-heterocyclic carbene) iridium(III) complexes as catalysts in transfer hydrogenation

Two novel di(N-heterocyclic carbene) complexes of formula (μ-PyrIm-CH2-ImPyr)[IrCp?Cl]2(PF6)2 (1) and μ-MeIm-CH2(p-C6H2)CH2-ImMe[IrCp? Cl]2 (2) (Im = imidazol-2-ylidene) have been synthesised by transmetallation of the dicarbene ligand from the corresponding dicarbene silver complex, using [IrCp?(μ-Cl)Cl]2 as an iridium precursor. The structure of complex 2 has been determined by X-ray diffraction and is characterized by a double ortho-metallation of the p-xylylene bridge between the carbene units. Both complexes show good activity in the transfer hydrogenation of ketones to alcohols in 2-propanol. Dinuclear iridium(III) complexes bearing a bridging di(NHC) ligand have been synthesised and tested as catalysts in transfer hydrogenation reactions.

SELF-REGENERATING ANTIOXIDANT CATALYSTS AND METHODS OF USING THE SAME

The present invention relates to self-regenerating antioxidant catalysts and methods of using the same.

Catalytic enantioselective addition of methyltriisopropoxititanium to aldehydes

An efficient catalyst for the enantioselective synthesis of chiral methyl carbinols from aldehydes is presented. The system uses methyltriisopropoxytitanium as a nucleophile and a readily available binaphthyl derivative as a chiral ligand. The enantioselective methylation of both aromatic and aliphatic aldehydes proceeds with good yields and high enantioselectivities under mild conditions.

Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes

Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral methyl carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times.

ALKANE OXIDATION BY MODIFIED HYDROXYLASES

This invention relates to modified hydroxylases. The invention further relates to cells expressing such modified hydroxylases and methods of producing hydroxylated alkanes by contacting a suitable substrate with such cells.

New Type of 2,6-Bis(imidazo[1,2-a]pyridin-2-yl)pyridine-Based Ruthenium Complexes: Active Catalysts for Transfer Hydrogenation of Ketones

Neutral and cationic ruthenium(II) complexes bearing a symmetrical 2,6-bis(imidazo[1,2-a]pyridin-2-yl)pyridine were synthesized and structurally characterized by NMR analysis and X-ray crystallographic determinations. These complexes have exhibited good catalytic activity in the transfer hydrogenation of ketones. In refluxing isopropyl alcohol, the conversion of the substrates reached up to 99%, and a TOF value of 356400 h-1 with 0.1 mol % catalyst was achieved. (Figure Presented).

Identification of an ε-keto ester reductase for the efficient synthesis of an (R)-α-lipoic acid precursor

Abstract A novel reductase (CpAR2) with unusually high activity toward an ε-keto ester, ethyl 8-chloro-6-oxooctanoate, was isolated from Candida parapsilosis. The asymmetric reduction of ethyl 8-chloro-6-oxooctanoate using Escherichia coli cells coexpressing CpAR2 and glucose dehydrogenase genes gave ethyl (R)-8-chloro-6-hydroxyoctanoate, a key precursor for the synthesis of (R)-α-lipoic acid, in high space-time yield (530 gL-1d-1) and with excellent enantiomeric excess (>99%). This bioprocess was shown to be viable on a 10-L scale. This method provides a greener and more cost-effective method for the industrial production of (R)-α-lipoic acid.

Identification of key residues in Debaryomyces hansenii carbonyl reductase for highly productive preparation of (S)-aryl halohydrins

Key residues of Debaryomyces hansenii carbonyl reductase in the determination of the reducing activity towards aryl haloketones were identified through combinatorial mutation of conserved residues. This study provides a green and efficient biocatalyst for the synthesis of (S)-aryl halohydrins.