6939-95-3

Usage

Uses

Used in Perfumery and Fragrance Industry:
1-(3-Chlorophenyl)-1-ethanol is used as a fragrance ingredient for its distinctive and pleasant scent, contributing to the formulation of perfumes, colognes, and other scented products to enhance their olfactory appeal.
Used in Organic Synthesis:
In the realm of organic chemistry, 1-(3-Chlorophenyl)-1-ethanol is utilized as a reagent or intermediate in the synthesis of complex organic molecules, facilitating the creation of a wide array of chemical compounds.
Used in Pharmaceutical Manufacturing:
1-(3-Chlorophenyl)-1-ethanol is employed as a precursor in the development and production of various pharmaceuticals, underscoring its importance in the medicinal chemistry sector for creating new and existing drugs.

InChI:InChI=1/C8H9ClO/c1-6(10)7-3-2-4-8(9)5-7/h2-6,10H,1H3

Upstream product

• 75-07-0 acetaldehyde 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 587-04-2 m-Chlorobenzaldehyde 
• 75-16-1 methylmagnesium bromide 
• 99-02-5 3'-Chloroacetophenone 
• 108-37-2 1-bromo-3-chlorobenzene 
• 2039-85-2 3-Chlorostyrene 
• 620-16-6 3-chloroethylbenzene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 67-63-0 isopropyl alcohol 
• 108-90-7 chlorobenzene 
• 1309380-77-5 3-(m-chlorophenyl)-2-butanone oxime 
• 1262155-52-1 C₂₀H₁₈ClNO₃S 

Downstream Products

• 99-02-5 3'-Chloroacetophenone 
• 34887-78-0 1-chloro-3-(1-chloroethyl)benzene 
• 117780-31-1 1-(3-chlorophenyl)ethyl vinyl ether 
• 135145-34-5 (S)-1-(m-chlorophenyl)ethanol 
• 120121-01-9 (R)-1-(3-chlorophenyl)-ethanol 
• 2039-85-2 3-Chlorostyrene 
• 872180-68-2 2-fluoro-6-[1-(3-chlorophenyl)ethoxy]benzonitrile 
• 86728-93-0 methyl (S)-4-chloro-3-hydroxybutanoate 
• 136705-69-6 (R)-1-(3-chloroethylphenyl)ethyl acetate 
• 1103679-61-3 (S)-1-(3-chlorophenyl)ethanol acetate 
• 1236375-78-2 C₁₁H₁₃ClO₂ 
• 1342259-89-5 (R)-1-(3-chlorophenyl)ethyl valerate 
• 1330776-76-5 2-hydroxy-5,5-dimethyl-2-(3-oxo-1,3-diphenylpropyl)cyclohexane-1,3-dione 
• 1610950-01-0 1-chloro-3-(1-(o-tolyl)ethyl)benzene 

Relevant academic research and scientific papers

Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol

We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.

Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water

A green, efficient, and high active catalytic system for the hydrogenation of ketones and aldehydes to produce corresponding alcohols under atmospheric-pressure H2 gas and ambient temperature conditions was developed by a water-soluble metal–ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(OH)][Na] in water without addition of a base. The catalyst exhibited high activity for the hydrogenation of ketones and aldehydes. Furthermore, it was worth noting that many readily reducible or labile functional groups in the same molecule, such as cyan, nitro, and ester groups, remained unchanged. Interestingly, the unsaturated aldehydes can be also selectively hydrogenated to give corresponding unsaturated alcohols with remaining C=C bond in good yields. In addition, this reaction could be extended to gram levels and has a large potential of wide application in future industrial.

Selective C-alkylation Between Alcohols Catalyzed by N-Heterocyclic Carbene Molybdenum

The first implementation of a molybdenum complex with an easily accessible bis-N-heterocyclic carbene ligand to catalyze β-alkylation of secondary alcohols via borrowing-hydrogen (BH) strategy using alcohols as alkylating agents is reported. Remarkably high activity, excellent selectivity, and broad substrate scope compatibility with advantages of catalyst usage low to 0.5 mol%, a catalytic amount of NaOH as the base, and H2O as the by-product are demonstrated in this green and step-economical protocol. Mechanistic studies indicate a plausible outer-sphere mechanism in which the alcohol dehydrogenation is the rate-determining step.

Ruthenium complex based on [N,N,O] tridentate -2-ferrocenyl-2-thiazoline ligand for catalytic transfer hydrogenation

A method for the synthesis of a new phosphine-free [N,N,O]-tridentate Schiff base ligand L1 using the 2-Ferrocenyl-2-thiazoline as scaffold was developed. The 1,2-disubstituted ferrocene-based ligand was assembled using as key strategy the directed ortho-metalation (DoM) in 2-ferrocenyl-2-thiazoline. L1 was successfully obtained in 83% of overall yield after two-step synthesis. The coordination ability of L1 towards Ru(II) was evidenced and the resulting complex was characterized by IR, UV-vis and EPR. Its catalytic performance was tested in transfer hydrogenation of a variety of substrates giving moderate to excellent conversions.

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.

Postsynthetic Modification of Half-Sandwich Ruthenium Complexes by Mechanochemical Synthesis

A mild and environmentally friendly method to synthesize half-sandwich ruthenium complexes through the Wittig reaction between an aldehyde-tagged half-sandwich ruthenium complex and phosphorus ylide mechanochemically is reported herein. The mechanochemical synthesis of valuable half-sandwich ruthenium complexes resulted in a fast reaction, good yield with simple workup, and the avoidance of harsh reaction conditions and organic solvents. The synthesized half-sandwich ruthenium complexes exhibited high catalytic activity for transfer hydrogenation of ketones using 2-propanol as the hydrogen source and solvent. Density functional theory was carried out to propose a mechanism for the transfer hydrogenation process. The modeling suggests the importance of the labile p-cymene ligand in modulating the reactivity of the catalyst.

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones

A novel silylene supported iron hydride [Si, C]FeH (PMe3)3 (1) was synthesized by C (sp3)-H bond activation with zero-valent iron complex Fe (PMe3)4. Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp3)?H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.

Mn(i) phosphine-amino-phosphinites: a highly modular class of pincer complexes for enantioselective transfer hydrogenation of aryl-alkyl ketones

A series of Mn(i) catalysts with readily accessible and more π-accepting phosphine-amino-phosphinite (P′(O)N(H)P) pincer ligands have been explored for the asymmetric transfer hydrogenation of aryl-alkyl ketones which led to good to high enantioselectivities (up to 98%) compared to other reported Mn-based catalysts for such reactions. The easy tunability of the chiral backbone and the phosphine moieties makes P′(O)N(H)P an alternative ligand framework to the well-known PNP-type pincers.

Pincerlike molybdenum complex and preparation method thereof, catalytic composition and application thereof, and alcohol preparation method

The invention discloses a clamp-type molybdenum complex, a preparation method, a corresponding catalyst composition and application. The method comprises the steps: obtaining 9 molybdenum complexes with different structures through coordination reaction of 2-(substituent ethyl)-(5, 6, 7, 8-tetrahydroquinolyl) amine and a corresponding carbonyl molybdenum metal precursor; and catalyzing a ketone compound transfer hydrogenation reaction through a molybdenum complex to generate 40 alcohol compounds. The preparation method of the molybdenum complex is simple, high in yield and good in stability. For a transfer hydrogenation reaction of ketone, the molybdenum-based catalytic system has high catalytic activity and small molybdenum loading capacity, is used for production of aromatic and aliphatic alcohols, and has the advantages of simple method, small environmental pollution and high yield.

Hydrogen-Catalyzed Acid Transformation for the Hydration of Alkenes and Epoxy Alkanes over Co-N Frustrated Lewis Pair Surfaces

Hydrogen (H2) is widely used as a reductant for many hydrogenation reactions; however, it has not been recognized as a catalyst for the acid transformation of active sites on solid surface. Here, we report the H2-promoted hydration of alkenes (such as styrenes and cyclic alkenes) and epoxy alkanes over single-atom Co-dispersed nitrogen-doped carbon (Co-NC) via a transformation mechanism of acid-base sites. Specifically, the specific catalytic activity and selectivity of Co-NC are superior to those of classical solid acids (acidic zeolites and resins) per micromole of acid, whereas the hydration catalysis does not take place under a nitrogen atmosphere. Detailed investigations indicate that H2 can be heterolyzed on the Co-N bond to form Hδ-Co-N-Hδ+ and then be converted into OHδ-Co-N-Hδ+ accompanied by H2 generation via a H2O-mediated path, which significantly reduces the activation energy for hydration reactions. This work not only provides a novel catalytic method for hydration reactions but also removes the conceptual barriers between hydrogenation and acid catalysis.