1475-11-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(3,4-DICHLOROPHENYL)ETHANOL, 97 is used as a synthetic intermediate for the production of various drugs and pharmaceuticals, contributing to the development of new chemical compounds in research and development settings. Its role in the synthesis process is vital for creating effective medications.

InChI:InChI=1/C8H8Cl2O/c1-5(11)6-2-3-7(9)8(10)4-6/h2-5,11H,1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 555-31-7 aluminum isopropoxide 
• 2642-63-9 3',4'-dichloroacetophenone 
• 52909-94-1 2-(3,4-dichlorophenyl)oxirane 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 75-16-1 methylmagnesium bromide 
• 95-50-1 1,2-dichloro-benzene 

Downstream Products

• 2642-63-9 3',4'-dichloroacetophenone 
• 2039-83-0 3,4-dichlorostyrene 
• 820260-69-3 1-(3,4-dichlorophenyl)ethyl 2,2,2-trichloroacetimidate 
• 459451-08-2 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(3,4-dichlorophenyl)-ethyl ester 
• 872181-29-8 2-[1-(3,4-dichlorophenyl)-ethoxy]-6-fluorobenzonitrile 
• 338776-97-9 3-(chloromethyl)-5-(3,4-dichlorophenyl)isoxazole 
• 93618-67-8 ethyl 4-(3,4-dichlorophenyl)-2,4-dioxobutanoate 
• 192702-37-7 4-(1-bromoethyl)-1,2-dichlorobenzene 
• 52909-94-1 2-(3,4-dichlorophenyl)oxirane 

Relevant academic research and scientific papers

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.

Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes

We utilized acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD), wild type and Trp288Ala mutant, to reduce halogenated acetophenone analogs to their corresponding (S)- and (R)-alcohols beneficial as pharmaceutical intermediates. Reduction by wild type resulted in excellent (S)-enantioselectivity for all of the substrates tested. Meanwhile, reduction by Trp288Ala resulted in high (R)-enantioselectivity for the reduction of 4′ substituted acetophenone and 2′-trifluoromethylacetophenone. In addition to that, we were able to control the enantioselectivity of Trp288Ala by the positions and sizes of the halogen substituents.

Method for synthesizing secondary alcohol

The invention discloses a method for synthesizing secondary alcohol, which utilizes transition metal catalysis and uses isopropanol as a hydrogen source to synthesize the secondary alcohol. The reaction not only uses inexpensive and environmentally friendly isopropanol as the hydrogen source and a solvent, but also has the advantages of high yield, environmental protection, and the like, and therefore the reaction has broad development prospects.

Ambient-pressure hydrogenation of ketones and aldehydes by a metal-ligand bifunctional catalyst [Cp*Ir(2,2′-bpyO)(H2O)] without using base

An efficient catalytic system for hydrogenation of ketones and aldehydes using a Cp*Ir complex [Cp*Ir(2,2′-bpyO)(H2O)] bearing a bipyridine-based functional ligand as catalyst has been developed. A wide variety of secondary and primary alcohols were synthesized by the catalyzed hydrogenation of ketones and aldehydes under facile atmospheric-pressure without a base. The catalyst also displays an excellent chemoselectivity towards other carbonyl functionalities and unsaturated motifs. This catalytic system exhibits high activity for hydrogenation of ketones and aldehydes with H2 gas.

Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators

Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.

Heterogenization of cobalt nanoparticles on hollow carbon capsules: Lab-in-capsule for catalytic transfer hydrogenation of carbonyl compounds

Incorporation of cobalt nanoparticles (Co NPs) in porous iron oxide nanospheres (Fe3O4 NSs) templated, glucose derived hollow carbon capsules (HCCs), with an objective to achieve activity and stability simultaneously, facilitates higher catalytic activity of Co NPs in transfer hydrogenation of ketones and aldehydes. A variety of ketones and aldehydes are hydrogenated successfully with excellent yields and high turnover number (TON). This system constitutes one of the most general, heterogeneous, highly stable catalyst, which does not require additives for activation and employs mild reaction conditions. Other significant advantages are low Co content (0.38 mol%) for a catalytic hydrogenation reaction, functional-group tolerance, inexpensive, environmentally benign nature and reusability.

A comparative study on asymmetric reduction of ketones using the growing and resting cells of marine-derived fungi

Whole-cell biocatalysts offer a highly enantioselective, minimally polluting route to optically active alcohols. Currently, most of the whole-cell catalytic performance involves resting cells rather than growing cell biotransformation, which is one-step process that benefits from the simultaneous growth and biotransformation, eliminating the need for catalysts preparation. In this paper, asymmetric reduction of 14 aromatic ketones to the corresponding enantiomerically pure alcohols was successfully conducted using the growing and resting cells of marine-derived fungi under optimized conditions. Good yields and excellent enantioselectivities were achieved with both methods. Although substrate inhibition might be a limiting factor for growing cell biotransformation, the selected strain can still completely convert 10-mM substrates into the desired products. The resting cell biotransformation showed a capacity to be recycled nine times without a significant decrease in the activity. This is the first study to perform asymmetric reduction of ketones by one-step growing cell biotransformation.

GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein A, R, W, Q, n and m have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.

Reduction of acetophenones using Borohydride Exchange Resins (BER) and a BER-Lithium salt system

Borohydride reduction of acetophenones was carried out with the borohydride-form of an anion exchange polystyrene-divinylbenzene resin. High yields were achieved and reaction rates were significantly increased by the addition of LiNO3, LiCl, LiBr or LiI without decreasing yield.

N-hydroxyalkyl derivatives of 3β-phenyltropane and 1-methylspiro[1H- indoline-3,4'-piperidine]: Vesamicol analogues with affinity for monoamine transporters

As part of our ongoing structure-activity studies of the vesicular acetylcholine transporter ligand 2-(4-phenylpiperidino)cyclohexanol [vesamicol, 1), 22 N-hydroxy(phenyl)alkyl derivatives of 3β-phenyltropane, 6, and 1-methylspiro[1H-indoline-3,4'-piperidine], 7, were synthesized and tested for binding in vitro. Although a few compounds displayed moderately high affinity for the vesicular acetylcholine transporter, no compound was more potent than the prototypical vesicular acetylcholine transporter ligand vesamicol. However, a few derivatives of 6 displayed higher affinity for the dopamine transporter than cocaine. We conclude that modification of the piperidyl fragment of 1 will not lead to more potent vesicular acetylcholine transporter ligands.