877397-65-4

Basic information

• Product Name: (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol
• Synonyms: BenzeneMethanol,2,6-dichloro-3-fluoro-a-Methyl-, (aS)-;(1S)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol;(S)-1-(2,6-dichloro-4-fluorophenyl)ethanol;(1S)-1-(2,6-Dichloro-3-fluorophenyl)ethane-1-ol;(aS)-2,6-Dichloro-3-fluoro-a-methyl-benzenemethanol;-1-(2,6-Dichloro-3-fluorophenyl);(S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol;(S)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol
• CAS NO: 877397-65-4
• Molecular Formula: C₈H₇Cl₂FO
• Molecular Weight: 209.04
• EINECS: 1308068-626-2
• Product Categories: Aromatic Ring;Chiral Compounds
• Mol File: 877397-65-4.mol

Chemical Properties

• Boiling Point: 261.329 °C at 760 mmHg
• Flash Point: 111.848 °C
• Appearance: White/Solid
• Density: 1.407 g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: 2-8°C
• PKA: 13.30±0.20(Predicted)
• CAS DataBase Reference: (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol(877397-65-4)
• EPA Substance Registry System: (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol(877397-65-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 877397-65-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol is used as an intermediate in the synthetic preparation of Crizotinib (C785000), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK). Crizotinib is a potential antitumor agent, making this intermediate essential for the development of cancer treatments.
Additionally, (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol is utilized in the synthesis of (R)-3-[l-(2,6-dichloro-3-fluoro-benzene)-ethoxy-5-(l-piperidine-4-hydroxy-1 hydrogen-pyrazole-4-hydroxy)-pyrimidine-2-indane, a small molecule kinase inhibitor. (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol is specifically designed for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) that is positive for anaplastic lymphohematokinase (ALK), further highlighting the importance of (S)-1-(2,6-Dichloro-3-fluorophenyl)ethanol in the development of targeted cancer therapies.

InChI:InChI=1/C8H7Cl2FO/c1-4(12)7-5(9)2-3-6(11)8(7)10/h2-4,12H,1H3/t4-/m0/s1

Upstream product

• 877397-68-7 (1S)-1-(2,6-dichloro-3-fluorophenyl)ethyl acetate 
• 756520-66-8 1-(2,6-dichloro-3-fluorophenyl)ethanol 
• 290835-85-7 2',6'-dichloro-3'-fluoroacetophenone 
• 877397-67-6 1-(2,6-dichloro-3-fluorophenyl)ethyl acetate 
• 330156-50-8 (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol 
• 877399-98-9 C₉H₉Cl₂FO₃S 
• 141-78-6 ethyl acetate 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 877397-70-1 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine 
• 1175296-50-0 (1S)-1-(2,6-dichloro-3-fluorophenyl)ethyl methanesulfonate 
• 1236301-32-8 C₁₇H₁₁BrCl₂FNO 
• 877397-71-2 (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-aminopyridine 
• 877399-52-5 crizotinib 
• 1332837-62-3 1-benzenesulfonyl-7-chloro-4-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-nitro-1H-pyrrolo[2,3-c]pyridine 
• 1332837-57-6 C₂₀H₁₇Cl₃FN₃O₅ 

Relevant articles and documents

Biotransformation of a crizotinib intermediate using a mutant alcohol dehydrogenase of Lactobacillus kefir coupled with glucose dehydrogenase

(S)-1-(2, 6-dichloro-3-fluorophenyl) ethanol, the key chiral intermediate of crizotinib, was prepared from 1-(2, 6-dichloro-3-fluorophenyl) ethanone using the alcohol dehydrogenases from Lactobacillus kefir (ADH-LK) with a tetrad mutant (ADH-LKM, F147L/Y1

Abiotic reduction of ketones with silanes catalysed by carbonic anhydrase through an enzymatic zinc hydride

Enzymatic reactions through mononuclear metal hydrides are unknown in nature, despite the prevalence of such intermediates in the reactions of synthetic transition-metal catalysts. If metalloenzymes could react through abiotic intermediates like these, then the scope of enzyme-catalysed reactions would expand. Here we show that zinc-containing carbonic anhydrase enzymes catalyse hydride transfers from silanes to ketones with high enantioselectivity. We report mechanistic data providing strong evidence that the process involves a mononuclear zinc hydride. This work shows that abiotic silanes can act as reducing equivalents in an enzyme-catalysed process and that monomeric hydrides of electropositive metals, which are typically unstable in protic environments, can be catalytic intermediates in enzymatic processes. Overall, this work bridges a gap between the types of transformation in molecular catalysis and biocatalysis. [Figure not available: see fulltext.]

Preparation method of deuterated crizotinib and derivatives thereof

The invention relates to a preparation method of deuterated crizotinib and derivatives thereof, and belongs to the technical field of synthesis of medical compounds. Four deuterated crizotinib with different configurations are synthesized, the influence of the deuterated position and different chirality of the deuterated crizotinib on the biological activity and the drug metabolism property of thecrizotinib is investigated, and the result shows that the deuterated crizotinib and the crizotinib have similar anti-cancer activity. Compared with a deuterated crizotinib raceme and crizotinib, thedeuterated crizotinib has certain physicochemical property advantages, has good anticancer application prospects, and provides a new compound for synthesis of novel antitumor drugs. The resolution ofthe racemate phenylethanol derivative is a key step for synthesizing the deuterated crizotinib, the ee value of the racemate phenylethanol derivative directly influences the ee value of a final product, and the resolution method has the characteristics of easiness in operation, low cost and the like.

Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand

A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable 'side arm' groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5percent ee). This protocol features wide substrate scope and functional group tolerance, thereby providing easy access to a key intermediate of crizotinib.

Synthesis method of (S)-1-(2, 6-dichloro-3-fluorophenyl)-ethanol

The invention relates to a synthesis method of (S)-1-(2, 6-dichloro-3-fluorophenyl)-ethanol. The synthesis method comprises the following steps: mixing 2, 6-dichloro-3- fluoroacetophenone, a chiral catalyst, alkali and a solvent, and carrying out a reacti

Chiral ferrocene phosphine-nitrogen-nitrogen tridentate ligand as well as preparation method and application thereof

The invention discloses a chiral ferrocene phosphine-nitrogen-nitrogen tridentate ligand as well as a preparation method and an application thereof. The general structural formula of the chiral ferrocene phosphine-nitrogen-nitrogen tridentate ligand is shown in formula (I) or formula (II), wherein R1 and R2 are independently selected from C1-C6 alkyl, C3-C6 cycloalkyl, aryl or heterocyclic aryl respectively; R3 is aryl, heterocyclic aryl or C1-C6 alkyl, and R4 is hydrogen, C1-C6 alkyl, aryl or heterocyclic aryl; the general structural formula in the formula (I) and the formula (II) contains animidazole group or a substituted benzimidazole group respectively; one or more substituent groups exist on a benzene ring of the substituted benzimidazole group, and each substituent group is independently selected from H or C1-C4 alkyl. The chiral ferrocene phosphine-nitrogen-nitrogen tridentate ligand has the advantages that the tridentate ligand is convenient to synthesize, exists in the air stably and can be coordinated with cheap metal to prepare a cheap metal catalyst, and the cheap metal catalyst is well applied to asymmetric hydrogenation reactions of ketone.

Towards practical earth abundant reduction catalysis: Design of improved catalysts for manganese catalysed hydrogenation

Manganese catalysts derived from tridentate P,N,N ligands can be activated easily using weak bases for both ketone and ester hydrogenations. Kinetic studies indicate the ketone hydrogenations are 0th order in acetophenone, positive order in hydrogen and 1st order in the catalyst. This implies that the rate determining step of the reaction was the activation of hydrogen. New ligand systems with varying donor strength were studied and it was possible to make the hydrogen activation significantly more efficient; a catalyst displaying around a 3-fold increase in initial turn-over frequencies for the hydrogenation of acetophenone relative to the parent system was discovered as a result of these kinetic investigations. Ester hydrogenations and ketone transfer hydrogenation (isopropanol as reductant) are first order for both the substrate and catalysts. Kinetic studies also gained insight into catalyst stability and identified a working range in which the catalyst is stable throughout the catalytic reaction (and a larger working range where high yields can still be achieved). The new more active catalyst, combining an electron-rich phosphine with an electron-rich pyridine is capable of hydrogenating acetophenone using as little as 0.01 mol% catalyst at 65 °C. In all, protocols for reduction of 21 ketones and 15 esters are described.

MANUFACTURING METHOD OF OPTICAL ACTIVE SECONDARY ALCOHOL

PROBLEM TO BE SOLVED: To provide a method for manufacturing optical active secondary alcohol with high optical purity by hydrogenating a substrate carbonyl compound using a ruthenium complex with a specific optical active diphosphine compound and an amine compound of which synthesis is easy as ligands as a catalyst. SOLUTION: The manufacturing method of optical active secondary alcohol including reacting a substrate carbonyl compound (excluding 3-quinuclidinone, a 3-quinuclidinone derivative having a substituent, and ketone having an aromatic hydrocarbon group and a heterocycle) with hydrogen and/or a hydrogen-donating compound in a presence of a ruthenium complex selected from a compound represented by the following general formula (1) RuXYAB (1) [X and Y are same or different, represent a hydrogen atom or an anionic group, A represents optical active diphosphine represented by the general formula (2), and B represents an amine compound represented by the following general formula (3)]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT

Method for preparing crizotinib intermediate by using immobilized chiral catalyst

The invention relates to a method for preparing a crizotinib intermediate by using an immobilized chiral catalyst. The method can effectively solve the problems that according to existing methods, thematerial consumption is high, the cost is high and cata