1006376-60-8

Basic information

• Product Name: (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol
• Synonyms: (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol;(1S)-2-Chloro-1-(3,4-difluorophenyl)ethan-1-ol;(alphaS)-alpha-(Chloromethyl)-3,4-difluorobenzenemethanol;Benzenemethanol, α-(chloromethyl)-3,4-difluoro-, (αS)-;Benzenemethanol, α-(chloromethyl)-3,4-difluoro-
• CAS NO: 1006376-60-8
• Molecular Formula: C₈H₇ClF₂O
• Molecular Weight: 192.5903864
• Mol File: 1006376-60-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 256.3±35.0 °C(Predicted)
• Appearance: /
• Density: 1.372±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 12.49±0.20(Predicted)
• CAS DataBase Reference: (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol(1006376-60-8)
• EPA Substance Registry System: (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol(1006376-60-8)

Safety Data

• Hazardous Substances Data: 1006376-60-8(Hazardous Substances Data)

Usage

Uses

(S)-2-Chloro-1-(3,4-difluorophenyl)ethanol is a building block used in organic synthesis including bein an intermediate in the synthesis of Ticagrelor (T437700), the first reversible oral P2Y12 receptor antagonist, provides faster, greater, and more consistent ADP-receptor inhibition than Clopidogrel.

Upstream product

• 51336-95-9 2-chloro-1-(3,4-difluorophenyl)ethan-1-one 
• 367-11-3 ortho-difluorobenzene 

Downstream Products

• 1006376-61-9 (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester 
• 220352-36-3 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid 
• 1006614-49-8 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine 
• 274693-27-5 ticagrelor 
• 220347-05-7 AR-C₁₂₄₉₁₀XX 
• 274693-49-1 (3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 1381841-44-6 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy) thyl carbonate 
• 1381841-46-8 2-((1S,2S,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl)oxy)ethyl isobutyl carbonate 
• 1381841-52-6 (1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl butyrate 
• 1381841-55-9 (1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl ethyl carbonate 
• 1381841-56-0 (1S,2S,3S,4R)-4-(7-((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino-5-propylthio-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,3-dihydroxycyclopentyl isobutyl carbonate 
• 274693-26-4 [3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol 
• 376608-70-7 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl chloride 
• 1006376-62-0 (1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide 

Relevant articles and documents

Development of a Practical Enzymatic Process for Preparation of (S)-2-Chloro-1-(3,4-difluorophenyl)ethanol

(S)-2-Chloro-1-(3,4-difluorophenyl)ethanol (1) is a vital chiral intermediate for the synthesis of Ticagrelor - an effective treatment for acute coronary syndromes. A ketoreductase (KRED) KR-01 in our KRED library was screened to transform 2-chloro-1-(3,4

Ketone Reductase Biocatalysis in the Synthesis of Chiral Intermediates Toward Generic Active Pharmaceutical Ingredients

A range of generic active pharmaceutical ingredients were examined for potential chiral alcohol motifs and derivatives within their structures that could be employed as key synthetic intermediates. For seven generic active pharmaceutical ingredients (APIs), eight precursor ketones were acquired and then subjected to reduction by >400 commercially available ketone reductases from different suppliers. Positive screening results were achieved for five ketones screened, with multiple ketone reductases available for each successful ketone. Selectivity was typically >99.5% ee in most cases, including for the opposite enantiomer. The three best examples were then optimized and quickly scaled up to 1 L scale in high conversion and isolated yield while retaining selectivity of >99.5% ee for the desired chiral alcohol enantiomer. This work illustrates that where a wide range of enzymes are available, productive enzymes to give either alcohol enantiomer can be readily identified for many ketones and rapidly scaled up to produce chiral alcohols. This approach is particularly applicable to generating chiral API intermediates.

Method for preparing ticagrelor intermediate

The invention discloses a method for preparing a ticagrelor intermediate. The method comprises the following steps: taking o-difluorobenzene and chloroacetyl chloride as initial raw materials, carrying out an F-K reaction, a bio-enzyme fermentation technology asymmetric reduction reaction, a ring-closure reaction and a cyclopropanation reaction, so as to obtain the key intermediate (1R, 2R)-2-(3,4-difluorophenyl) cyanocyclopropane carboxylate of the ticagrelor at high yield, high enantioselectivity and high purity. The method can realize industrialized production. The method is low in energy consumption, less in pollution, green, clean, high in yield and high in purity, the cost is reduced, the product quality is stable, and the method is suitable for large-scale stable industrial production.