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

Description

(1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol, also known as (S)-2-Chloro-1-(3,4-difluorophenyl)ethanol, is an organic compound with a chloro and difluorophenyl group attached to an ethanol molecule. It is characterized by its unique chemical structure and properties, making it a versatile compound in various applications.

Uses

Used in Pharmaceutical Industry:
(1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol is used as a building block in organic synthesis for the development of new pharmaceutical compounds. Its application is particularly significant in the synthesis of Ticagrelor (T437700), which is the first reversible oral P2Y12 receptor antagonist. Ticagrelor provides faster, greater, and more consistent ADP-receptor inhibition compared to Clopidogrel, making it a valuable addition to the treatment of cardiovascular conditions.

Upstream product

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

Downstream Products

• 1006376-63-1 (S)-2-(3,4-difluorophenyl)ethylene oxide 
• 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 

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.

Preparation method of ticagrelor

The invention discloses a preparation method of ticagrelor. The preparation method comprises the following steps: (1) preparation of ticagrelor intermediate product 1-TK acid; (2) preparation of ticagrelor intermediate product 2-TK-amide; (3) preparation of ticagrelor intermediate product 3-TK-amino compound hydrochloride; (4) preparation of ticagrelor intermediate product 4-TK-amino compound R-tartrate; ( 5) preparation of ticagrelor intermediate product 5-TK-amino compound L-mandelate; and (6) preparation of ticagrelor-TK. The preparation method has the advantages of cost advantage, mature and stable process, stable product quality, and safe and reliable production process.