(1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid

Base Information

• Chemical Name: (1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid
• CAS No.: 220352-36-3
• Molecular Formula: C10H8F2O2
• Molecular Weight: 198.169
• Hs Code.: 2916200090
• DSSTox Substance ID: DTXSID60431457
• Nikkaji Number: J2.688.118H
• Mol file: 220352-36-3.mol

Synonyms:220352-36-3;(1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid;(1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carboxylic Acid;trans-2-(3,4-Difluoro-phenyl)-cyclopropanecarboxylic acid;1006614-50-1;trans-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid;(1R,2R)-2-(3,4-Difluorophenyl)-cyclopropanecarboxylic Acid;MFCD22201080;SCHEMBL248384;AMY3283;DTXSID60431457;CS-M1813;Cyclopropanecarboxylic acid, 2-(3,4-difluorophenyl)-, (1R,2R)-;AC9689;AKOS016844814;CS-14545;EN300-1655713;trans-2-(3,4-Difluorophenyl)cyclopropanecarboxylicacid;Z2307311644;(1R,2R)-2-(3,4-Difluorophenyl) Cyclopropane Carboxylic Acid;(1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid;(1R,2R)-2-(3,4-Difluorophenyl)Cyclopropane Carboxylic Acid;rac-(1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carboxylic acid;(1r,2s)-2-(3,4-difluorophenyl)cyclopropanaminium (2r)hydroxy(phenyl)ethanoate

Chemical Property of (1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid

Chemical Property:

• Boiling Point: 308.1±42.0 °C(Predicted)
• PKA: 4.53±0.10(Predicted)
• PSA: 37.30000
• Density: 1.435±0.06 g/cm3(Predicted)
• LogP: 2.15290
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 198.04923582
• Heavy Atom Count: 14
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

(1R,2R)-2-(3,4-Difluorophenyl)-cyclopropanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1C(=O)O)C2=CC(=C(C=C2)F)F
• Isomeric SMILES: C1[C@H]([C@@H]1C(=O)O)C2=CC(=C(C=C2)F)F
• Uses: (1R,2R)-2-(3,4-Difluorophenyl)-cyclopropanecarboxylic Acid is an intermediate used to prepare AZD6140 as an orally active reversible P2Y12 receptor antagonist for prevention of thrombosis. It is also used to synthesize triazolopyrimidine derivatives as P2T receptor antagonists.

Technology Process of (1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid

There total 25 articles about (1R,2R)-2-(3,4-Difluorophenyl)cyclopropanecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

[3aS-[1(1R,2R),3a,6,7a]]-1-[[2-(3,4-difluorophenyl)cyclopropyl]carbonyl]-hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide → trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid (220352-36-3,1006614-50-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/j.bmcl.2007.07.057

Reference yield: 98.1%

(4R,5R)-2-[(1R,2R)-2-(3,4-difluorophenyl)cyclopropyl]-1,3-dioxolane-4,5-dicarboxylic acid diisopropyl ester → trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid (220352-36-3,1006614-50-1)

Guidance literature:

With Jones reagent; In acetone; at 0 - 5 ℃;

Reference yield: 98.0%

(1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester (1006376-61-9) → trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid (220352-36-3,1006614-50-1)

Guidance literature:

(1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester; With methanol; sodium hydroxide; water; In toluene; at 65 ℃; for 2h;

With hydrogenchloride; In water; toluene;

upstream raw materials:

(1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester

(E)-3-(3,4-difluorophenyl)acrylic acid

3,4-difluorocinnamoyl chloride

3,4 difluorobenzaldehyde

Downstream raw materials:

trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl chloride

(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine

[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

Refernces

• 1、 -. "Preparation method of ticagrelor key intermediate". Paragraph 0044-0050. . Retrieved 2021/05/29.
• 2、 -. "Method for synthesizing (1R,2R)-2-(3,4-difluorophenyl)cyclopropane-carboxylic acid". Paragraph 0025-0049. . Retrieved 2019/06/05.