(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid

Base Information

• Chemical Name: (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid
• CAS No.: 20445-31-2
• Molecular Formula: C10H9F3O3
• Molecular Weight: 234.175
• Hs Code.: 29189900
• European Community (EC) Number: 243-829-5
• UNII: 27O5L9T1WM
• DSSTox Substance ID: DTXSID10897009
• Nikkaji Number: J66.197J
• Wikidata: Q27254219
• Mol file: 20445-31-2.mol

Synonyms:20445-31-2;(2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid;(+)-Mtpa;(R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid;(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid;(+)-Mosher's Acid;(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid;(R)-MTPA;UNII-27O5L9T1WM;(r)-(+)-a-methoxy-a-trifluoromethylphenylacetic acid;27O5L9T1WM;EINECS 243-829-5;C10H9F3O3;(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid;alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, (+)-;C10-H9-F3-O3;Moshers's acid;(R)-MOSHER ACID;(R)-(+)-Mosher's acid;SCHEMBL236358;(R)-(+)-MTPA ACID;(R)-(+)-MOSHER ACID;DTXSID10897009;(R)-(+)-alpha-Methoxy-alpha-trifluoromethyl-phenylacetic acid;(R)-(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic Acid;AMY32681;MFCD00004184;AKOS005254473;SB35195;BP-12316;M0831;MOSHER'S REAGENT (R)-(+)-FORM [MI];T72051;A814569;(+)-A-Methoxy-A-(trifluoromethyl)phenylacetic acid;J-013327;(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoicacid;Q27254219;(+)-alpha-methoxy-alpha-trifluoromethylphenylacetic acid;Benzeneacetic acid, a-methoxy-a-(trifluoromethyl)-, (aR)-;(2R)-(+)-2-Methoxy-2-phenyl-3,3,3-trifluoropropanoic acid;(R)-(+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid;r-(+)-alpha-methoxy-alpha-(trifluoromethyl)phenyl acetic acid;r-(+)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid;(R)-(+)-3,3,3-TRIFLUORO-2-PHENYL-2-METHOXYPROPANOIC ACID;(R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, 99%;(R)-(+)-.ALPHA.-METHOXY-.ALPHA.-(TRIFLUOROMETHYL)PHENYLACETIC ACID;.ALPHA.-METHOXY-.ALPHA.-TRIFLUOROMETHYLPHENYLACETIC ACID, (+)-;(R)-(+)-ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)PHENYLACETIC ACID [OPTICAL RESOLVING];BENZENEACETIC ACID, .ALPHA.-METHOXY-.ALPHA.-(TRIFLUOROMETHYL)-, (.ALPHA.R)-;(R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, for chiral derivatization, >=99.0%

Chemical Property of (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid

Chemical Property:

• Vapor Pressure: 0.164mmHg at 25°C
• Melting Point: 46-49 °C(lit.)
• Refractive Index: n20/D 1.473(lit.)
• Boiling Point: 287.226 °C at 760 mmHg
• PKA: 1.47±0.10(Predicted)
• Flash Point: 134.154 °C
• PSA: 46.53000
• Density: 1.35 g/cm³
• LogP: 2.17520
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Soluble in methanol (50 mg/ 1 ml).
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 234.05037863
• Heavy Atom Count: 16
• Complexity: 259

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-α-Methoxy-α-(trifluoromethyl)phenylaceticacid[OpticalResolving],98%(GC)(T) 98%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(C1=CC=CC=C1)(C(=O)O)C(F)(F)F
• Isomeric SMILES: CO[C@](C1=CC=CC=C1)(C(=O)O)C(F)(F)F
• Uses: (R)-(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid is widely used reagent for determination of optical purities of alcohols and amines by 1H or 19F NMR. Mosher′s acid chloride is used as a dervatization agent for β-arylethylamines, enantiomeric alcohols, and enantiomeric amines. It is also a reagent used for the determination of enantiomeric purity and absolute configuration of alcohols and amines by NMR.

Technology Process of (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid

There total 64 articles about (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic 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%

C26H31F3O3 → R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2) + (-)-8-phenylmenthol (65253-04-5)

Guidance literature:

With potassium hydroxide; In methanol; at 70 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b01517

Reference yield: 82.0%

(R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanol (537695-87-7) → R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; acetonitrile; at 55 ℃; for 4h;

DOI:10.1016/S0957-4166(03)00023-5

Reference yield: 64.0%

(+)-(R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionaldehyde → R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In diethyl ether; water; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.5b03412

upstream raw materials:

methanol

α-(Chlordifluormethyl)-α-(trifluormethyl)-benzylalkohol

Trimethyl-(2,2,2-trichloro-1-phenyl-1-trifluoromethyl-ethoxy)-silane

α-methoxy-α-trifluoromethyl-phenyl-acetonitrile

Downstream raw materials:

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,4S)-4-acetoxy-cyclopent-2-enyl ester

(R)-3,3,3-Trifluoro-N-((R)-2-hydroxy-1-methyl-ethyl)-2-methoxy-2-phenyl-propionamide

Refernces

• 1、 Wang, Pan,Feng, Liang-Wen,Wang, Lijia,Li, Jun-Fang,Liao, Saihu,Tang, Yong. "Asymmetric 1,2-Perfluoroalkyl Migration: Easy Access to Enantioenriched α-Hydroxy-α-perfluoroalkyl Esters". supporting information. p. 4626 - 4629. Retrieved 2015/04/27.
• 2、 Chavda, Sameer,Coulbeck, Elliot,Dingjan, Marco,Eames, Jason,Motevalli, Majid. "Probing the parallel resolution of Mosher's acid using a combination of quasi-enantiomeric oxazolidin-2-ones". . p. 1274 - 1284. Retrieved 2008/12/20.