(S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid

Base Information

• Chemical Name: (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
• CAS No.: 17257-71-5
• Molecular Formula: C10H9 F3 O3
• Molecular Weight: 234.1719
• Hs Code.: 29189900
• European Community (EC) Number: 241-292-1
• UNII: 172HCJ1IQV
• DSSTox Substance ID: DTXSID80897011
• Nikkaji Number: J66.198H
• Wikidata: Q27251856
• Mol file: 17257-71-5.mol

Synonyms:17257-71-5;(S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid;(S)-3,3,3-Trifluoro-2-methoxy-2-phenylpropanoic acid;(-)-Mosher's Acid;(2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid;(-)-Mtpa;(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid;(s)-mtpa;UNII-172HCJ1IQV;172HCJ1IQV;EINECS 241-292-1;(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid;C10H9F3O3;alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, (-)-;Benzeneacetic acid, .alpha.-methoxy-.alpha.-(trifluoromethyl)-, (.alpha.S)-;C10-H9-F3-O3;(S)-(-)-MTPA;(+)-MTPA' Mosher's acid;SCHEMBL246914;(-)-A-Methoxy-A-(trifluoromethyl)phenylacetic acid;(S)-(-)-MOSHER ACID;DTXSID80897011;(-)-(S)-MTPA;CS-DA-00617;STR04436;MFCD00064200;AKOS005254536;AKOS015888435;CS-W014166;PS-6677;SB34237;M0832;MOSHER'S REAGENT (S)-(-)-FORM [MI];T71917;(-)-a-methoxy-a-trifluoromethylphenylacetic acid;A811432;(S)-(-)-methoxy(trifluoromethyl)phenyl-acetic acid;J-010831;Q27251856;(-)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid;Benzeneacetic acid, a-methoxy-a-(trifluoromethyl)-, (aS)-;(2S)-(-)-2-Methoxy-2-phenyl-3,3,3-trifluoropropanoic acid;(S)-(-)-alpha-Methoxy-alpha-trifluoromethyl-phenylacetic acid;(S)-(-)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid;(R)-(+)- alpha -Methoxy- alpha -trifluoromethylphenylacetic acid;(S)-(-)- alpha -Methoxy- alpha -(trifluoromethyl)phenylacetic acid;(S)-(-)-3,3,3-TRIFLUORO-2-PHENYL-2-METHOXYPROPANOIC ACID;(S)-(-)-alpha-methoxy-alpha-(trifluoromethyl) phenylacetic acid;(s)-(-)-alpha-methoxy-alpha-(trifluoromethyl)-phenylacetic acid;(-)-.ALPHA.-METHOXY-.ALPHA.-(TRIFLUOROMETHYL)PHENYLACETIC ACID;(S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid, >=99%;.ALPHA.-METHOXY-.ALPHA.-TRIFLUOROMETHYLPHENYLACETIC ACID, (-)-;(S)-(-)-.BETA.,.BETA.,.BETA.-TRIFLUORO-.ALPHA.-METHOXYHYDRATROPIC ACID;(S)-(-)-ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)PHENYLACETIC ACID [OPTICAL RESOLVING];(S)-(-)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, for chiral derivatization, >=99.0%

Chemical Property of (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid

Chemical Property:

• Vapor Pressure: 0.00117mmHg at 25°C
• Melting Point: 46-49 °C(lit.)
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 95-97 °C0.05 mm Hg(lit.)
• PKA: 1.47±0.10(Predicted)
• Flash Point: 113 ºC
• PSA: 46.53000
• Density: 1.303
• LogP: 2.17520
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Readily soluble in hexane, ether, THF, CH2Cl2, benzene.
• 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

(S)-(?)-α-Methoxy-α-trifluoromethylphenylacetic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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: (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid is used as a chiral derivatizing agent, it reacts with an alcohol or amine of unknown stereochemistry to form an ester or amide. The absolute configuration of the ester or amide is then determined by proton and/or 19F NMR spectroscopy.

Technology Process of (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid

There total 32 articles about (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic 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: 80.0%

(S,R)-4-phenyl-3-(2-methoxy-2-phenyl-2-trifluoromethyl-acetyl)oxazolidin-2-one (1044204-03-6) → C18H18F3NO3 (1044204-62-7) + (S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6) + (4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2008.04.032

Reference yield: 78.0%

(S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanol (52356-17-9) → (S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6)

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:

MTPA (20445-31-2,56135-03-6,81655-41-6,17257-71-5) → R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2) + (S)-Mosher acid (17257-71-5,20445-31-2,56135-03-6,81655-41-6)

Guidance literature:

MTPA; With (1S,2R)-1-amino-2-indanol; In ethanol; ethyl acetate; at 30 ℃; for 12h;

With hydrogenchloride; Further stages.;

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 (S)-1-ethynyl-hexyl ester

(S)-1-(3,6-Dihydro-2H-pyridin-1-yl)-3,3,3-trifluoro-2-methoxy-2-phenyl-propan-1-one

(S)-α-methoxy-N-<(S)-1-phenylethyl>-α-(trifluoromethyl)benzeneacetamide

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (7S,8S)-8-hydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-7-yl ester

Refernces

• 1、 Ishii, Akihiro,Kanai, Masatomi,Yasumoto, Manabu,Inomiya, Kenjin,Kuriyama, Yokusu,Katsuhara, Yutaka. "Synthetic application of 3,3-dichloro-1, 1, 1-trifluoroacetone (DCTFA) and 3,3,3-trichloro-1, 1, 1-trifluoroacetone (TCTFA) for trifluorolactic acid derivatives". . p. 567 - 571. Retrieved 2007/10/03.
• 2、 Buszek, Keith R.,Sato, Nagaaki. "An improved synthesis of α-methoxy-α-(trifluoromethyl)-phenylacetic acid (Mosher's acid)". . p. 488 - 490. Retrieved 2007/10/03.