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

• ChemBase ID: 10382
• Molecular Formular: C10H9F3O3
• Molecular Mass: 234.1718696
• Monoisotopic Mass: 234.05037881
• SMILES: c1cccc(c1)C(C(=O)O)(C(F)(F)F)OC
• Canonical SMILES: COC(C(F)(F)F)(c1ccccc1)C(=O)O
• InChI: InChI=1S/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15)
• InChIKey: JJYKJUXBWFATTE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid; (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid; 3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid
• IUPAC Traditional name: (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid; (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid; mosher's acid
• Synonyms: (+/-)-Mosher's acid; (+/-)-MTPA; (±)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid; (+/-)-1-Methoxy-1-(trifluoromethyl)phenylacetic acid 98%; (S)-(-)-α-Methoxy-α-trifluoromethylphenylacetic acid; α-Methoxy-α-(trifluoromethyl)phenylacetic acid; (+)-MTPA; (R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid; [+]-MTPA; (+)-α-METHOXY-α-TRIFLUOROMETHYLPHENYL-ACETIC ACID; Methoxy(trifluoromethyl)phenylacetic acid; MTPA; Mosher's acid; Mosher′s acid; (±)-α-Methoxy-α-trifluoromethylphenylacetic acid; (-)-MTPA; Mosher’s acid; (S)-(-)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid; (±)-α-Methoxy-α-trifluoromethylphenylacetic acid; (+/-)-a-甲氧基-α-(三氟甲基)苯乙酸; (S)-(-)-α-甲氧基-α-三氟甲基苯乙酸; α-甲氧基-α-(三氟甲基)苯乙酸; (R)-(+)-α-甲氧基-α-三氟甲基苯乙酸; (±)-α-甲氧基-α-三氟甲基苯乙酸; Mosher 酸; (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸

Database IDs

• CAS Number: 81655-41-6; 17257-71-5; 56135-03-6; 20445-31-2
• EC Number: 241-292-1; 000-000-0; 243-829-5
• MDL Number: MFCD00004184; MFCD00064200; MFCD00066637
• Beilstein Number: 4684048; 3591560; 2215439
• PubChem SID: 24849618; 24883972; 24859111; 160973689; 24883982; 24849508; 24883979; 24883971
• PubChem CID: 86531
• Wikipedia Title: Mosher's_acid

CALCULATED PROPERTIES

• Acid pKa: 3.3649635
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.44897783
• LogD (pH = 7.4): -0.84149176
• Log P: 2.5700164
• Molar Refractivity: 48.8698 cm^3
• Polarizability: 18.41779 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid
• Melting Point: 40-44°C; 40-45 °C; 41-46 °C(lit.); 43-45°C; 46-49 °C(lit.); 46-49°C (319-322 K)
• Boiling Point: 105 - 107 °C at 1 torr; 105-107 °C/1 mmHg(lit.); 105-107°C/1mm; 105-107°C/1mm; 90 °C/0.1 mmHg; 95-97 °C/0.05 mmHg(lit.); 95-98 °C/0.05 mmHg(lit.)
• Flash Point: 110°C; 113 °C; 235.4 °F
• Density: 1.303 g/mL at 25 °C(lit.); 1.344 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.473(lit.); n20/D 1.474(lit.); n20/D 1.476(lit.)
• Optical Rotation: [α]18/D -72°, c = 1.6 in methanol; [α]20/D +72±2°, c = 2% in methanol; [α]20/D +72°, c = 1.6 in methanol; [α]20/D +73±1°, c = 2% in methanol; [α]20/D -70°, c = 1.6 in methanol; [α]20/D -72±2°, c = 2% in methanol; [α]20/D -73±1°, c = 2% in methanol

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic; Irritant; IRRITANT, HYGROSCOPIC, KEEP COLD
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R36/37/38
• Safety Statements: 26-36; 26-37; S26-36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T); ≥99%; ≥99.0%; ≥99.0% (T); 97%; 98%; 99%
• Grade: for chiral derivatization; for GC derivatization; puriss.
• Optical Purity: ee: 95% (GLC); ee: 99% (GLC); enantiomeric ratio: ~98.5 (GC); enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: C6H5C(OCH3)(CF3)CO2H
• Empirical Formula (Hill Notation): C10H9F3O3

DETAILS

MP Biomedicals - 02155444

([+]-MTPA)

Sigma Aldrich - 155616

Application
Derivatizing reagent for determination of enantiomeric excess by NMR.1,2
Packaging
1 g in glass bottle

Sigma Aldrich - 155268

Application
Derivatizing reagent for determination of enantiomeric excess by NMR.1,2
Other Notes
doi:10.1038/nprot.2007.354
Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 156558

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 318035

Other Notes
doi:10.1038/nprot.2007.354
Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 65369

Application
Determination of absolute configuration of stereogenic carbinol carbons; doi:10.1038/nprot.2007.3541

Sigma Aldrich - 65361

Application
Reagent used for the determination of the enantiomeric purity and the absolute configuration of alcohols and amines by NMR1,2; doi:10.1038/nprot.2007.3543; Review4