2-(Trifluoromethyl)-D-phenylalanine

Base Information

• Chemical Name: 2-(Trifluoromethyl)-D-phenylalanine
• CAS No.: 130930-49-3
• Molecular Formula: C₁₀H₁₀F₃NO₂
• Molecular Weight: 233.19
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID30426491
• Mol file: 130930-49-3.mol

Synonyms:130930-49-3;2-(Trifluoromethyl)-D-phenylalanine;(R)-2-AMINO-3-(2-(TRIFLUOROMETHYL)PHENYL)PROPANOIC ACID;(2R)-2-amino-3-[2-(trifluoromethyl)phenyl]propanoic acid;2-Trifluoromethyl-D-Phenylalanine;D-2-Trifluoromethylphenylalanine;D-Phenylalanine, 2-(trifluoromethyl)-;D-2-TRIFLUOROMETHYLPHE;(2R)-2-azaniumyl-3-[2-(trifluoromethyl)phenyl]propanoate;MFCD01860877;SCHEMBL503201;DTXSID30426491;IOABLDGLYOGEHY-MRVPVSSYSA-N;AKOS016843045;AC-5861;AM83481;CS-W010345;HY-W009629;PS-12174;2-(Trifluoromethyl)-D-phenylalanine, >=98.0%;A850818;J-005904;2-(Trifluoromethyl)-D-phenyalanine (H-D-Phe(2-CF3)-OH)

Chemical Property of 2-(Trifluoromethyl)-D-phenylalanine

Chemical Property:

• Boiling Point: 299.4 °C at 760 mmHg
• PKA: 2.09±0.10(Predicted)
• Flash Point: 134.9 °C
• PSA: 63.32000
• Density: 1.364 g/cm³
• LogP: 2.36010
• Storage Temp.: Store at -15°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 233.06636305
• Heavy Atom Count: 16
• Complexity: 255

Purity/Quality:

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

2-(Trifluoromethyl)-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC(C(=O)O)N)C(F)(F)F
• Isomeric SMILES: C1=CC=C(C(=C1)C[C@H](C(=O)O)N)C(F)(F)F
• Uses: 2-(Trifluoromethyl)-D-phenylalanine is a useful reactant for the synthesis of a second-?generation DNA-?templated library for the discovery of bioactive small molecules.

Technology Process of 2-(Trifluoromethyl)-D-phenylalanine

There total 6 articles about 2-(Trifluoromethyl)-D-phenylalanine 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:

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-[(2R,3S)-3-(2-trifluoromethyl-phenyl)-aziridin-2-yl]-methanone → (R)-2-amino-3-(2-trifluoromethyl-phenyl)-propionic acid (130930-49-3)

Guidance literature:

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-[(2R,3S)-3-(2-trifluoromethyl-phenyl)-aziridin-2-yl]-methanone; With hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; ethyl acetate; at 20 ℃; for 14h; atmospheric pressure;

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2003-41470

Reference yield:

((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-[(2R,3S)-1-diphenylphosphanyl-3-(2-trifluoromethyl-phenyl)-aziridin-2-yl]-methanone → (R)-2-amino-3-(2-trifluoromethyl-phenyl)-propionic acid (130930-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / BF₃*OEt₂ / CH₂Cl₂; methanol

2.1: H₂; aq. TFA / Pd(OH)2 / ethyl acetate; methanol / 14 h / 20 °C / atmospheric pressure

2.2: aq. LiOH / tetrahydrofuran / 20 °C

With boron trifluoride diethyl etherate; hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; dichloromethane; ethyl acetate;

DOI:10.1055/s-2003-41470

Reference yield:

2-acetylamino-3-(2-trifluoromethyl-phenyl)-acrylic acid (3094-32-4) → 2-(trifluoromethyl)-dl-phenylalanine (3832-73-3,130930-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C

2: (hydrolysis)

With hydrogen; palladium on activated charcoal;

DOI:10.1021/jo01075a015

upstream raw materials:

o-(trifluoromethyl)phenylpyruvic acid

(+/-)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridophane

2-Acetamino-3-<2-trifluormethyl-phenyl>-propionsaeure

2-methyl-4-(2-trifluoromethyl-benzylidene)-4H-oxazol-5-one

Downstream raw materials:

(2R,3R)-3-Amino-2-hydroxy-4-(2-trifluoromethyl-phenyl)-butyric acid ethyl ester

2-{3-[(1R,2R)-2-ethoxycarbonyl-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic acid

2-{3-[(1R,2R)-2-carboxy-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic acid

N^α-[(tert-butoxy)carbonyl]-2-(trifluoromethyl)-L-phenylalanine

Refernces

• 1、 Ando,Kuzuhara. "Asymmetric synthesis of fluorophenylalanines and (trifluoromethyl)phenylalanines; the use of chiral pyridoxamine-like pyridinophane-zinc complex as an enzyme mimic". . p. 1925 - 1928. Retrieved 2007/10/02.