3-Fluoro-D-phenylalanine

Base Information

• Chemical Name: 3-Fluoro-D-phenylalanine
• CAS No.: 110117-84-5
• Molecular Formula: C9H10FNO2
• Molecular Weight: 183.182
• Hs Code.: 2922498590
• European Community (EC) Number: 686-374-1
• Nikkaji Number: J231.858J
• Mol file: 110117-84-5.mol

Synonyms:3-Fluoro-D-phenylalanine;110117-84-5;H-D-PHE(3-F)-OH;(2R)-2-amino-3-(3-fluorophenyl)propanoic acid;D-3-fluorophenylalanine;3-FLUORO-D-PHE;(R)-2-AMINO-3-(3-FLUOROPHENYL)PROPANOIC ACID;(2R)-2-azaniumyl-3-(3-fluorophenyl)propanoate;m-Fluoro-D-phenylalanine;MFCD00066449;D-PHENYLALANINE, 3-FLUORO-;SCHEMBL288728;VWHRYODZTDMVSS-MRVPVSSYSA-N;AKOS016842878;AC-5828;AM83337;DS-13612;HY-79294;CS-0011436;3-Fluoro-D-phenylalanine (H-D-Phe(3-F)-OH);EN300-1297344;A802145

Chemical Property of 3-Fluoro-D-phenylalanine

Chemical Property:

• Vapor Pressure: 0.000369mmHg at 25°C
• Refractive Index: 1.555
• Boiling Point: 305 °C at 760 mmHg
• PKA: 2.17±0.10(Predicted)
• Flash Point: 138.3 °C
• PSA: 63.32000
• Density: 1.293g/cm³
• LogP: 1.48040
• Storage Temp.: Store at 0-5°C
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 183.06955672
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

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

3-Fluoro-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(=CC(=C1)F)CC(C(=O)O)N
• Isomeric SMILES: C1=CC(=CC(=C1)F)C[C@H](C(=O)O)N

Technology Process of 3-Fluoro-D-phenylalanine

There total 21 articles about 3-Fluoro-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: 99.0%

3-fluoro-(RS)-phenylalaninamide hydrochloride → (R)-2-amino-3-(3-fluorophenyl)propionic acid (110117-84-5,2629-54-1)

Guidance literature:

With pyridoxal 5'-phosphate monohydrate; In aq. buffer; at 40 ℃; for 8h; pH=8.0; Enzymatic reaction;

DOI:10.1002/adsc.201100923

Reference yield: 96.0%

3-fluorophenylalanine (456-88-2,2629-54-1) → (R)-2-amino-3-(3-fluorophenyl)propionic acid (110117-84-5,2629-54-1)

Guidance literature:

With borane-ammonia complex; L-amino acid oxidase; bovine serum catalase; at 40 ℃; for 24h;

DOI:10.1002/cctc.202101296

Reference yield: 56.0%

3-fluorocinnamic acid (20595-30-6,458-46-8) → (R)-2-amino-3-(3-fluorophenyl)propionic acid (110117-84-5,2629-54-1)

Guidance literature:

With ammonium hydroxide; borane-ammonia complex; In aq. buffer; at 37 ℃; pH=9.6; Enzymatic reaction;

DOI:10.1002/anie.201410670

upstream raw materials:

N-acetyl-3-fluorophenylalanine methyl ester

glycine

1-(Bromomethyl)-3-fluorobenzene

3-fluoro-DL-phenylalanine methyl ester hydrochloride

Downstream raw materials:

C₁₈H₁₄FNO₃S

3-(3-fluoro-phenyl)-2-oxo-propionic acid

boc-L-3-(3-fluorophenyl)alanine

C₂₀H₁₆FNO₃

Refernces

• 1、 Cox, Brad M.,Bilsborrow, Joshua B.,Walker, Kevin D.. "Enhanced conversion of racemic α-arylalanines to (R)-β- arylalanines by coupled racemase/aminomutase catalysis". . p. 6953 - 6959. Retrieved 2009.
• 2、 Ishida, Chiharu,Miyata, Ryo,Hasebe, Fumihito,Miyata, Azusa,Kumazawa, Shigenori,Ito, Sohei,Nakano, Shogo. "Reconstruction of Hyper-Thermostable Ancestral L-Amino Acid Oxidase to Perform Deracemization to D-Amino Acids". . p. 5228 - 5235. Retrieved 2021/11/05.
• 3、 Nakano, Shogo,Minamino, Yuki,Hasebe, Fumihito,Ito, Sohei. "Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase". . p. 10152 - 10158. Retrieved 2019/10/19.