4-Borono-D-phenylalanine

Base Information

• Chemical Name: 4-Borono-D-phenylalanine
• CAS No.: 111821-49-9
• Molecular Formula: C₉H₁₂BNO₄
• Molecular Weight: 209.01
• Hs Code.: 29310099
• European Community (EC) Number: 635-122-9
• DSSTox Substance ID: DTXSID30370208
• Nikkaji Number: J505.253J
• Wikidata: Q82157499
• Mol file: 111821-49-9.mol

Synonyms:4-Borono-D-phenylalanine;111821-49-9;(R)-2-amino-3-(4-boronophenyl)propanoic acid;(2R)-2-amino-3-(4-boronophenyl)propanoic acid;D-Phenylalanine,4-borono-;D-Phenylalanine, 4-borono-;d-4-boronophenylalanine;(R)-2-Amino-3-(4-boronophenyl)propanoicacid;4-BORONO-D-PHENYLALANINE B10 ENRICHED;SCHEMBL502901;DTXSID30370208;(2R)-2-amino-3-[4-(dihydroxyboranyl)phenyl]propanoic acid;AKOS015833708;AKOS015907946;AC-31009;PD063254;BB 0260313;CS-0134555;4-Borono-D-phenylalanine, >=97.0% (HPLC);A802419;J-002638;J-514523

Chemical Property of 4-Borono-D-phenylalanine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.39E-09mmHg at 25°C
• Refractive Index: 1.59
• Boiling Point: 449.281 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 225.517 °C
• PSA: 103.78000
• Density: 1.347 g/cm³
• LogP: -0.97890
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 209.0859380
• Heavy Atom Count: 15
• Complexity: 216

Purity/Quality:

98%min ^*data from raw suppliers

4-Borono-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)CC(C(=O)O)N)(O)O
• Isomeric SMILES: B(C1=CC=C(C=C1)C[C@H](C(=O)O)N)(O)O
• Uses: 4-Borono-D-phenylalanine is a melanin precursor analog used to deliver 10B to melanoma tissue for B neutron capture therapy.

Technology Process of 4-Borono-D-phenylalanine

There total 4 articles about 4-Borono-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: 83.0%

Methyl 2-amino-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]propionate → DL-4-boronophenylalanine (76410-58-7,77374-29-9,90580-64-6,111821-49-9)

Guidance literature:

Methyl 2-amino-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]propionate; With sodium hydroxide; water; at 45 - 50 ℃; for 2h;

With hydrogenchloride; water; at 30 ℃; for 3h;

DOI:10.1055/s-1999-3624

Reference yield:

N-acetyl-4-dihydroxyboranyl-phenylalanine (147529-10-0) → DL-4-boronophenylalanine (76410-58-7,77374-29-9,90580-64-6,111821-49-9)

Guidance literature:

N-acetyl-4-dihydroxyboranyl-phenylalanine; With hydrogenchloride; In water; at 85 - 100 ℃; for 12 - 18h;

With sodium hydroxide; In water; at 18 - 25 ℃; pH=6;

Reference yield:

Methyl (E/Z)-2-(benzyloxycarbonylamino)-3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acrylate → DL-4-boronophenylalanine (76410-58-7,77374-29-9,90580-64-6,111821-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / H₂ / 10 percent Pd/C / methanol; CH₂Cl₂ / 19 h / 20 °C / 2280 Torr

2.1: NaOH; H₂O / 2 h / 45 - 50 °C

2.2: 83 percent / HCl; H₂O / 3 h / 30 °C

With sodium hydroxide; water; hydrogen; 10% palladium on active carbon; In methanol; dichloromethane; 1.1: Hydrogenation / 2.1: Hydrolysis / 2.2: Hydrolysis;

DOI:10.1055/s-1999-3624

upstream raw materials:

N-acetyl-4-dihydroxyboranyl-phenylalanine

Downstream raw materials:

t-butyl(phenyl)nitroxide

4-(N-t-butyl-N-oxylamino)methoxybenzene

C₁₂H₁₆NO₂

C₁₅H₂₂BNO₆

Refernces

• 1、 -. "Compositions, methods of preparing amino acids, and nuclear magnetic resonance spectroscopy". Page/Page column 13; sheet 3. . Retrieved 2010/11/27.