3-Bromo-D-phenylalanine

Base Information

• Chemical Name: 3-Bromo-D-phenylalanine
• CAS No.: 99295-78-0
• Molecular Formula: C₉H₁₀BrNO₂
• Molecular Weight: 244.088
• Hs Code.: 2922498590
• DSSTox Substance ID: DTXSID10427562
• Mol file: 99295-78-0.mol

Synonyms:3-BROMO-D-PHENYLALANINE;99295-78-0;(R)-2-Amino-3-(3-bromophenyl)propanoic acid;(2R)-2-amino-3-(3-bromophenyl)propanoic acid;H-D-PHE(3-BR)-OH;D-Phenylalanine, 3-bromo-;D-3-Bromophenylalanine;MFCD06659100;D-PHE(3-BR)-OH;SCHEMBL14935980;DTXSID10427562;AMY40610;AKOS017482176;CS-W003318;DS-3159;HY-W003318;PD196411;EN300-1297447;A845993;3-Bromo-D-phenylalanine

Chemical Property of 3-Bromo-D-phenylalanine

Chemical Property:

• Boiling Point: 368.4 °C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 176.6 °C
• PSA: 63.32000
• Density: 1.588 g/cm³
• LogP: 2.10380
• Storage Temp.: Store at RT.
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.98949
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99%, ^*data from raw suppliers

3-Bromo-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)Br)CC(C(=O)O)N
• Isomeric SMILES: C1=CC(=CC(=C1)Br)C[C@H](C(=O)O)N
• Uses: 3-Bromo-D-phenylalanine, can be used in the synthesis of various chemical compounds, such as 3-(Methylsulfonyl)-D-phenylalanine Hydrochloride, which has been found to be a potent LFA-1/ICAM-1 Antagonist SAR 1118 as an Ophthalmic Solution for treating dry eye. 3-Bromo-D-phenylalanine, can be used in the synthesis of various chemical compounds, such as 3-(Methylsulfonyl)-D-phenylalanine Hydrochloride (M326188), which has been found to be a potent LFA-1/ICAM-1 Antagonist SAR 1118 as an Ophthalmic Solution for treating dry eye.

Technology Process of 3-Bromo-D-phenylalanine

There total 20 articles about 3-Bromo-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: 96.0%

C36H37BrClN3NiO3 → (2R)-2-amino-3-(3-bromophenyl)propanoic acid (99295-78-0) + (S)-N-(2-benzoyl-4-chlorophenyl)-2-(1-(1-adamantyl)ethylamino)acetamide

Guidance literature:

C₃₆H₃₇BrClN₃NiO₃; With hydrogenchloride; In methanol; at 50 ℃; for 4h;

With ammonium hydroxide;

DOI:10.1039/c8ob00963e

Reference yield: 89.0%

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (82278-73-7) → (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 16h;

Reference yield:

2-amino-3-(3-bromophenyl)propanoic acid (30163-20-3,99295-78-0) → (2R)-2-amino-3-(3-bromophenyl)propanoic acid (99295-78-0) + (S)-2-amino-3-(3-bromophenyl)propanoic acid (82311-69-1,99295-78-0)

Guidance literature:

With phenylalanine ammonia-lyase from Pseudozyma antarctica yeast; In aq. buffer; at 30 ℃; for 168h; pH=8.5; Time; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

upstream raw materials:

diethyl (acetylamino)<(3-bromophenyl)methyl>propanedioate

meta-bromobenzyl bromide

3-bromocinnamic acid

(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid

Downstream raw materials:

C₁₀H₁₂BrNO₂

Refernces

• 1、 Weise, Nicholas J.,Thapa, Prasansa,Ahmed, Syed T.,Heath, Rachel S.,Parmeggiani, Fabio,Turner, Nicholas J.,Flitsch, Sabine L.. "Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines". . p. 995 - 998. Retrieved 2020/01/21.
• 2、 Meng, Kaicheng,Shim, Paul,Wang, Qingtin,Zhao, Shuai,Gu, Ting,Kahsai, Alem W.,Ahn, Seungkirl,Chen, Xin. "Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor". . p. 2320 - 2330. Retrieved 2018/03/29.