(2S)-2-azaniumyl-3-(3,5-dibromo-4-hydroxyphenyl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(3,5-dibromo-4-hydroxyphenyl)propanoate
• CAS No.: 300-38-9
• Molecular Formula: C9H9 Br2 N O3
• Molecular Weight: 338.983
• Mol file: 300-38-9.mol

Synonyms:

Chemical Property of (2S)-2-azaniumyl-3-(3,5-dibromo-4-hydroxyphenyl)propanoate

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Melting Point: 245°C
• Refractive Index: 0.8 ° (C=5, 1mol/L HCl)
• Boiling Point: 416.6°Cat760mmHg
• PKA: 2.17, 6.45, 7.60(at 25℃)
• Flash Point: 205.7°C
• PSA: 83.55000
• Density: 2.014g/cm³
• LogP: 2.57190
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Base (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 338.89287
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

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

3,5-Dibromo-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1Br)O)Br)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=C(C=C(C(=C1Br)O)Br)C[C@@H](C(=O)[O-])[NH3+]
• Uses: 3,5-Dibromo-L-tyrosine is a dibrominated derivative of L-Tyrosine (T899975), one of the 22 proteinogenic amino acids that are used by cells to synthesize proteins.

Technology Process of (2S)-2-azaniumyl-3-(3,5-dibromo-4-hydroxyphenyl)propanoate

There total 10 articles about (2S)-2-azaniumyl-3-(3,5-dibromo-4-hydroxyphenyl)propanoate 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: 100.0%

3',5'-dibromo-L-tyrosine methyl ester (67470-21-7,173383-29-4) → 3,5-dibromo-L-tyrosine (300-38-9)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 24h;

DOI:10.21577/0103-5053.20180136

Reference yield: 92.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 3,5-dibromo-L-tyrosine (300-38-9)

Guidance literature:

With bromine; In acetic acid; at 80 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00553-0

Reference yield: 29.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 3,5-dibromo-L-tyrosine (300-38-9) + (2S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid (38739-13-8,7298-91-1)

Guidance literature:

With bromoisocyanuric acid monosodium salt; sulfuric acid; at 0 ℃; for 2h;

DOI:10.1248/cpb.54.1715

upstream raw materials:

L-tyrosine

bromine

acetic acid

(+)-(S)-methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-(2-methylprop-2-yloxycarbamoyl)propanoate

Downstream raw materials:

2-(4-hydroxyphenyl)acetamide

(S)-3-(3,5-Dibromo-4-hydroxy-phenyl)-2-(3-ethylcarbamoylsulfanyl-propionylamino)-propionic acid

3,5,3',5'-tetrabromo-L-thyronine

(2S)-2-benzyloxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid

Refernces

• 1、 Gao, Hongfeng,Kelly, Michelle,Hamann, Mark T.. "Bromotyrosine-derived Metabolites from the Sponge Aiolochoria crassa". . p. 9717 - 9726. Retrieved 1999.
• 2、 Puratchikody, Ayarivan,Umamaheswari, Appavoo,Irfan, Navabshan,Sinha, Shweta,Manju,Ramanan, Meera,Ramamoorthy, Gayathri,Doble, Mukesh. "A novel class of tyrosine derivatives as dual 5-LOX and COX-2/mPGES1 inhibitors with PGE2 mediated anticancer properties". supporting information. p. 834 - 846. Retrieved 2019/01/09.
• 3、 Restrepo, Manuel Pastrana,Jaramillo, Elkin Galeano,Martínez, Alejandro Martínez,Arango, Ana Mesa,Restrepo, Sara Robledo. "Anti-parasite and cytotoxic activities of chloro and bromo L-tyrosine derivatives". . p. 2569 - 2579. Retrieved 2018/11/06.