3-Bromo-L-tyrosine

Base Information

• Chemical Name: 3-Bromo-L-tyrosine
• CAS No.: 38739-13-8
• Molecular Formula: C9H10BrNO3
• Molecular Weight: 260.087
• Hs Code.: 2922509090
• European Community (EC) Number: 869-789-4
• ChEMBL ID: CHEMBL3808609
• Nikkaji Number: J678.997H
• Wikidata: Q27124150
• Mol file: 38739-13-8.mol

Synonyms:3-Bromo-L-tyrosine;38739-13-8;(S)-2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid;(2S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid;3-?Bromo-?L-?tyrosine;L-Tyrosine, 3-bromo-;H-Tyr(3-Br)-OH;BRY;MFCD09836116;SCHEMBL455225;CHEMBL3808609;CHEBI:53668;HGWOSUKIFQMEIF-ZETCQYMHSA-N;AKOS015891273;AKOS016035824;CS-W019172;HY-W018386;AS-10308;PD070425;EN300-215162;Q27124150;(S)-2-Amino-3-(3-bromo-4-hydroxyphenyl)propanoicacid;Z1269188313

Chemical Property of 3-Bromo-L-tyrosine

Chemical Property:

• Melting Point: 247-248 °C
• Boiling Point: 402.8±45.0 °C(Predicted)
• PKA: 2.21±0.20(Predicted)
• PSA: 83.55000
• Density: 1.710±0.06 g/cm3(Predicted)
• LogP: 1.80940
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Aqueous Acid (Sparingly), DMSO (Heated), Methanol (Heated)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 258.98441
• Heavy Atom Count: 14
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)Br)O
• Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)Br)O
• Uses: 3-Bromo-L-tyrosine is used in the preparation and synthesis of polyclonal antibodies that work against brominated protein related allergic responses and afflictions. Also effective in asthma control a nd prediction in children.

Technology Process of 3-Bromo-L-tyrosine

There total 10 articles about 3-Bromo-L-tyrosine 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%

C10H12BrNO3 → (2S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid (38739-13-8,7298-91-1)

Guidance literature:

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

DOI:10.21577/0103-5053.20180136

Reference yield: 65.2%

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

Guidance literature:

With hydrogen bromide; dimethyl sulfoxide; In acetic acid; at 20 - 65 ℃; Mechanism;

DOI:10.1007/s00726-012-1366-z

Reference yield: 51.0%

2-hydroxybromobenzene (95-56-7) + piruvate (57-60-3) → (2S)-2-amino-3-(3-bromo-4-hydroxyphenyl)propanoic acid (38739-13-8,7298-91-1)

Guidance literature:

With ethylenediaminetetraacetic acid; pyridoxal 5'-phosphate; Ammonium; thermophilic tyrosine phenol lyases M₃₈₀V mutant from thermophilic microorganism Symbiobacterium toebii; In aq. phosphate buffer; at 37 ℃; pH=8; stereoselective reaction; Green chemistry; Enzymatic reaction;

DOI:10.1002/ejoc.202000061

upstream raw materials:

L-tyrosine

formic acid

bromine

2-hydroxybromobenzene

Downstream raw materials:

(S)-N-Boc-3-bromotyrosine

3-bromotyrosine

Fmoc-3-nitro-O-(dibenzylphosphoryl)tyrosine

N-(tert-butoxycarbonyl)-L-tyrosyl-3-bromo-L-tyrosine methyl ester

Refernces

• 1、 Jiang, Yiqi,Ju, Shuyun,Li, Guosi,Lian, Jiazhang,Lin, Jianping,Wu, Mianbin,Xue, Hailong,Yang, Lirong. "Biocascade Synthesis of L-Tyrosine Derivatives by Coupling a Thermophilic Tyrosine Phenol-Lyase and L-Lactate Oxidase". supporting information. . Retrieved 2020/02/25.
• 2、 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.