300-38-9

Basic information

• Product Name: 3,5-Dibromo-L-tyrosine
• Synonyms: H-PHE(3,5-BR2, 4-OH)-OH DIHYDRATE;H-TYR(3,5-BR 2)-OH 2H2O;L-(3,5-DIBROMO, 4-HYDROXY)PHENYLALANINE DIHYDRATE;L-(3,5-DIBROMO)TYROSINE DIHYDRATE;L-Tyr(3',5'-Br2);5,5'-Dibromo-2,2'-dihydroxybenzil;Dibromotyrosine;3,5-Dibromo-L-tyrosine
• CAS NO: 300-38-9
• Molecular Formula: C₉H₉Br₂NO₃
• Molecular Weight: 338.98
• EINECS: 206-091-5
• Product Categories: Pharmaceutical Raw Materials
• Mol File: 300-38-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 245°C
• Boiling Point: 416.6°Cat760mmHg
• Flash Point: 205.7°C
• Appearance: /
• Density: 1.9706 (rough estimate)
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 0.8 ° (C=5, 1mol/L HCl)
• Storage Temp.: Store at RT.
• Solubility: Aqueous Base (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 2.17, 6.45, 7.60(at 25℃)
• Merck: 14,3030
• CAS DataBase Reference: 3,5-Dibromo-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibromo-L-tyrosine(300-38-9)
• EPA Substance Registry System: 3,5-Dibromo-L-tyrosine(300-38-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 300-38-9(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

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.

Definition

ChEBI: A bromoamino acid that is L-tyrosine carrying bromo- substituents at positions C-3 and C-5 of the benzyl group.

InChI:InChI=1/C9H9Br2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1

Upstream product

• 60-18-4 L-tyrosine 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 355857-30-6 (+)-(S)-methyl 3-(3,5-dibromo-4-hydroxyphenyl)-2-(2-methylprop-2-yloxycarbamoyl)propanoate 
• 67470-21-7 3',5'-dibromo-L-tyrosine methyl ester 
• 3417-91-2 L-tyrosine methyl ester HCl 

Downstream Products

• 134755-34-3 3,5-dibromo-4-hydroxy-β-phenethylamine 
• 67470-21-7 3',5'-dibromo-L-tyrosine methyl ester 
• 17194-82-0 2-(4-hydroxyphenyl)acetamide 
• 57203-13-1 (S)-3-(3,5-Dibromo-4-hydroxy-phenyl)-2-(3-ethylcarbamoylsulfanyl-propionylamino)-propionic acid 
• 6893-00-1 3,5,3',5'-tetrabromo-L-thyronine 
• 111820-85-0 (2S)-2-benzyloxycarbonylamino-3-(3,5-dibromo-4-hydroxyphenyl)propionic acid 
• 537-24-6 3,5-dibromo-DL-tyrosine 
• 91384-03-1 3,5-dibromo-L-tyrosine ethyl ester 
• 1212918-50-7 (S)-methyl 2-amino-3-(3,4,5-trimethoxyphenyl)propanoate 

Relevant articles and documents

Preparation of 3-bromo-l-tyrosine and 3,5-dibromo-l-tyrosine

l-Tyrosine is converted to 3-bromo-l-tyrosine in good yield by reaction with 1.2 equiv. of DMSO in HBr/AcOH, while reaction with 2.2 equiv. of DMSO under comparable conditions results in formation of 3,5-dibromo-l-tyrosine in good yield. This is the simplest, safest and most efficient method for the preparation of gram quantities of either 3-bromo-l-tyrosine or 3,5-dibromo-l-tyrosine.

Convenient access to L-3,4,5-trioxygenated phenylalanine compounds from L-tyrosine

A convenient and efficient synthesis of L-3,4,5-trioxygenated phenylalanine derivatives from L-tyrosine was developed. Dibromo phenylalanine is converted easily to bis-phenol via copper-catalyzed hydroxylation. The synthetic potential of this methodology has been demonstrated by efficient synthesis of L-3,4,5-trimethoxyphenylalanine methyl ester and one key intermediate of Trabectedin.

Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives

Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity were evaluated over monocytic cell line U-937. Compound 25 was the most active against T. cruzi with a EC50 of 75.52 μM compared with benznidazole with a EC50 of 58.79 μM. Compounds 3, 4, 7, and 15 were the derivatives with the best selectivity index (SI) with values of 7.5, 8.3,12.1, and 8.6, respectively. Finally, compound 7 was the safer and the more promising derivative against T. cruzi.