148613-12-1

Basic information

• Product Name: 2-AMINO-3-(2-FLUORO-5-HYDROXY-PHENYL)-PROPIONIC ACID
• Synonyms: 2-FLUORO-M-L-TYROSINE;2-AMINO-3-(2-FLUORO-5-HYDROXY-PHENYL)-PROPIONIC ACID;F-M-L-TYROSINE;FMT;L-PHENYLALANINE, 2-FLUORO-5-HYDROXY-;6-fluoro-3-tyrosine;2-Fluoro-m-Tyrosine;(2S)-2-AMINO-3-(6-FLUORO-3-HYDROXYPHENYL)PROPANOIC ACID
• CAS NO: 148613-12-1
• Molecular Formula: C9H10FNO3
• Molecular Weight: 199.18
• Mol File: 148613-12-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 398.9 °C at 760 mmHg
• Flash Point: 195 °C
• Appearance: /
• Density: 1.421 g/cm³
• Vapor Pressure: 4.44E-07mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 2-AMINO-3-(2-FLUORO-5-HYDROXY-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-(2-FLUORO-5-HYDROXY-PHENYL)-PROPIONIC ACID(148613-12-1)
• EPA Substance Registry System: 2-AMINO-3-(2-FLUORO-5-HYDROXY-PHENYL)-PROPIONIC ACID(148613-12-1)

Safety Data

• Hazardous Substances Data: 148613-12-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

InChI:InChI=1/C9H10FNO3/c10-7-2-1-6(12)3-5(7)4-8(11)9(13)14/h1-3,8,12H,4,11H2,(H,13,14)/t8-/m0/s1

Upstream product

• 1354973-63-9 (Z)-4-(2-(tert-butyl)-5-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one 
• 1354973-62-8 (Z)-4-(2-(tert-butyl)-5-((tert-butyldimethylsilyl)oxy)benzylidene)-2-phenyloxazol-5(4H)-one 
• 1354973-61-7 2-(tert-butyl)-5-((tert-butyldimethylsilyl)oxy)benzaldehyde 
• 1354973-60-6 (3-bromo-4-(tert-butyl)phenoxy) (tert-butyl)dimethylsilane 
• 14034-12-9 3-bromo-4-(tert-butyl)phenol 
• 129167-73-3 3-bromo-4-(tert-butyl)benzaldehyde 
• 1354973-59-3 9-hydroxy-6,6-dimethyl-2-propyl-11,11a-dihydro-2H-pyrazino[1,2-b]isoquinoline-1,4(3H, 6H)-dione 
• 1354973-58-2 9-{[tert-butyl(dimethyl)silyl]oxy}-6,6-dimethyl-2-propyl-11,11a-dihydro-2H-pyrazino[1,2-b]isoquinoline-1,4(3H, 6H)-dione 
• 1354973-57-1 methyl 2-(bromoacetyl)-6-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 1354973-56-0 methyl 6-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 1354973-54-8 methyl 6-hydroxy-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride 
• 38473-89-1 3-bromo-4-(tert-butyl)benzoic acid 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 91319-42-5 2-(bromomethyl)-1-fluoro-4-methoxybenzene 

Relevant articles and documents

Selective fluorination of m-tyrosine by OF2

Fluorine-18 labeled aromatic amino acids are routinely used as tracers in positron emission tomography (PET) to study in vivo metabolic processes. The most versatile method for the production of such radiotracers is electrophilic fluorination of the aroma

FLUORINE RADIOLABELLING PROCESS

The invention relates to a process for producing a process for producing an 18F-labelled compound, the process comprising treating a compound of formula (I): wherein EDG is an electron-donating group selected from -OH, -OR4, -NHR5 and -NR55R5; R1, R2, X1 and X2 are as defined herein; and R3 is selected from H, X3 and X4, wherein X3 is a monodentate cleavable surrogate group, and X4 is a bidentate cleavable surrogate group which is bonded (a) to said X or X and (b) to the ring carbon atom para to EDG; with [18F]fluoride in the presence of an oxidant, thereby producing, when R3 in the compound of formula (I) is H, an 18F-labelled compound of formula (II), wherein EDG is as defined above and R1, R2, X1 and X2 are as defined herein; or thereby producing, when R3 in the compound of formula (I) is said monodentate cleavable surrogate group X4, a compound of formula (Ilc), wherein EDG' is O, NR5, -NR55R5 or [OR4]+, and wherein R4, R5, R55, R1, R2, X1, X2 and X3 are as defined herein; or thereby producing, when R3 in the compound of formula (I) is said bidentate cleavable surrogate group X4, a compound of formula (IIc) or a compound of formula (IId), wherein EDG' is O, NR5, -NR55R5 or [OR4]+, and wherein R4, R5, R55, R1, R2, X1, X2 and X4 are as defined herein.

Asymmetric synthesis of fluorinated L-tyrosine and meta-L-tyrosines

A convenient asymmetric synthesis of (2S)-2-amino-3-(2-fluoro-5-hydroxyphenyl) propanoic acid, (2S)-2-amino-3-(4-fluoro-3-hydroxyphenyl) propanoic acid and (2S)-2-amino-3-(2-fluoro-4-hydroxyphenyl) propanoic acid is described.Key steps include the synthes