119290-61-8

Basic information

• Product Name: DL-PHENYLALANINE-OBZL P-TOSYLATE
• Synonyms: DL-Phe-OBzl HCl;H-DL-Phe-OBzl;H-D,L-Phe-OBzl·HCl;DL-Phe-OBzl·TosOH;DL-PHENYLALANINE-OBZL P-TOSYLATE;DL-PHENYLALANINE BENZYL ESTER 4-TOLUENESULFONATE SALT;DL-PHENYLALANINE BENZYL ESTER P-TOLUENE-SULFONATE;DL-PHENYLALANINE-BENZYL ESTER P-TOSYLATE
• CAS NO: 119290-61-8
• Molecular Formula: C₇H₈O₃S*C₁₆H₁₇NO₂
• Molecular Weight: 427.51
• Product Categories: Amino hydrochloride
• Mol File: 119290-61-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 149 °C(Solv: water (7732-18-5))
• Boiling Point: 382.8 °C at 760 mmHg
• Flash Point: 220.3 °C
• Appearance: /
• Storage Temp.: Store at RT.
• CAS DataBase Reference: DL-PHENYLALANINE-OBZL P-TOSYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-PHENYLALANINE-OBZL P-TOSYLATE(119290-61-8)
• EPA Substance Registry System: DL-PHENYLALANINE-OBZL P-TOSYLATE(119290-61-8)

Safety Data

• Hazardous Substances Data: 119290-61-8(Hazardous Substances Data)

Usage

General Description

DL-Phenylalanine-obzl p-tosylate is a chemical compound that is primarily used in scientific research. It is a derivative of phenylalanine, an essential amino acid that plays a crucial role in various physiological functions. DL-Phenylalanine-obzl p-tosylate is modified with a benzyl (obzl) group and a tosylate group, which can influence its reactivity and properties. DL-Phenylalanine-obzl p-tosylate is often used in the synthesis of peptides and proteins, and it may also be utilized in the development of pharmaceuticals and biologically active compounds. Despite its use in research, information about its toxicity or potential health effects is limited, emphasizing the need for careful handling and use.

Upstream product

• 150-30-1 Phenylalanine 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 14390-34-2 (+/-)-N-Diphenyl-phosphoro-phenyl-alanin-benzylester 
• 37534-65-9 D-2-carbamoylamino-3-phenylpropionic acid 

Relevant articles and documents

One-step preparation of enantiopure l- or d-amino acid benzyl esters avoiding the use of banned solvents

The enantiomers of amino acid benzyl esters are very important synthetic intermediates. Many of them are currently prepared by treatment with benzyl alcohol and p-toluenesulfonic acid in refluxing benzene or carbon tetrachloride, to azeotropically remove water, and then precipitated as tosylate salt by adding diethyl ether. Here, we report a very efficient preparation of eight l- or d-amino acid benzyl esters (Ala, Phe, Tyr, Phg, Val, Leu, Lys, Ser), in which these highly hazardous solvents are dismissed using cyclohexane as a water azeotroping solvent and ethyl acetate to precipitate the tosylate salt. With some work-up modifications and lower yield, the procedure can be applied also to methionine. Chiral HPLC analysis shows that all the benzyl esters, including the highly racemizable ones such as those of phenylglycine, tyrosine and methionine, are formed enantiomerically pure under these new reaction conditions thus validating the solvents replacement. Contrariwise, toluene cannot be used in place of benzene or carbon tetrachloride because leading to partially or totally racemized amino acid benzyl esters depending on the polar effect of the amino acid α-side chain as expressed by Taft’s substituent constant (σ*).