29739-88-6

Basic information

• Product Name: N-(p-Tosyl)-L-phenylalaninyl chloride
• Synonyms: Tos-Phe-Cl~N-p-Tosyl-L-phenylalaninyl chloride;N-P-TOSYL-L-PHENYLALANINYL CHLORIDE 99%;N-p-Toluenesulfonyl-L-phenylalaninylchloride;N-(p-Toluenesulfonyl)-L-phenylalanyl Chloride [Optical Resolving Reagent for Alcohols];[Optical Resolving Reagent for Alcohols];N-(p-Toluenesulfonyl)-L-phenylalanyl Chloride (S)-(+)-(P-TOLYLSULFONYLAMINO)HYDROCINNAMOYL CHLORIDE;(S)-N-TOSYL-PHENYLALANYL CHLORIDE
• CAS NO: 29739-88-6
• Molecular Formula: C₁₆H₁₆ClNO₃S
• Molecular Weight: 337.82
• EINECS: 1533716-785-6
• Product Categories: chiral;for Resolution of Alcohols & Thiols;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 29739-88-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 132 °C (dec.)(lit.)
• Boiling Point: 492.108 °C at 760 mmHg
• Flash Point: 251.418 °C
• Appearance: /
• Density: 1.305 g/cm³
• Vapor Pressure: 7.91E-10mmHg at 25°C
• Refractive Index: 10 ° (C=3, CHCl3)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: N-(p-Tosyl)-L-phenylalaninyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-Tosyl)-L-phenylalaninyl chloride(29739-88-6)
• EPA Substance Registry System: N-(p-Tosyl)-L-phenylalaninyl chloride(29739-88-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 29739-88-6(Hazardous Substances Data)

Usage

General Description

N-(p-Tosyl)-L-phenylalaninyl chloride, also known as Tos-Phe-Cl, is a chemical compound that is commonly used in peptide synthesis and organic chemistry. It is a derivative of L-phenylalanine and contains a tosyl group, which is often used as a protecting group in organic synthesis. Tos-Phe-Cl is a reactive compound that can be used to introduce the phenylalanine amino acid into peptides and proteins, and it is commonly used as a building block in the synthesis of bioactive peptides. It is also used as a reagent in the preparation of various pharmaceuticals and chemical compounds. Due to its reactivity and versatility, Tos-Phe-Cl is a valuable tool in the field of organic chemistry and drug discovery.

InChI:InChI=1/C16H16ClNO3S/c1-12-7-9-14(10-8-12)22(20,21)18-15(16(17)19)11-13-5-3-2-4-6-13/h2-10,15,18H,11H2,1H3/t15-/m0/s1

Upstream product

• 13505-32-3 N-tosyl-(S)-phenylalanine 
• 63-91-2 L-phenylalanine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 115211-02-4 N-(toluene-4-sulfonyl)-L-phenylalanyl=>L-glutaminyl=>L-asparagine 
• 32556-70-0 (R)-1-octyn-3-ol 
• 13505-32-3 N-tosyl-(S)-phenylalanine 
• 135628-89-6 (S)-1-octyn-3-yl N-(p-toluenesulfonyl)-(S)-phenylalaninate 
• 120402-85-9 N-tosyl-L-phenylalanyl-4-methylcoumaryl-7-amide 
• 99033-29-1 7-<(N-tosylphenylalanyl)amino>-4-chloro-3-methoxyisocoumarin 
• 80613-68-9 6-(N-tosyl-L-Phe)aminocoumarin-3-carboxylic acid 
• 88955-90-2 7-(N-tosyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole 
• 10119-00-3 tosyl-L-phenylalanyl diazomethane 
• 206441-84-1 3-tert-butoxycarbonylamino-2-methyl-6-[3-phenyl-2-(toluene-4-sulfonylamino)-propionylamino]-benzoic acid 2-trimethylsilanyl-ethyl ester 

Relevant articles and documents

Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides

The synthesis and structural studies of N-(p-Toluenesulfonyl)amino acid o-phenolamides was discussed. The structure and conformation of these amides were established by NMR spectroscopy and x-ray crystallography. Variable temperature experiments showed th

Metal-Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids

We have developed a method for the synthesis of dihydroquinoxalinones via intramolecular N–H/C–H coupling using hypervalent iodine. The starting materials were prepared from inexpensive and readily available aniline and amino acid derivatives. Various functional groups were tolerated to give multisubstituted dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without a loss of enantiomeric excess. Preliminary mechanistic studies indicated that the reaction proceeds via an ionic mechanism.

Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity

A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)