29588-07-6

Basic information

• Product Name: PHENYLTHIOHYDANTOIN PHENYLALANINE)
• Synonyms: (5S)-3-phenyl-5-(phenylmethyl)-2-thioxo-4-Imidazolidinone;(5S)-5-benzyl-3-phenyl-2-sulfanylideneimidazolidin-4-one
• CAS NO: 29588-07-6
• Molecular Formula: C₁₆H₁₄N₂OS
• Molecular Weight: 282.36
• Mol File: 29588-07-6.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 410.6°C at 760 mmHg
• Flash Point: 202.1°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 5.93E-07mmHg at 25°C
• Refractive Index: 1.699
• CAS DataBase Reference: PHENYLTHIOHYDANTOIN PHENYLALANINE)(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLTHIOHYDANTOIN PHENYLALANINE)(29588-07-6)
• EPA Substance Registry System: PHENYLTHIOHYDANTOIN PHENYLALANINE)(29588-07-6)

Safety Data

• Hazardous Substances Data: 29588-07-6(Hazardous Substances Data)

Usage

General Description

Phenylthiohydantoin phenylalanine is a chemical compound used in the laboratory to derivatize amino acids for analysis. It is formed by reacting phenylalanine with phenylisothiocyanate, resulting in the formation of a phenylthiohydantoin derivative of phenylalanine. This derivative has a high stability and is widely used in chromatographic and mass spectrometric analysis of amino acids. It allows for the specific and sensitive detection of phenylalanine in biological samples and is particularly useful in the diagnosis and monitoring of phenylketonuria, a genetic disorder that results in the buildup of phenylalanine in the body.

InChI:InChI=1/C16H14N2OS/c19-15-14(11-12-7-3-1-4-8-12)17-16(20)18(15)13-9-5-2-6-10-13/h1-10,14H,11H2,(H,17,20)/t14-/m0/s1

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 103-72-0 phenyl isothiocyanate 
• 63-91-2 L-phenylalanine 
• 49645-33-2 phenyl thioisocyanate 
• 1219278-46-2 BF₄^(1-)*C₂₈H₃₀N₅OS⁽¹⁺⁾ 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 74734-11-5 1H-imidazole-1-carbodithioic acid methyl ester 
• 62-53-3 aniline 
• 35661-40-6 N-Fmoc L-Phe 
• 150-30-1 Phenylalanine 
• 154738-10-0 N-phenyl-N'-(2-phenyl-1-carboxyethyl)thiocarbamide 
• 15028-44-1 DL-phenylalanine methyl ester 
• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 701-73-5 methyl N-phenyldithiocarbamate 

Downstream Products

• 32832-07-8 (E)-5-benzylidene-3-phenyl-2-thioxoimidazolidin-4-one 
• 1393347-01-7 (Z)-4-benzylidene-1-phenyl-1H-imidazol-5-one 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 155496-29-0 2-thioxo-3-phenyl-5-phenylmethylene-4-imidazolidinone 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 716-79-0 2-phenyl-1H-benzoimidazole 

Relevant articles and documents

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Microwave-assisted traceless synthesis of thiohydantoin

An efficient, microwave-assisted method for the liquid-phase combinatorial synthesis of 3,5-disubstituted-thiohydantoin has been developed. Fmoc-protected amino acids were coupled with HO-PEG-OH and after deprotection, reacted with various isothiocyanates

Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes

A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface (B3LYP/6–31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction.

NOVEL AZULENYL COMPOUND

PROBLEM TO BE SOLVED: To provide: a method for determining amino acid sequences such as trace peptides and proteins; as well as a compound that can be used as an Edman reagent suitable for said method, specifically a compound that has a high UV absorbance and efficiently reacts with peptides. SOLUTION: Provided is an azulenyl isothiocyanate compound represented by the formula (1). (Each R independently is a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group or heteroaryl group having 6 to 10 carbon atoms; n is an integer from 0 to 7; in particular, R preferably is an alkyl group having 1 to 10 carbon atoms, and further preferably has substituent group at 1 or more of the carbon 3-, 5-, 8-position.). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT