15988-11-1 Usage
Description
4-Phenylurazole is a laboratory chemical used as a precursor in the synthesis of various compounds, including the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione. It is known for its ability to undergo oxidation, acetylation, and polymerization reactions, and has been recently demonstrated in the traceless, chemoselective labeling of peptides and proteins through electrochemical tyrosine-click (e-Y-CLICK) chemistry. It is characterized by its white to light beige crystalline powder or granule appearance.
Uses
Used in Chemical Synthesis:
4-Phenylurazole is used as a precursor for the synthesis of the Diels-Alder trapping agent, 4-phenyl-1,2,4-triazoline-3,5-dione, which is an important intermediate in the production of various chemical compounds.
Used in Dyes Industry:
The derivative of 4-Phenylurazole, azo dyes, has wide applications in the dyes industry due to their diverse color properties and versatility in use.
Used in Polymer Synthesis:
4-Phenylurazole is used as a monomer in the polymerization process, yielding insoluble polymers when reacted with phosgene, terephthaloyl chloride, and epichlorohydrin. These polymers can be utilized in various applications, such as coatings, adhesives, and plastics.
Used in Pharmaceutical and Biotechnology Research:
4-Phenylurazole has been demonstrated in the traceless, chemoselective labeling of peptides and proteins through electrochemical tyrosine-click (e-Y-CLICK) chemistry, making it a valuable tool in pharmaceutical and biotechnology research for the development of new drugs and therapies.
Purification Methods
Crystallise 4-phenylurazole from water or 95% EtOH. Dissolve 35g in 80mL of boiling 95% EtOH and on cooling 90-95% is recovered with m 209-210o. It has IR with 1685 and 3120cm-1. [Cookson et al. Org max Synth 51 121 1971, Beilstein 26 I 64, 26 III/IV 540.]
References
http://www.sigmaaldrich.com/catalog/product/aldrich/188956?lang=en®ion=US&gclid=EAIaIQobChMI6r7k0eu71gIV1IZoCh0nwgLjEAAYASAAEgI0tvD_BwE
http://nopr.niscair.res.in/handle/123456789/21799
Check Digit Verification of cas no
The CAS Registry Mumber 15988-11-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,9,8 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 15988-11:
(7*1)+(6*5)+(5*9)+(4*8)+(3*8)+(2*1)+(1*1)=141
141 % 10 = 1
So 15988-11-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H7N3O2/c12-7-9-10-8(13)11(7)6-4-2-1-3-5-6/h1-5H,(H,9,12)(H,10,13)
15988-11-1Relevant articles and documents
A reliable multi-kilogram preparation of 4-phenylurazole
Chandrasekhar,Kumar,Mallela,Bhirud
, p. 469 - 472 (2004)
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Tandem Functionalization in a Highly Branched Polymer with Layered Structure
Cao, Xiaosong,Shi, Yi,Gan, Weiping,Gao, Haifeng
supporting information, p. 5974 - 5981 (2018/03/26)
A hyperbranched polymer with multilayer structure was developed to demonstrate the possibility of highly efficient tandem functionalization reactions at different domains within one nanostructured platform. The polymer scaffold was constructed by chain-growth copper-catalyzed azide–alkyne cycloaddition polymerization of three functional monomers with sequential monomer addition in one pot. Subsequent reactions with different monomer units resulted in efficient functionalization of each segment with construction of a highly sophisticated polymer structure by a robust procedure. As a proof of concept, the ability of this polymer structure to quantitatively load six species of guest molecules through three different types of conjugation reactions was demonstrated.
Reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with 2-pyrazolines
Novikov,Korolev,Tomilov
experimental part, p. 1685 - 1693 (2012/09/05)
4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) acts as an efficient Michael acceptor in reactions with 1-unsubstituted 2-pyrazolines, giving substituted (3,5-dioxo-4-phenyl-1,2,4-triazol-idin-1-yl)-1-pyrazolines in quantitative yields. Through elimination of molecular nitrogen, the latter are easily transformed into the corresponding cyclopropanes. A reaction of methyl 5-methyl-2-pyrazoline-5-carboxylate with a twofold excess of PTAD leads to an intermediate bisadduct, which undergoes dediazotization to form a 1,3,5-triazabicyclo[3.3.0]octane-2,4-dione derivative. 1-Substituted 2-pyrazolines also add to PTAD with the exception that the 2-pyrazoline structure is retained in the product because of the migration of the C(3)H proton to PTAD.