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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The reaction of oximes with 4-phenyl-1,2,4-triazoline-3,5-dione to produce nitric oxide – Model compounds for nitric oxide synthase
Jensen, Anton W.,Flotka, Daryl,Xu, Tianzuo,Pullizzi, Alexis E.,Dilling, Wendell L.,Doverspike, Joshua C.,Meyerhoff, Mark E.,Mohanty, Dillip K.
supporting information, p. 2173 - 2175 (2018/05/08)
Certain oximes form nitric oxide upon reaction with 4-phenyl-1,2,4-triazole-3,5-dione (PTAD). The oximes appear to undergo an Alder-ene reaction with the PTAD enophile to form a nitroso intermediate capable of dimerization and/or nitric oxide formation. Upon exposure to oxygen, the nitroso compounds eventually form ketones. This reaction may serve as a model for the study of nitric oxide synthase (NOS), the enzyme responsible for physiological production of nitric oxide. NOS is known to produce an oxime intermediate which reacts with oxygen to produce nitric oxide and citrulline.
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.