881-05-0

Basic information

• Product Name: 1H-Pyrazole-4,5-dione,3-Methyl-1-phenyl-
• Synonyms: 1H-Pyrazole-4,5-dione,3-Methyl-1-phenyl-
• CAS NO: 881-05-0
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18272
• Mol File: 881-05-0.mol

Chemical Properties

• Melting Point: 118-120 °C
• Boiling Point: 289.9±23.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• PKA: -0.11±0.40(Predicted)
• CAS DataBase Reference: 1H-Pyrazole-4,5-dione,3-Methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-4,5-dione,3-Methyl-1-phenyl-(881-05-0)
• EPA Substance Registry System: 1H-Pyrazole-4,5-dione,3-Methyl-1-phenyl-(881-05-0)

Safety Data

• Hazardous Substances Data: 881-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1H-Pyrazole-4,5-dione,3-Methyl-1-phenylis used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals for its versatile chemical structure and potential to be modified for specific therapeutic or pesticidal effects.
Used in Organic Synthesis:
As a versatile building block, 1H-Pyrazole-4,5-dione,3-Methyl-1-phenylis used in organic synthesis to create a range of chemical compounds with diverse applications, leveraging its reactive functional groups and structural features.
Used in Medicinal Chemistry:
1H-Pyrazole-4,5-dione,3-Methyl-1-phenylis utilized in medicinal chemistry for the development of new drugs, taking advantage of its potential biological activities, such as anti-inflammatory and analgesic properties, to treat various medical conditions.
Used in Photochromic Materials:
1H-Pyrazole-4,5-dione,3-Methyl-1-phenylhas been investigated for its potential use in photochromic materials, where its properties may allow it to change color upon exposure to light, offering applications in smart materials and devices.
Used in the Synthesis of New Functional Materials:
1H-Pyrazole-4,5-dione,3-Methyl-1-phenylserves as a building block for the synthesis of new functional materials, where its unique structure and properties can be harnessed to create materials with specific functions in various industries, such as electronics, sensors, or energy storage.

Upstream product

• 99694-71-0 4-aminoantipyrine 
• 117985-07-6 4-Diethylamino-phenylimino-3-methyl-1-phenyl-2-pyrazolin-5-on 
• 1456-89-9 1-Phenyl-3-methyl-4-(4-dimethylaminophenylimino)-pyrazolin-5-on 
• 60-80-0 antipyrine 
• 62947-11-9 4,4-Dibromo-3-methyl-1-phenyl-2-pyrazolin-5-one 
• 58-15-1 aminopyrine 
• 3615-24-5 ramifenazone 
• 2139-47-1 nifenazone 
• 6536-18-1 Morazone 
• 117985-05-4 (E)-5-methyl-2-phenyl-4-(phenylimino)-2,4-dihydro-3H-pyrazol-3-one 
• 4593-76-4 1-phenyl-3-methyl-4-benzhydryl-2-pyrazolin-5-one 
• 60-29-7 diethyl ether 
• 7664-93-9 sulfuric acid 
• 7705-08-0 iron(III) chloride 

Downstream Products

• 909-59-1 4-<3-methyl-1-phenyl-5-oxo-2-pyrazoline-4-ylideneamino>-3-methyl-1-phenyl-2-pyrazoline-5-one 
• 1055-31-8 1,5,5'-trimethyl-2,2'-diphenyl-1,2,2',4'-tetrahydro-4,4'-azanylylidene-bis-pyrazol-3-one 
• 36013-41-9 5-methyl-2-phenyl-2H-pyrazole-3,4-dione 4-(methyl-phenyl-hydrazone) 
• 292620-42-9 4-(2-aminophenylimino)-5-methyl-2-phenyl-3,4-dihydro-2H-pyrazol-3-one 
• 19374-75-5 3-methyl-1-phenylpyrazole-4,5-dione 4-phenylhydrazone 
• 1080-89-3 4-hydroxyimino-3-methyl-1-phenyl-2-pyrazolin-5-one 
• 32273-66-8 9-methyl-7-phenyl-1,4-dioxa-7,8-diaza-spiro[4.4]non-8-en-6-one 
• 62094-95-5 rubazonic acid 
• 75380-47-1 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazole-3,4-dione 4-bis(quinoxaline-2,3-diylhydrazone) 
• 94724-62-6 3-methyl-1-phenyl-5-oxopyrazolo-4-yl-methylidene-2-(quinolium-1-ethiodide)cyanine 
• 94724-63-7 3-Ethyl-2-[3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-(4Z)-ylidenemethyl]-benzooxazol-3-ium; iodide 
• 96498-76-9 3-Methyl-1-phenyl-5-p-tolyl-1H-pyrazolo[4,3-d]oxazole 

Relevant articles and documents

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

Organocatalytic Direct Asymmetric Indolization from Anilines by Enantioselective [3 + 2] Annulation

We report the efficient syntheses of chiral tetrahydroindole pyrazolinones by the asymmetric [3 + 2] cascade cyclizations (indolizations) of simple aniline derivatives with pyrazolinone ketimines as 2C synthons. The chiral phosphoric-acid-catalyzed system uses a concerted π-πinteraction/dual H-bond control strategy to catalytically direct the asymmetric aniline, which undergoes a highly chemo-, regio-, and enantioselective [3 + 2] cascade annulation, furnishing a series of optically active tetra-hydroindole pyrazolinones with two contiguous chiral aza-quaternary carbon centers in excellent yields with excellent enantioselectivities. This method features a relatively broad substrate scope for amines and 2-naphthylamines and highlights the emerging value of direct chiral indolizations from simple amine sources in organic synthesis.

Iodine-Catalyzed Construction of Dihydrooxepines via 3-Methyl-5-Pyrazolones C?H Oxidation/Functionalization of Quinolines Cascade

An efficient iodine-catalyzed [3+3+1] annulation for the construction of dihydrooxepine scaffolds with quinoline units was developed. This strategy involves a seven-membered dihydrooxepine with a broad substrate scope through a formal three-component tandem reaction. Further derivation of the target product produced a trioxabicycle scaffold, which formed the basic core of natural products and pharmaceutical molecules.

Squaramide-catalyzed asymmetric Mannich reactions between 3-fluorooxindoles and pyrazolinone ketimines

An enantioselective Mannich reaction between 3-fluorooxindoles and pyrazolinone ketimines has been developed for the construction of amino-pyrazolone-oxindoles containing stereogenic C-F units. Based on this new protocol that allows for the generation of two adjacent tetrasubstituted stereocenters, a variety of structurally diverse fluorinated amino-pyrazolone-oxindoles were obtained in good to excellent yields with excellent diastereoselectivities and enantioselectivities (up to 98% yield, >20:1 dr and >99% ee). What's more, good yield and high stereoselectivities were obtained in the gram-scale reaction.

Asymmetric Organocatalytic Friedel-Crafts Hydroxyalkylation of Indoles Using Electrophilic Pyrazole-4,5-diones

The electrophilic reactivity of a series of novel pyrazole-4,5-dione derivatives in the organocatalytic Friedel-Crafts reaction with various substituted indoles has been tested. The disclosed procedure catalyzed by a cinchona alkaloid derivative allows the conjugation of two very important aza-heterocyclic scaffolds to generate a new class of indolylpyrazolones bearing a tetrasubstituted stereocenter in excellent yields (up to 99%) and with enantioselectivities of up to 94:6 er.

Enantioselective synthesis of pyrazolone α-aminonitrile derivatives: Via an organocatalytic Strecker reaction

A new organocatalytic enantioselective Strecker reaction of pyrazolone-derived ketimine electrophiles has been developed. Using pseudo-enantiomeric squaramide catalysts the nucleophilic 1,2-addition of trimethylsilyl cyanide to the ketimines efficiently provides a direct entry to both enantiomers of pyrazolone α-aminonitrile derivatives at will in good yields and high enantioselectivities for a wide variety of substrates.

Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction

A new series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in asymmetric Mannich reactions with pyrazolones. The amino-bis-pyrazolone products are obtained in excellent yields and stereoselectivities by employing a very low loading of 1 mol % of a bifunctional squaramide organocatalyst. Depending on the substitution at position 4 of the pyrazolones, the new protocol allows for the generation of one or two tetrasubstituted stereocenters, including a one-pot version combing the Mannich reaction with a base-mediated halogenation.

Squaramide-Catalyzed Asymmetric aza-Friedel–Crafts/N,O-Acetalization Domino Reactions Between 2-Naphthols and Pyrazolinone Ketimines

N-Boc ketimines derived from pyrazolin-5-ones were explored to develop an unprecedented domino aza-Friedel–Crafts/N,O-acetalization reaction with 2-naphthols. The novel method requires a catalyst loading of only 0.5 mol % of a bifunctional squaramide catalyst, is scalable to gram amounts, and provides a new series of furanonaphthopyrazolidinone derivatives bearing two vicinal tetra-substituted stereogenic centers in excellent yields (95–98 %) and stereoselectivity (>99:1 d.r. and 97–98 % ee). A different reactivity was observed in the case of 1-naphthols and other electron-rich phenols, which led to the aza-Friedel–Crafts adducts in 70–98 % yield and 47–98 % ee.

A new regiospecific synthesis method of 1H-pyrazolo[3,4-b]quinoxalines – Potential materials for organic optoelectronic devices, and a revision of an old scheme

A series of 6-substituted-1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxalines were prepared using a new synthetic pathway: reductive cyclization of appropriate 5-(o-nitrophenyl)-pyrazoles with ferrous oxalate or triphenylphosphine. The main advantage of this procedure is that, contrary to the older protocols of pyrazolo[3,4-b]quinoxaline synthesis, this method allows for a substituent to be introduced to the carbocyclic ring without the formation of isomers. The pyrazole ring can also be modified to some extent. Furthermore, we propose a new mechanism for the oldest reported pyrazolo[3,4-b]quinoxaline synthesis, based on the condensation between o-phenylenediamine and 3,4-pyrazolin-5-diones.

Development of new dyeing photoinitiators for free radical polymerization based on the 1H-pyrazolo[3,4-b]quinoxaline skeleton. Part 2

Several dyes containing a pyrazoloquinoxaline moiety have been synthesized and evaluated as novel photoinitiators for free radical polymerization induced with the argon-ion laser. The kinetic study of photoinitiated polymerization, performed for viscous monomeric formulations with the use of the most effective dye-N-phenylglycine derivative photoinitiating systems has shown unusual kinetic properties. The experimental data show the presence of "Marcus inverted region"-like kinetic behavior. Analysis of possible reasons for this specific feature suggests that one of the processes that may be responsible for such a specific property is the back electron transfer process. Study of photo-initiated polymerization has shown that there is a linear relationship between the rate of polymerization and the square root of the efficiency of singlet oxygen formation. This finding clearly indicates that the electron transfer process between the tested dyes and electron donors occurs via a triplet state. The observed relationship is also in good agreement with the general equation describing the rate of polymerization, which is (among other parameters) a function of the square root of the quantum yield of triplet state formation. In the paper, it is also shown that the structure of the dye has a strong effect on its polymerization photoinitiation ability. The dyes tested were prepared in such a way as to, (i) restrict the rotational freedom of selected parts of the molecule and (ii) increase the quantum yield of the triplet state formation. The latter was achieved by introducing to the molecule a heavy atom (ZCl2, CI) or different heavy atoms (CICl2).