4702-90-3

Basic information

• Product Name: Solvent Yellow 93
• Synonyms: transparent yellow 3g;3H-Pyrazol-3-one, 4-(1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)methyl-2,4-dihydro-5-methyl-2-phenyl-;Solvent yellow 93 (C.I. 48160);4-[(1,5-Dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)methyl]-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one;C.I. 48160;Solvent Yellow 93;Kayaset Yellow GN;Oplas Yellow 140
• CAS NO: 4702-90-3
• Molecular Formula: C₂₁H₁₈N₄O₂
• Molecular Weight: 358.39
• EINECS: 225-184-1
• Product Categories: Solvent Dyestuff
• Mol File: 4702-90-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 180 °C
• Boiling Point: 556.2 °C at 760 mmHg
• Flash Point: 290.2 °C
• Appearance: COA
• Density: 1.27 g/cm³
• Vapor Pressure: 2.07E-12mmHg at 25°C
• Refractive Index: 1.668
• PKA: 1.73±0.70(Predicted)
• Water Solubility: 4.7μg/L at 23℃
• CAS DataBase Reference: Solvent Yellow 93(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Yellow 93(4702-90-3)
• EPA Substance Registry System: Solvent Yellow 93(4702-90-3)

Safety Data

• Hazardous Substances Data: 4702-90-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

Properties and Applications

yellow. Green light yellow powder. Insoluble in water, soluble in ethanol, Chloroform, Acetone and organic solvent. Mainly used in polyester protoplasmic coloring, also used in the manufacture of polyester masterbatch. Standard Light Fastness Heat-resistant(℃) water Sodium Carbonate(5%) Hydrochloric acid(5%) Melting point Stable ISO Well 300 Well Well Well

Standard

Light Fastness

Melting point

Stable

ISO

Well

InChI:InChI=1/C21H18N4O2/c1-14-18(20(26)24(22-14)16-9-5-3-6-10-16)13-19-15(2)23-25(21(19)27)17-11-7-4-8-12-17/h3-13,18H,1-2H3/b19-13+

Synthetic route

6-[allyl(methyl)amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde (1188497-81-5) + edaravone (89-25-8) → 1,3-dimethyl-6-N,N-(allylmethyl)aminouracil (105459-37-8) + 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol for 2.5h; Reflux;	A 80% B n/a

6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde (139958-85-3) + edaravone (89-25-8) → 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3) + 6-hydroxy-1,3-dimethyluracil (41949-07-9)

Conditions	Yield
With piperidine In ethanol at 20℃; for 0.5h;	A 80% B 80%

edaravone (89-25-8) + 1,3-Dimethyl-2,4-dioxo-6-pyrrolidin-1-yl-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde (193696-10-5) → N,N-dimethyl-6-pyrrolidino uracil (74151-85-2) + 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol for 2.5h; Reflux;	A 80% B n/a

6-(Allyl-phenyl-amino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde (114143-07-6) + edaravone (89-25-8) → C15H17N3O2 (1188497-84-8) + 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3)

Conditions	Yield
With piperidine In ethanol at 20℃; for 0.666667h;	A 75% B n/a

edaravone (89-25-8) + 6-chloro-5-formyl-1,3-dimethyluracil (35824-85-2) → 1,3-Dimethyl-6-chlorouracil (6972-27-6) + 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3)

Conditions	Yield
With piperidine In ethanol at 20℃; for 0.5h;	A 75% B n/a

6-hydroxy-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde + edaravone (89-25-8) → 1-phenyl-3-methyl-4-(1-phenyl-3-methyl-5-oxo-4-pyrazolylidene)methylene-5-pyrazolone (4702-90-3) + 6-Hydroxy-1-methyl-1H-pyrimidine-2,4-dione

Conditions	Yield
With piperidine In ethanol at 20℃; for 0.666667h;	A n/a B 70%

Upstream product

• 89-25-8 edaravone 
• 1188497-81-5 6-[allyl(methyl)amino]-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 
• 1188497-82-6 C₆H₅ClN₂O₃ 
• 54660-80-9 6-amino-1,3-dimethyl-5-formyluracil 
• 139958-85-3 6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 114143-07-6 6-(Allyl-phenyl-amino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 35824-85-2 6-chloro-5-formyl-1,3-dimethyluracil 
• 193696-10-5 1,3-Dimethyl-2,4-dioxo-6-pyrrolidin-1-yl-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 947-95-5 5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole 
• 109-77-3 malononitrile 
• 51751-34-9 4-hydroxycoumarin-3-carboxaldehyde 
• 942-32-5 5-methyl-2-phenyl-2H-pyrazol-3-ol 
• 122-51-0 orthoformic acid triethyl ester 
• 151-50-8 potassium cyanide 

Relevant articles and documents

A mild and efficient method for the deformylation of 5-formyl uracils and synthesis of 4,4￠-methylidenebis(1-phenyl-3-methyl-5-pyrazolone)

6-Substituted 5-formyl uracils undergo an interesting reaction with 1-phenyl-3-methyl-5-pyrazolone in the presence of base catalyst to afford deformylated uracils and 4,4￠-methylidenebis(1-phenyl-3-methyl-5- pyrazolone) in excellent yields. Georg Thieme V

Novel reactions of 5-chloro-4-formyl-3-methyl-1-phenylpyrazole with active methylene compounds

Condensation of 5-chloro-4-formyl-3-methyl-1-phenylpyrazole (1) with malononitrile in the presence of piperidine or ammonium acetate affords the corresponding pyrazole derivatives (2-4). Base-catalyzed cyclocondensation of 1 with hippuric acid or ethyl glycinate hydrochloride gives the oxazolone 6 and 5-amino-3-methyl-6-oxo-1-phenyl-1,6-dihydropyrano[2,3-c]pyrazole (7) respectively. Treatment of 1 with ethyl cyanoacetate in basic medium produce ethyl α-cyano-β-(5-chloro-3-methyl-1-phenylpyrazol-4-yl)acrylate (8) which reacts with nitrogen nucleophiles to give compounds 9-12. Transesterification and/or hydrolysis of ester group has been observed on treatment of 8 with methyl alcohol in basic medium leading to the formation of acrylate derivatives (13-15). Compound 8 on treatment with ethyl acetoacetate or cyclohexanone undergoes condensation with subsequent cyclization and/or dearylation to give the adducts 16 and 17 respectively. Structures of all the products have been established by elemental analysis, IR, PMR and mass spectral data.