31108-57-3

Basic information

• Product Name: 4-CYANOPYRAZOLE
• Synonyms: 4-CYANOPYRAZOLE;4-Pyrazolecarbonitrile;4-CYANOPYRAZOLE 97%;4-Cyano-1H-pyrazole;1H-Pyrazole-4-carbonitrile;1H-Pyrazole-4-carbonitrle;1H-Pyrazole-4-carbonitrile (as hydrochloride)
• CAS NO: 31108-57-3
• Molecular Formula: C₄H₃N₃
• Molecular Weight: 93.09
• Product Categories: Pyrazole series
• Mol File: 31108-57-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 317.4 °C at 760 mmHg
• Flash Point: 114 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 0.000385mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.30±0.50(Predicted)
• CAS DataBase Reference: 4-CYANOPYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANOPYRAZOLE(31108-57-3)
• EPA Substance Registry System: 4-CYANOPYRAZOLE(31108-57-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 31108-57-3(Hazardous Substances Data)

Usage

Uses

4-Cyanopyrazole is used to catalyze epoxidation of ethene by hydrogen peroixde.

InChI:InChI=1/C4H3N3/c5-1-4-2-6-7-3-4/h2-3H,(H,6,7)

Synthetic route

4-bromo-1H-pyrazole (2075-45-8) + potassiumhexacyanoferrate(II) trihydrate → 1H-pyrazole-4-carbonitrile (31108-57-3)

Conditions	Yield
With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;	90%

α-cyano-β-dimethylaminoacrolein (149139-41-3) → 1H-pyrazole-4-carbonitrile (31108-57-3)

Conditions	Yield
With hydrogenchloride; hydrazine In ethanol for 1h; Heating;	55%

4-bromo-1H-pyrazole (2075-45-8) + [11C]hydrogen cyanide (14904-70-2) → 1H-pyrazole-4-carbonitrile (31108-57-3)

Conditions	Yield
Stage #1: 4-bromo-1H-pyrazole With XPhos In toluene at 20℃; for 0.5h; Stage #2: [11C]hydrogen cyanide In tetrahydrofuran at 100℃; for 0.0166667h;

C24H41BrO + 1H-pyrazole-4-carbonitrile (31108-57-3) → C28H43N3O

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;	97.5%

(2R,5S)-tert-butyl 5-(4-chlorobenzyl)-2-(((methylsulfonyl)oxy)methyl)morpholine-4-carboxylate + 1H-pyrazole-4-carbonitrile (31108-57-3) → (2R,5S)-tert-butyl 5-(4-chlorobenzyl)-2-((4-cyano-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃; Sealed tube;	97%

3,4-dihydro-2H-pyran (110-87-2) + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbonitrile (1448317-12-1)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 3 - 20℃;	96%

trimethylamine-borane (75-22-9) + 1H-pyrazole-4-carbonitrile (31108-57-3) → {1-(4-cyano)pyrazolyl}borane (18601-58-6)

Conditions	Yield
	95%
	95%

triethyl borane (97-94-9) + 1H-pyrazole-4-carbonitrile (31108-57-3) → bis-[μ-(4-cyano-pyrazolato-N1:N2)]-tetraethyl-bis-boron (14695-72-8)

Conditions	Yield
	93%
	93%

C23H38O2 + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-((R)-2-hydroxy-2-((3R,5R,8R,9R,10S,13S,14S,15R,17S)-3-hydroxy-3,13,15-trimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propyl)-1H-pyrazole-4-carbonitrile + 1-((S)-2-hydroxy-2-((3R,5R,8R,9R,10S,13S,14S,15R,17S)-3-hydroxy-3,13,15-trimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)propyl)-1H-pyrazole-4-carbonitrile

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 25 - 120℃; for 16h;	A 43% B 93%

methyl 3-(((methylsulfonyl)oxy)methyl)bicyclo[1.1.1]pentane-1-carboxylate + 1H-pyrazole-4-carbonitrile (31108-57-3) → methyl 3-((4-cyano-1H-pyrazol-1-yl)methyl)bicyclo[1.1.1]pentane-1-carboxylate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	93%

ethyl iodide (75-03-6) + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-ethyl-1H-pyrazole-4-carbonitrile

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 16h;	92%

C25H42O3 + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-((R)-2-((3R,5R,8S,9S,10S,13S,14S,17S)-10-ethyl-3-hydroxy-3-(methoxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxypropyl)-1H-pyrazole-4-carbonitrile + 1-((S)-2-((3R,5R,8S,9S,10S,13S,14S,17S)-10-ethyl-3-hydroxy-3-(methoxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxypropyl)-1H-pyrazole-4-carbonitrile

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 48h;	A 53.4% B 92%

C23H39BrO + 1H-pyrazole-4-carbonitrile (31108-57-3) → C27H41N3O

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 15 - 80℃; for 2h; Inert atmosphere;	91.5%

3-chloromethyl-6-(trifluoromethyl)pyridine (386715-33-9) + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-((6-(trifluoromethyl)pyridin-3-yl)methyl)-1H-pyrazole-4-carbonitrile

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	90.7%

p-Methoxybenzyl bromide (2746-25-0) + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-(4-methoxybenzyl)-1H-pyrazole-4-carbonitrile (1448317-15-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃;	87%

ethyl 1-(6-(2-(4-(3-bromopropoxy)-2-methylphenethyl)-5-fluorophenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate + 1H-pyrazole-4-carbonitrile (31108-57-3) → ethyl 1-(6-(2-(4-(3-(4-cyano-1H-pyrazol-1-yl)propoxy)-2-methylphenethyl)-5-fluorophenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃; for 16h;	87%

1H-pyrazole-4-carbonitrile (31108-57-3) + benzene (71-43-2) → 1-phenyl-1H-pyrazole-4-carbonitrile (709-04-6)

Conditions	Yield
With 10-phenyl-10H-phenothiazine; 1,1,1,3',3',3'-hexafluoro-propanol; oxygen; lithium perchlorate In 2,2,2-trifluoroethanol under 760.051 Torr; Irradiation; Cooling;	87%

C21H34O2 + 1H-pyrazole-4-carbonitrile (31108-57-3) → C25H37N3O2

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;	84%

C24H41BrO2Si + 1H-pyrazole-4-carbonitrile (31108-57-3) → C28H43N3O2Si

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	82%

1H-pyrazole-4-carbonitrile (31108-57-3) → 4-cyano-N-nitropyrazole

Conditions	Yield
With Iron(III) nitrate nonahydrate; tetrabutylammonium tetrafluoroborate In acetonitrile at 70℃; Inert atmosphere; Electrolysis; Green chemistry;	80%

C30H44O5S + 1H-pyrazole-4-carbonitrile (31108-57-3) → 1-((3-((3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)oxetan-3-yl)methyl)-1H-pyrazole-4-carbonitrile

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 16h;	79%

Upstream product

• 149139-41-3 α-cyano-β-dimethylaminoacrolein 
• 2075-45-8 4-bromo-1H-pyrazole 
• 14904-70-2 [11C]hydrogen cyanide 

Downstream Products

• 18601-58-6 {1-(4-cyano)pyrazolyl}borane 
• 1333-74-0 hydrogen 
• 75-50-3 trimethylamine 
• 1144022-92-3 1-[2-cyano-4-[5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]phenyl]-1H-pyrazole-4-carbonitrile 
• 1219601-60-1 C₁₁H₉N₃O₂S 
• 1413065-66-3 1-(3-bromo-2-formylphenyl)-1H-pyrazole-4-carbonitrile 
• 1448317-15-4 1-(4-methoxybenzyl)-1H-pyrazole-4-carbonitrile 
• 1622426-52-1 1-(6-phenylhexanoyl)-1H-pyrazole-4-carbonitrile 
• 1622426-61-2 1-(5-phenylpentanoyl)-1H-pyrazole-4-carbonitrile 
• 1632051-40-1 zuranolone 
• 37599-59-0 C-(1H-pyrazol-4-yl)methylamine 

Relevant articles and documents

Virtually instantaneous, room-temperature [11C]-cyanation using biaryl phosphine Pd(0) complexes

A new radiosynthetic protocol for the preparation of [11C]aryl nitriles has been developed. This process is based on the direct reaction of in situ prepared L·Pd(Ar)X complexes (L = biaryl phosphine) with [11C]HCN. The strategy is operationally simple, exhibits a remarkably wide substrate scope with short reaction times, and demonstrates superior reactivity compared to previously reported systems. With this procedure, a variety of [11C]nitrile-containing pharmaceuticals were prepared with high radiochemical efficiency.

Cyanoacetaldehyde - New Synthetic Applications of an Old Compound Syntheses with Nitriles, XCI

Various reactions of cyanoacetaldehyde (1), freshly prepared by ozonization of (E)-1,4-dicyano-2-butene or allylcyanide, are described.Thus, conversion of 1 with anilines gave β-phenylaminoacrylonitriles 2a-e.Reaction of 1 with hydrazines led to the corresponding hydrazones 3a-e, which could be cyclized under alkaline conditions to 5-aminopyrazoles 4a-d.An aldol-type condensation product 5a could be obtained by reaction of 1 with sodiumphenoxide.Treatment of 1 with dimethylformamide-dimethylacetal led to the formation of (E)-3-dimethylamino-2-formylpropenenitrile (6), a very useful synthon in synthetic chemistry.For the determination of the structure of 6 the method of steady state diffferential NOEs was used.Reaction of 6 with hydrazines gave 1-substituted-4-cyanopyrazoles 7a-k. Keywords.Cyanoacetaldehyde; Hydrazones; Cyanopyrazoles; Aminopyrazoles.