36650-74-5

Usage

Uses

Used in Chemical Synthesis:
1H-Pyrazole-3-carbonitrile is used as a building block for the synthesis of various organic compounds, contributing to the development of new chemical entities with potential applications in different industries.
Used in Pharmaceutical Industry:
1H-Pyrazole-3-carbonitrile is utilized as a reagent in organic synthesis, playing a crucial role in the development of pharmaceuticals. Its potential biological and pharmacological activities make it a valuable component in the creation of novel drug candidates.
Used in Agrochemical Production:
1H-Pyrazole-3-carbonitrile serves as a precursor in the production of agrochemicals, contributing to the development of effective and safe products for agricultural applications.

InChI:InChI=1/C4H3N3/c5-3-4-1-2-6-7-4/h1-2H,(H,6,7)

Synthetic route

1H-pyrazole-3-carboxamide (33064-36-7) → pyrazolecarbonitrile (36650-74-5)

Conditions	Yield
at 335℃; for 1h; Temperature;	85%
With sodium chloride; trichlorophosphate In acetonitrile at 80℃;

3-bromo-3-cyano-4,5-dihydropyrazole → pyrazolecarbonitrile (36650-74-5)

Conditions	Yield
at 20℃; for 1h; Elimination;	65%

4-diazo-1,1,1,2,2-pentafluoro-3-pentafluoroethyl-3-trifluoromethylbutane (87879-93-4) + acrylonitrile (107-13-1) → pyrazolecarbonitrile (36650-74-5)

Conditions	Yield
for 240h;	47%

diazomethane (186581-53-3, 908094-01-9) + (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile (205251-17-8) → pyrazolecarbonitrile (36650-74-5)

Conditions	Yield
In diethyl ether at -10℃;

1H-pyrazole-3-carbxaldehyde oxime (30192-58-6) → pyrazolecarbonitrile (36650-74-5)

Conditions	Yield
With acetic anhydride at 100℃; for 5h;

tert-butyl N-(3,4-dichloro-6-fluoro-9H-pyrido[2,3-b]indol-8-yl)-N-ethylcarbamate + pyrazolecarbonitrile (36650-74-5) → tert-butyl N-[3-chloro-4-(3-cyanopyrazol-1-yl)-6-fluoro-9H-pyrido[2,3-b]indol-8-yl]-N-ethyl-carbamate

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 12h;	87.6%

ethanol (64-17-5) + pyrazolecarbonitrile (36650-74-5) → ethyl 1H-pyrazole-3-carboximidoate hydrochloride

Conditions	Yield
With hydrogenchloride In chloroform for 3.83333h; Cooling with acetone-dry ice;	81%
With hydrogenchloride In chloroform for 3h; Cooling with acetone-dry ice;

pyrazolecarbonitrile (36650-74-5) → 1-nitro-1H-pyrazole-3-carbonitrile

Conditions	Yield
With nitric acid; acetic anhydride; trifluoroacetic acid at 5 - 10℃; for 2h;	80%

pyrazolecarbonitrile (36650-74-5) → 5-(1H-pyrazol-3-yl)tetrazole

Conditions	Yield
With sodium azide; triethylamine hydrochloride In toluene at 110℃; for 10h;	79%
With sodium azide; zinc dibromide In N,N-dimethyl-formamide at 175℃; for 0.333333h; microwave irradiation;

pyrazolecarbonitrile (36650-74-5) + alpha-bromo-3,4-difluorotoluene (85118-01-0) → 1-(3,4-difluorobenzyl)-1H-pyrazole-3-carbonitrile + C11H7F2N3

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	A 75% B n/a

2-bromo-6-fluorobenzaldehyde (360575-28-6) + pyrazolecarbonitrile (36650-74-5) → 1-(3-bromo-2-formylphenyl)-1H-pyrazole-3-carbonitrile (1413065-58-3)

Conditions	Yield
Stage #1: pyrazolecarbonitrile With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: 2-bromo-6-fluorobenzaldehyde In dimethyl sulfoxide at 20℃;	73%

C24H41BrO + pyrazolecarbonitrile (36650-74-5) → C28H43N3O + C28H43N3O

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 12h;	A 71% B 13%

2-bromo-N,N-dimethylethanamide (5468-77-9) + pyrazolecarbonitrile (36650-74-5) → C8H10N4O + C8H10N4O

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; magnesium bromide In tetrahydrofuran at 0℃; for 2h; Glovebox; regioselective reaction;	A n/a B 60%
With potassium carbonate In acetonitrile at 25℃; for 1h; regioselective reaction;	A 54% B n/a

C25H43BrO2 + pyrazolecarbonitrile (36650-74-5) → C29H45N3O2 + C29H45N3O2

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 25 - 80℃; for 16h;	A 57% B 28%

C23H37BrO3 + pyrazolecarbonitrile (36650-74-5) → C27H39N3O3

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 16h; Solvent; Temperature; Inert atmosphere;	56%

2,3-dichloro-pyridine (2402-77-9) + pyrazolecarbonitrile (36650-74-5) → C9H5ClN4

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130 - 140℃;	55%

2-bromo-1-((3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one (1430063-93-6) + pyrazolecarbonitrile (36650-74-5) → 3α-hydroxy-3β-methyl-21-(3-cyano-1H-pyrazol-1'-yl)-19-nor-5β-pregnan-20-one

Conditions	Yield
With potassium carbonate In tetrahydrofuran	53%
With potassium carbonate In tetrahydrofuran at 35℃; for 15h;	24%

C23H39BrO + pyrazolecarbonitrile (36650-74-5) → C27H41N3O + C27H41N3O

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 85℃; for 12h;	A 53% B 16%

C25H41BrO3 + pyrazolecarbonitrile (36650-74-5) → 1-(2-((3R,5S,8S,9S,10S,13S,14S,17S)-3-(ethoxymethyl)-10-ethyl-3-hydroxy-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With potassium carbonate In acetone at 15℃; for 16h;	44.1%

ethyl 1-(6-(2-(4-(3-bromopropoxy)-2-methylphenethyl)-5-fluorophenyl)pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate + pyrazolecarbonitrile (36650-74-5) → ethyl 1-(6-(2-(4-(3-(3-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;	43.5%

2-mercaptopropanoic acid (79-42-5) + pyrazolecarbonitrile (36650-74-5) → 2-(3-pyrazolyl)-4-hydroxy-5-methylthiazole (133833-90-6)

Conditions	Yield
With pyridine at 100℃; for 2h;	42%

2-Amino-2-methyl-1-propanol (124-68-5) + pyrazolecarbonitrile (36650-74-5) → C8H11N3O

Conditions	Yield
With zinc(II) chloride at 95℃; for 4h; Microwave irradiation;	41.6%

4-((tert-butoxycarbonylamino)methyl)phenylboronic acid (489446-42-6) + pyrazolecarbonitrile (36650-74-5) → tert-butyl (4-(3-cyano-1H-pyrazol-1-yl)benzyl)carbamate

Conditions	Yield
With pyridine; copper diacetate; triethylamine In dichloromethane at 40℃; for 18h;	39%

C24H39BrO3 + pyrazolecarbonitrile (36650-74-5) → 1-(2-((3R,5S,8S,9S,10S,13S,14S,17S)-10-ethyl-3-hydroxy-3-(methoxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With potassium carbonate In acetone at 15℃; for 16h;	39%

C22H37BrO2 + pyrazolecarbonitrile (36650-74-5) → C26H39N3O2 + C26H39N3O2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25 - 85℃; for 12h;	A 39% B 3.3%

2-Amino-6-chloropurin (10310-21-1) + pyrazolecarbonitrile (36650-74-5) → 1-(2-amino-9H-purin-6-yl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;	37.4%

6-allyloxy-3-iodo-1,6-diazabicyclo[3.2.1]oct-3-en-7-one + pyrazolecarbonitrile (36650-74-5) → N-(6-allyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-3-yl)pyrazole-3-carbonitrile

Conditions	Yield
With copper(l) iodide; N,N-dimethylglycine hydrochoride; potassium carbonate In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;	37%

C21H32BrFO2 (1430065-01-2) + pyrazolecarbonitrile (36650-74-5) → C25H34FN3O2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	28%

C23H37BrO2 + pyrazolecarbonitrile (36650-74-5) → C27H39N3O2

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	26.09%

2-bromo-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole + pyrazolecarbonitrile (36650-74-5) → 1-[7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl]pyrazole-3-carbonitrile

Conditions	Yield
With copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate In 1,4-dioxane at 140℃; for 3h; Microwave irradiation; Sealed tube;	26%

2-bromo-1-((3R,5R,8S,10R,13S,14S)-10-fluoro-3-hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one + pyrazolecarbonitrile (36650-74-5) → 1-(2-((3R,5R,8S,9S,10R,13S,14S,17S)-10-fluoro-3-hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)-1H-pyrazole-3-carbonitrile + 1-(2-((3R,5R,8S,9S,10R,13S,14S,17R)-10-fluoro-3-hydroxy-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl)-1H-pyrazole-3-carbonitrile

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 5h;	A 21.9% B 6%

C22H35BrO2 + pyrazolecarbonitrile (36650-74-5) → C26H37N3O2

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 70℃;	19.4%

Upstream product

• 87879-93-4 4-diazo-1,1,1,2,2-pentafluoro-3-pentafluoroethyl-3-trifluoromethylbutane 
• 107-13-1 acrylonitrile 
• 30192-58-6 1H-pyrazole-3-carbxaldehyde oxime 
• 33064-36-7 1H-pyrazole-3-carboxamide 
• 186581-53-3 diazomethane 
• 205251-17-8 (Z)-3-[(R)-p-tolylsulfinyl]propenonitrile 

Downstream Products

• 135641-90-6 1-p-chlorobenzyl-3-cyano-1H-pyrazole 
• 135641-89-3 1-p-chlorobenzyl-5-cyano-1H-pyrazole 
• 860807-23-4 1-(hydroxymethyl)-3-cyano-1H-pyrazole 
• 1006471-40-4 1-ethyl-1H-pyrazole-3-carbonitrile 
• 79080-39-0 1-Methylpyrazole-3-carboxylic acid nitrile 
• 1413065-58-3 1-(3-bromo-2-formylphenyl)-1H-pyrazole-3-carbonitrile 
• 1138450-08-4 1-[2,4-dioxo-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]-1H-pyrazole-3-carbonitrile 

Relevant academic research and scientific papers

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Fluorinated pyrazole acids are agonists of the high affinity niacin receptor GPR109a

A series of 5-alkyl pyrazole-3-carboxylic acids were prepared and found to act as potent and selective agonists of the human GPCR, GPR109a, the high affinity nicotinic acid receptor. No activity was observed at the highly homologous low affinity niacin receptor, GPR109b. A further series of 4-fluoro-5-alkyl pyrazole-3-carboxylic acids were shown to display similar potency. One example from the series was shown to have improved properties in vivo compared to niacin.

MALONONITRILE COMPOUND AND USE THEREOF

A nitrile compound shown by the formula (1) has an excel lent pesticidal activity and it is useful as an active ingredient of pesticide.

(Z)-3-p-tolylsulfinylacrylonitriles as chiral dipolarophiles: Reactions with diazoalkanes

(figure presented) The dipolarophilic reactivity of enantiopure (Z)-3-p-tolylsulfinylacrylonitriles (1) has been evaluated with diazoalkanes. 3-Cyanopyrazoles are obtained when R = H, but with R = alkyl (Bn, n-Bu, and t-Bu) only one cycloadduct (4 or 5) is formed in high yield under mild conditions, therefore evidencing a complete control of the regioselectivity and the endolexo and π-facial selectivities. These reactions are a new straightforward entry to the synthesis of pyrazolines and related structures and reveal the excellent dipolarophilic features of (Z)-sulfinylacrylonitriles.

Reactions of spirocyclopropane-containing 1- and 2-pyrazolines with electrophilic reagents

Hydrochlorination of spiro(1-pyrazoline-3, 1′-cyclopropanes) proceeds regioselectively at the azocyclopropane group to form 3-(2-haloethyl)pyrazoline derivatives. If the latter contain a halogen atom in the heterocycle, they are readily converted into (2-haloethyl)pyrazole hydrohalides. Bromination of 3-cyanospiro(2-pyrazoline-5,1′-cyclopropane) with N-bromosuccinimide at 20 °C proceeds with retention of the cyclopropane ring to form 3-bromo-3-cyanospiro(1-pyrazoline-5,1′-cyclopropane), which is converted into (2-bromoethyl)cyanopyrazole in ～60% yield at ～20 °C after 3 - 4 days.

REACTIONS OF TETRAFLUOROETHENE OLIGOMERS. PART XII. CYCLOADDITION REACTIONS OF 3,3,4,4,4-PENTAFLUORO-2-PENTAFLUOROETHYL-2-TRIFLUOROMETHYLDIAZOBUTANE. A NOVEL SYNTHESIS OF PYRAZOLES

The title diazoalkane (1) reacts smoothly with a variety of electron deficient alkenes to give, unexpectedly, the corresponding pyrazole derivatives.Thus, reaction with methyl or ethyl propenoate affords the methyl and ethyl esters of pyrazole-3-carboxylic acid (2) and (3).Reaction with diethyl maleate yields 3,4-bis-(ethoxycarbonyl)pyrazole (4), and dimethyl maleate gives the corresponding dimethyl ester (5).Treatment of (1) with propenonitrile afforded 3-cyanopyrazole (6), and with propenoic acid the corresponding pyrazole-3-carboxylic acid (7) was obtained.In all of these reactions two side products were isolated, namely perfluoro-(3-methylpent-2-ene) (8) and 3H-3-trifluoromethyldecafluoropentane (9).A mechanistic rationale for these unusual and potentially useful reactions is given.