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288-13-1 Usage

Chemical Description

Pyrazole is a heterocyclic organic compound with the formula C3H4N2.

Uses

Different sources of media describe the Uses of 288-13-1 differently. You can refer to the following data:
1. Used as a ligand to prepare organometallic compounds.1,2
2. Chelating agent; in organic synthesis.
3. Pyrazole is used in organic synthesis and asa chelating agent.

Definition

Different sources of media describe the Definition of 288-13-1 differently. You can refer to the following data:
1. ChEBI: The 1H-tautomer of pyrazole.
2. A heterocyclic crystalline aromatic compound with a five-membered ring containing three carbon atoms and two nitrogen atoms.
3. pyrazole: An unsaturated heterocycliccompound having two nitrogenatoms in a five-membered ring,C3H4N2; m.p. 66–70°C; b.p. 168–188°C. Pyrazine is a symmetricdiazine.

Hazard

Toxic by ingestion and inhalation, irritant to skin and eyes.

Health Hazard

The acute toxic symptoms from oral administrationof pyrazole in experimental animalswere ataxia, muscle weakness, and respiratorydepression. It is less toxic than pyrroleand pyrrolidine. The oral LD50 value in miceis within the range 1450 mg/kg.Pyrazole exhibited reproductive toxicityin rats and mice when administered by oralor intraperitoneal route. The effects includefetal death, developmental abnormalities pertainingto the urogenital system, and postimplantationmortality.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise pyrazole from pet ether, cyclohexane, or water. Its solubility in H2O at 9.6o is 2.7moles/L, and at 24.8o it is 19.4moles/L; in cyclohexane at 31.8o it is 0.577moles/L, and at 56.2o it is 5.86moles/L; and in benzene at 5.2o it is 0.31moles/L, and at 46.5o it is 16.8moles/1000mL. [Barszcz et al. J Chem Soc, Dalton Trans 2025 1986, Beilstein 23 H 39, 23 I 15, 23 II 33, 23 III/IV 550, 23/4 V 122.]

Check Digit Verification of cas no

The CAS Registry Mumber 288-13-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 8 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 288-13:
(5*2)+(4*8)+(3*8)+(2*1)+(1*3)=71
71 % 10 = 1
So 288-13-1 is a valid CAS Registry Number.
InChI:InChI=1/C3H4N2/c1-2-4-5-3-1/h1-3H,(H,4,5)

288-13-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A14186)  1H-Pyrazole, 98%   

  • 288-13-1

  • 25g

  • 488.0CNY

  • Detail
  • Alfa Aesar

  • (A14186)  1H-Pyrazole, 98%   

  • 288-13-1

  • 100g

  • 1336.0CNY

  • Detail
  • Aldrich

  • (P56607)  Pyrazole  98%

  • 288-13-1

  • P56607-5G

  • 219.96CNY

  • Detail
  • Aldrich

  • (P56607)  Pyrazole  98%

  • 288-13-1

  • P56607-25G

  • 624.78CNY

  • Detail
  • Aldrich

  • (P56607)  Pyrazole  98%

  • 288-13-1

  • P56607-100G

  • 1,601.73CNY

  • Detail
  • Vetec

  • (V900639)  Pyrazole  Vetec reagent grade, 98%

  • 288-13-1

  • V900639-25G

  • 115.83CNY

  • Detail
  • Vetec

  • (V900639)  Pyrazole  Vetec reagent grade, 98%

  • 288-13-1

  • V900639-100G

  • 397.80CNY

  • Detail

288-13-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1H-pyrazole

1.2 Other means of identification

Product number -
Other names 1H-Pyrazole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:288-13-1 SDS

288-13-1Synthetic route

tert-butyl 1H-pyrazole-1-carboxylate
219580-32-2

tert-butyl 1H-pyrazole-1-carboxylate

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
In methanol at 120℃; under 5171.62 Torr; for 0.333333h; Microwave irradiation;99%
With water at 100℃; for 0.166667h;99%
With sodium carbonate In 1,2-dimethoxyethane; water for 0.25h; Heating;60%
ethyl 2-(difluoroacetyl)-3-(dimethylamino)acrylate

ethyl 2-(difluoroacetyl)-3-(dimethylamino)acrylate

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With sodium hydroxide In water95.8%
With potassium hydroxide In water91.4%
4-iodopyrazole
3469-69-0

4-iodopyrazole

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With sodium sulfite In water at 130℃; for 1h; Sealed tube; Microwave irradiation; Green chemistry;94%
methylhydrazine
60-34-4

methylhydrazine

A

NH-pyrazole
288-13-1

NH-pyrazole

B

ethyl 2-(difluoroacetyl)-3-(dimethylamino)acrylate

ethyl 2-(difluoroacetyl)-3-(dimethylamino)acrylate

Conditions
ConditionsYield
In water; tolueneA 93.6%
B n/a
glycerol
56-81-5

glycerol

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
Stage #1: glycerol With hydrazine hydrate; potassium iodide; sodium iodide under 3750.38 Torr; for 0.5h; Large scale;
Stage #2: With sulfuric acid at 160℃; for 2h; Temperature; Pressure; Large scale;
91.1%
4-bromo-1H-pyrazole
2075-45-8

4-bromo-1H-pyrazole

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With sodium sulfite In water at 130℃; for 5h; Sealed tube; Microwave irradiation; Green chemistry;91%
malonaldehydebis(dimethylacetal)
102-52-3

malonaldehydebis(dimethylacetal)

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With hydrazine hydrate; acetic acid at 85℃; for 1.5h;90%
(Z)-1-(2-methyl-4,5-diphenylpent-4-en-2-yl)-1H-pyrazole

(Z)-1-(2-methyl-4,5-diphenylpent-4-en-2-yl)-1H-pyrazole

A

NH-pyrazole
288-13-1

NH-pyrazole

B

(Z)-(4-methylpenta-1,3-diene-1,2-diyl)dibenzene

(Z)-(4-methylpenta-1,3-diene-1,2-diyl)dibenzene

Conditions
ConditionsYield
With n-butyllithium In hexane; tert-butyl methyl ether at 20℃; for 0.05h; Catalytic behavior; Temperature; Inert atmosphere;A n/a
B 87%
3-nitropyridone
6332-56-5

3-nitropyridone

A

NH-pyrazole
288-13-1

NH-pyrazole

B

carbonodihydrazide
497-18-7

carbonodihydrazide

Conditions
ConditionsYield
With hydrazine hydrate at 90 - 95℃; for 7h;A 74%
B 75%
With hydrazine hydrate at 90 - 95℃; for 7h; Product distribution; also 3,5-dinitropyridone investigated;A 74%
B 75%
2-methyl-3-(1H-pyrazol-1-yl)propanoic acid

2-methyl-3-(1H-pyrazol-1-yl)propanoic acid

A

NH-pyrazole
288-13-1

NH-pyrazole

B

5-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-4-one

5-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-4-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran -78 deg C 15 min, -45 deg C 1 h and room t., 3.5 h;A 75%
B 22%
malonaldehydebis(dimethylacetal)
102-52-3

malonaldehydebis(dimethylacetal)

1,1,3-trimethoxy-3-acethoxypropane
98561-07-0

1,1,3-trimethoxy-3-acethoxypropane

1,3-diacetoxy-1,3-dimethoxy-propane
15874-25-6

1,3-diacetoxy-1,3-dimethoxy-propane

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With hydrogenchloride; hydrazine hydrochloride In water at 30℃; for 1h;69%
N,N-dimethyl-1H-pyrazole-1-sulfonamide
133228-21-4

N,N-dimethyl-1H-pyrazole-1-sulfonamide

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With hydrogenchloride for 21h; Heating;62%
Dimethyldisulphide
624-92-0

Dimethyldisulphide

1,2-bis(1H-pyrazol-1-yl)ethane
92146-02-6

1,2-bis(1H-pyrazol-1-yl)ethane

A

NH-pyrazole
288-13-1

NH-pyrazole

B

1-vinylpyrazole
20173-98-2

1-vinylpyrazole

C

5-methylthio-1-vinylpyrazole

5-methylthio-1-vinylpyrazole

D

1-(5-methylthiopyrazol-1-yl)-2-pyrazol-1-ylethane

1-(5-methylthiopyrazol-1-yl)-2-pyrazol-1-ylethane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) 0 deg C, 1 h; 2.) room temp., 14 h; Yields of byproduct given;A 62%
B n/a
C n/a
D n/a
With n-butyllithium In tetrahydrofuran; hexane 1.) 0 deg C, 1 h; 2.) room temp., 14 h; Yields of byproduct given;A n/a
B n/a
C 12%
D n/a
With n-butyllithium In tetrahydrofuran; hexane 1.) 0 deg C, 1 h; 2.) room temp., 14 h; Yields of byproduct given;A n/a
B n/a
C n/a
D 2%
With n-butyllithium In tetrahydrofuran; hexane Product distribution; 1.) 0 deg C. 1 h; 2.) room temp., 14 h; varying amounts of reag.;
(1-chloro-2-methylpropylidene)methane-1,1-dicarbonitrile
40797-97-5

(1-chloro-2-methylpropylidene)methane-1,1-dicarbonitrile

(2,6-dichlorophenyl)hydrazine monohydrochloride
50709-36-9

(2,6-dichlorophenyl)hydrazine monohydrochloride

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With sodium hydrogencarbonate; triethylamine In tetrahydrofuran62%
With sodium hydrogencarbonate; triethylamine In tetrahydrofuran62%
Metazachlor
67129-08-2

Metazachlor

A

NH-pyrazole
288-13-1

NH-pyrazole

B

4,4'-methylenebis(2,6-dimethylaniline)
4073-98-7

4,4'-methylenebis(2,6-dimethylaniline)

Conditions
ConditionsYield
hydrogenchloride In water for 8h; Heating;A 59%
B 35%
gem-dichlorocyclopropanol
42039-22-5

gem-dichlorocyclopropanol

NH-pyrazole
288-13-1

NH-pyrazole

Conditions
ConditionsYield
With hydrazine; dibenzo-18-crown-6 In ethanol58%
NH-pyrazole
288-13-1

NH-pyrazole

3,6-dichlorpyridazine
141-30-0

3,6-dichlorpyridazine

3,6‑di(pyrazol‑1‑yl)pyridazine
79091-11-5

3,6‑di(pyrazol‑1‑yl)pyridazine

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane at 20℃; for 24h;100%
Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide for 1h; Inert atmosphere;
Stage #2: 3,6-dichlorpyridazine In N,N-dimethyl-formamide at 0 - 20℃; for 13h; Inert atmosphere;
86%
In ethanol for 2h; Heating;65%
NH-pyrazole
288-13-1

NH-pyrazole

Hexafluorobenzene
392-56-3

Hexafluorobenzene

hexakis(pyrazol-1-yl)benzene
148807-09-4

hexakis(pyrazol-1-yl)benzene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 6h; Product distribution; Mechanism; Heating; other diazole sodium salts, var solvents, var. time, var. temp.;100%
With sodium hydride In tetrahydrofuran for 6h; Heating;91%
With sodium hydride 1.) THF, 65 deg C, 2.) THF, reflux, 6 h; Yield given. Multistep reaction;
NH-pyrazole
288-13-1

NH-pyrazole

3-fluoro-6-nitrotoluene
446-33-3

3-fluoro-6-nitrotoluene

1-(3-methyl-4-nitrophenyl)-1H-pyrazole
102792-12-1

1-(3-methyl-4-nitrophenyl)-1H-pyrazole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;100%
With sodium carbonate In N,N-dimethyl-formamide at 100℃;
NH-pyrazole
288-13-1

NH-pyrazole

4-bromo-1H-pyrazole
2075-45-8

4-bromo-1H-pyrazole

Conditions
ConditionsYield
With bromine In dichloromethane at 0℃;100%
With N-Bromosuccinimide In water at 20 - 25℃;100%
With N-Bromosuccinimide In water at 20℃;100%
NH-pyrazole
288-13-1

NH-pyrazole

sodium pyrazolide
40958-82-5

sodium pyrazolide

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran100%
With sodium hydride In tetrahydrofuran for 0.5h;
With sodium hydride
With sodium hydroxide In diethylene glycol dimethyl ether; water; toluene at 40 - 80℃; Inert atmosphere; Large scale reaction;
With sodium hydroxide In ethanol; water at 20℃; for 3h;
NH-pyrazole
288-13-1

NH-pyrazole

iodobenzene
591-50-4

iodobenzene

1-phenylpyrazole
1126-00-7

1-phenylpyrazole

Conditions
ConditionsYield
With copper; caesium carbonate; iron(III)-acetylacetonate In N,N-dimethyl-formamide at 100℃; for 15h;100%
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;99%
With caesium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere;99%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

NH-pyrazole
288-13-1

NH-pyrazole

1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole
449758-17-2

1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With trifluoroacetic acid Heating;100%
at 125℃; for 24h; Green chemistry;100%
With trifluoroacetic acid at 100℃; for 12h; Inert atmosphere;100%
NH-pyrazole
288-13-1

NH-pyrazole

1-(4-bromophenyl)-1H-pyrazole
13788-92-6

1-(4-bromophenyl)-1H-pyrazole

1-[4-(1H-pyrazol-1-yl)phenyl]-1H-pyrazole
67673-42-1

1-[4-(1H-pyrazol-1-yl)phenyl]-1H-pyrazole

Conditions
ConditionsYield
With caesium carbonate; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine In acetonitrile at 82℃; for 48h; Conversion of starting material;100%
With caesium carbonate; copper(I) oxide In acetonitrile at 82℃; for 48h;91%
NH-pyrazole
288-13-1

NH-pyrazole

Isobutyl bromide
78-77-3

Isobutyl bromide

1-isobutyl-1H-pyrazole
725746-81-6

1-isobutyl-1H-pyrazole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In water; methyl cyclohexane at 110℃; for 5.5h; Product distribution / selectivity; Heating / reflux;100%
With potassium hydroxide In ethanol at 78℃; for 1.5h;64%
NH-pyrazole
288-13-1

NH-pyrazole

4-tolyl iodide
624-31-7

4-tolyl iodide

1-(4-methylphenyl)-1H-pyrazole
20518-17-6

1-(4-methylphenyl)-1H-pyrazole

Conditions
ConditionsYield
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;100%
With Cu6[1,4-bis(imidazol-1-yl)butane]3I6; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;97%
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;96%
NH-pyrazole
288-13-1

NH-pyrazole

{(C2H5)2B(C3H3N2)2}Mo(CO)2(C3H5)

{(C2H5)2B(C3H3N2)2}Mo(CO)2(C3H5)

{(C2H5)2B(C3H3N2)2}Mo(CO)2(C3H5)(C3H4N2)

{(C2H5)2B(C3H3N2)2}Mo(CO)2(C3H5)(C3H4N2)

Conditions
ConditionsYield
100%
100%
NH-pyrazole
288-13-1

NH-pyrazole

diethylboryl-pivalate
34574-27-1

diethylboryl-pivalate

2,2-dimethylpropanoyloxydiethylborane pyrazole complex
217324-49-7

2,2-dimethylpropanoyloxydiethylborane pyrazole complex

Conditions
ConditionsYield
In chloroform Ar-atmosphere; dropwise addn. of pyrazole to equimolar amt. of B-compd.(0°C); solvent removal (vac.);100%
NH-pyrazole
288-13-1

NH-pyrazole

trimethyl gallium
1445-79-0

trimethyl gallium

1-dimethylgallylpyrazole
79422-25-6

1-dimethylgallylpyrazole

Conditions
ConditionsYield
In benzene byproducts: CH4; under argon atm., reflux, 1 h; evapn. of solvent;100%
NH-pyrazole
288-13-1

NH-pyrazole

2-fluoro-4-methoxy-1-nitro-benzene
446-38-8

2-fluoro-4-methoxy-1-nitro-benzene

1-(5-methoxy-2-nitro-phenyl)-1H-pyrazole
1022974-77-1

1-(5-methoxy-2-nitro-phenyl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.216667h;
Stage #2: 2-fluoro-4-methoxy-1-nitro-benzene In tetrahydrofuran at 20℃; for 0.35h;
100%
NH-pyrazole
288-13-1

NH-pyrazole

5-sec-butyl-4-chloro-6-methyl-2-methylsulfonylpyrimidine
944740-28-7

5-sec-butyl-4-chloro-6-methyl-2-methylsulfonylpyrimidine

5-sec-butyl-4-chloro-6-methyl-2-(1H-pyrazol-1-yl)pyrimidine
944740-29-8

5-sec-butyl-4-chloro-6-methyl-2-(1H-pyrazol-1-yl)pyrimidine

Conditions
ConditionsYield
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: 5-sec-butyl-4-chloro-6-methyl-2-methylsulfonylpyrimidine In tetrahydrofuran at -70℃; for 0.166667h;
100%
NH-pyrazole
288-13-1

NH-pyrazole

4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

1-(4-fluorobenzyl)-1H-pyrazole
500367-31-7

1-(4-fluorobenzyl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: NH-pyrazole With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;
Stage #2: 4-Fluorobenzyl bromide In DMF (N,N-dimethyl-formamide) for 1h;
Stage #3: With water In DMF (N,N-dimethyl-formamide) at 0℃;
100%
Stage #1: NH-pyrazole With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃;
Stage #2: 4-Fluorobenzyl bromide In dimethyl sulfoxide; mineral oil at 50℃;
84%
NH-pyrazole
288-13-1

NH-pyrazole

3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester
142253-57-4

3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester

3-pyrazol-1-ylmethyl-azetidine-1-carboxylic acid tert-butyl ester
1228230-84-9

3-pyrazol-1-ylmethyl-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: 3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h;
100%
Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h;
Stage #2: 3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h;
76%
NH-pyrazole
288-13-1

NH-pyrazole

3-chlorofluorobenzene
625-98-9

3-chlorofluorobenzene

1-(3-chloro-phenyl)-1H-pyrazole
57211-65-1

1-(3-chloro-phenyl)-1H-pyrazole

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 190℃; for 1h; Microwave irradiation;100%
NH-pyrazole
288-13-1

NH-pyrazole

tert-butyl ((ethylthio)(phenyl)methyl)carbamate
1323902-49-3

tert-butyl ((ethylthio)(phenyl)methyl)carbamate

tert-butyl (phenyl(1H-pyrazol-1-yl)methyl)carbamate
1612786-59-0

tert-butyl (phenyl(1H-pyrazol-1-yl)methyl)carbamate

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at -78℃; for 0.0833333h; Friedel-Crafts Alkylation; Sealed tube; Inert atmosphere; chemoselective reaction;100%
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; tert-butyl alcohol In acetonitrile at 20℃; for 24h; Irradiation;60%
NH-pyrazole
288-13-1

NH-pyrazole

1,1-dimethylethyl (2R,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate
924907-62-0

1,1-dimethylethyl (2R,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate

C19H35N3O3Si
1432128-64-7

C19H35N3O3Si

Conditions
ConditionsYield
Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.166667h; Cooling with ice;
Stage #2: 1,1-dimethylethyl (2R,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate In N,N-dimethyl-formamide; mineral oil at 60℃; for 1.5h;
100%
NH-pyrazole
288-13-1

NH-pyrazole

2,4-dichloro-1-iodo-benzene
29898-32-6

2,4-dichloro-1-iodo-benzene

1-(2,4-dichlorophenyl)-1H-pyrazole

1-(2,4-dichlorophenyl)-1H-pyrazole

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 180℃; for 0.5h; Inert atmosphere; Microwave irradiation;100%
NH-pyrazole
288-13-1

NH-pyrazole

copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

(Bu4N)2[SO4{Cu(OH)(pyrazole)}31]

(Bu4N)2[SO4{Cu(OH)(pyrazole)}31]

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran for 72h;100%
NH-pyrazole
288-13-1

NH-pyrazole

sodium hydride
7646-69-7

sodium hydride

phenylboronic acid
98-80-6

phenylboronic acid

sodium phenyltris(pyrazolyl)borate
80583-77-3

sodium phenyltris(pyrazolyl)borate

Conditions
ConditionsYield
at 200℃; for 0.25h; Microwave irradiation; Inert atmosphere;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

NH-pyrazole
288-13-1

NH-pyrazole

1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole
449758-17-2

1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 12h;100%
NH-pyrazole
288-13-1

NH-pyrazole

7-(bromomethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
691857-35-9

7-(bromomethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

7-((1H-pyrazol-1-yl)methyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

7-((1H-pyrazol-1-yl)methyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h;100%
NH-pyrazole
288-13-1

NH-pyrazole

acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

butyl 3-(1H-pyrazol-1-yl)propanoate

butyl 3-(1H-pyrazol-1-yl)propanoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 12h;88%
NH-pyrazole
288-13-1

NH-pyrazole

methyl cyanoformate
17640-15-2

methyl cyanoformate

pyrazole-1-carboxylic acid methyl ester
28188-08-1

pyrazole-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With C14H18N2 (14)99%
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene for 2h; Ambient temperature;95%
NH-pyrazole
288-13-1

NH-pyrazole

dimethylamino sulfonyl chloride
13360-57-1

dimethylamino sulfonyl chloride

N,N-dimethyl-1H-pyrazole-1-sulfonamide
133228-21-4

N,N-dimethyl-1H-pyrazole-1-sulfonamide

Conditions
ConditionsYield
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran for 1.5h;
99%
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: dimethylamino sulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
99%
With sodium hydride In tetrahydrofuran; mineral oil for 1.33333h; Inert atmosphere;91%
NH-pyrazole
288-13-1

NH-pyrazole

N-aminopyrazole
3994-46-5

N-aminopyrazole

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water for 0.5h; Ambient temperature;99%
With potassium hydroxide; hydroxylamine-O-sulfonic acid for 15h; Ambient temperature;42%
With potassium hydroxide; aminosulfonic acid at 70℃;
NH-pyrazole
288-13-1

NH-pyrazole

Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

1-cyclopentyl-1H-pyrazole

1-cyclopentyl-1H-pyrazole

Conditions
ConditionsYield
With sodium hydrogencarbonate at 120℃; for 12h;99%

288-13-1Relevant articles and documents

Copper (II) complexes with novel Schiff-based ligands: synthesis, crystal structure, thermal (TGA–DSC/FT-IR), spectroscopic (FT-IR, UV-Vis) and theoretical studies

Moreira, Jeniffer Meyer,Campos, Guilherme Fava,de Campos Pinto, Leandro Moreira,Martins, Gabriel Rodrigues,Tirloni, Bárbara,Schwalm, Cristiane Storck,de Carvalho, Cláudio Teodoro

, p. 4087 - 4098 (2022)

This study aimed to synthesize two novel Schiff-base ligands through the condensation between N-(2-aminoethyl)pyrazoles and 2-hydroxy-1-naphthaldehyde, which are: NaphPz ((E)-1-(((2-(1H-pyrazol-1-yl)ethyl)imino)methyl)naphthalen-2-ol)) and NaphDPz ((E)-1-(((2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)imino)methyl)naphthalen-2-ol). These novel pyrazole-imines were synthesized, characterized and used as copper (II) ion complexing agents. Different synthetic routes have been adapted to obtain the [Cu(NaphPz)Cl], [Cu(NaphDPz)Cl] and [Cu(NaphPz)2] complexes in the solid state, the first two in the crystalline form and the latter as a powder. The minimum metal–ligand stoichiometry for the three complexes was defined by TGA–DSC thermoanalytical data and by single-crystal X-ray diffraction for the crystalline samples which belong to the P21/n space group. The products of the thermal decomposition of the material were also monitored by TGA–DSC/FT-IR in air and N2 atmospheres in order to suggest how thermal decomposition of the organic portion of the complex occurs. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations compared to experimental results (UV-Vis and FT-IR) show a high degree of correlation. From HOMO/LUMO orbitals, the main major charge distributions, responsible for the absorption bands of the complexes, were determined.

Unexpected ring opening of pyrazolines with activated alkynes: synthesis of 1H-pyrazole-4,5-dicarboxylates and chromenopyrazolecarboxylates

Bhimapaka, China Raju,Kolla, Sai Teja,Rayala, Nageswara Rao,Sridhar, Balasubramanian

supporting information, p. 334 - 338 (2022/01/20)

1H-Pyrazole-4,5-dicarboxylates and chromenopyrazole carboxylates were prepared by reacting pyrazolines with activated alkynes under neat conditions without a catalyst. The products were formed via unexpected ring opening of pyrazolines with the elimination of styrene/ethylene. These types of transformations are unknown and the products formed were confirmed using their spectral/analytical data. In addition, the structures of compounds 5e and 5n were confirmed by single-crystal X-ray analysis. Control experiments were conducted to support the proposed reaction mechanism.

Preparation method of dinotefuran

-

Paragraph 0013; 0048-0053, (2021/08/07)

The invention provides a preparation method of dinotefuran, and belongs to the field of organic synthesis. The invention provides a preparation method of dinotefuran, which is characterized by comprising the following steps: step 1, adding a compound I, a compound II and a solvent into a reaction container, heating to 50 DEG C which is the reflux temperature of the solvent, reacting for 1-24 hours, then adding tetrahydrofuran-3-methylamine, and continuously reacting for 1-24 hours to obtain a reaction solution; and 2, cooling the reaction solution to 0-20 DEG C, standing, filtering, separating the solid and filtrate, and purifying the solid to obtain dinotefuran, wherein the structural formula of the compound I is shown in the specification, the structural formula of the compound II is shown in the specification, and R1 and R2 are independently selected from any one of H, C1-C5 alkyl and C1-C5 alkyl substituted by at least one halogen atom. According to the invention, a brand new dinotefuran synthesis route is developed, the synthesis route is greatly shortened, and the production efficiency is improved.

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