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Cas Database

75640-14-1

75640-14-1

Identification

  • Product Name:5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

  • CAS Number: 75640-14-1

  • EINECS:

  • Molecular Weight:326.398

  • Molecular Formula: C22H18N2O

  • HS Code:

  • Mol File:75640-14-1.mol

Synonyms:5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

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Relevant articles and documentsAll total 6 Articles be found

PTSA-catalyzed Mannich-type-cyclization-oxidation tandem reactions: One-pot synthesis of 1,3,5-substituted pyrazoles from aldehydes, hydrazines and alkynes

Liu, Pei,Pan, Ying-Ming,Xu, Yan-Li,Wang, Heng-Shan

, p. 4696 - 4698 (2012)

A convenient one-pot Mannich-type-cyclization-oxidation tandem process has been developed for the synthesis of 1,3,5-trisubstituted pyrazoles derivatives from aldehydes, hydrazines and alkynes using p-toluenesulfonic acid monohydrate (PTSA) as a multifunctional catalyst. This method provides a flexible and rapid route to 1,3,5-trisubstituted pyrazoles.

Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration

Cipagauta Esquivel, Edna Carolina,Rufino, Virgínia Camila,Trindade Nogueira, Matheus Henrique,Carbonaro Souza, Ana Carolina,Pliego Júnior, Josefredo Rodriguez,Valle, Marcelo Siqueira

, (2019/12/23)

The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.

Photooxidation of 3,5-diaryl-1-phenyl-2-pyrazolines: Experimental and computational studies

Soltani, Marzieh,Memarian, Hamid Reza,Sabzyan, Hassan

, (2019/12/23)

Photooxidation of various 2-pyrazolines is studied experimentally and computationally. Experimental results show that the electron-donating/withdrawing substituents increases/decreases the rate of this photoreaction. The proposed light-induced electron-tr

A convenient and efficient protocol for the synthesis of 5-aryl-1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation

Li, Ji-Tai,Yin, Ying,Li, Ling,Sun, Ming-Xuan

experimental part, p. 11 - 13 (2010/11/16)

The synthesis of 5-aryl-1,3-diphenylpyrazole via the reactions of 3-aryl-2,3-epoxy-1-phenyl-1-propanone with phenylhydrazine was carried out in 69-99% yields at room temperature under ultrasound irradiation. This method provides several advantages such as

Solvent-free synthesis of 1, 3-diphenyl-5-arylpyrazole derivatives

Li, Ji-Tai,Yin, Ying,Meng, Xian-Tao

experimental part, p. 384 - 386 (2010/04/23)

The synthesis of 1, 3-diphenyl-5-arylpyrazoles via the reactions of 2, 3-epoxy-1-phenyl-3-aryl-1-propanones with phenylhydrazine was carried out in 48-84% yields at 230 °C under solvent-free condition within 1.5 h. This method provides several advantages

Process route upstream and downstream products

Process route

1-ethynyl-2-methoxybenzene
767-91-9

1-ethynyl-2-methoxybenzene

benzaldehyde
100-52-7

benzaldehyde

phenylhydrazine
100-63-0

phenylhydrazine

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 8h;
82%
5-(2-methoxyphenyl)-1,3-dyphenyl-4,5-dihydro-1H-pyrazol-4-ol

5-(2-methoxyphenyl)-1,3-dyphenyl-4,5-dihydro-1H-pyrazol-4-ol

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
With hydrogenchloride; In methanol; Reflux;
80%
phenylhydrazine
100-63-0

phenylhydrazine

2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one
68235-45-0

2,3-epoxy-3-(2-metoxyphenyl)-1-phenylpropan-1-one

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
at 230 ℃; for 1.5h; Neat (no solvent);
82%
With hydrogenchloride; In ethanol; water; at 20 ℃; for 1.41667h; Ultrasound irradiation;
80%
5-(2-methoxyphenyl)-1,3-diphenyl-2-pyrazoline
7245-44-5

5-(2-methoxyphenyl)-1,3-diphenyl-2-pyrazoline

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
With lead(IV) acetate; In dichloromethane; for 12h; Ambient temperature;
88%
In chloroform; for 0.0166667h; UV-irradiation;
1,3-diphenyl-5-orthomethoxyphenyl pyrazole-4-carboxylic acid
119824-80-5

1,3-diphenyl-5-orthomethoxyphenyl pyrazole-4-carboxylic acid

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
With copper; In quinoline; for 4h; Heating;
75%
coumarin
91-64-5

coumarin

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 65 percent / Et3N / benzene / 4 h / Heating
2: 83 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
3: 65 percent / aq. 1 N KOH / ethanol / 1 h / Heating
4: KOH / methanol / 0.5 h / Heating
5: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; triethylamine; In quinoline; methanol; ethanol; dichloromethane; benzene;
Multi-step reaction with 5 steps
1: 65 percent / Et3N / benzene / 4 h / Heating
2: 76 percent / aq. 1 N KOH / ethanol / 1 h / Heating
3: 80 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
4: KOH / methanol / 0.5 h / Heating
5: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; triethylamine; In quinoline; methanol; ethanol; dichloromethane; benzene;
1,3-diphenyl-3a,9b-dihydro-4-oxo-1H-benzopyrano<4,3-c>pyrazole
93232-47-4

1,3-diphenyl-3a,9b-dihydro-4-oxo-1H-benzopyrano<4,3-c>pyrazole

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 83 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
2: 65 percent / aq. 1 N KOH / ethanol / 1 h / Heating
3: KOH / methanol / 0.5 h / Heating
4: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; In quinoline; methanol; ethanol; dichloromethane;
Multi-step reaction with 4 steps
1: 76 percent / aq. 1 N KOH / ethanol / 1 h / Heating
2: 80 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
3: KOH / methanol / 0.5 h / Heating
4: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; In quinoline; methanol; ethanol; dichloromethane;
N-phenylbenzohydrazonoyl chloride
15424-14-3

N-phenylbenzohydrazonoyl chloride

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 65 percent / Et3N / benzene / 4 h / Heating
2: 83 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
3: 65 percent / aq. 1 N KOH / ethanol / 1 h / Heating
4: KOH / methanol / 0.5 h / Heating
5: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; triethylamine; In quinoline; methanol; ethanol; dichloromethane; benzene;
Multi-step reaction with 5 steps
1: 65 percent / Et3N / benzene / 4 h / Heating
2: 76 percent / aq. 1 N KOH / ethanol / 1 h / Heating
3: 80 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
4: KOH / methanol / 0.5 h / Heating
5: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; triethylamine; In quinoline; methanol; ethanol; dichloromethane; benzene;
2-methoxychalcone
5416-70-6

2-methoxychalcone

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 78 percent / acetic acid / 6 h / Heating
2: 88 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
With lead(IV) acetate; In dichloromethane; acetic acid;
1,3-diphenyl-5-orthomethoxyphenyl-4-methoxycarbonyl-pyrazoline
119824-78-1

1,3-diphenyl-5-orthomethoxyphenyl-4-methoxycarbonyl-pyrazoline

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole
75640-14-1

5-(2-methoxyphenyl)-1,3-diphenyl-1H-pyrazole

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 80 percent / Pb(OAc)4 / CH2Cl2 / 12 h / Ambient temperature
2: KOH / methanol / 0.5 h / Heating
3: 75 percent / Cu powder / quinoline / 4 h / Heating
With lead(IV) acetate; potassium hydroxide; copper; In quinoline; methanol; dichloromethane;

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