3-(1-Methyl-1H-pyrazol-4-YL)benzaldehyde

Base Information

• Chemical Name: 3-(1-Methyl-1H-pyrazol-4-YL)benzaldehyde
• CAS No.: 179055-93-7
• Molecular Formula: C11H10 N2 O
• Molecular Weight: 186.2099
• DSSTox Substance ID: DTXSID40443018
• Wikidata: Q82260685
• Mol file: 179055-93-7.mol

Synonyms:3-(1-METHYL-1H-PYRAZOL-4-YL)BENZALDEHYDE;179055-93-7;3-(1-methylpyrazol-4-yl)benzaldehyde;SCHEMBL8807378;DTXSID40443018;MFCD08669917;AKOS010262736;AT30374;3-(1-Methyl-1H-pyrazol-4-yl)-benzaldehyde;EN300-121805;A1-32640

Chemical Property of 3-(1-Methyl-1H-pyrazol-4-YL)benzaldehyde

Chemical Property:

• PSA: 34.89000
• LogP: 1.89960
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.079312947
• Heavy Atom Count: 14
• Complexity: 208

Purity/Quality:

95% ^*data from raw suppliers

3-(1-Methyl-1H-pyrazol-4-yl)benzaldehyde 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C=N1)C2=CC=CC(=C2)C=O

Technology Process of 3-(1-Methyl-1H-pyrazol-4-YL)benzaldehyde

There total 3 articles about 3-(1-Methyl-1H-pyrazol-4-YL)benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

m-bromobenzoic aldehyde (3132-99-8) + (1-methyl-1H-pyrazol-4-yl)boronic acid (847818-55-7) → 3-(1-methyl-1H-pyrazol-4-yl)benzaldehyde (179055-93-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; at 100 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cmdc.201600327

Reference yield: 78.0%

m-bromobenzoic aldehyde (3132-99-8) + 1-methyl-4-tributylstannanyl-1H-pyrazole (179055-21-1) → 3-(1-methyl-1H-pyrazol-4-yl)benzaldehyde (179055-93-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In xylene; at 140 ℃; for 3h;

DOI:10.1021/jm9800853

Reference yield: 45.0%

1-methyl-1H-pyrazole (930-36-9) + m-bromobenzoic aldehyde (3132-99-8) → 3-(1-methylpyrazol-5-yl)benzaldehyde (179056-80-5) + 3-(1-methyl-1H-pyrazol-4-yl)benzaldehyde (179055-93-7)

Guidance literature:

With potassium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150 ℃; for 20h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1260076

upstream raw materials:

m-bromobenzoic aldehyde

1-methyl-4-tributylstannanyl-1H-pyrazole

1-methyl-1H-pyrazole

(1-methyl-1H-pyrazol-4-yl)boronic acid

Downstream raw materials:

Benzyl-[3-(1-methyl-1H-pyrazol-4-yl)-benzyl]-amine

Cycloheptyl-[3-(1-methyl-1H-pyrazol-4-yl)-benzyl]-amine

Refernces

• 1、 Beladhria, Anissa,Beydoun, Kassem,Ammar, Hamed Ben,Salem, Ridha Ben,Doucet, Henri. "Pd-catalysed direct 5-arylation of 1-methylpyrazole with aryl bromides". experimental part. p. 2553 - 2560. Retrieved 2011/10/04.