methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate

Base Information

• Chemical Name: methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate
• CAS No.: 164295-93-6
• Molecular Formula: C₁₅H₁₂N₂O₂
• Molecular Weight: 252.272
• Hs Code.: 2933199090
• DSSTox Substance ID: DTXSID30378103
• Nikkaji Number: J643.200J
• Wikidata: Q82167586
• Pharos Ligand ID: NASVY8MB5BX9
• ChEMBL ID: CHEMBL349087
• Mol file: 164295-93-6.mol

Synonyms:164295-93-6;methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate;methyl 3-naphthalen-2-yl-1H-pyrazole-5-carboxylate;5-Naphthalen-2-yl-1H-pyrazole-3-carboxylic acid methyl ester;methyl 3-(2-naphthyl)-1H-pyrazole-5-carboxylate;Methyl 5-(naphth-2-yl)-1H-pyrazole-3-carboxylate;MFCD06245485;5-(Naphth-2-yl)-1H-pyrazole-3-carboxylic acid methyl ester;MLS-0111546.0001;methyl 3-(naphthalen-2-yl)-1H-pyrazole-5-carboxylate;CHEMBL349087;SCHEMBL2460252;SCHEMBL13539290;BDBM41866;cid_2771808;DTXSID30378103;BBL030477;STK942748;AKOS000276446;AKOS005254519;CCG-139358;VS-09833;BB 0241036;FT-0758086;EN300-238120;SR-01000099753;SR-01000099753-1;F2130-0109;3-(2-naphthyl)-1H-pyrazole-5-carboxylic acid methyl ester;3-(2-naphthalenyl)-1H-pyrazole-5-carboxylic acid methyl ester;5-Naphthalen-2-yl-2H-pyrazole-3-carboxylic acid methyl ester

Chemical Property of methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate

Chemical Property:

• Vapor Pressure: 5.69E-10mmHg at 25°C
• Refractive Index: 1.657
• Boiling Point: 495.9°Cat760mmHg
• PKA: 10.56±0.10(Predicted)
• Flash Point: 253.7°C
• PSA: 54.98000
• Density: 1.272g/cm³
• LogP: 3.01650
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 252.089877630
• Heavy Atom Count: 19
• Complexity: 334

Purity/Quality:

97% ^*data from raw suppliers

Methyl 5-(naphth-2-yl)-1H-pyrazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=NN1)C2=CC3=CC=CC=C3C=C2
• Uses: Methyl 3-(2-naphthyl)-1h-pyrazole-5-carboxylate is a useful reagent for synthesizing potent histone deacetylase inhibitors with in vitro and in vivo anti-tumor efficacy

Technology Process of methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate

There total 6 articles about methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate 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: 78.0%

(E)-methyl 2-diazo-4-(naphthalen-2-yl)but-3-enoate (234084-71-0) → methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate (164295-93-6)

Guidance literature:

With α,α,α-trifluorotoluene; for 0.166667h; Reflux;

DOI:10.1055/s-0040-1707111

Reference yield:

4-naphthalen-2-yl-2,4-dioxo-butyric acid methyl ester (144252-18-6) → methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate (164295-93-6)

Guidance literature:

With hydrazine; In ethanol; water; Heating / reflux;

Reference yield:

methyl (E)-4-(naphthalen-2-yl)-3-butenoate → methyl 5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate (164295-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 4-acetamidobenzenesulfonyl azide / acetonitrile / 12 h / Inert atmosphere

2: α,α,α-trifluorotoluene / 0.17 h / Reflux

With α,α,α-trifluorotoluene; 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile;

DOI:10.1055/s-0040-1707111

upstream raw materials:

4-naphthalen-2-yl-2,4-dioxo-butyric acid methyl ester

methyl 2-naphthyl ketone

(E)-methyl 2-diazo-4-(naphthalen-2-yl)but-3-enoate

β-naphthaldehyde

Downstream raw materials:

5-(naphthalen-2-yl)-1H-pyrazole-3-carboxylic acid

5-naphthalen-2-yl-1H-pyrazol-3-carboxylic acid hydrazide

Refernces

• 1、 -. "SPHINGOSINE KINASE INHIBITORS". Page 47, 48. . Retrieved 2008/06/13.