Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate

Base Information

• Chemical Name: Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate
• CAS No.: 105486-72-4
• Molecular Formula: C7H9BrN2O2
• Molecular Weight: 233.065
• Hs Code.: 2933199090
• DSSTox Substance ID: DTXSID70693302
• Wikidata: Q72473288
• Mol file: 105486-72-4.mol

Synonyms:105486-72-4;ETHYL 5-BROMO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE;ETHYL 5-BROMO-1-METHYLPYRAZOLE-4-CARBOXYLATE;5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester;MFCD13189831;1H-Pyrazole-4-carboxylic acid, 5-bromo-1-methyl-, ethyl ester;SCHEMBL2315523;DTXSID70693302;OMQVPOJHVUMCGK-UHFFFAOYSA-N;AMY11961;STL587370;AKOS015899813;AB69212;FD10518;DS-11410;SY128882;CS-0007675;FT-0752969;EN300-160210;5-Bromo-1-methyl-1H-pyrazole-4-carboxylicacidethylester;ETHYL5-BROMO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLATE

Chemical Property of Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.578
• Boiling Point: 290.717 °C at 760 mmHg
• PKA: -1.13±0.10(Predicted)
• Flash Point: 129.621 °C
• PSA: 44.12000
• Density: 1.588 g/cm³
• LogP: 1.35930
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 231.98474
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

Ethyl5-bromo-1-methyl-1H-pyrazole-4-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N(N=C1)C)Br

Technology Process of Ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate

There total 3 articles about Ethyl 5-bromo-1-methyl-1H-pyrazole-4-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: 96.0%

ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate (31037-02-2) → 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (105486-72-4)

Guidance literature:

With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1039/d1ra00314c

Reference yield: 16.8%

ethyl 3-bromo-1H-pyrazole-4-carboxylate (1353100-91-0) + methyl iodide (74-88-4) → 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (105486-72-4) + ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate (139308-52-4)

Guidance literature:

ethyl 3-bromo-1H-pyrazole-4-carboxylate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at 0 - 25 ℃; for 19h;

Reference yield:

3-amino-4-pyrazolecarboxylic acid ethyl ester (6994-25-8,103259-35-4,19750-02-8) → 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (105486-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tert.-butylnitrite; copper(ll) bromide / acetonitrile / 12 h / 70 °C / Inert atmosphere

2: caesium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C

With tert.-butylnitrite; caesium carbonate; copper(ll) bromide; In N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

3-amino-4-pyrazolecarboxylic acid ethyl ester

ethyl 3-bromo-1H-pyrazole-4-carboxylate

methyl iodide

Downstream raw materials:

1-methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid

ethyl 5-(trifluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

ethyl 1-methyl-5-phenyl-1H-pyrazole-4-carboxylate

Refernces

• 1、 Helal, Christopher J.,Arnold, Eric,Boyden, Tracey,Chang, Cheng,Chappie, Thomas A.,Fisher, Ethan,Hajos, Mihaly,Harms, John F.,Hoffman, William E.,Humphrey, John M.,Pandit, Jayvardhan,Kang, Zhijun,Kleiman, Robin J.,Kormos, Bethany L.,Lee, Che-Wah,Lu, Jiemin,Maklad, Noha,McDowell, Laura,McGinnis, Dina,O'Connor, Rebecca E.,O'Donnell, Christopher J.,Ogden, Adam,Piotrowski, Mary,Schmidt, Christopher J.,Seymour, Patricia A.,Ueno, Hirokazu,Vansell, Nichole,Verhoest, Patrick R.,Yang, Edward X.. "Identification of a Potent, Highly Selective, and Brain Penetrant Phosphodiesterase 2A Inhibitor Clinical Candidate". . p. 1001 - 1018. Retrieved 2018/02/17.
• 2、 -. "CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF". Paragraph 0573-0575. . Retrieved 2018/09/25.