1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid

Base Information

• Chemical Name: 1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid
• CAS No.: 5932-32-1
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.15
• Hs Code.: 2933199090
• European Community (EC) Number: 675-518-9
• DSSTox Substance ID: DTXSID90974746
• Wikidata: Q72505429
• ChEMBL ID: CHEMBL128604
• Mol file: 5932-32-1.mol

Synonyms:5932-32-1;1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid;884497-47-6;1,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid;2,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid;1H,4H,5H,6H-Cyclopenta[C]Pyrazole-3-Carboxylic Acid;1,4,5,6-tetrahydrocyclopentapyrazole-3-carboxylic acid;3-cyclopentapyrazolecarboxylic acid, 1,4,5,6-tetrahydro-;CYCLOPENTAPYRAZOLE-3-CARBOXYLIC ACID;MFCD01248822;2,4,5,6-Tetrahydro-3-cyclopentapyrazolecarboxylic acid;CHEMBL128604;2,4,5,6-Tetrahydrocyclopentapyrazole-3-carboxylic acid;2,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid;ChemDiv3_014408;EC-000.1364;Oprea1_415453;SCHEMBL1663622;SCHEMBL16629837;2,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylicacid;DTXSID90974746;HMS1513O20;CS-D1767;BBL018891;BDBM50132140;MFCD05863684;STK387519;AKOS000271376;AKOS000441635;AB08420;AB89910;CS-W000372;DG-0059;IDI1_030206;AM804102;BB 0219108;FT-0646366;EN300-41431;AB00667834-01;A832267;SR-01000597146;J-503951;SR-01000597146-1;2H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylic acid;Z57683732;2,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate;3-Cyclopentapyrazolecarboxylic acid, 2,4,5,6-tetrahydro;3-Cyclopentapyrazolecarboxylicacid,2,4,5,6-tetrahydro-;F0452-7554;F8880-5931;1,4,5,6-tetrahydrocyclopenta [c]pyrazole-3-carboxylic acid;1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid, AldrichCPR

Chemical Property of 1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.5E-08mmHg at 25°C
• Melting Point: 245-248 °C
• Refractive Index: 1.66
• Boiling Point: 430.7 °C at 760 mmHg
• PKA: 16.31±0.20(Predicted)
• Flash Point: 214.3 °C
• PSA: 65.98000
• Density: 1.482 g/cm³
• LogP: 0.59660
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

99% ^*data from raw suppliers

1H,4H,5H,6H-Cyclopenta[c]pyrazole-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C1)NN=C2C(=O)O
• Uses: 1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic Acid is used in the synthetic preparation of pyrazole derivatives as partial agonists for nicotinic acid receptor.

Technology Process of 1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid

There total 6 articles about 1,4,5,6-Tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid 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: 98.0%

1,2-diazabicyclo[3,3,04,8]octa-3,8-diene-3-carboxylic acid ethyl ester (5932-31-0) → 1,4,5,6-tetrahydro-cyclopenta[c]pyrazole-3-carboxylic acid (5932-32-1)

Guidance literature:

With potassium hydroxide; In methanol; water; at 43 ℃; for 1.5h;

DOI:10.1021/op800290t

Reference yield:

cyclopentanone (120-92-3) → 1,4,5,6-tetrahydro-cyclopenta[c]pyrazole-3-carboxylic acid (5932-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1: EtONa / ethanol / 18 h / 20 °C

2: N₂H₄*H₂O; AcOH / 8 h / Heating

3: 42 percent / aq. NaOH / dioxane / 18 h / 20 °C

With sodium hydroxide; sodium ethanolate; hydrazine hydrate; acetic acid; In 1,4-dioxane; ethanol; 1: Claisen condensation;

DOI:10.1021/jm030888c

Reference yield:

(2-oxocyclopentyl)glycoxylic acid ethyl ester sodium salt → 1,4,5,6-tetrahydro-cyclopenta[c]pyrazole-3-carboxylic acid (5932-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: N₂H₄*H₂O; AcOH / 8 h / Heating

2: 42 percent / aq. NaOH / dioxane / 18 h / 20 °C

With sodium hydroxide; hydrazine hydrate; acetic acid; In 1,4-dioxane;

DOI:10.1021/jm030888c

upstream raw materials:

1,2-diazabicyclo[3,3,0^4,8]octa-3,8-diene-3-carboxylic acid ethyl ester

cyclopentanone

oxo-(2-oxo-cyclopentyl)-acetic acid ethyl ester

Downstream raw materials:

methyl cyclopenta[c]pyrazole-3-carboxylate

N-[(4R)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-yl]-1,4,5,6-tetrahydrocyclopenta[a]pyrazole-3-carboxamide

1,4,5,6-tetrahydro-cyclopentapyrazole-3-carboxylic acid amide

5,6-dihydro-1H,4H-cyclopenta[c]pyrazole

Refernces

• 1、 Semple, Graeme,Skinner, Philip J.,Gharbaoui, Tawfik,Shin, Young-Jun,Jung, Jae-Kyu,Cherrier, Martin C.,Webb, Peter J.,Tamura, Susan Y.,Boatman, P. Douglas,Sage, Carleton R.,Schrader, Thomas O.,Chen, Ruoping,Colletti, Steven L.,Tata, James R.,Waters, M. Gerard,Cheng, Kang,Taggart, Andrew K.,Cai, Tian-Quan,Carballo-Jane, Ester,Behan, Dominic P.,Connolly, Daniel T.,Richman, Jeremy G.. "3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (MK-0354): A partial agonist of the nicotinic acid receptor, G-protein coupled receptor 109a, with antilipolytic but no vasodilatory activity in mice". experimental part. p. 5101 - 5108. Retrieved 2009/08/07.