ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate

Base Information

• Chemical Name: ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate
• CAS No.: 133261-06-0
• Molecular Formula: C9H12N2O2
• Molecular Weight: 180.206
• Hs Code.: 2933199090
• European Community (EC) Number: 851-296-0
• DSSTox Substance ID: DTXSID70429022
• Nikkaji Number: J3.289.413E
• Wikidata: Q82241904
• Mol file: 133261-06-0.mol

Synonyms:ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate;133261-06-0;ethyl 3-cyclopropyl-1H-pyrazole-5-carboxylate;5-Cyclopropyl-1H-pyrazole-3-carboxylic acid ethyl ester;5-cyclopropyl-2H-pyrazole-3-carboxylic acid ethyl ester;1H-Pyrazole-3-carboxylic acid, 5-cyclopropyl-, ethyl ester;SCHEMBL1281530;SCHEMBL19100014;DTXSID70429022;KGGGSOGFJKVURE-UHFFFAOYSA-N;BBL021587;MFCD08277218;STK894300;AKOS000135959;AKOS005264669;SB22095;AM803161;AS-70558;CS-0049440;FT-0730319;EN300-59056;A888146;ETHYL5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE;ETHYL 5-CYCLOPROPYL-2H-PYRAZOLE-3-CARBOXYLATE;3-Cyclopropyl-1H-pyrazole-5-carboxylic acid ethyl ester;Z326118958;5-Cyclopropyl-1H-pyrazole-3-carboxylic acid ethyl ester, AldrichCPR

Chemical Property of ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate

Chemical Property:

• Melting Point: 90-92 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 352.0±30.0 °C(Predicted)
• PKA: 11.60±0.10(Predicted)
• PSA: 54.98000
• Density: 1.256±0.06 g/cm3(Predicted)
• LogP: 1.46380
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 180.089877630
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl 5-cyclopropyl-1h-pyrazole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NNC(=C1)C2CC2

Technology Process of ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate

There total 8 articles about ethyl 5-cyclopropyl-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: 87.0%

C11H15NO6 + toluene-4-sulfonic acid hydrazide (1576-35-8) → ethyl 3-cyclopropyl-1H-pyrazole-5-carboxylate (133261-06-0)

Guidance literature:

With sodium carbonate; In methanol; at 65 ℃; for 2h; regioselective reaction;

DOI:10.1016/j.tet.2013.12.046

Reference yield: 60.0%

Cyclopropyl methyl ketone (765-43-5) + oxalic acid diethyl ester (95-92-1) → ethyl 3-cyclopropyl-1H-pyrazole-5-carboxylate (133261-06-0)

Guidance literature:

Cyclopropyl methyl ketone; oxalic acid diethyl ester; With potassium tert-butylate; In tetrahydrofuran; at 0 - 30 ℃; for 15h;

With acetic acid; hydrazine; In tetrahydrofuran; for 2h; Heating / reflux;

Reference yield:

ethyl 4-cyclopropyl-2,4-dioxobutanoate (21080-80-8) → ethyl 3-cyclopropyl-1H-pyrazole-5-carboxylate (133261-06-0)

Guidance literature:

With hydrazine;

DOI:10.1016/j.bmcl.2007.06.028

upstream raw materials:

ethyl 4-cyclopropyl-2,4-dioxobutanoate

Cyclopropyl methyl ketone

oxalic acid diethyl ester

toluene-4-sulfonic acid hydrazide

Downstream raw materials:

5-cyclopropyl-1H-pyrazole-3-carboxylic acid

ethyl 1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazole-5-carboxylate

3-(N-methylaminomethyl)-5-cyclopropyl-1H-pyrazole

(E)-3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}-N-(pentylsulfonyl)propenamide

Refernces

• 1、 Shao, Nana,Chen, Tong,Zhang, Taotao,Zhu, Huajian,Zheng, Qunxiong,Zou, Hongbin. "Cascade regioselective synthesis of pyrazoles from nitroallylic acetates and N-tosyl hydrazine". . p. 795 - 799. Retrieved 2014/01/23.
• 2、 Musatov,Starodubtseva,Rakishev,Turova,Vinogradov. "Synthesis of 3-aminomethyl-substituted pyrazoles and isoxazoles". experimental part. p. 1199 - 1203. Retrieved 2011/12/15.