3-Amino-1H-pyrazole-4-carboxamide

Base Information

• Chemical Name: 3-Amino-1H-pyrazole-4-carboxamide
• CAS No.: 5334-31-6
• Molecular Formula: C4H6N4O
• Molecular Weight: 126.118
• Hs Code.: 2933199090
• European Community (EC) Number: 226-252-3
• NSC Number: 1402
• UNII: G43E3B7590
• DSSTox Substance ID: DTXSID50201489
• Nikkaji Number: J231.954C,J25.250F
• Wikidata: Q27278715
• Mol file: 5334-31-6.mol

Synonyms:3-Amino-1H-pyrazole-4-carboxamide;5334-31-6;3-AMINOPYRAZOLE-4-CARBOXAMIDE;5-amino-1h-pyrazole-4-carboxamide;3-AMINO-4-PYRAZOLECARBOXAMIDE;3-Amino-pyrazole-4-carboxylic acid amide;1H-Pyrazole-4-carboxamide, 3-amino-;3-Amino-4-carbamoylpyrazole;5-Amino-1H-pyrazole-4-carboxylic acid amide;UNII-G43E3B7590;NSC-1402;EINECS 226-252-3;MFCD00082808;G43E3B7590;SR-01000945176;NSC1402;5-Amino-1H-pyrazole-4-carboxylic amide;MLS006011394;5-aminopyrazole-4-carboxamide;SCHEMBL918559;(R)-Modafinil-d10 Carboxylate;LEFSNWUSTYESGC-UHFFFAOYSA-;DTXSID50201489;NSC 1402;BBL010022;MFCD01812304;STK711120;5-AMINO-4-PYRAZOLECARBOXAMIDE;3-Amino-1(H)-pyrazole-4-carboxamide;AKOS000145542;AKOS005530692;CS-W021829;PB13014;AS-18400;SMR002529996;SY004722;ALLOPURINOL IMPURITY A [EP IMPURITY];AM20100307;FT-0614992;EN300-30536;AB00373924-03;3-amino-2H-pyrazole-4-carboxamide;sulfuric acid;A829524;3-AMINO-1H-PYRAZOLE-4-CARBOXYLIC ACID AMIDE;J-516659;Q-100348;SR-01000945176-1;SR-01000945176-2;Q27278715;Z300087852

Chemical Property of 3-Amino-1H-pyrazole-4-carboxamide

Chemical Property:

• Melting Point: 187-189 °C(Solv: water (7732-18-5))
• Boiling Point: 454.3°Cat760mmHg
• PKA: 13.26±0.50(Predicted)
• Flash Point: 228.5°C
• PSA: 97.79000
• Density: 1.538g/cm³
• LogP: 0.37230
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 126.05416083
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-4-pyrazolecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NNC(=C1C(=O)N)N
• Uses: 5-Amino-4-pyrazolecarboxamide is used in the synthesis of 4H-3,1-Benzothiazinone analogs as antiproliferative agents against human cancer cell lines. Also, it is an intermediate used in the synthesis of 3-(4H-1,2,4-Triazol-4-yl)-1H-pyrazole-4-carboxamide (T767570), which is an impurity of Allopurinol (A547300), which is a xanthine oxidase inhibitor; decreases uric acid production. Used in treatment of hyperuricemia and chronic gout. Antiurolithic.

Technology Process of 3-Amino-1H-pyrazole-4-carboxamide

There total 4 articles about 3-Amino-1H-pyrazole-4-carboxamide 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: 90.0%

3-amino-4-cyano-2H-pyrazole (16617-46-2) → 5-amino-1H-pyrazole-4-carboxylic acid amide (5334-31-6)

Guidance literature:

With ammonium hydroxide; sulfuric acid; In water; at 50 ℃; for 5h;

DOI:10.1016/j.bioorg.2018.02.030

Reference yield:

→ 5-amino-1H-pyrazole-4-carboxylic acid amide (5334-31-6)

Guidance literature:

Allopurinol, Hydrolyse;

DOI:10.1002/jps.2600570225

Reference yield:

3-Amino-4-cyanopyrazole (16617-46-2,882231-01-8) → 3-aminopyrazole-4-carboxylic acid amide (5334-31-6,52906-16-8)

Guidance literature:

DOI:10.1021/ja01585a023

upstream raw materials:

3-Amino-4-cyanopyrazole

3-amino-4-cyano-2H-pyrazole

Downstream raw materials:

6-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

6-(2,4-Dichloro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

6-(p-methylphenyl)-1H-pyrazolo<3,4-d>pyrimidin-4(5H)-one

7-(3-(N-ethylacetamido)phenyl)pyrazolo[1,5-a]pyrimidin-3-carboxamide

Refernces

• 1、 Chandrasekaran, Balakumar,Cherukupalli, Srinivasulu,Karunanidhi, Sivanandhan,Kajee, Afsana,Aleti, Rajeshwar Reddy,Sayyad, Nisar,Kushwaha, Babita,Merugu, Srinivas Reddy,Mlisana, Koleka P.,Karpoormath, Rajshekhar. "Design and synthesis of novel heterofused pyrimidine analogues as effective antimicrobial agents". . p. 246 - 255. Retrieved 2019/02/15.
• 2、 Singla, Prinka,Luxami, Vijay,Singh, Raja,Tandon, Vibha,Paul, Kamaldeep. "Novel pyrazolo[3,4-d]pyrimidine with 4-(1H-benzimidazol-2-yl)-phenylamine as broad spectrum anticancer agents: Synthesis, cell based assay, topoisomerase inhibition, DNA intercalation and bovine serum albumin studies". . p. 24 - 35. Retrieved 2016/10/26.