28466-26-4|4-Aminopyrazole| Ambeed

Structure of 4-Amino-1H-pyrazole
CAS No.: 28466-26-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 28466-26-4 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 28466-26-4 ]

CAS No. :	28466-26-4
Formula :	C₃H₅N₃
M.W :	83.09
SMILES Code :	C1=N[NH]C=C1N
MDL No. :	MFCD01693729
InChI Key :	AXINVSXSGNSVLV-UHFFFAOYSA-N
Pubchem ID :	78035

Safety of [ 28466-26-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Computational Chemistry of [ 28466-26-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	6
Num. arom. heavy atoms	5
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	22.99
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.7 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.16
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-1.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.0
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-1.13
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.56
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.3

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.29
Solubility	43.1 mg/ml ; 0.519 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	0.43
Solubility	224.0 mg/ml ; 2.7 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.76
Solubility	14.3 mg/ml ; 0.173 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.58 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.2

Application In Synthesis of [ 28466-26-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 28466-26-4 ]

[ 28466-26-4 ] Synthesis Path-Downstream 1~35

1
[ 2075-46-9 ]
[ 28466-26-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃; under 760.051 Torr; for 12h;	Under hydrogen (1 atm), to a solution of 4-nitropyrazole (1.13 g, 10 mmol) in methanol (10 mL) was added 10% Pd-C (0.1 g). The mixture was stirred at 25 C. for 12 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give compound 31-a (860 mg, yield: 100%), which was used directly for the next step without purification.
100%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃;	5.0g 4-nitropyrazole was dissolved in 160mL of ethanol and 0.8g of 10% Pd/C was added. The reaction was subjected to hydrogen and reacted overnight at room temperature. TLC was used to monitor reaction completion. By celite was filtered off Pd/C. Ethanol solvent was evaporated to give 3.6g of the pure intermediate 8 as a red solid, quantitative reaction.
99%	With palladium 10% on activated carbon; hydrogen; In methanol; for 16h;	A suspension of 4-nitro-1H-pyrazole (2.05 g, 18.13 mmol), and Pd/C (10% w/w palladium on activated carbon, 0.96 g, 0.90 mmol) in MeOH (20 mL) was stirred under H2 atmosphere (balloon) for 16 h. The reaction mixture was filtered through Celite, rinsed with MeOH (3x 30 mL) and concentrated, affording 1.50 g of 1H-pyrazol-4- amine (pale pink solid, 99% yield). HPLC-MS (Method H): Ret, 1.16 min; ESI+-MS m/z: 84 (M+1).

95%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2068.65 Torr; for 3h;	Compound Ia (15.0 g, 133 mmol) was added to a suspension of palladium on carbon 10% (7.0 g, 6.65 mmol) in ethanol (100 mL). The mixture was shaken for 3 hours under hydrogen pressure (40 psi) at room temperature. The catalyst was removed by filtration through a pad of Celite and the solvent was evaporated. Compound Ib was obtained as a burgundy oil (10.5 g, 126 mmol, 95%) which was used in the following step without purification; GC/MS: m/z = 83 (100%).
49%	With hydrogen;1% Pd/C; In ethanol; under 1034.32 - 1551.49 Torr;	A mixture of 4-nitro-l/f-pyrazole (1.13 g, 10 mmol), Pd/C (10%, 57 mg) in ethanol (20 mL) was hydrogenated at 20-30 psi on a parr apparatu overnight. The reaction mixture was filtered through celite, washed with ethanol (10 mL). The filtrate was concentrated to get desired compound 0113-42 (404 mg, 49%) as a brown solid. LC-MS: 84 [M+l]+; 1H-NMR (400 MHz, DMSO-d6) delta 3.11 (br s, 2H), 6.99 (s, 2H), 11.92 (s, IH).
	palladium; In ethanol;	4-aminopyrazole (10) The 4-nitropyrazole (9) (15.0 g, 133 mmol) was added to a suspension of palladium on carbon 10% (7.0 g, 6.65 mmol, 5% mmol) in ethanol (100 ml). The mixture was shaken for 3 hours under hydrogen pressure (40 psi) at room temperature. The end of reaction checked by TLC (Ethylacetate/Hexane 1/1, 4-nitropyrazole Rf=0.6, UV active, 4-aminopyrazole Rf 0.1, UV active). The catalyst was removed by filtration through a pad of Celite and the solvent was evaporated. The product (10) was obtained as a burgundy oil (10.5 g, 126 mmol, 95%), which was used in the following step without purification. GC/MS: m/z=83 (100%).
	With hydrogen;platinum(IV) oxide; In ethanol; ethyl acetate; under 2280.15 Torr; for 2h;	The 4-amino-l/i-pyrazole used as a starting material was prepared as follows :-A mixture of 4-nitro-l/J-pyrazole (0.7 g), platinum oxide (0.05 g), ethyl acetate (5 ml) <n="110"/>and ethanol (15 ml) was stirred under 3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. There was thus obtained the required starting material (0.5 g).
	With iron; ammonium chloride; In ethanol; water; at 80℃; for 2h;	Step2:[00394] To a stirred mixture of iron (1.68g, 30 mmol), ammonium chloride (540mg, 10 mmol), water (2ml_) and ethanol (8ml_) at 800C was added 4-nitro-1 H-pyrazol (1 .13g, lOmmol) in portions. After completion of addition, the mixture was stirred at 800C for additional 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, and the resultant mixture was filtered through a pad of celite. The filtrate was concentrated to afford the crude title compound which was used at next step without further purification. MS (ES) [M+H]+ expected 84.0, found 84.0.
	With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 22h;	Intermediate (1e), 4-nitro-1 H-pyrazole (2.8g, 24.8mmol), was stirred in ethanol (20OmL) and the flask was evacuated and then flushed with nitrogen. Palladium, 10wt. % on activated carbon (300mg, catalytic amount) was added and after two vacuum / H2 cycles to replace the nitrogen inside with hydrogen, the mixture was shaken for 18 hours under ordinary hydrogen pressure (1atm). Palladium, 10wt. % on activated carbon (300mg) was added and after two vacuum / H2 cycles to replace the nitrogen inside with hydrogen, the mixture was shaken for a further 4 hours. The reaction mixture was filtered through celite and the filter cake was washed through with ethanol (2x50ml_). The combined washings and the filtrate were concentrated in vacuo. The residue obtained was triturated with ethyl acetate to yield a light pink solid, 1.48g, 72%. The filtrate subsequently obtained was concentrated in vacuo to yield another batch of sufficiently pure material, 0.54g, 26%, as a dark pink solid.
		4-Nitro-1 /-/-pyrazole (Manchester organics; 1.13 g, 9.99 mmol) was dissolved in ethanol (50 ml). This solution was added carefully to 10% palladium on carbon (Aldrich; 102 mg) under a nitrogen atmosphere. The atmosphere was exchanged to hydrogen, and the mixture was stirred vigorously at room temperature under a hydrogen atmosphere. After 45 min, ca. 700 ml of hydrogen had been taken up, and no further hydrogen was taken up over the next 30 min. Stirring was stopped and the atmosphere was exchanged to nitrogen. The solution was filtered through cellite (10 g cartridge) and washed with further ethanol (150 ml). Relevant fractions (as verified by TLC) were combined and concentrated in vacuo to give a red oil. Trituration with DCM gave the title compound (815 mg) as a red solid; 1 H NMR (MeOH-d4, 400 MHz) delta (ppm) 7.20 (2 H, s).
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 1.25h;Inert atmosphere;	Intermediate 5: 1 H-Pyrazol-4-amine. 4-Nitro-1H-pyrazole (Manchester organics; 1.13 g, 9.99 mmol) was dissolved in ethanol (50 ml). This solution was added carefully to 10% palladium on carbon (Aldrich; 102 mg) under a nitrogen atmosphere. The atmosphere was exchanged to hydrogen, and the mixture was stirred vigorously at room temperature under a hydrogen atmosphere. After 45 min, ca. 700 ml of hydrogen had been taken up, and no further hydrogen was taken up over the next 30 min. Stirring was stopped and the atmosphere was exchanged to nitrogen. The solution was filtered through cellite (10 g cartridge) and washed with further ethanol (150 ml). Relevant fractions (as verified by TLC) were combined and concentrated in vacuo to give a red oil. Trituration with DCM gave the title compound (815 mg) as a red solid; 1 H NMR (MeOH-d4, 400 MHz) delta (ppm) 7.20 (2 H, s).
	With hydrogen;palladium on activated charcoal; In ethanol; at 20℃; for 18h;	A -(1H-Pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide Step 1 : To a round bottom flask, 4-nitro-1 /-/-pyrazole (2.0 g, 17.68 mmol), Pd/C (200 mg, 1.89 mmol) and EtOH (15.0 mL, degassed) was added. The flask was evacuated and backfilled with H2 and the reaction mixture was stirred under H2-atmosphere at rt for 18 h. The reaction mixture was filtered over celite, washed with MeOH and the solvent was removed under reduced pressure to yield 1 H-pyrazol-4-amine as a red oil which was used without further purification. 1 H-NMR (400 MHz, DMSO) delta 3.72 (brs, 2H), 6.99 (s, 2H), 1 1.9 (brs, 1 H).
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 1h;	Synthesis of compound 96.2[00605] A solution of 4-nitro-lH-pyrazole (200 mg, 1.77 mmol, 1.00 equiv) and 10% Palladium on carbon (40 mg) in methanol (5 mL) was degassed with H2 three times and the reaction mixture was stirred for 1 h at room temperature. The catalyst was filtered out and the filtrate was concentrated under vacuum to give 120 mg (crude) of compound 96.2 as a light yellow solid.
3.6 g	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃;	Dissolving 5.0 g of 4-nitropyrazole in 160 mL of ethanol, and then adding 0.8 g of 10 wt% Pd/C to the above solution; Hydrogen was introduced into the reaction solution and allowed to react overnight at room temperature; after the TLC detection reaction was completed, the insoluble matter was filtered off with diatomaceous earth; Evaporation of the ethanol solvent gave pure intermediate 2 as a red solid 3.6 g.

References: [1]Patent: US2015/336982,2015,A1 .Location in patent: Paragraph 0252; 0253.
[2]ChemMedChem,2016,p. 1695 - 1699.
[3]Patent: CN105418616,2016,A .Location in patent: Paragraph 0118; 0119.
[4]Organic and Biomolecular Chemistry,2013,vol. 11,p. 395 - 399.
[5]Patent: WO2017/178510,2017,A1 .Location in patent: Page/Page column 297.
[6]Patent: WO2006/44821,2006,A1 .Location in patent: Page/Page column 23.
[7]Journal of Medicinal Chemistry,2019,vol. 62,p. 3898 - 3923.
[8]Patent: WO2010/75542,2010,A1 .Location in patent: Page/Page column 73.
[9]Chemische Berichte,1904,vol. 37,p. 3501.
[10]Journal of the Chemical Society,1945,p. 114.
[11]Journal of the Chemical Society,1925,vol. 127,p. 2939.
[12]Journal of Medicinal Chemistry,2005,vol. 48,p. 5780 - 5793.
[13]Patent: US6531475,2003,B1 .
[14]Patent: WO2007/99326,2007,A1 .Location in patent: Page/Page column 108-109.
[15]Patent: WO2008/8375,2008,A2 .Location in patent: Page/Page column 83.
[16]Patent: WO2009/93012,2009,A1 .Location in patent: Page/Page column 20; 35.
[17]Journal of Medicinal Chemistry,2011,vol. 54,p. 4350 - 4364.
[18]Patent: WO2012/52459,2012,A1 .Location in patent: Page/Page column 38-39.
[19]Patent: WO2012/52458,2012,A1 .Location in patent: Page/Page column 34.
[20]Patent: WO2012/110986,2012,A1 .Location in patent: Page/Page column 52-53.
[21]Patent: WO2014/194242,2014,A2 .Location in patent: Paragraph 00603-0605.
[22]Patent: CN108864057,2018,A .Location in patent: Paragraph 0105; 0206-0208.

2
[ 28466-26-4 ]
[ 121-60-8 ]
sulfanilic acid-(1H-pyrazol-4-ylamide) [ No CAS ]

References: [1]Journal of the Chemical Society,1945,p. 114.

3
[ 28466-26-4 ]
[ 3469-69-0 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 3501.

4
[ 28466-26-4 ]
1H-pyrazole-4-diazonium ; chloride [ No CAS ]

References: [1]Journal of the Chemical Society,1925,vol. 127,p. 2939.

5
[ 116008-52-7 ]
[ 28466-26-4 ]

References: [1]Justus Liebigs Annalen der Chemie,1927,vol. 457,p. 292.

6
[ 28466-26-4 ]
[ 448-61-3 ]
C₂₆H₂₀N₃⁽¹⁺⁾*BF₄^(1-)*BF₃*FH [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1984,vol. 20,p. 1245 - 1254.
Khimiya Geterotsiklicheskikh Soedinenii,1984,p. 1509 - 1518.

7
[ 698-63-5 ]
[ 28466-26-4 ]
[1-(5-Nitro-furan-2-yl)-meth-(E)-ylidene]-(1H-pyrazol-4-yl)-amine [ No CAS ]