5930-94-9|3-Nitro-1H-pyrrole| Ambeed

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Quality Control of [ 5930-94-9 ] Purity: 98% SDS Specification

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Product Details of [ 5930-94-9 ]

CAS No. :	5930-94-9
Formula :	C₄H₄N₂O₂
M.W :	112.09
SMILES Code :	[O-][N+](=O)C1=CNC=C1
MDL No. :	MFCD00059714
InChI Key :	LOJNBPNACKZWAI-UHFFFAOYSA-N
Pubchem ID :	145813

Safety of [ 5930-94-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 5930-94-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	5
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	29.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	61.61 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.77
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	0.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.92
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.	-0.33
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	-0.62
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.26

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.27
Solubility	6.0 mg/ml ; 0.0535 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.	-1.41
Solubility	4.41 mg/ml ; 0.0393 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.93
Solubility	13.2 mg/ml ; 0.118 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	Yes
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.	-6.6 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	2.0 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)	1.76

Application In Synthesis of [ 5930-94-9 ]

* 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 [ 5930-94-9 ]

[ 5930-94-9 ] Synthesis Path-Downstream 1~35

1
[ 109-97-7 ]
[ 5919-26-6 ]
[ 5930-94-9 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 6879 - 6881.
[2]Canadian Journal of Chemistry,1957,vol. 35,p. 21,26.

3
[ 16851-82-4 ]
[ 5919-26-6 ]
[ 5930-94-9 ]
[ 97188-21-1 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 4899 - 4900.

4
[ 55315-56-5 ]
[ 5930-94-9 ]
2,5-bis(1,3-benzodithiol-2-yl)-3-nitropyrrole [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 2939 - 2944.

5
[ 5930-94-9 ]
[ 65018-89-5 ]
[ 127486-48-0 ]
[ 140614-02-4 ]
[ 140614-03-5 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 1109 - 1112.

6
[ 5930-94-9 ]
[ 71984-04-8 ]
[ 87427-32-5 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 552 - 562.

7
[ 5930-94-9 ]
[ 42778-73-4 ]
[ 87427-20-1 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 552 - 562.

8
[ 5930-94-9 ]
C₄H₃⁽²⁾HN₂O₂ [ No CAS ]
C₄H₃⁽²⁾HN₂O₂ [ No CAS ]
C₄H₃⁽²⁾HN₂O₂ [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1475 - 1480.

9
[ 87630-39-5 ]
[ 5930-94-9 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 6317 - 6328.
[2]Journal of Heterocyclic Chemistry,2021,vol. 58,p. 1836 - 1848.
[3]Tetrahedron Letters,1983,vol. 24,p. 3455 - 3456.

10
[ 97188-21-1 ]
[ 5930-94-9 ]

References: [1]Canadian Journal of Chemistry,1985,vol. 63,p. 896 - 902.

11
[ 5930-94-9 ]
[ 4330-21-6 ]
1-(2'-deoxy-3',5'-di-O-toluoyl-β-D-ribofuranosyl)-3-nitropyrrole [ No CAS ]

References: [1]Journal of the American Chemical Society,1995,vol. 117,p. 1201 - 1209.

12
[ 5930-94-9 ]
[ 75-03-6 ]
[ 216591-43-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2.5h;	Method G Synthesis of 5-tert-Butyl-3-[3-(1-ethyl-1H-pyrrol-3-yl)-ureido]-thiophene-2-carboxylic acid methyl ester. (Example 18) [Show Image] step 1; A solution of <strong>[5930-94-9]3-nitropyrrole</strong> (446 mg, 4.16 mmol), cesium carbonate (1.63 g, 4.99 mmol), iodoethane (998 ul, 12.48 mmol) in DMF (10 ml) was stirred for 2.5 hours at 20C. The reaction was diluted with ethyl acetate, washed 1N hydrochloric acid (3x), dried with sodium sulfate and the solvent removed in vacuo. The crude material was purified by flash chromatography with 100% dichloromethane affording 480 mg (82%) as an oil.

References: [1]Patent: EP986382,2008,B1 .Location in patent: Page/Page column 22.
[2]European Journal of Organic Chemistry,1999,p. 955 - 958.

15
[ 109-97-7 ]
[ 7697-37-2 ]
[ 108-24-7 ]
[ 5919-26-6 ]
[ 5930-94-9 ]

References: [1]Canadian Journal of Chemistry,1957,vol. 35,p. 21,26.

16
[ 60-29-7 ]
[ 625-58-1 ]
sodium compound of pyrrole [ No CAS ]
[ 5930-94-9 ]

References: [1]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1911,vol. <5> 20 I,p. 311.

17
[ 5930-94-9 ]
[ 616236-59-0 ]
[ 616236-60-3 ]

References: [1]Chemistry - A European Journal,2003,vol. 9,p. 3353 - 3366.

18
[ 5930-94-9 ]
[ 96-32-2 ]
[ 250647-51-9 ]

References: [1]Organic Letters,1999,vol. 1,p. 1639 - 1641.
[2]Acta Pharmacologica Sinica,2018,vol. 39,p. 1902 - 1912.

19
[ 50-00-0 ]
[ 5930-94-9 ]
[ 1213269-56-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; water; at 20℃; for 0.5h;	Reference Production Example 35 1-chloromethyl-3-nitro-1H-pyrole 840 mg of 3-nitro-1H-pyrole, 15 ml of tetrahydrofuran and 15 ml of formaldehyde 36 % in water were mixed. 0.5 ml of tetrabutylammonium hydroxide 10 % in water was added at room temperature, followed by stirring at room temperature for 30 minutes. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 1-hydroxymethyl-3-nitro-1H-pyrole.

References: [1]Patent: EP1710234,2006,A1 .Location in patent: Page/Page column 72.

20
2,3,3-triiodoallyl-p-toluenesulfonate [ No CAS ]
[ 5930-94-9 ]
[ 87427-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;	EXAMPLE 2 1-(2',3',3'-Triiodoallyl)-<strong>[5930-94-9]3-nitropyrrole</strong> To a solution of 112 mg (1 mmole) of <strong>[5930-94-9]3-nitropyrrole</strong> in 5.0 ml of dry N,N-dimethylformamide were added 606 mg of 2,3,3-triiodoallyl-p-toluenesulfonate and 60 mg (1.5 mmoles) of powdery sodium hydroxide and the reaction was carried out with stirring for 15 minutes. To the reaction mixture were added 50 ml of ethyl acetate and 50 ml of water, extraction was effected and the ethyl acetate layer was separated. The layer was washed with water, dried and concentrated under reduced pressure. To the residue were added 2.5 ml of methanol and the so separated crystalline substance, 1-(2',3',3'-triiodoallyl)-<strong>[5930-94-9]3-nitropyrrole</strong>, was recovered by filtration. Yield 306 mg (56%), mp 107-109 C. Analysis for C7 H5 N2 O2 I3 (%): Calc'd: C, 15.86; H, 0.95; N, 5.29; I, 71.85. Found: C, 15.85; H, 0.85; N, 5.14; I, 71.82.

References: [1]Patent: US4563472,1986,A .

21
[ 5930-94-9 ]
1-(1'-iodopropyn-3'-yl)-3-nitropyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; N,N-dimethyl-formamide;	EXAMPLE 13 1-(1'-Iodopropyn-3'-yl)-<strong>[5930-94-9]3-nitropyrrole</strong> To a solution of 224 mg (2 mmoles) of <strong>[5930-94-9]3-nitropyrrole</strong> in 5 ml of dry N,N-dimethylformamide were added 0.67 g (2 mmoles) of p-toluenesulfonic acid ester of iodopropargyl alcohol and 100 mg of powdery sodium hydroxide and the resulting mixture was stirred at 10-5 C. for one hour. The reaction mixture was extracted with each 50 ml portion of ethyl acetate and water and the ethyl acetate layer was separated, washed with water and dried. The ethyl acetate layer was concentrated under reduced pressure, to the residue were added 1.5 ml of methanol and the so separated 1-(1'-iodopropyn-3'-yl)-<strong>[5930-94-9]3-nitropyrrole</strong> crystal was recovered by filtration. Yield 236 mg (43%), mp 138-140 C. Analysis for C3 H5 N2 O2 I (%): Calc'd: C, 30.47; H, 1.83; N, 10.14; I, 45.97. Found: C, 31.31; H, 1.89; N, 10.06; I, 45.34.

References: [1]Patent: US4563472,1986,A .

22
[ 108-30-5 ]
[ 5930-94-9 ]
[ 1015196-35-6 ]

References: [1]Synthesis,2008,p. 788 - 794.

23
[ 5930-94-9 ]
[ 4584-46-7 ]
[ 1197333-04-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	A mixture of <strong>[5930-94-9]3-nitropyrrole</strong> (500 mg, 4.46 mmol), cesium carbonate (3.63 g, 11.2 mmol, 2.5 equiv), 1-chloro-2-dimethylaminoethane (835 mg, 5.8 mmol, 1.3 equiv) and DMF (5 mL) was stirred for 16 h at rt. The reaction mixture was quenched by addition of a saturated aqueous solution of NaHCOs and extracted with DCM/MeOH (9:1 , v/v). The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM → DCM/MeOH, 97:3) to afford 656 mg of the title compound as a yellow oil. Title compound: ESI-MS: 184.1 [M+H]+; TLC: Rf = 0.38 (DCM/MeOH, 9:1 ).

References: [1]Patent: WO2009/141386,2009,A1 .Location in patent: Page/Page column 142.

24
[ 1255171-72-2 ]
[ 5930-94-9 ]
[ 1255172-19-0 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 15800 - 15807.

25
[ 890122-43-7 ]
[ 5930-94-9 ]
[ 1373527-15-1 ]

References: [1]Organic Letters,2012,vol. 14,p. 2254 - 2257.

26
[ 5930-94-9 ]
cis-2,5-dibenzoxy-2,5-dihydrofuran [ No CAS ]
[ 1373527-22-0 ]

References: [1]Organic Letters,2012,vol. 14,p. 2254 - 2257.

27
[ 5930-94-9 ]
[ 368-66-1 ]
[ 1449787-97-6 ]