Home Cart Sign in  
Chemical Structure| 613-50-3 Chemical Structure| 613-50-3

Structure of 613-50-3

Chemical Structure| 613-50-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Alternative Products

Product Details of [ 613-50-3 ]

CAS No. :613-50-3
Formula : C9H6N2O2
M.W : 174.16
SMILES Code : C1=C([N+](=O)[O-])C=CC2=NC=CC=C12
MDL No. :MFCD00006799
InChI Key :SMHPLBXIVNQFBA-UHFFFAOYSA-N
Pubchem ID :11945

Safety of [ 613-50-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 613-50-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 50.57
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

58.71 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.46
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.84
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.14
Log Po/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.

0.66
Log Po/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

0.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.27

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.58
Solubility 0.456 mg/ml ; 0.00262 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.69
Solubility 0.353 mg/ml ; 0.00203 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < 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

-3.08
Solubility 0.146 mg/ml ; 0.000836 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

Yes
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.

-6.06 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

1.0
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)

1.72

Application In Synthesis of [ 613-50-3 ]

* 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 [ 613-50-3 ]

[ 613-50-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 613-50-3 ]
  • [ 580-15-4 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 2h; Synthesis of 89 To a methanol (50 ml)-tetrahydrofuran (50 ml) suspension of 88 (5.00 g, 28.71 mmol), 10% Pd-C (moisture of about 50%; 1.00 g) was added under a hydrogen atmosphere, and the mixture was stirred at room temperature for 2 hours. The catalyst was removed by filtration and the solvent of the filtrate was distilled off under reduced pressure to obtain 89 (4.14 g, 100%) as a pale yellow solid. mp 116-117C APCI-MS m/z 145[M+H]+
> 99% With lithium hydroxide monohydrate; palladium diacetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In dichloromethane; at 25℃; for 12h;Schlenk technique; Inert atmosphere; Replace the gas environment in the Shrek tube with a nitrogen environment, add 6-nitroquinoline 0.25 mmol, palladium acetate 0.005 mmol, methylene chloride 0.5 mL, add pinacol borane 0.775 mmol, water 0.55 mmol, room temperature with stirring The reaction was carried out under conditions for 12 hours. The reaction solution obtained after the reaction was completed was subjected to column chromatography, and the target product obtained with a yield of> 99% was a pale yellow solid.
95% With hydrogen; In methanol; N,N-dimethyl-formamide; at 50℃; under 6080.41 Torr; for 22h;Inert atmosphere; Autoclave; General procedure: The hydrogenation of nitrobenzene (Table 1, entry 2) is given as an example.Nitrobenzene (2a) (1.88 g, 15.3 mmol) was charged into an Ar-filled 100 mL glass autoclaveequipped with a Teflon-coated magnetic stirring bar. Methanol (10 mL) degassed by three freeze-thaw cycles was introduced via Teflon cannula, followed by the addition of a solution of thePd-NPs catalyst in DMF (5.0 mM, 60 μL, 0.30 μmol, S/Pd = 51,000:1). Hydrogen wasintroduced into the reaction vessel until the pressure gauge indicated 8 atm, and then the pressurewas carefully released to 1 atm by opening the stop valve. This procedure was repeated five times,and finally hydrogen was pressurized to 8 atm. The vessel was placed into a water bath controlledat 50 C, and the reaction mixture was vigorously stirred for 40 h. After careful venting of thehydrogen, the reaction mixture was concentrated under a reduced pressure.1,3,5-Trimethoxylbenzene (101.0 mg, 0.601 mmol) was added as an internal standard for the NMRanalysis, and the produced aniline (3a) was quantified (99%).The reaction mixture was concentrated to approximately half the original volume under a reducedpressure, followed by dilution with ether (15 mL). The ethereal solution was extracted by 3 Mhydrochloric acid (15 mL 3, 10 mL 2) to remove the internal standard for NMR analysis.The combined aqueous solution was basified by the addition of 3 M NaOH until the pH of thesolution became >12, and the alkaline solution was extracted by ether (15 mL 3). Thecombined extracts were washed with brine and dried over anhydrous sodium sulfate. Afterremoval of the drying agent by filtration, the solution was concentrated under a reduced pressure.The residual oil was purified by bulb-to-bulb distillation, giving pure aniline as a colorless oil (1.14g, 80%).
93% With palladium diacetate; hydrazine hydrate monohydrate; potassium hydroxide; In lithium hydroxide monohydrate; at 50℃; for 8h;Inert atmosphere; Green chemistry; General procedure: To an oven-dried reaction flask with Teflon coated stir bar purgedwith argon, Pd(OAc)2 0.01 mmol, IL4 0.08 mmol, KOH (or K2CO3)0.30 mmol, nitroarene 1 1.0 mmol and degassed HPLC grade water1.5 mL were added, and the mixture was stirred for 5 min under argonat room temperature. Then, 0.5 mL of hydrazine hydrate aqueous solution(~5.0 mmol) was syringed into the flask at the same temperature.After stirring for additional 5 min, the reaction was heat to 50 C,and stirring for 8 h under argon. After completion, the reaction mixturewas extracted by methyl tertiary butyl ether (MTBE) (3 × 2 mL), andthe organic layer was collected and filtered through a bed of silica gellayered over Celite. The volatiles were removed in vacuo to afford theproduct 2. In some cases, further column chromatography on silica gelwas required to afford the pure desired products.
91% With hydrogen; In methanol; at 20℃; The solution of 6-nitroquinoline (174.2 mg, 1 mmol) in methanol (10 mL) wastreated with Pd/C (10%, 14.0 mg). the reaction mixture wasvigorously stirred under an atmosphere of hydrogen at roomtemperature. +e progress of the reaction was monitored byTLC. After completion of the reaction, the reaction mixturewas then filtered and concentrated in vacuo to give the crudeproduct. The crude product was purified by column (ethylacetate : petroleum ether: 4) to afford the product 2(131.1 mg, 91.0%) as white solid. m.p. 116.8-119.0C. 1HNMR (600 MHz, CDCl3) 2: 8.64 (d, J 4.0 Hz, 1H), 7.89 (t,J 9.7 Hz, 2H), 7.25 (t, J 4.8 Hz, 1H), 7.14 (dd, J 9.0 Hz,2.6 Hz, 1H), 6.88 (d, J 2.5 Hz, 1H), 3.84 (brs, 2H).
90% With tetrahydroxydiborane; copper (II) acetate; In acetonitrile; at 100℃; for 24h;Inert atmosphere; 6-nitroquinoline (0.6mmol, 114.1mg), Cu(OAc)2 (0.03mmol, 6.0mg) and tetrahydroxydiboron (0.9mmol, 80.7mg), acetonitrile (1mL), under nitrogen protection, 100 C After reacting for 24 hours, the reaction was monitored by TLC, 10 mL of water was added, ethyl acetate (10 mL×3) was added, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by column chromatography (V petroleum ether: V ethyl acetate = 3:1) to obtain 77.9 mg of white solid, which is to obtain the target compound with a yield of 90%.
87% With hydrazine hydrate monohydrate; In ethanol; at 80℃; for 1h;Inert atmosphere; General procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.
83% With tetrahydroxydiborane; 5%-palladium/activated carbon; lithium hydroxide monohydrate; In acetonitrile; at 50℃; for 24h; General procedure: Nitrobenzene (0.6mmol), 5wt% Pd/C (0.5mmol %, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99%).
83% General procedure: The nitro compound (1 equiv), HFIP (10 equiv), Fe powder (5 equiv) were mixed in a tube. Then 2 N HCl aqueous solutions was added to the reaction mixture. After stirring at room temperature for 30 min, the reaction mixture was neutralized with sat. NaHCO3 (aq.) and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was then purified by column chromatography on silica gel to furnish the desired amine product.
75% With tetrahydroxydiborane; copper (II) acetate; In acetonitrile; at 80℃; for 24h;Schlenk technique; General procedure: A 20 mL Schlenk tube was charged with 8-nitroquinoline (1k; 87 mg, 0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4(135 mg, 1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 80 C for 24 h, then cooled to room temperature and concentrated under reduced pressure. Similar workup to 2a gave a brown solid (4a: 63 mg, 87% yield).
65% With tetrahydroxydiborane; lithium hydroxide monohydrate; at 80℃; for 8h; General procedure: Nitro aromatic (1.0 mmol), B2(OH)4 (5.0 equiv, 5.0 mmol), and H2O (3.0 mL) were added in a10 mL tube. The reaction mixture was stirred at 80 C for 8 h. When the reaction was completemonitored by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate (3 ×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography.
46% With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 24h; INTERMEDIATE 1 Synthesis of 6-Amino-quinoline A suspension of 6-nitro-quinoline (8.7 g, 5 mmol), palladium on charcoal (10 %) (0.1 g) in methanol (0.2 L) was hydrogenated at room temperature for 24 with stirring. The catalyst was filtered and the solvent evaporated to yield a yellow solid. Crystallisation from ethyl acetate yielded the pure title compound as a pale yellow solid (3.3 g, 46 %). MS m/z: 145 [[M+H+]. IH] NMR (270 MHz, [CHC13-D)] [8] ppm 3.89 (s, 2 H) 6.87 (d, [J=2.] 64 Hz, 1 H) 7.14 [(DD,] [J=8.] 97,2. 64 Hz, 1 H) 7.25 [(DD,] [J=8.] 44,4. 22 Hz, [1] H) 7. [88 (DD, J=7.] 92,1. [58] Hz, 1 H) 7.90 (d, [J=8.] 97 Hz, 1 H) 8.63 [(DD,] [J=4.] 22,1. [58] Hz, 1 H).
98%Chromat. With hydrazine hydrate monohydrate; In ethanol; at 70℃; for 1h;Schlenk technique; Sealed tube;Catalytic behavior; General procedure: Pd cNPs/CFe3O4 (20mg, 0.73mol% of Pd), aromatic nitro compounds (1mmol),N2H4.H2O (3mmol), and EtOH (3mL) were taken in a schlenk tube with a teflon stopcock, sealed and heated at 70C for a given time with constant stirring. After the completion of reaction, the catalyst was separated by an external magnet and reaction mixture was decanted. The solvent was evaporated and the residue was subjected to GC analysis (retention time of nitroaromatic compounds was used as internal standard) followed by column chromatography for further purification. The purified compounds were characterized by 1H NMR spectroscopy using CDCl3 as solvent and TMS as internal standard. The spectral details and spectra are given in supporting information section (Fig. S4a-S4l).
With hydrogen; In methanol; at 120℃; under 11251.1 Torr; for 3h; General procedure: Typically, 0.5 mmol of nitrobenzene, 20 mg of Co-NSPC-X catalyst and 5 mL of methanol were added into a 30 mL stainless steel autoclave, and the autoclave was pressurized to 1.5 MPa. Then the reactor was placed into oil bath and heated to 120 C with vigorous stirring. After 2 h, the autoclave cooled down to room temperature and the hydrogen gas was carefully released. After the catalysts were removed by filtration, the remaining liquid mixture was analyzed on GC 9890 equipped with a DB-1701 column and a flame ionization detector (FID).

References: [1]Synthesis,2006,p. 3316 - 3340.
[2]Patent: EP2634177,2013,A1 .Location in patent: Paragraph 0269; 0270.
[3]Angewandte Chemie - International Edition,2012,vol. 51,p. 10190 - 10193.
[4]Journal of Organic Chemistry,2013,vol. 78,p. 4530 - 4542.
[5]Chemistry - A European Journal,2014,vol. 20,p. 16732 - 16737.
[6]Journal of the American Chemical Society,2017,vol. 139,p. 17089 - 17097.
[7]Patent: CN111099986,2020,A .Location in patent: Paragraph 0034; 0309-0312.
[8]Advanced Synthesis and Catalysis,2020,vol. 362,p. 4119 - 4129.
[9]Organic Process Research and Development,2021,vol. 25,p. 2100 - 2109.
[10]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 2515 - 2518.
[11]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 631 - 638.
[12]Organic Letters,2017,vol. 19,p. 6518 - 6521.
[13]Organic Letters,2014,vol. 16,p. 98 - 101.
[14]ChemSusChem,2019.
[15]Tetrahedron Letters,1990,vol. 31,p. 1181 - 1182.
[16]Tetrahedron Letters,1993,vol. 34,p. 7445 - 7446.
[17]Tetrahedron Letters,1985,vol. 26,p. 6233 - 6234.
[18]Tetrahedron Letters,2015,vol. 56,p. 3913 - 3915.
[19]Catalysis science and technology,2016,vol. 6,p. 152 - 160.
[20]Journal of Organic Chemistry,2022,vol. 87,p. 910 - 919.
[21]Tetrahedron Letters,2005,vol. 46,p. 3987 - 3990.
[22]Catalysis science and technology,2015,vol. 5,p. 286 - 295.
[23]Green Chemistry,2019,vol. 21,p. 614 - 626.
[24]Catalysis Communications,2017,vol. 99,p. 57 - 60.
[25]Chemical Communications,2012,vol. 48,p. 7982 - 7984.
[26]RSC Advances,2014,vol. 4,p. 22567 - 22574.
[27]ChemSusChem,2019,vol. 12,p. 3178 - 3184.
[28]Journal of Chemistry,2020,vol. 2020.
[29]Catalysis Letters,2014,vol. 144,p. 439 - 446.
[30]New Journal of Chemistry,2015,vol. 39,p. 5360 - 5365.
[31]Organic Letters,2016,vol. 18,p. 2774 - 2776.
[32]Applied Organometallic Chemistry,2020.
[33]Chemical Science,2020,vol. 11,p. 4332 - 4339.
[34]Patent: CN106800493,2020,B .Location in patent: Paragraph 0193-0196; 0245-0248; 0285-0288.
[35]Advanced Synthesis and Catalysis,2011,vol. 353,p. 281 - 286.
[36]Advanced Synthesis and Catalysis,2012,vol. 354,p. 321 - 327.
[37]Heterocycles,1990,vol. 31,p. 2201 - 2204.
[38]Catalysis Communications,2016,vol. 84,p. 25 - 29.
[39]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 816 - 818.
[40]Journal of Chemical Research - Part S,2000,p. 290 - 291.
[41]Journal of Organic Chemistry,2008,vol. 73,p. 6867 - 6870.
[42]Tetrahedron,2017,vol. 73,p. 3898 - 3904.
[43]Tetrahedron Letters,2017,vol. 58,p. 3646 - 3649.
[44]Synlett,1998,p. 1028 - 1028.
[45]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 955 - 977.
[46]Tetrahedron Letters,1990,vol. 31,p. 4065 - 4066.
[47]ChemCatChem,2019,vol. 11,p. 4189 - 4195.
[48]Tetrahedron,2018,vol. 74,p. 2121 - 2129.
[49]Russian Journal of General Chemistry,2000,vol. 70,p. 298 - 303.
[50]Organic Letters,2019,vol. 21,p. 3764 - 3768.
[51]Dalton Transactions,2016,vol. 45,p. 7421 - 7426.
[52]Synlett,2018,vol. 29,p. 1765 - 1768.
[53]Patent: WO2004/828,2003,A1 .
[54]Justus Liebigs Annalen der Chemie,1940,vol. 544,p. 280,284.
[55]Chemische Berichte,1883,vol. 16,p. 673.
[56]Journal fur praktische Chemie (Leipzig 1954),1896,vol. &lt;2&gt; 53,p. 112.
[57]Proceedings of the Royal Society of London. Series B, Biological sciences,1917,vol. 93,p. 335,348.
    Chemisches Zentralblatt,1922,vol. 93,p. 742.
[58]Justus Liebigs Annalen der Chemie,1940,vol. 544,p. 280,284.
[59]Justus Liebigs Annalen der Chemie,1940,vol. 544,p. 280,284.
[60]Journal of Organic Chemistry,1953,vol. 18,p. 1317,1326.
[61]Journal of Organic Chemistry,1953,vol. 18,p. 1317,1326.
[62]Justus Liebigs Annalen der Chemie,1938,vol. 536,p. 89,95.
[63]Journal of the Chemical Society,1956,p. 3087,3090.
[64]Journal of Organic Chemistry,1958,vol. 23,p. 680,683.
[65]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1954,vol. 74,p. 1274.
    Chem.Abstr.,1955,p. 3192.
[66]Tetrahedron,1991,vol. 47,p. 8587 - 8600.
[67]Australian Journal of Chemistry,2005,vol. 58,p. 368 - 374.
[68]Journal of Medicinal Chemistry,2006,vol. 49,p. 7095 - 7107.
[69]Angewandte Chemie - International Edition,2009,vol. 48,p. 9538 - 9541.
[70]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1876 - 1879.
[71]Advanced Synthesis and Catalysis,2011,vol. 353,p. 1306 - 1316.
[72]Arzneimittel-Forschung/Drug Research,2011,vol. 61,p. 373 - 378.
[73]Chemical Communications,2011,vol. 47,p. 10972 - 10974.
[74]RSC Advances,2014,vol. 4,p. 60873 - 60877.
[75]ChemSusChem,2015,vol. 8,p. 3029 - 3035.
[76]ChemSusChem,2014,vol. 7,p. 3122 - 3131.
[77]RSC Advances,2015,vol. 5,p. 102736 - 102740.
[78]Journal of Molecular Catalysis A: Chemical,2016,vol. 423,p. 511 - 519.
[79]RSC Advances,2016,vol. 6,p. 100532 - 100545.
[80]Catalysis science and technology,2018,vol. 8,p. 1454 - 1467.
[81]Green Chemistry,2018,vol. 20,p. 2821 - 2828.
[82]Patent: DE567923,1931,C .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 1105.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 1105.
[83]Patent: DE567923,1931,C .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 1105.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 1105.
[84]Patent: DE567923,1931,C .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 1105.
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 1105.
[85]ChemSusChem,2019,vol. 12,p. 487 - 494.
[86]Organic Letters,2019,vol. 21,p. 3764 - 3768.
[87]Applied Catalysis A: General,2019,vol. 579,p. 99 - 105.
[88]RSC Advances,2020,vol. 10,p. 10689 - 10694.
[89]Analytical Chemistry,2022,vol. 94,p. 1769 - 1777.
[90]ACS Catalysis,2022,p. 5786 - 5794.
 

Historical Records

Categories

Related Functional Groups of
[ 613-50-3 ]

Nitroes

Chemical Structure| 4253-81-0

A194926 [4253-81-0]

2-(2-Nitrophenyl)pyridine

Similarity: 0.86

Chemical Structure| 7557-00-8

A173329 [7557-00-8]

7-Nitroquinazoline

Similarity: 0.84

Chemical Structure| 194032-17-2

A244192 [194032-17-2]

4-Methyl-5-nitroisoquinoline

Similarity: 0.83

Chemical Structure| 607-32-9

A129555 [607-32-9]

5-Nitroisoquinoline

Similarity: 0.81

Chemical Structure| 84531-36-2

A208601 [84531-36-2]

3-Nitro-6,7-dihydro-5H-cyclopenta[b]pyridine

Similarity: 0.79

Related Parent Nucleus of
[ 613-50-3 ]

Quinolines

Chemical Structure| 613-51-4

A722991 [613-51-4]

7-Nitroquinoline

Similarity: 0.75

Chemical Structure| 99185-71-4

A147058 [99185-71-4]

2-Methyl-6-nitroquinolin-4-amine

Similarity: 0.71

Chemical Structure| 607-34-1

A343861 [607-34-1]

5-Nitroquinoline

Similarity: 0.67

Chemical Structure| 607-35-2

A104022 [607-35-2]

8-Nitroquinoline

Similarity: 0.66

Chemical Structure| 100516-88-9

A224626 [100516-88-9]

Quinolin-6-ylmethanol

Similarity: 0.66