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 2 weeks

{[ 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 [ 5683-43-2 ] Purity: 98% 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 Online Technical Q&A

Product Citations

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

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

DOI: 10.1021/acs.joc.1c01431 PubMed ID: 34983185 JOC,2022,87(2):910-919.

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.

Purchased from AmBeed: 607-35-2 ; 578-66-5 ; 613-50-3 ; 100-19-6 ; 579-71-5 ; 3034-94-4 ; 5683-43-2 ; 99-92-3 ; 13534-97-9 ; 5676-60-8 ; 5470-18-8 ; 619-45-4 ; 553-26-4 ; 580-15-4 ; 611-34-7 ; 619-72-7 ; 100-13-0 ; 540-37-4 ; 1849-25-8 ; 4487-59-6 ; 555-16-8 ; 6298-19-7 ; 556-08-1 ; 953-26-4 ; 54060-30-9 ; 62-23-7 ; 607-34-1 ; 3867-18-3 ; 873-74-5 ; 3544-24-9 ; 94-52-0 ; 1520-21-4 ; 5470-34-8 ; 619-50-1 ; 586-39-0 ; 934-22-5 ; 402-54-0 ; 15411-43-5 ; 455-14-1 ; 17763-80-3 ; 3085-54-9 ; 1942-30-9 ; 1694-20-8 ; 6305-66-4 ; 41656-75-1 ; 6393-17-5 ; 4309-66-4

Product Details of [ 5683-43-2 ]

CAS No. :	5683-43-2
Formula :	C₈H₆N₂O₃
M.W :	178.14
SMILES Code :	CC1=NC2=C(O1)C=C(C=C2)[N+]([O-])=O
MDL No. :	MFCD00022848
InChI Key :	DPVZLXWUFYMLBK-UHFFFAOYSA-N
Pubchem ID :	79766

Safety of [ 5683-43-2 ]

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

Calculated chemistry of [ 5683-43-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	47.8
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.85 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.6
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	1.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.04
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.	0.23
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	0.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.64
Solubility	0.404 mg/ml ; 0.00227 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.	-3.13
Solubility	0.134 mg/ml ; 0.00075 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	-2.68
Solubility	0.371 mg/ml ; 0.00208 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.	-5.97 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)	2.56

Application In Synthesis of [ 5683-43-2 ]

* 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 [ 5683-43-2 ]

[ 5683-43-2 ] Synthesis Path-Downstream 1~29

1
[ 5683-43-2 ]
[ 5676-60-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron; ammonium chloride; In methanol; water; at 70℃; for 2.0h;	INTERMEDIATE Bl2-Methyl- 1 ,3-benzoxazol-6-amine To a heated suspension (70 0C) of <strong>[5683-43-2]6-nitro-2-methyl-benzoxazole</strong> (4.00 g, 22.4 mmol) in MeOH (60 mL) was added a solution of ammonium chloride (12.1 g, 0.227 mol) in water (40 mL) followed by iron powder (4.52 g, 80.1 mmol). The mixture was stirred for 2 h at 70 0C and then filtered through Celite and washed with MeOH. The filtrate was concentrated and the residue was partitioned between water and EtOAc. The organic layers were combined and the solvent was removed under reduced pressure to give the title compound. Yield 2.83 g (85%). Analytical HPLC: purity 100% (System A); LRESIMS (ESI+) m/z = 149 (M+H)+.
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16.0h;	2-methylbenzo[d]oxazol-6-amine 2-Methyl-6-nitrobenzoxazole (10.0 g, 56 mmol) and 10% Pd/C (3.4 g) in MeOH (10 mL) were hydrogenated at rt for 16 h. The reaction mixture was filtered through Celite and wash with MeOH (100 mL). The filtrate was concentrated under vacuum to obtained crude 2-methylbenzo[d]oxazol-6-amine (8.4 g), (MS: ESI +ve, 149.07 [M+H]); 1H NMR: (400 MHz, DMSO) delta: 2.47 (s, 3H), 5.24 (s, 2H), 6.56-6.53 (dd, J=2, 1H), 6.70-6.70 (d, J=1.6, 1H), 7.25-7.23 (d, J=8.4, 1H).
	With iron; ammonium chloride; In methanol; water; at 70℃; for 4.0h;	The synthetic route for 1 was outlined in Scheme 1, and the detailed procedures were presented as follows: (a) To a solution of 2-amino-5-nitrophenol (7.70g, 50.0mmol) and pyridine (3.96g, 50.0mmol) in dry xylene (150mL) at 0C was added dropwise acetyl chloride (4.32g, 55.0mmol). The solution was stirred at ambient temperature for 2h. To above solution was added p-toluenesulfonic acid (1.72g, 10.0mmol), the solution was refluxed till no water was discharged. After cooling to room temperature, the solution was washed with water (100mL×3) and a saturated solution of NaCl (50.0mL), respectively. The organic solution was collected and dried over Na2SO4, after evaporation of the solvent, the crude <strong>[5683-43-2]2-methyl-6-nitrobenzoxazole</strong> (pale solid, 8.80g, 95% yield) was obtained for next step without purification. (b) To a solution of 13 <strong>[5683-43-2]2-methyl-6-nitrobenzoxazole</strong> (3.92g, 22.0mmol) in 14 methanol (60.0mL) at 70C was added 15 NH4Cl (11.77g, 220mmol) in 16 H2O (40.0mL) and Fe (4.48g, 80.0mmol). The mixture solution was stirred at 70C for 4h till the starting material disappeared (TLC detection). The mixture solution was cooled to ambient temperature and filtered, the solution was extracted with ethyl acetate (30.0mL×3). The combined organic solution was dried over Na2SO4, after evaporation of the solvent, the crude 17 2-methylbenzoxazol-6-amine (2.77g, 85% yield) was obtained for next step reaction without purification. (c) To a solution of 2-methylbenzoxazol-6-amine (2.66g, 18.0mmol) in methanol (30.0mL) was added 18 formaldehyde (37%, 12mL, 144mmol) and 19 NaBH3CN (2.27g, 36.0mmol). The solution was stirred at ambient temperature for 36h till the starting material disappeared (TLC detection). The solution was poured into H2O (30.0mL), and the mixture solution was extracted with ethyl acetate (30.0mL×3). The combined organic solution was dried over Na2SO4, the solution is concentrated and 20 2-methyl-6-(N, N-dimethylamino) benzoxazole (2.50g, 79% yield) is obtained by flash column chromatography (elute: petroleum ether / ethyl acetate=10 / 1, v/v, Rf =0.11).

References: [1]Patent: WO2009/150144,2009,A1 .Location in patent: Page/Page column 137.
[2]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5082 - 5088.
[3]Journal of the Chemical Society,1928,p. 121.
[4]Journal of the Chemical Society,1930,p. 2685,2687.
[5]Patent: DE724160,1938, .
DRP/DRBP Org.Chem.,.
[6]Journal of general chemistry of the USSR,1960,vol. 30,p. 2640 - 2646.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 2658 - 2664.
[7]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275.
[8]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380.
[9]Tetrahedron Letters,1999,vol. 40,p. 8085 - 8088.
[10]Patent: US2014/274933,2014,A1 .Location in patent: Paragraph 0081; 0082.
[11]Chemical Communications,2015,vol. 51,p. 16312 - 16315.
[12]Journal of Photochemistry and Photobiology A: Chemistry,2018,vol. 361,p. 62 - 66.
[13]Patent: US2326497,1939, .

2
[ 1516-60-5 ]
[ 64-19-7 ]
[ 5683-43-2 ]

References: [1]Journal of the Chemical Society C: Organic,1966,p. 1980 - 1983.

3
[ 5683-43-2 ]
[ 25351-89-7 ]

References: [1]Heterocycles,1988,vol. 27,p. 881 - 884.
[2]Heterocycles,1988,vol. 27,p. 881 - 884.

4
[ 5683-43-2 ]
[ 33884-41-2 ]
3-[(2-Phenyl-benzooxazol-6-ylamino)-methylene]-pentane-2,4-dione [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380.

6
[ 95-21-6 ]
[ 5683-43-2 ]
[ 32046-51-8 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 8659 - 8664.

7
[ 5683-43-2 ]
1-butyl-3-(2-methyl-benzooxazol-6-yl)-urea [ No CAS ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 8085 - 8088.

8
[ 5683-43-2 ]
7-Acetyl-2-methyl-5H-oxazolo[4,5-g]quinolin-8-one [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380.

9
[ 5683-43-2 ]
8-Acetyl-2-methyl-6H-oxazolo[5,4-f]quinolin-9-one [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380.

10
[ 5683-43-2 ]
3-[(2-Methyl-benzooxazol-6-ylamino)-methylene]-pentane-2,4-dione [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380.

11
[ 5683-43-2 ]
2-[1-(2-Methyl-benzooxazol-6-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 371 - 380.

12
[ 5683-43-2 ]
2-Methyl-8-oxo-5,8-dihydro-oxazolo[4,5-g]quinoline-7-carboxylic acid ethyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275.

13
[ 5683-43-2 ]
2-Methyl-9-oxo-6,9-dihydro-oxazolo[5,4-f]quinoline-8-carboxylic acid ethyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275.

14
[ 5683-43-2 ]
2-[(2-Methyl-benzooxazol-6-ylamino)-methylene]-malonic acid diethyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1996,vol. 61,p. 268 - 275.

15
[ 5683-43-2 ]
[ 101278-78-8 ]

References: [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 2640 - 2646.
Zhurnal Obshchei Khimii,1960,vol. 30,p. 2658 - 2664.

16
[ 123-75-1 ]
[ 5683-43-2 ]
[ 4637-24-5 ]
[ 933988-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 100℃; for 16.0h;	Example 11; 2-Phenyl-pyrimidine-5-carboxylic acid r2-(2-pyrrolidin-l-yl-ethyl)-benzooxazol-6-yl1 -amide; Step 1; A solution of <strong>[5683-43-2]2-methyl-6-nitro-benzoxazole</strong> (30 mmol), dimethyl formamide dimethyl acetal (60 mmol) and pyrrolidine (60 mmol) in DMF (45 mL) is stirred at 1000C for 16 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water and brine, dried (Na2SO4) and filtered. The filtrate is concentrated. The residue is washed with cooled EtOAc to afford 6-nitro-2-f 2-pyrrolidin- 1 -yl-vinyl Vbenzooxazole as a solid. 1H NMR (300 MHz, CDCl3): delta 1.80-2.25 (broad, 4H), 3.10-3.80 (broad, 4H), 5.06 (d, H), 7.44 (d, H), 7.96 (d, H), 8.21 (m, 2H).

References: [1]Patent: WO2007/41634,2007,A1 .Location in patent: Page/Page column 39.

17
[ 5683-43-2 ]
[ 110-54-3 ]
[ 7439-89-6 ]
[ 5676-60-8 ]

Yield	Reaction Conditions	Operation in experiment
69 mg (83%)	With sodium carbonate; In dichloromethane; water; acetic acid; ethyl acetate;	A. 2-Methyl-6-aminobenzoxazole (479A) To a solution of <strong>[5683-43-2]2-methyl-6-nitrobenzoxazole</strong> (100 mg, 0.560 mmol) in AcOH (2 mL) was added iron powder (325 mesh, 63.0 mg, 1.12 mmol) at 70 C. in a single portion. After 15 min at 70 C. additional iron powder (325 mesh, 63.0 mg, 1.12 mmol) was added and stirring was continued for 15 min. The mixture was cooled and concentrated under reduced pressure. The resulting residue was taken up into EtOAc and washed with sat. Na2CO3 followed by H2O. The organic layer was dried over MgSO4, concentrated under reduced pressure and purified by flash chromatography on silica gel eluding with a gradient of 0 to 25% EtOAc in CH2Cl2 to yield 69 mg (83%) of compound 479A as a solid. HPLC: 97% at 0.24 min (retention time) (YMC S5 ODS column, 4.6*50 mm Ballistic, 10-90% aqueous methanol over 4 min containing 0.2% H3PO4, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 149.2 [M+H]+.

References: [1]Patent: US2004/77605,2004,A1 .

18
[ 78-39-7 ]
[ 121-88-0 ]
[ 5683-43-2 ]

References: [1]ARKIVOC,2012,vol. 2012,p. 262 - 279.

19
[ 25351-89-7 ]
[ 5683-43-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With Amberlyst-15; In water; at 90℃; for 1.0h;Irradiation;	General procedure: To a mixture of N-acyl or benzoy lderivative (6, 1 mmol) in water (5 mL) was added amberlyst-15 (10%, w/w) and the mixture was irradiated with ultrasound (40 KHz) continuously at 90 C till the completion of the reaction (monitored by TLC) as indicated in Table 4. The solid separated was filtered, washed with diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid obtained was purified by recrystallization (column chromatography in few cases) to afford the desired products 7, 8 or 9.

References: [1]Synthetic Communications,2013,vol. 43,p. 3083 - 3092.

20
[ 5683-43-2 ]
2-bromo-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl) acetamide [ No CAS ]