6665-97-0|1,3-Dimethoxy-2-nitrobenzene| Ambeed

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Quality Control of [ 6665-97-0 ] Purity: 98% SDS Specification

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Product Details of [ 6665-97-0 ]

CAS No. :	6665-97-0
Formula :	C₈H₉NO₄
M.W :	183.16
SMILES Code :	O=[N+](C1=C(OC)C=CC=C1OC)[O-]
MDL No. :	MFCD00474587
Boiling Point :	No data available
InChI Key :	MVBXGGHFJZBKFJ-UHFFFAOYSA-N
Pubchem ID :	324784

Safety of [ 6665-97-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 6665-97-0 ]

* 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 [ 6665-97-0 ]

[ 6665-97-0 ] Synthesis Path-Downstream 1~35

1
[ 6665-97-0 ]
[ 1150-40-9 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 4006.
[2]Recueil des Travaux Chimiques des Pays-Bas,1919,vol. 38,p. 108.

2
[ 6665-97-0 ]
[ 3114-61-2 ]

References: [1]Patent: US2385282,1942,A .

3
[ 6665-97-0 ]
[ 18523-14-3 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1919,vol. 38,p. 108.
[2]Chemische Berichte,1907,vol. 40,p. 4006.

4
[ 6665-97-0 ]
[ 2734-70-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron(0); glacial acetic acid; In ethanol; water monomer; at 90℃;	To a solution of 78 (170 mg, 0.93 mmol) in AcOH (5 mL), EtOH (5 mL) and H2O (2.5 mL) was added iron powder (311 mg, 325 mesh, 5.57 mmol) portion wise. The mixture was then heated at 90 C. under N2 overnight. After cooling to room temperature, the mixture was poured onto ice, basified using solid Na2CO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 79 as a pale yellow solid (139 mg, 98%). MS (APCD): m/z 154 (100%, [M+H]+) which was used in the next step without further purification.
80%	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 - 30℃; under 7500.75 Torr;Autoclave;	In a 150-ml autoclave, 2,6-dimethoxynitrobenzene (10 g, 55 mmol) was added in that order,30ml absolute ethanol,0.2 g of 10% Pd / C catalyst,Into high purity hydrogen to 1.0MPa,Reaction at room temperature.When the hydrogen pressure gauge is not falling as the end of the reaction.Filtration, the filtrate spin dry,A white solid 6.7g, 80% yield.
60%	With hydrogenchloride; dichloro-λ2-stannane dihydrate; In diethyl ether; at 20℃; for 30.0h;	To conc. hydrochloric acid (15 mL) was added dihydrated tin chloride (69.6 g, 308 mmol) at rt. In another flask, compound 50 (5.6 g, 30.6 mmol) was solubilized in ethyl ether (60 mL). The resulting mixture was added by small portions to dissolved tin chloride in hydrochloric acid. The reaction was run to completion over 12 hours at rt. The mixture was then poured into cold water and basified to pH = 9 with aqueous sodium hydroxide and stirred at rt for 3 hours. The final suspension was filtered on Celite. After dilution of the filtrate with ethyl acetate and washing with water, the organic layer was dried over MgSO4 and concentrated under reduced pressure. The off-white solid obtained 51 (2.81 g, 60%) presented the same physico-chemical properties as the commercial product. TLC Rf (EtOAc) = 0.83; 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.81 (s, 2H, NH2), 3.86 (s, 6H, 2OCH3), 6.53 (d, J = 8.2 Hz, 2H, ArH), 6.69 (t, J = 8.2 Hz, 1H, ArH).

With iron(0); glacial acetic acid; In ethanol; water monomer; at 90℃;Inert atmosphere;

2,6-Dimethoxy-phenylamine (79): To a solution of 78 (170 mg, 0.93 mmol) in AcOH (5 mL), EtOH (5 mL) and H2O (2.5 mL) was added iron powder (311 mg, 325 mesh, 5.57 mmol) portion wise. The mixture was then heated at 90 C. under N2 overnight. After cooling to room temperature, the mixture was poured onto ice, basified using solid Na2CO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 79 as a pale yellow solid (139 mg, 98%). MS (APCI): m/z 154 (100%, [M+H]+) which was used in the next step without further purification.

References: [1]Patent: US2007/179164,2007,A1 .Location in patent: Page/Page column 56.
[2]Organic Letters,2011,vol. 13,p. 4320 - 4323.
[3]Chemistry - A European Journal,2018,vol. 24,p. 14933 - 14937.
[4]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2929 - 2934.
[5]Patent: CN107286036,2017,A .Location in patent: Paragraph 0088; 0089.
[6]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6042 - 6054.
[7]Journal of the American Chemical Society,1933,vol. 55,p. 4225,4227.
[8]Scientific Papers of the Institute of Physical and Chemical Research (Japan),1939,vol. 35,p. 365,369.
Chemisches Zentralblatt,1939,vol. 110,p. 4188.
[9]Journal of the American Chemical Society,1953,vol. 75,p. 5280,5282.
[10]Acta Chemica Scandinavica (1947),1952,vol. 6,p. 1016,1017.
[11]Justus Liebigs Annalen der Chemie,1910,vol. 372,p. 139.
[12]Patent: US9486455,2016,B2 .Location in patent: Page/Page column 155.
[13]Chemical Communications,2020,vol. 56,p. 10002 - 10005.
[14]Angewandte Chemie - International Edition,2022,vol. 61.
Angew. Chem.,2022,vol. 134.

5
[ 6665-97-0 ]
[ 860687-63-4 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 4006.

6
[ 6665-97-0 ]
1,5-dibromo-2,4-dimethoxy-3-nitrobenzene [ No CAS ]

References: [1]Chemische Berichte,1907,vol. 40,p. 4006.
[2]Monatshefte fur Chemie,1939,vol. 72,p. 373,374, 375.

7
[ 6665-97-0 ]
[ 107-06-2 ]
[ 3114-61-2 ]

References: [1]Journal of Organic Chemistry,1951,vol. 16,p. 586,606.

8
[ 6665-97-0 ]
[ 107-06-2 ]
[ 601-89-8 ]

References: [1]Journal of Organic Chemistry,1951,vol. 16,p. 586,606.

9
[ 601-89-8 ]
[ 77-78-1 ]
[ 3114-61-2 ]
[ 6665-97-0 ]

References: [1]Patent: US2385282,1942,A .

10
[ 601-89-8 ]
[ 77-78-1 ]
[ 6665-97-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In acetone; for 1.0h;Inert atmosphere; Reflux;	To a solution of 2-nitroresorcinol 49 (4.80 g, 30.9 mmol) in acetone (30 mL) was added K2CO3 (21.39 g, 155 mmol) under nitrogen atmosphere. Dimethylsulfate (8.80 mL, 92.8 mmol) was then added and the mixture obtained was heated to reflux for 1 h. After cooling to room temperature, the solvent was removed in vacuo. The solid obtained was washed with triethylamine and water, then filtered and dried (MgSO4) to give pure compound 5055 (5.6 g, 99%) as a white solid; TLC Rf (EtOAc) = 0.73; 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.88 (s, 6H, 2OCH3), 6.63 (d, J = 8.6 Hz, 2H, ArH), 7.33 (t, J = 8.6 Hz, 1H, ArH).

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6042 - 6054.
[2]Tetrahedron Letters,2009,vol. 50,p. 4087 - 4091.
[3]Chemistry - A European Journal,2018,vol. 24,p. 14933 - 14937.
[4]Recueil des Travaux Chimiques des Pays-Bas,1906,vol. 25,p. 17.
[5]Chemische Berichte,1906,vol. 39,p. 2725.
[6]Justus Liebigs Annalen der Chemie,1910,vol. 372,p. 139.
[7]Journal of the American Chemical Society,1933,vol. 55,p. 4225,4227.

11
[ 6665-97-0 ]
[ 2785-97-9 ]
[ 19177-22-1 ]

References: [1]Journal of the American Chemical Society,1964,vol. 86,p. 646 - 650.

12
[ 50-00-0 ]
[ 6665-97-0 ]
[ 7169-00-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1966,vol. 694,p. 98 - 109.

13
[ 50-00-0 ]
[ 6665-97-0 ]
[ 7169-02-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1966,vol. 694,p. 98 - 109.

14
[ 151-10-0 ]
[ 16147-07-2 ]
[ 4920-84-7 ]
[ 6665-97-0 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 1201 - 1208.

15
[ 601-89-8 ]
[ 74-88-4 ]
[ 6665-97-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In acetone; at 60 - 70℃;	MeI (3.0 mL, 48.3 mmol) was added to mixture of 77 (2.50 g, 16.1 mmol) and K2CO3 (4.46 g, 325 mesh, 32.3 mmol) in acetone (250 mL). The reaction mixture was heated to 60-70 C. (bath temperature) over night under N2. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to yield 78 as a yellow solid (2.87 g, 97%) which was used in the next step without further purification.
	With potassium carbonate; In acetone;Heating; Inert atmosphere;	1,3-Dimethoxy-2-nitro-benzene (78) MeI (3.0 mL, 48.3 mmol) was added to mixture of 77 (2.50 g, 16.1 mmol) and K2CO3 (4.46 g, 325 mesh, 32.3 mmol) in acetone (250 mL). The reaction mixture was heated to 6070 C. (bath temperature) over night under N2. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to yield 78 as a yellow solid (2.87 g, 97%) which was used in the next step without further purification.

References: [1]Patent: US2007/179164,2007,A1 .Location in patent: Page/Page column 56.
[2]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2929 - 2934.
[3]Organic Letters,2011,vol. 13,p. 4320 - 4323.
[4]Patent: US9486455,2016,B2 .Location in patent: Page/Page column 155.

16
[ 7446-70-0 ]
[ 6665-97-0 ]
[ 71-43-2 ]
[ 3114-61-2 ]

References: [1]Patent: US2385282,1942,A .

17
[ 151-10-0 ]
[ 4920-84-7 ]
[ 6665-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bismuth (III) nitrate pentahydrate; for 1.5h;Schlenk technique; Ionic liquid; Inert atmosphere; Heating;	General procedure: The ionic liquid (3.5-4.0 mL) was charged into an oven-dried Schlenk tube under a nitrogen atmosphere and Bi(NO3)3·5H2O (1.5 mmol) was added. The respective aromatic compound (1 mmol) was then introduced into the Schlenk tube under a nitrogen atmosphere. The reaction mixture was magnetically stirred, initially at rt for about 10 min followed by stirring in a pre-heated oil bath at 80-85 C, until completion (as monitored by GC-MS). Once the reaction was over, the contents were cooled to rt and extracted with EtOAc-Hexane (2:3 vol/vol), until the final extraction did not show a spot corresponding to the starting material or to the product. The combined organic extracts were washed with 10% NaHCO3 solution, dried with MgSO4, and concentrated to give the crude product. Isomer distributions were determined by GC-MS, and/or by 1H NMR.

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 267 - 275.
[2]Tetrahedron Letters,2012,vol. 53,p. 6782 - 6785,4.

18
[ 6665-97-0 ]
[ 87119-03-7 ]