16947-63-0|2,6-Dimethyl-4-nitroaniline| Ambeed

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Quality Control of [ 16947-63-0 ] Purity: 98% SDS Specification

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Product Details of [ 16947-63-0 ]

CAS No. :	16947-63-0
Formula :	C₈H₁₀N₂O₂
M.W :	166.18
SMILES Code :	CC1=CC(=CC(C)=C1N)[N+]([O-])=O
MDL No. :	MFCD02093072
InChI Key :	NSBSVUUVECHDDX-UHFFFAOYSA-N
Pubchem ID :	28159

Safety of [ 16947-63-0 ]

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

Application In Synthesis of [ 16947-63-0 ]

* 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 [ 16947-63-0 ]

[ 16947-63-0 ] Synthesis Path-Downstream 1~35

1
[ 2423-71-4 ]
[ 16947-63-0 ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 2995,3001.

2
[ 16947-63-0 ]
[ 53906-84-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1956,vol. 75,p. 1137,1138, 1149.
[2]Journal of the American Chemical Society,1940,vol. 62,p. 2995,3001.
[3]Canadian Journal of Chemistry,1988,vol. 66,p. 1454 - 1458.

3
[ 16947-63-0 ]
2,6-dimethyl-4-nitro-phenyl thiocyanate [ No CAS ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1954,vol. 73,p. 819,829.

4
[ 67083-22-1 ]
[ 16947-63-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid; In water; at 40℃;	K43-c(1.9g, 5.9mmol) and water(0.75mL) were added into a round- bottomed flask, concentrated sulfuric acid(10mL) was added thereto, and the mixture was kept under 40 C overnight. The mixture was cooled to room temperature,and crushed ice and 2M aqeous sodium hydroxide solution (15mL) were poured thereto. The mixture was extractedwith ethyl acetate(50mL), and the organic phase obtained was washed with water(20mL) twice, and then with saturatedsaline(20mL) once, dried with anhydrous sodium sulfate and concentrated to to give K43-d as a yellow sold(980mg,yield: 100%), which was directly used in the next step
66%	With sulfuric acid; at 60℃; for 1.0h;	A solution of 3 (23 g, 72 mmol, 1.0 eq) in concentrated H2SO4 (232 mL, c = 0.3) was heated to 60 C with stirring for 1 hour. The reaction was then poured into ice (1000 mL), adjusted to pH 8 with 20% NaOH and extracted with EA (200 mL). The organic phase was washed with brine (15 mL), dried over anhydrous Na2SO4 and filtered to give a residue. The residue after rotary evaporation was purified by column chromatography to give the desired product 4 (8 g, 66% yield).
53%	With sulfuric acid; at 50℃; for 1.0h;	N-Tosyl-2,6-dimethyl-4-nitroaniline (20) (3.2 g, 10.0 mmol) wasdissolved in H2SO4 (32 mL) and warmed at 50 C for 1 h. The reactionmixture was poured slowly into an ice/water mixture. Theprecipitate was filtered and washed with water. The crude productwas purified by recrystallization (ethyl acetate) to give 21 as yellowcrystals (1.0 g, 53%). Rf: 0.34 (n-hexane/ethyl acetate, 5/1, v/v). Mp:164e165 C. 1H NMR (DMSO-d6, 400 MHz) d 7.79 (s, 2H), 6.16 (s,2H), 2.16 (s, 6H). MS (ESI) m/z: 166.8 [MH], 188.8 [MNa].

References: [1]Patent: EP3138833,2017,A1 .Location in patent: Paragraph 0040; 0043.
[2]European Journal of Organic Chemistry,2009,p. 739 - 748.
[3]Journal of Medicinal Chemistry,1983,vol. 26,p. 1625 - 1630.
[4]Heterocycles,2008,vol. 76,p. 1313 - 1328.
[5]Patent: KR2018/69782,2018,A .Location in patent: Paragraph 0422; 0424; 0431-0433.
[6]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1062 - 1080.
[7]European Journal of Medicinal Chemistry,2017,vol. 131,p. 1 - 13.
[8]Recueil des Travaux Chimiques des Pays-Bas,1954,vol. 73,p. 809,815.

5
[ 99841-87-9 ]
[ 16947-63-0 ]

References: [1]Acta Chemica Scandinavica (1947),1957,vol. 11,p. 1350,1354.

6
[ 855227-21-3 ]
[ 16947-63-0 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1954,vol. 73,p. 809,815.

7
[ 16947-63-0 ]
[ 541-41-3 ]
[ 99841-87-9 ]

References: [1]Acta Chemica Scandinavica (1947),1957,vol. 11,p. 1350,1354.

8
[ 16947-63-0 ]
[ 108-24-7 ]
[ 114166-18-6 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1954,vol. 73,p. 809,815.

9
[ 583-06-2 ]
[ 16947-63-0 ]
[ 56428-54-7 ]

References: [1]Patent: US4130661,1978,A .

10
[ 80-58-0 ]
[ 16947-63-0 ]
2-Chloro-N-(2,6-dimethyl-4-nitro-phenyl)-butyramide [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1982,vol. 71,p. 680 - 686.

11
[ 584-93-0 ]
[ 16947-63-0 ]
2-Chloro-pentanoic acid (2,6-dimethyl-4-nitro-phenyl)-amide [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1982,vol. 71,p. 680 - 686.

12
[ 616-05-7 ]
[ 16947-63-0 ]
2-Chloro-hexanoic acid (2,6-dimethyl-4-nitro-phenyl)-amide [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1982,vol. 71,p. 680 - 686.

13
[ 14150-94-8 ]
[ 96-22-0 ]
[ 16947-63-0 ]
[ 68541-85-5 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 1203 - 1206.
[2]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2820 - 2827.

14
[ 16947-63-0 ]
C₈H₈N₃O₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Chemische Berichte,1980,vol. 113,p. 3610 - 3620.

15
[ 16947-63-0 ]
[ 62272-80-4 ]

References: [1]Journal of the American Chemical Society,1984,vol. 106,p. 2758 - 2761.

16
[ 16947-63-0 ]
[ 501-53-1 ]
[ 86955-76-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	In toluene; at 25 - 30℃;Reflux;	Example 4 Synthesis of 3,5-dimethyl-4-carboxybenzylamine-1-nitrobenzene (IV) A solution of benzylchloroformate (1027 gms; 50% solution in toluene) was slowly added to a suspension of <strong>[16947-63-0]2,6-dimethyl-4-nitroaniline</strong> (100 gms) in toluene (1000 ml) at 25 to 30 C. The mixture was refluxed till completion of the reaction. The reaction mixture was cooled at 10-15 C., filtered and dried to give 3,5-dimethyl-4-carboxybenzylamine-1-nitrobenzene (IV). Yield: 160 g % Yield: 88%

References: [1]Patent: US2014/275538,2014,A1 .Location in patent: Paragraph 0052; 0053; 0054.
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 1625 - 1630.

17
[ 294853-97-7 ]
[ 16947-63-0 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 1454 - 1458.

18
[ 16947-63-0 ]
[ 79-04-9 ]
[ 67083-23-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; triethylamine; In dichloromethane; at 0 - 20℃;	To a mixture of 4 (4 g, 24 mmol, 1.0 eq) in DCM (30 mL, c = 0.8) was added pyridine (2.28 g, 28.8 mmol, 1.2 eq) 2-Chloroacetyl chloride (3.25 g, 28.8 mmol, 1.2 eq) was dropped at 0 C, The mixture was stirred at room temperature overnight. The reaction product was then filtered, the filter cake was poured into water, adjusted to pH 4 with 2N HCl, then filtered and the filter cake was dried to give the desired product 5 (4.4 g, 76% yield).
	With pyridine; In benzene;	EXAMPLE 4 Preparation of alpha-chloro-4-nitro-2,6-dimethylacetanilide At room temperature, a solution of 6ml (76mmoles) of chloroacetylchloride in 30ml of seive-dried benzene was added dropwise to a rapidly stirring solution of 12g (72mmoles) of the product of Ex. 3 and 5.8ml (72mmoles) of dry pyridine in 500ml of benzene. A precipitate formed at once. Forty-five min. after the addition was completed, the reaction mixture was chilled, the precipitate collected, washed with water and dried in a vacuum desiccator overnight. Crystallization was achieved by dissolving the product in 2.5 1. of boiling benzene, which, after concentration to ca. 1.5 1. deposited the product (12.73g, 73%) as very long, thin light yellow needles, m.p. 227-228.

References: [1]Journal of Pharmaceutical Sciences,1982,vol. 71,p. 680 - 686.
[2]Patent: KR2018/69782,2018,A .Location in patent: Paragraph 0422; 0424; 0434-0436.
[3]Patent: US4069105,1978,A .

19
[ 7623-09-8 ]
[ 16947-63-0 ]
2-Chloro-N-(2,6-dimethyl-4-nitro-phenyl)-propionamide [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1982,vol. 71,p. 680 - 686.

20
[ 16947-63-0 ]
[ 76-05-1 ]
[ 86955-83-1 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1625 - 1630.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 6 2,6-Dimethyl-4-nitroaniline The nitrated intermediate prepared by the method of Example 5 (100 g, 0.34 mole) was stirred at room temperature in a mixture of 300 ml of sulfuric acid and 30 ml of water for one hour. The reaction mixture was poured into one liter of ice-water and the mixture made basic with ammonium hydroxide, giving the title compound (53 g). Structure assignment of the final product was confirmed by nmr spectroscopy and by elemental analysis. Calcd. for C8 H10 N2 O2: C, 57.82; H, 6.07; N, 16.86. Found: C, 58.10; H, 6.06; N, 16.91.
		EXAMPLE 3 Preparation of 1-amino-2,6-dimethyl-4-nitrobenzene The nitrosulphonamide, (Ex. 2) (31.9g. was suspended in a solution of 100ml of conc. H2 SO4 and 10ml of water and heated in a water bath (~95) and occasionally swirled until all material had dissolved. The resulting dark brown mixture was poured into 300ml of ice water and made basic (pH 12) with concentrated ammonium hydroxide. The resulting yellowish-brown precipitate was collected, washed with water, and crystallized from hot ethanol-water to give 11.3g of fine yellow needles (m.p. 156-160). Concentration of the mother liquor and addition of water gave 2.7g of the product, for a combined yield of 14g (82%). An analytical sample was cyrstallized from chloroform, m.p. 158-159.

23
2.5-dinitro-m-xylene [ No CAS ]
[ 16947-63-0 ]

References: [1]Journal of the Chemical Society,1923,vol. 123,p. 1268.

24
[ 74709-95-8 ]
aqueous-methanolic ammonia [ No CAS ]
[ 16947-63-0 ]

References: [1]Journal of the Chemical Society,1923,vol. 123,p. 1268.

25
[ 632300-21-1 ]
[ 16947-63-0 ]

References: [1]Journal of Chemical Research, Miniprint,2003,p. 701 - 714.

26
[ 16947-63-0 ]
2-azido-1,3-dimethyl-5-nitrobenzene [ No CAS ]

References: [1]Helvetica Chimica Acta,2005,vol. 88,p. 1589 - 1609.

27
[ 16947-63-0 ]
(1S,9aR)-(octahydro-2H-quinolizin-1-yl)ethanoyl chloride [ No CAS ]
[ 927267-30-9 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 334 - 343.

28
[ 16947-63-0 ]
[ 99-63-8 ]
N,N'-bis(2,6-dimethyl-4-nitro-phenyl)-isophthalamide [ No CAS ]