[ CAS No. 14804-39-8 ]

Name: 14804-39-8|2-Methoxy-1,3-dimethyl-5-nitrobenzene|96%
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Quality Control of [ 14804-39-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 14804-39-8 ]

CAS No. :	14804-39-8	MDL No. :	MFCD00024537
Formula :	C₉H₁₁NO₃	Boiling Point :	299.6°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	181.19 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 14804-39-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.69
TPSA :	55.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	2.45
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	2.07
Log Po/w (SILICOS-IT) :	0.59
Consensus Log Po/w :	1.86

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.72
Solubility :	0.348 mg/ml ; 0.00192 mol/l
Class :	Soluble
Log S (Ali) :	-3.25
Solubility :	0.102 mg/ml ; 0.000563 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.68
Solubility :	0.379 mg/ml ; 0.00209 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 14804-39-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14804-39-8 ]

* 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.

Upstream synthesis route of [ 14804-39-8 ]
Downstream synthetic route of [ 14804-39-8 ]

[ 14804-39-8 ] Synthesis Path-Upstream 1~3

1
[ 14804-39-8 ]
[ 2423-71-4 ]

Reference： [1] Journal of the Society of Chemical Industry, London, 1931, vol. 50, p. 79 T

2
[ 1004-66-6 ]
[ 2423-71-4 ]
[ 14804-39-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986, p. 1097 - 1102

3
[ 14804-39-8 ]
[ 14804-38-7 ]

Reference： [1] Journal of Organic Chemistry, 1953, vol. 18, p. 83,87

[ 14804-39-8 ] Synthesis Path-Downstream 1~31

1
[ 1004-66-6 ]
[ 14804-39-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sulfuric acid; nitric acid; acetic acid at 0 - 20℃; for 3h;
68%	With sulfuric acid; nitric acid; acetic acid at 0 - 20℃; for 3h;
65%	With nitric acid; acetic acid at 0 - 65℃;

62%	With nitric acid	3 Synthesis of 2,6-Dimethyl-4-nitroanisole (3) EXAMPLE 3 Synthesis of 2,6-Dimethyl-4-nitroanisole (3) 2,6-Dimethylanisole (2, 36 g, 260 mmol) was added dropwise over 0.5 h to stirred cold cone. nitric acid (200 mL) contained in round-bottom flask; stirring at room temperature was continued for 18 h. The mixture was poured onto crushed ice contained in a 1-L beaker. The resulting bright yellow solid was vacuum-filtered and dried. Recrystallization from ethanol-water gave 2,6-dimethyl-4-nitroanisole (3, 29 g, 62% yield) as a pale yellow solid, mp 90°-91° C. (lit.: Burton, G. W.; Joyce, A.; Ingold, K. U. Arch. Biochem. Biophys., 1982, 221, 281; 89°-91° C.).
61%	With nitric acid; acetic acid In water at 0 - 65℃;	2,6-dimethyl-4-nitroanisole (16a) To an ice-cold, stirred solution of 2,6-dimethylanisole 15 (40.00 g,294 mmol) in glacial acetic acid (60 mL) was added dropwise 70% nitric acid (60 mL). After the addition was complete and gas evolution began to subside, the solution was slowly heated to 65 oC resulting in the formation of a pale yellow solution. [CAUTION: It is essential to keep the reaction temperature below 70 oC at all times as, above this, the mixture on occasions detonated with extreme violence; protection by a blast screen in recommended in any event]. The solution was then allowed to cool to ambient temperature and diluted with water (300 mL). Nitrogen was bubbled through the resulting deep brown solution for ca. 0.5 h to remove most of the nitrogen oxides present. The resulting yellow precipitate was separated by vacuum filtration and washed with copious water then crystallised from ethanol to give the nitroanisole 16a (32.6 g, 61%), mp 91.5-93.5 oC (lit.18 mp89-91 oC); 1H NMR δ 2.28 (s, 6H, 2 x Me), 3.71 (s, 3H, OMe), 7.83 (s, 2H, ArH); 13C NMR δ 16.8 (2x Me), 60.3 (OMe), 124.6 (2 x ArCH), 132.7 (2 x ArC), 143.8 (ArC), 162.8 (ArC); m/z (APCI) 152(M-29, 100%).
	With nitric acid; acetic anhydride
	With tetrachloromethane; Nitrogen dioxide
	With nitric acid; acetic acid at 60 - 70℃;
	(nitration);
	With nitric acid In acetic acid

Reference： [1]Khan, Taukeer A.; Fornefeld, Torsten; Hübner, Dennis; Vana, Philipp; Tietze, Lutz F. [Organic Letters, 2018, vol. 20, # 7, p. 2007 - 2010]
[2]Khan, Taukeer A.; Tietze, Lutz F. [Heterocycles, 2019, vol. 99, # 2, p. 1183 - 1195]
[3]Location in patent: scheme or table Knight, David W.; Qing, Xu [Tetrahedron Letters, 2009, vol. 50, # 26, p. 3534 - 3537]
[4]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - US5674876, 1997, A
[5]Knight, David W.; Xu, Qing [Heterocycles, 2016, vol. 93, # 2, p. 647 - 672]
[6]Bruice et al. [Journal of Organic Chemistry, 1953, vol. 18, p. 83,87]
[7]Horner; Huebenett [Chemische Berichte, 1952, vol. 85, p. 804,817][Justus Liebigs Annalen der Chemie, 1953, vol. 579, p. 193,202]
[8]Baldwin; Robinson [Journal of the Chemical Society, 1934, p. 1264,1266] Rowe; Bannister; Storey [Journal of the Society of Chemical Industry, 1931, vol. 50, p. 79 T]
[9]Degani,J. et al. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 1967, vol. 23, p. 1351 - 1372]
[10]Dix, Leslie R.; Moodie, Roy B. [Journal of the Chemical Society. Perkin transactions II, 1986, p. 1097 - 1102]

2
[ 14804-38-7 ]
[ 14804-39-8 ]

Reference： [1]Journal of Organic Chemistry,1953,vol. 18,p. 83,87

3
[ 14804-39-8 ]
[ 2423-71-4 ]

Reference： [1]Journal of the Society of Chemical Industry,1931,vol. 50,p. 79 T

4
[ 14804-39-8 ]
[ 39785-37-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride; acetic acid; zinc In water; ethyl acetate at 0 - 20℃; for 4h;
98%	In ethanol	4 Synthesis of 4-Amino-2,6-dimethylanisole (4) EXAMPLE 4 Synthesis of 4-Amino-2,6-dimethylanisole (4) 2,6-Dimethyl-4-nitroanisole (3, 29 g, 160 mmol), 10% Pd-C (200 mg) and ethanol (300 mL) were placed in a 500-mL Parr hydrogenation flask and hydrogenated at 50 psi for 24 h. The resulting solution was filtered through a silica gel column using ethyl acetate as eluent. Concentration of the solvent and drying under vacuum gave 23.7 g (98% yield) of 4-amino-2,6-dimethylanisole (4) as a brown-colored solid, mp 59°-60° C. (lit.: Bruice, T. C.; Kharasch, N.; Winzler, R. J. J. Org. Chem. 1953, 18, 83; 63° C.).
97%	With hydrogenchloride; acetic acid; zinc In ethyl acetate at 0 - 20℃; for 4h;

96%	With iron(III) chloride; pyrographite; hydrazine hydrate In methanol Heating;
91%	With palladium 10% on activated carbon; cyclohexene In ethanol at 80℃;
91%	With palladium 10% on activated carbon In ethanol; cyclohexane at 80℃; for 14h;	4-amino-2,6-dimethylanisole (16b) To a suspension of 10% Pd-C (0.65 g) in ethanol (130 mL) at rt was added portion wise the foregoing nitroanisole 16a (10.00 g, 55 mmol) followed by cyclohexene (32 mL, 330 mmol). The mixture was then heated under reflux for 14 h, cooled to rt and filtered through celite. The filter cake was washed with ethanol and the combined filtrates evaporated to leave the sensitive aniline 16b (7.56 g, 91%) as a brown solid which was sufficiently pure for further use and which showed mp 62-63 oC (lit.33 mp 60-61 oC), IR (KBr) 3772, 3612, 3397, 1605, 1487, 1340,1219, 1150, 1016 cm-1; 1H NMR δ 2.24 (s, 6H, 2 x Me), 3.47-3.51 (br s, 2H, NH2), 3.69 (s, 3H, OMe),6.39 (2, 2H, 2 x ArH); 13C NMR δ 16.5 (2 x Me), 60.4 (OMe), 115.7 (2 x ArCH), 131.9 (2 x ArC),142.5 (ArC), 150.0 (ArC); m/z (APCI) 152 (M + 1, 100%).
67%	With hydrogenchloride; tin; acetic acid for 18h;	3,5-Dimethyl-4-methoxyaniline. 2,6-Dimethyl-4-nitroanisole(1.18 g, 6.53 mmol) and tin powder (2.52 g, 21.2 mmol) were stirred in an HCl/AcOH mixture (1.3/13.0 mL).After 18 h, the reaction was diluted with H2O (100 mL) and neutralized with NaHCO3, then extracted into EtOAc (100 mL).The organics were washed with H2O (2x25 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to afford 3,5-dimethyl-4-methoxyaniline as a pale orange solid (657 mg, 67%).1H-NMR (500 MHz, CDCl3)d6.34-6.36 (m, 2H), 3.65 (s, 3H), 3.40 (br s, 2H), 2.20-2.21 (m, 6H);13C-NMR (125 MHz, CDCl3)d149.62, 142.08, 131.45, 115.29, 59.97, 16.07; ESI-MS 152m/z[MH]+, C9H14NO requires 152.
	With diethyl ether; nickel Hydrogenation;
	With ethanol; platinum Hydrogenation;
	With hydrogenchloride; iron
	With hydrazine hydrate
	With hydrogen In ethanol	60.3 6'-Methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline] Step 3: 4-Methoxy-3,5-dimethylaniline To a solution of 2-methoxy-1,3-dimethyl-5-nitrobenzene (12 g) in ethanol in a Parr hydrogenation bottle, was added Pd/C (0.24 g, 10%). The mixture was shaken at 50 psi of H2 in the hydrogenator overnight. The reaction mixture was filtered through Celite and the solvent was removed by evaporation. The crude residue was purified by column chromatography (10% ethyl acetate/hexane), giving 4-methoxy-3,5-dimethylaniline as a light yellow solid (8.2 g). 1H-NMR (300 MHz, CDCl3) δ=6.18 (s, 1H), 3.711 (s, 3H), 2.29 (s, 6H) ppm. MS: m/z 152 (100, M+H)+
	With palladium on activated charcoal; hydrogen In ethanol at 20℃;
	With 5%-palladium/activated carbon; hydrogen In methanol; water at 20℃; for 24h;

Reference： [1]Khan, Taukeer A.; Fornefeld, Torsten; Hübner, Dennis; Vana, Philipp; Tietze, Lutz F. [Organic Letters, 2018, vol. 20, # 7, p. 2007 - 2010]
[2]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - US5674876, 1997, A
[3]Khan, Taukeer A.; Tietze, Lutz F. [Heterocycles, 2019, vol. 99, # 2, p. 1183 - 1195]
[4]Cheemala, Murthy N.; Knochel, Paul [Organic Letters, 2007, vol. 9, # 16, p. 3089 - 3092]
[5]Location in patent: scheme or table Knight, David W.; Qing, Xu [Tetrahedron Letters, 2009, vol. 50, # 26, p. 3534 - 3537]
[6]Knight, David W.; Xu, Qing [Heterocycles, 2016, vol. 93, # 2, p. 647 - 672]
[7]Connelly, Stephen; Mortenson, David E.; Choi, Sungwook; Wilson, Ian A.; Powers, Evan T.; Kelly, Jeffery W.; Johnson, Steven M. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3441 - 3449]
[8]Bruice et al. [Journal of Organic Chemistry, 1953, vol. 18, p. 83,87]
[9]Bielig et al. [Angewandte Chemie, 1953, vol. 65, p. 599]
[10]Baldwin; Robinson [Journal of the Chemical Society, 1934, p. 1264,1266] Rowe; Bannister; Storey [Journal of the Society of Chemical Industry, 1931, vol. 50, p. 79 T]
[11]Baliah,V.; Kanagasabapathy,V.M. [Tetrahedron, 1978, vol. 34, p. 3611 - 3615]
[12]Current Patent Assignee: ELI LILLY & CO - US2006/128790, 2006, A1 Location in patent: Page/Page column 97
[13]Location in patent: scheme or table Ozeki, Minoru; Muroyama, Atsushi; Kajimoto, Tetsuya; Watanabe, Tetsushi; Wakabayashi, Keiji; Node, Manabu [Synlett, 2009, # 11, p. 1781 - 1784]
[14]Yasui, Kosuke; Kamitani, Miharu; Fujimoto, Hayato; Tobisu, Mamoru [Organic Letters, 2021, vol. 23, # 5, p. 1572 - 1576]

5
[ 2423-71-4 ]
[ 77-78-1 ]
[ 14804-39-8 ]

Reference： [1]Journal of Organic Chemistry,1953,vol. 18,p. 83,87

6
[ 1004-66-6 ]
[ 2423-71-4 ]
[ 14804-39-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1986,p. 1097 - 1102

7
[ 2423-71-4 ]
[ 74-88-4 ]
[ 14804-39-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 72h;	2,6-Dimethyl-4-nitrophenol(1.18 g, 7.06 mmol), iodomethane (0.53 mL, 8.51 mmol), and K2CO3(1.18 g, 8.54 mmol) were stirred in DMF (7.0 mL) at room temperature.After 3 days, the reaction was diluted with H2O and the precipitate was filtered, rinsed with H2O, and dried to afford2,6-dimethyl-4-nitroanisoleas a pale yellow powder (1.23 g, 96%).1H-NMR (500 MHz, CDCl3)d7.92 (s, 2H), 3.79 (s, 3H), 2.36 (s, 6H);13C-NMR (125 MHz, CDCl3)d162.41, 143.49, 132.32, 124.25, 59.88, 16.38; ESI-MS 182m/z[MH]+, C9H12NO3requires 182; RP-HPLC: >99% pure.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3441 - 3449
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 2639 - 2646
[3]Synlett,2009,p. 1781 - 1784

8
[ 14804-38-7 ]
[ 14804-39-8 ]
Bis(4-methoxy-3,5-dimethylphenyl)nitroxid [ No CAS ]

Reference： [1]Chemische Berichte,1974,vol. 107,p. 2362 - 2382

9
[ 92100-74-8 ]
[ 14804-39-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With nitric acid; acetic acid In dichloromethane for 0.5h; Ambient temperature;

Reference： [1]Yamato, Takehiko; Kamimura, Hideo; Furukawa, Tsuyoshi [Journal of Organic Chemistry, 1997, vol. 62, # 22, p. 7560 - 7564]

10
[ 14804-39-8 ]
4,4'-Dimethoxy-3,3',5,5'-tetramethylazobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h;

Reference： [1]Sawada, Tsuyoshi; Yamada, Masaki; Thiemann, Thies; Mataka, Shuntaro [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 16, p. 2623 - 2627]

11
[ 14804-39-8 ]
[ 948018-39-1 ]