[ CAS No. 2423-71-4 ] {[proInfo.proName]}

Name: 2423-71-4|2,6-Dimethyl-4-nitrophenol|98%
Brand: Ambeed
SKU: A213449
Price: 7.0 USD
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2D 3D

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Quality Control of [ 2423-71-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2423-71-4 ]

SDS Specification

Alternatived Products of [ 2423-71-4 ]

Product Details of [ 2423-71-4 ]

CAS No. :	2423-71-4	MDL No. :	MFCD00007339
Formula :	C₈H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FNORUNUDZNWQFF-UHFFFAOYSA-N
M.W :	167.16	Pubchem ID :	17030
Synonyms :

Calculated chemistry of [ 2423-71-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.22
TPSA :	66.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.5
Log Po/w (XLOGP3) :	1.18
Log Po/w (WLOGP) :	1.92
Log Po/w (MLOGP) :	0.94
Log Po/w (SILICOS-IT) :	0.1
Consensus Log Po/w :	1.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.99 mg/ml ; 0.0119 mol/l
Class :	Very soluble
Log S (Ali) :	-2.16
Solubility :	1.15 mg/ml ; 0.00687 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.97
Solubility :	1.79 mg/ml ; 0.0107 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.56

Safety of [ 2423-71-4 ]

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

Application In Synthesis of [ 2423-71-4 ]

* 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 [ 2423-71-4 ]
Downstream synthetic route of [ 2423-71-4 ]

[ 2423-71-4 ] Synthesis Path-Upstream 1~23

1
[ 576-26-1 ]
[ 2423-71-4 ]
[ 4906-22-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With bismuth (III) nitrate pentahydrate In acetone at 20℃; for 20 h;	General procedure: To a solid mixture of phenol (1–3 equiv) and Bi(NO₃)₃5H₂O (1 equiv) or Fe(NO₃)₃9H₂O (1 equiv) was added acetone (10 ml/mmol). The resulting mixture was stirred at room temperature under air or at reflux for 2–24 hours, Tables 1 and 2. When the reaction was completed the insoluble materials were filtered off using a pad of Celite and the residue was washed by acetone (ca. 5 ml/mmol). The filtrate was treated by NaHCO₃ (0.1 g/mmol) until evolution of CO₂ stopped. Insoluble material was filtered off again, and the solvent was removed under vacuum in a water bath 25–35°C. The nitrated products were separated or purified using silica gel chromatography, to give pure phenolic compounds. All products were characterized by 1H NMR,13C NMR and IR and were identified by comparison of the spectral data and melting points with those reported in literature and characterized.

Reference： [1] Synthetic Communications, 2015, vol. 45, # 1, p. 143 - 150

2
[ 576-26-1 ]
[ 2423-71-4 ]

Reference： [1] Journal of Chemical Sciences, 2011, vol. 123, # 1, p. 63 - 67
[2] Chinese Chemical Letters, 2010, vol. 21, # 11, p. 1283 - 1286
[3] Synthetic Communications, 2003, vol. 33, # 5, p. 703 - 710
[4] Synthetic Communications, 2005, vol. 35, # 2, p. 263 - 270
[5] Synthetic Communications, 1986, vol. 16, # 1, p. 63 - 68
[6] Phosphorus, Sulfur and Silicon and the Related Elements, 2003, vol. 178, # 5, p. 1027 - 1035
[7] Journal of Organic Chemistry, 1942, vol. 7, p. 251,257
[8] Chemische Berichte, 1908, vol. 41, p. 2339
[9] Tetrahedron, 1978, vol. 34, p. 3611 - 3615
[10] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 2127 - 2133
[11] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1869 - 1872
[12] Journal of the Society of Chemical Industry, London, 1931, vol. 50, p. 79 T

3
[ 96-22-0 ]
[ 181294-58-6 ]
[ 2423-71-4 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 24, p. 10169 - 10171

4
[ 14150-94-8 ]
[ 96-22-0 ]
[ 2423-71-4 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180

5
[ 576-26-1 ]
[ 2423-71-4 ]
[ 115822-08-7 ]
[ 94045-98-4 ]

Reference： [1] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1869 - 1872

6
[ 4397-14-2 ]
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1] Tetrahedron Letters, 1998, vol. 39, # 16, p. 2261 - 2264

7
[ 576-26-1 ]
[ 108-95-2 ]
[ 13331-93-6 ]
[ 2423-71-4 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 49, p. 14111 - 14122

8
[ 123-75-1 ]
[ 14150-94-8 ]
[ 96-22-0 ]
[ 2423-71-4 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 7, p. 2174 - 2180

9
[ 5384-21-4 ]
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 11, p. 2376 - 2379

10
[ 576-26-1 ]
[ 2423-71-4 ]
[ 527-61-7 ]
[ 94045-98-4 ]

Reference： [1] Canadian Journal of Chemistry, 1984, vol. 62, p. 1446 - 1451

11
[ 94045-98-4 ]
[ 2423-71-4 ]

Reference： [1] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1869 - 1872
[2] Canadian Journal of Chemistry, 1984, vol. 62, p. 1446 - 1451

12
[ 14804-39-8 ]
[ 2423-71-4 ]

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

13
[ 1004-66-6 ]
[ 2423-71-4 ]

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

14
[ 576-26-1 ]
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 1842,1850

15
[ 34461-00-2 ]
[ 96-22-0 ]
[ 2423-71-4 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 1842,1850

16
[ 576-26-1 ]
[ 123871-57-8 ]
[ 2423-71-4 ]
[ 89-64-5 ]
[ 106-48-9 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310

17
[ 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

18
[ 60-29-7 ]
[ 4919-37-3 ]
[ 7782-77-6 ]
[ 2423-71-4 ]

Reference： [1] Comment. phys. math., 1956, vol. 19, # 1, p. 38,40

19
[ 576-26-1 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1] Journal of the Chemical Society, 1931, p. 1842,1850

20
[ 2423-71-4 ]
[ 14804-38-7 ]

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

21
[ 2423-71-4 ]
[ 59557-90-3 ]

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

22
[ 2423-71-4 ]
[ 16947-63-0 ]

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

23
[ 2423-71-4 ]
[ 1736-85-2 ]

Reference： [1] Chemical Communications, 2013, vol. 49, # 21, p. 2151 - 2153
[2] Chemistry of Materials, 2015, vol. 27, # 5, p. 1772 - 1779

[ 2423-71-4 ] Synthesis Path-Downstream 1~88

1
[ 576-26-1 ]
[ 2423-71-4 ]

Reference： [1]Journal of Chemical Sciences,2011,vol. 123,p. 63 - 67
[2]Chinese Chemical Letters,2010,vol. 21,p. 1283 - 1286
[3]Synthetic Communications,2003,vol. 33,p. 703 - 710
[4]Synthetic Communications,2005,vol. 35,p. 263 - 270
[5]Synthetic Communications,1986,vol. 16,p. 63 - 68
[6]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 1027 - 1035
[7]Journal of Organic Chemistry,1942,vol. 7,p. 251,257
[8]Chemische Berichte,1908,vol. 41,p. 2339
[9]Tetrahedron,1978,vol. 34,p. 3611 - 3615
[10]Bulletin of the Chemical Society of Japan,1975,vol. 48,p. 2127 - 2133
[11]Tetrahedron Letters,1988,vol. 29,p. 1869 - 1872
[12]Journal of the Society of Chemical Industry,1931,vol. 50,p. 79 T

2
[ 576-26-1 ]
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1]Journal of the Chemical Society,1931,p. 1842,1850

3
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1]Journal of the Chemical Society,1931,p. 1842,1850
[2]Journal of the Chemical Society,1931,p. 1842,1850
[3]Journal of the Chemical Society,1931,p. 1842,1850
[4]Journal of the Chemical Society,1931,p. 1842,1850

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

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

5
[ 14804-39-8 ]
[ 2423-71-4 ]

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

6
[ 2423-71-4 ]
[ 768-95-6 ]
4-(1-Adamantyloxy)-3.5-dimethylanilin [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1979,vol. 22,p. 69 - 77

7
[ 2423-71-4 ]
[ 100-35-6 ]
[ 38519-16-3 ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 523 - 529

8
[ 2423-71-4 ]
[ 1499-21-4 ]
2,6-Dimethyl-4-nitrophenyl-diphenylphosphinat [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1972,vol. 94,p. 29 - 34

9
[ 123-75-1 ]
[ 14150-94-8 ]
[ 96-22-0 ]
[ 2423-71-4 ]
1,3-dimethyl-5-nitro-2-(1-pyrrolidinyl)benzene [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 2174 - 2180

10
[ 576-26-1 ]
[ 123871-57-8 ]
[ 2423-71-4 ]
[ 89-64-5 ]
[ 106-48-9 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 1299 - 1310

11
[ 576-26-1 ]
[ 2423-71-4 ]
[ 527-61-7 ]
[ 94045-98-4 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1446 - 1451

12
[ 576-26-1 ]
[ 2423-71-4 ]
[ 115822-08-7 ]
[ 94045-98-4 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1869 - 1872

13
[ 1004-66-6 ]
[ 2423-71-4 ]
[ 14804-39-8 ]

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

14
[ 2423-71-4 ]
[ 10486-48-3 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 568 - 574

15
[ 2423-71-4 ]
[ 91734-80-4 ]
[ 91734-80-4 ]
[ 104545-96-2 ]
[ 104545-97-3 ]

Reference： [1]Australian Journal of Chemistry,1985,vol. 38,p. 1693 - 1704
[2]Australian Journal of Chemistry,1985,vol. 38,p. 1693 - 1704

16
[ 5384-21-4 ]
[ 2423-71-4 ]
[ 527-61-7 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 2376 - 2379

17
[ 14150-94-8 ]
[ 96-22-0 ]
[ 2423-71-4 ]
1,3-dimethyl-5-nitro-2-(1-pyrrolidinyl)benzene [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 2174 - 2180

18
[ 94045-98-4 ]
[ 2423-71-4 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 1869 - 1872
[2]Canadian Journal of Chemistry,1984,vol. 62,p. 1446 - 1451

19
[ 2423-71-4 ]
[ 38560-96-2 ]

Reference： [1]Organic Preparations and Procedures International,1997,vol. 29,p. 128 - 131

20
[ 96-22-0 ]
[ 181294-58-6 ]
[ 2423-71-4 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 10169 - 10171

21
[ 23506-89-0 ]
[ 2423-71-4 ]
[ 927267-35-4 ]

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

22
[ 2423-71-4 ]
[ 647-42-7 ]
[ 928790-01-6 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1315 - 1325

23
[ 2423-71-4 ]
[ 34298-00-5 ]
[ 927267-41-2 ]

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

24
[ 108-01-0 ]
[ 2423-71-4 ]
[ 955369-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl (E)-azodicarboxylate; at 20℃; for 16h;	1) Production of 2-(2,6-dimethyl-4-nitrophenoxy)-N,N-dimethylethylamine 3.4 mL of diisopropyl azodicarboxylate was added to 1.9 g of <strong>[2423-71-4]2,6-dimethyl-4-nitrophenol</strong> and 1.71 mL of 2-dimethylaminoethanol, and stirred at room temperature for 16 hours. The reaction liquid was diluted with ethyl acetate, and the organic layer was extracted with 2 N hydrochloric acid. The aqueous layer was made basic with aqueous 2 N sodium hydroxide solution, and then extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure to obtain 667 mg of the entitled compound.

Reference： [1]Patent: US2007/254892,2007,A1 .Location in patent: Page/Page column 35

25
[ 358-23-6 ]
[ 2423-71-4 ]
[ 156740-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -15℃; for 0.25h;	2,6-dimethyl-4-nitro-phenol (4.93 g, 29.5 mmol) was suspended in anhydrous CH2Cl2 (30 mL). Huenig's base (12.4 mL, 70 mmol) was added to give a homogeneous, dark red solution. The reaction mixture was cooled to -15 C. and triflic anhydride (10 g, 35 mmol) was slowly added. The very dark reaction mixture was stirred at -15 C. for 15 minutes, then poured into 3N HCl (100 mL). The layers were separated and the aqueous layer was extracted 1×150 mL CH2Cl2. The combined organic layers were washed 1×50 mL sat. brine, dried over MgSO4, and concentrated to a dark red oil. This oil was filtered through a 2 cm plug of silica gel (eluting with 3:1 hexanes:ethyl acetate) and concentrated to an orange oil which was diluted with 10 mL of hexanes and allowed to stand at room temperature until crystallization of the product took place. The crystals were collected and dried under vacuum. The mother liquor was concentrated, then diluted with 5 mL of CH2Cl2 and 25 mL of hexanes and again allowed to stand until crystallization was complete. The second crop was collected by filtration and dried under vacuum. Combined yield of the two crops was 7.87 g of triflate 80.1. 1H NMR (CDCl3) delta 8.03 (s, 2H); 2.50 (s, 6H).
	With pyridine; In dichloromethane; at 0 - 20℃; for 2h;	Intermediate (82): 1-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole To a 0 C. solution of <strong>[2423-71-4]2,6-dimethyl-4-nitrophenol</strong> (3 g, 17.9 mmol) and pyridine (4.25 g, 53.7 mmol) in dichloromethane (30 mL) was slowly added triflic anhydride (7.6 g, 26.8 mmol). The solution was stirred at room temperature for 2 h. The mixture was concentrated poured into water (50 mL) and extracted with ethyl acetate (50 mL*3). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give crude 2,6-dimethyl-4-nitrophenyl trifluoromethanesulfonate (5.5 g) as a yellow solid.

Reference： [1]Chemical Communications,2013,vol. 49,p. 2151 - 2153
[2]Patent: US2005/250820,2005,A1 .Location in patent: Page/Page column 43-44
[3]Patent: US2012/202834,2012,A1 .Location in patent: Page/Page column 37
[4]Chemistry of Materials,2015,vol. 27,p. 1772 - 1779

26
[ 2423-71-4 ]
[ 927267-42-3 ]

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

27
[ 2423-71-4 ]
[ 927267-36-5 ]

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

28
[ 2423-71-4 ]
N-[3,5-dimethyl-4-(octahydro-quinolizin-1-ylmethoxy)-phenyl]-methanesulfonamide [ No CAS ]

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

29
[ 2423-71-4 ]
N-[3,5-dimethyl-4-(octahydro-quinolizin-1-ylmethoxy)-phenyl]-methanesulfonamide [ No CAS ]

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

30
[ 2423-71-4 ]
[ 928790-04-9 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1315 - 1325

31
[ 2423-71-4 ]
N-[3,5-dimethyl-4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxy)-phenyl]-2-(formyl-methyl-amino)-3-methyl-butyramide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1315 - 1325

32
[ 2423-71-4 ]
[ 928790-11-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 1315 - 1325

33
[ 2423-71-4 ]
6-(4-hydroxy-3-isopropyl-phenoxy)-5,7-dimethyl-quinoline-2-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1240 - 1244

34
[ 2423-71-4 ]
6-(4-hydroxy-3-isopropyl-phenoxy)-5,7-dimethyl-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1240 - 1244

35
[ 2423-71-4 ]
[ 880874-71-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1240 - 1244

36
[ 2423-71-4 ]
[ 880874-67-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1240 - 1244

37
[ 2423-71-4 ]
(E)-2-[4-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-phenylamino]-but-2-enedioic acid diethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1240 - 1244

38
[ 2423-71-4 ]
[ 156740-79-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1240 - 1244

39
[ 2423-71-4 ]
Trifluoro-methanesulfonate10-carboxymethyl-9-(2,6-dimethyl-4-nitro-phenoxycarbonyl)-acridinium; [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 8519 - 8522

40
[ 2423-71-4 ]
Trifluoro-methanesulfonate10-benzyloxycarbonylmethyl-9-(2,6-dimethyl-4-nitro-phenoxycarbonyl)-acridinium; [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 8519 - 8522

41
[ 576-26-1 ]
1,3,3,5,5,7-hexamethyl-(4at,8at)-1,3,4,4a,5,8a-hexahydro-1r,4c-etheno-naphthalene-2,6-dione [ No CAS ]
[ 2423-71-4 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1446 - 1451

42
[ 2423-71-4 ]
C₃₁H₂₆NO⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 568 - 574

43
[ 2423-71-4 ]
[ 14804-38-7 ]