6683-81-4|2-(tert-Butyl)-4-nitrophenol| Ambeed

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Quality Control of [ 6683-81-4 ] Purity: 95% SDS Specification

COA

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NMR

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Product Details of [ 6683-81-4 ]

CAS No. :	6683-81-4
Formula :	C₁₀H₁₃NO₃
M.W :	195.22
SMILES Code :	OC1=CC=C([N+]([O-])=O)C=C1C(C)(C)C
MDL No. :	MFCD01463425
Boiling Point :	No data available
InChI Key :	WPLSSAJHDAQNCO-UHFFFAOYSA-N
Pubchem ID :	528944

Safety of [ 6683-81-4 ]

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

Computational Chemistry of [ 6683-81-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	56.56
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.99
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	3.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.6
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.	1.56
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	0.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.53
Solubility	0.057 mg/ml ; 0.000292 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.	-4.73
Solubility	0.00367 mg/ml ; 0.0000188 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-2.42
Solubility	0.747 mg/ml ; 0.00383 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	Yes
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.	-4.9 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<2.0
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)	1.79

Application In Synthesis of [ 6683-81-4 ]

* 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.

Downstream synthetic route of [ 6683-81-4 ]

[ 6683-81-4 ] Synthesis Path-Downstream 1~35

1
[ 6683-81-4 ]
[ 1420-07-1 ]

References: [1]Journal of the American Chemical Society,1938,vol. 60,p. 2495.

2
[ 100-02-7 ]
[ 115-11-7 ]
[ 6683-81-4 ]

References: [1]Journal of the American Chemical Society,1938,vol. 60,p. 2495.

3
[ 6683-80-3 ]
[ 6683-81-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1966,vol. 85,p. 457 - 466.

4
[ 110-89-4 ]
[ 50-00-0 ]
[ 6683-81-4 ]
[ 158583-68-7 ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 1553 - 1560.

5
[ 6683-81-4 ]
[ 32750-26-8 ]

Yield	Reaction Conditions	Operation in experiment
96 - 100%	With Iodine monochloride; In methanol; water; for 2.16667h;	Part B. Preparation of 2-tert-butyl-6-iodo-4-nitrophenol.; To the product from Part A (4.5g, 23.05mmol) dissolved in MeOH (120ml) and water (3OmL) was added iodine monochloride (1.155ml, 23.05mmol) drop wise over a period of lOmin. The mixture was stirred for 2h and diluted into IL of water and allowed to stand overnight. The solid material was collected by filtration and washed 3x50mL with water and dried under vacuum overnight to give a tan solid (7.14g, 96%).; Part B. Preparation of 2-bromo-6-tert-butyl-4-nitrophenol.; A solution of the product from Part A (1.Og, 5.12mmol) in glacial acetic acid (10.25mL) was <n="172"/>treated portion wise with pyridine hydrobromide perbromide (1.8Og, 5.63mmol) followed by stirring at room temperature for 2h. Additional pyridinium hydrobromide perbromide (3.8Og) was added in two portions and after another 3h of stirring, the reaction was complete. The mixture was poured into ice water, and the mixture treated with a small amount of sodium sulfite. The resulting solid was filtered and dried under vacuum to give the title compound as a brown solid (1.4Og, 100 %).
96%	With Iodine monochloride; In methanol; water;	[00457] Part B. Preparation of 2-tert-butyl-6-iodo-4-nitrophenol.; [00458] To the product from Part A (4.5g, 23.05mmol) dissolved in MeOH (120ml) and water (3OmL) was added iodine monochloride (1.155ml, 23.05mmol) drop wise over a period of lOmin. The mixture was stirred for 2h and diluted into IL of water and allowed to stand overnight. The solid material was collected by filtration and washed 3x50mL with water and dried under vacuum overnight to give a tan solid (7.14g, 96%).; [00519] Example 2B. Preparation of N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-l(2H)-yl)-2- methoxyphenyl)naphthalen-2-yl)methanesulfonamide (compound IB-LO-2.3).; [00520] Part A. Preparation of 2-tert-butyl-6-iodo-4-nitrophenol.; [00521] To the product from Example 1, Part E (4.5g, 23.05mmol) dissolved in MeOH (120ml) and water (3OmL) was added iodine monochloride (1.155ml, 23.05mmol) drop wise over a period of lOmin.The mixture was stirred for 2h and diluted into IL of water and allowed to stand overnight. The solid material was collected by filtration and washed 3 x 5OmL with water and dried under vacuum overnight to give a tan solid (7.14g, 96%).
96%	With Iodine monochloride; In methanol; water; for 2.16667h;	Part B. Preparation of 2-tert-butyl-6-iodo-4-nitrophenol.; [00477] To the product from Part A (4.5g, 23.05mmol) dissolved in MeOH (120ml) and water (3OmL) was added iodine monochloride (1.155ml, 23.05mmol) drop wise over a period of lOmin. The mixture was stirred for 2h and diluted into IL of water and allowed to stand overnight. The solid material was collected by filtration and washed 3x50mL with water and dried under vacuum overnight to give a tan solid (7.14g, 96%).

References: [1]Patent: WO2009/39127,2009,A1 .Location in patent: Page/Page column 164; 170-171; 173; 179; 226.
[2]Patent: WO2009/39134,2009,A1 .Location in patent: Page/Page column 98; 108.
[3]Patent: WO2009/39135,2009,A1 .Location in patent: Page/Page column 100.
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 1153 - 1163.
[5]Justus Liebigs Annalen der Chemie,1971,vol. 746,p. 134 - 148.

6
[ 50-00-0 ]
[ 6683-81-4 ]
[ 124-40-3 ]
2-tert-Butyl-6-dimethylaminomethyl-4-nitro-phenol [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 1859 - 1868.

8
[ 50-00-0 ]
[ 6683-81-4 ]
[ 108-00-9 ]
N,N-bis[methyl-(2-hydroxy-3-tert-butyl-5-nitrophenyl)]-N',N'-dimethylethylenediamine [ No CAS ]

References: [1]Dalton Transactions,2003,p. 3082 - 3087.
[2]Macromolecules,2012,vol. 45,p. 5387 - 5396.

9
[ 6683-81-4 ]
2-tert-Butyl-6-(2-methylamino-naphthalen-1-ylmethyl)-4-nitro-phenol [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1995,vol. 50,p. 1859 - 1868.

10
[ 6683-81-4 ]
[ 158583-73-4 ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 1553 - 1560.

11
[ 6683-81-4 ]
2-t-butyl-4-(7'-chloroquinolin-4'-ylamino)-6-(piperidin-1''-ylmethyl)phenol [ No CAS ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 1553 - 1560.

12
[ 6683-81-4 ]
2-t-butyl-6-(piperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinolin-4''-ylamino)phenol [ No CAS ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 1553 - 1560.

13
[ 6683-78-9 ]
[ 6683-81-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1966,vol. 85,p. 457 - 466.

14
[ 6683-79-0 ]
[ 6683-81-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1966,vol. 85,p. 457 - 466.

15
[ 59255-98-0 ]
[ 6683-81-4 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1966,vol. 85,p. 457 - 466.

16
[ 88-18-6 ]
[ 6683-81-4 ]

Yield	Reaction Conditions	Operation in experiment
35.6%	With nitric acid; In n-heptane; water; for 2h;	Part A. Preparation of 2-tert-butyl-4-nitrophenol.; To a vigorously stirred solution of 2-tert-butylphenol (1Og, 66.6mmol) in heptane (67ml) was added at a fast drip a solution of 70% nitric acid (4.25ml, 66.6mmol) diluted with water (4.25ml). The resulting dark red/brown mixture was stirred vigorously for 2h. The suspended solid was collected by filtration washed with hexane (30OmL), water (20OmL) and once again with hexane (20OmL) to give a cocoa colored powder that was dried to constant mass (4.65g, 35.6%).
35.6%	With nitric acid; In n-heptane; water; for 2h;	[00454] Example A. Preparation of (E)-N-(3-tert-butyl-5-iodo-4-methoxyphenylcarbamoyl)-3-methoxy acrylamide.; [00455] Part A. Preparation of 2-tert-butyl-4-nitrophenol.; [00456] To a vigorously stirred solution of 2-tert-butylphenol (1Og, 66.6mmol) in heptane (67ml) was added at a fast drip a solution of 70% nitric acid (4.25ml, 66.6mmol) diluted with water (4.25ml). The resulting dark red/brown mixture was stirred vigorously for 2h. The suspended solid was collected by filtration washed with hexane (30OmL), water (20OmL) and once again with hexane (20OmL) to give a cocoa colored powder that was dried to constant mass (4.65g, 35.6%).; [00496] Part E. Preparation of 2-tert-butyl-4-nitrophenol.; [00497]To a vigorously stirred solution of 2-tert-butylphenol (1Og, 66.6mmol) in heptane (67ml) was added at a fast drip a solution of 70% nitric acid (4.25ml, 66.6mmol) diluted with water (4.25ml). The resulting dark red/brown mixture was stirred vigorously for 2h. The suspended solid was collected by filtration washed with hexane (30OmL), water (20OmL) and once again with hexane (20OmL) to give a <n="106"/>cocoa colored powder that was dried to constant mass (4.65g, 35.6%).
35.6%	With nitric acid; In n-heptane; water; for 2h;	Part A. Preparation of 2-tert-butyl-4-nitrophenol.; [00475] To a vigorously stirred solution of 2-tert-butylphenol (1Og, 66.6mmol) in heptane (67ml) was added at a fast drip a solution of 70% nitric acid (4.25ml, 66.6mmol) diluted with water (4.25ml). The resulting dark red/brown mixture was stirred vigorously for 2h. The suspended solid was collected by filtration washed with hexane (30OmL), water (20OmL) and once again with hexane (20OmL) to give a cocoa colored powder that was dried to constant mass (4.65g, 35.6%).; Part C. Preparation of 2-tert-butyl-4-nitrophenol.; [00593] To a vigorously stirred solution of 2-tert-butylphenol (1Og, 66.6mmol) in heptane (67ml) was added at a fast drip a solution of 70% nitric acid (4.25ml, 66.6mmol) diluted with water (4.25ml). The resulting dark red/brown mixture was stirred vigorously for 2h. The suspended solid was collected by filtration washed with hexane (30OmL), water (20OmL) and once again with hexane (20OmL) to give a cocoa colored powder that was dried to constant mass (4.65g, 35.6%).

References: [1]Patent: WO2009/39127,2009,A1 .Location in patent: Page/Page column 164; 170; 175-176; 226.
[2]Patent: WO2009/39134,2009,A1 .Location in patent: Page/Page column 98; 104-105.
[3]Patent: WO2009/39135,2009,A1 .Location in patent: Page/Page column 100; 119.
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 1153 - 1163.

17
[ 6683-81-4 ]
[ 20294-59-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridinium hydrobromide perbromide; acetic acid; at 20℃; for 5h;	Part F. Preparation of 2-bromo-6-tert-butyl-4-nitrophenol.; [00756] A solution of the product from Part E (l.Og, 5.12mmol) in glacial acetic acid (10.25mL) was treated portion wise with pyridine hydrobromide perbromide (1.8Og, 5.63mmol) followed by stirring at room temperature for 2h. Additional pyridinium hydrobromide perbromide (3.6g) was added in two portions and after another 3h of stirring, the reaction was complete. The mixture was poured into ice water, and the mixture treated with a small amount of sodium sulfite. The resulting solid was filtered and dried under vacuum to give the title compound as a brown solid (1.4Og, 100 %).
100%	With pyridinium perbromide hydrobromide; acetic acid; at 20℃; for 5h;	[00498] Part F. Preparation of 2-bromo-6-tert-butyl-4-nitrophenol.; [00499] A solution of the product from Part E (l.Og, 5.12mmol) in glacial acetic acid (10.25mL) was treated portion wise with pyridine hydrobromide perbromide (1.8Og, 5.63mmol) followed by stirring at room temperature for 2h. Additional pyridinium hydrobromide perbromide (3.6g) was added in two portions and after another 3h of stirring, the reaction was complete. The mixture was poured into ice water, and the mixture treated with a small amount of sodium sulfite. The resulting solid was filtered and dried under vacuum to give the title compound as a brown solid (1.4Og, 100 %).
100%	With pyridinium hydrobromide perbromide; acetic acid; at 20℃; for 5h;	Part D. Preparation of 2-bromo-6-tert-butyl-4-nitrophenol.; [00595] A solution of the product from Part C (l.Og, 5.12mmol) in glacial acetic acid (10.25mL) was treated portion wise with pyridine hydrobromide perbromide (1.8Og, 5.63mmol) followed by stirring at room temperature for 2h. Additional pyridinium hydrobromide perbromide (3.6g) was added in two portions and after another 3h of stirring, the reaction was complete. The mixture was poured into ice water, and the mixture treated with a small amount of sodium sulfite. The resulting solid was filtered and dried under vacuum to give the title compound as a brown solid (1.4Og, 100 %).

References: [1]Patent: WO2009/39127,2009,A1 .Location in patent: Page/Page column 176.
[2]Patent: WO2009/39134,2009,A1 .Location in patent: Page/Page column 105.
[3]Patent: WO2009/39135,2009,A1 .Location in patent: Page/Page column 119.

18
[ 88-18-6 ]
[ 6683-81-4 ]
[ 18515-04-3 ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 2538 - 2548.

19
[ 50-00-0 ]
[ 6683-81-4 ]
[ 4730-54-5 ]
1,4,7-tris(3-tert-butyl-2-hydroxy-5-nitrobenzyl)-1,4,7-triazacyclononane [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 2538 - 2548.

20
[ 50-00-0 ]
[ 6683-81-4 ]
[ 142-25-6 ]
[ 1570188-74-7 ]

References: [1]Organometallics,2014,vol. 33,p. 1112 - 1119.

21
[ 6683-81-4 ]
[ 1570188-80-5 ]

References: [1]Organometallics,2014,vol. 33,p. 1112 - 1119.

22
[ 6683-81-4 ]
[ 1570188-89-4 ]

References: [1]Organometallics,2014,vol. 33,p. 1112 - 1119.

23
[ 6683-81-4 ]
C₂₂H₂₉N₃O₆ [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.

24
[ 6683-81-4 ]
C₃₃H₄₂N₄O₉ [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.
[2]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.

25
[ 6683-81-4 ]
C₃₃H₃₉N₄O₁₀V [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.
[2]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.

26
[ 6683-81-4 ]
[ 100-97-0 ]
C₂₃H₂₉N₃O₆ [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.

27
[ 50-00-0 ]
[ 6683-81-4 ]
2-(bromomethyl)-6-(tert-butyl)-4-nitrophenol [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 15616 - 15619.

28
[ 6683-81-4 ]
[ 77-78-1 ]
[ 15353-20-5 ]