18542-98-8|4-Fluoro-N,N-dimethyl-3-nitroaniline| Ambeed

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Quality Control of [ 18542-98-8 ] Purity: 97% SDS Specification

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Product Details of [ 18542-98-8 ]

CAS No. :	18542-98-8
Formula :	C₈H₉FN₂O₂
M.W :	184.17
SMILES Code :	O=[N+](C1=CC(N(C)C)=CC=C1F)[O-]
MDL No. :	MFCD25960351
InChI Key :	OMHCRMSZWANSHP-UHFFFAOYSA-N
Pubchem ID :	12454244

Safety of [ 18542-98-8 ]

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

Computational Chemistry of [ 18542-98-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	49.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.06 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.63
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	1.88
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.22
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.	2.18
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	-0.34
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.38
Solubility	0.775 mg/ml ; 0.00421 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.	-2.53
Solubility	0.541 mg/ml ; 0.00294 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-2.17
Solubility	1.25 mg/ml ; 0.00678 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	No
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.	-6.09 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<1.0
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)	2.24

Application In Synthesis of [ 18542-98-8 ]

* 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.

Downstream synthetic route of [ 18542-98-8 ]

[ 18542-98-8 ] Synthesis Path-Downstream 1~20

1
[ 18542-98-8 ]
[ 19127-35-6 ]

References: [1]Journal of the Chemical Society B: Physical Organic,1968,p. 238 - 241.

2
[ 364-76-1 ]
[ 74-88-4 ]
[ 18542-98-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In N,N-dimethyl-d6-formamide; at 80℃; for 10.0h;	To a solution of compound 24 (0.31 g, 2 mmol) and K2CO3 (1.38 g, 10 mmol) in anhydrous N,N-dimethylformamide (DMF) (5 ml) was added CH3I (0.35 g, 2.5 mmol), and the reaction mixture was stirred for 10 h at 80 C. After cooling down the reaction to room temperature was added DCM (50 ml) to the solution, and washed with saturated NaHCO3. The organic layer dried over by MgSO4 and concentrated in vacuo to give the product 25 (0.34 g, 92%). 1H NMR (DMSO-d6, 400 MHz): delta 7.41-7.36 (m, 1H), 7.23-7.21 (m, 1H), 7.12-7.09 (m, 1H), 2.95 (s, 6H). ESI-HRMS: m/z calcd for C8H9FN2O2 [M+H]+ 185.0682 found 185.0749.
	With potassium carbonate; In N,N-dimethyl-formamide; at 5 - 20℃; for 63.0h;	The (4-fluoro-3-nitrophenyl)dimethylamine can be prepared in the following way: 13.27 g (96 mmol) of potassium carbonate are added, at a temperature in the region of 20 C., under an argon atmosphere, to 5 g (32 mmol) of 4-fluoro-3-nitroaniline in solution in 50 cm3 of dimethylformamide, followed, at a temperature in the region of 5 C., by 4.6 cm3 (73.6 mmol) of iodomethane. After stirring for 63 hours at a temperature in the region of 20 C., the reaction mixture is poured into 100 cm3 of water and then extracted with 3 times 100 cm3 of dichloromethane. The organic phases are combined, washed with 3 times 100 cm3 of water, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (2.7 kPa), to give 5.5 g of a residue which is purified by flash chromatography [eluent: ethyl acetate/cyclohexane (2/8 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 2.78 g of (4-fluoro-3-nitrophenyl)dimethylamine are obtained in the form of an orange-red solid; MS-ES+: m/z=185(+)=(M+H) (+)

References: [1]Tetrahedron,2019,vol. 75,p. 4010 - 4016.
[2]Journal of the Chemical Society B: Physical Organic,1968,p. 238 - 241.
[3]Patent: US2007/259910,2007,A1 .Location in patent: Page/Page column 17.

5
[ 18542-98-8 ]
[ 192819-46-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol; at 20 - 25℃; under 3750.38 Torr; for 0.5h;	3.23 g (17.54 mmol) of <strong>[18542-98-8](4-fluoro-3-nitrophenyl)-dimethylamine</strong> are added, at a temperature in the region of 20 C., to a suspension of 0.6 g (5.63 mmol) of 10% palladium-on-charcoal in 100 cm3 of methanol. After hydrogenation for 30 minutes in an autoclave under 5 bar of hydrogen, at a temperature in the, region of 25 C., the reaction mixture is filtered, the catalyst is rinsed with 3 times 10 cm3 of methanol, and the filtrate is then concentrated to dryness under reduced pressure (2.7 kPa), to give 2.7 g of 4-fluoro-N1,N1-dimethylbenzene-1,3-diamine, in the form of a brown oil; MS-EI: m/z=154(+)=(M)(+).
	With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate; for 5.0h;	General procedure: Compound 20 (1.00 g, 5 mmol) underwent hydrogenation in the solution of EtOAc (10 ml) and MeOH (10 ml) at H2 atmosphere for 5 h using Pd/C (0.10 g, 10%) as the catalyst. The reaction was then filtered and the solvent was removed in vacuo to afford the compound 21 (0.81 g, 96%).

References: [1]Patent: US2007/259910,2007,A1 .Location in patent: Page/Page column 17.
[2]Tetrahedron,2019,vol. 75,p. 4010 - 4016.

6
[ 18542-98-8 ]
[ 100-46-9 ]
C₁₅H₁₇N₃O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5652 - 5655.

7
[ 18542-98-8 ]
C₁₅H₁₅N₃O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5652 - 5655.

8
[ 18542-98-8 ]
4-Methoxy-3-nitro-N,N-dimethyl-anilin-N-oxid [ No CAS ]

References: [1]Journal of the Chemical Society B: Physical Organic,1968,p. 238 - 241.

9
[ 18542-98-8 ]
[ 890435-03-7 ]