[ CAS No. 14318-66-2 ] {[proInfo.proName]}

Name: 14318-66-2|3-Methoxy-N-methylaniline|98%
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SKU: A579742
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3d Animation Molecule Structure of 14318-66-2

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Quality Control of [ 14318-66-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 14318-66-2 ]

SDS Specification

Alternatived Products of [ 14318-66-2 ]

Product Details of [ 14318-66-2 ]

CAS No. :	14318-66-2	MDL No. :	MFCD05665953
Formula :	C₈H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZFMZSZMUFWRAOG-UHFFFAOYSA-N
M.W :	137.18	Pubchem ID :	84349
Synonyms :

Calculated chemistry of [ 14318-66-2 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.24
TPSA :	21.26 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) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	1.46
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.58

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 :	1.64 mg/ml ; 0.012 mol/l
Class :	Very soluble
Log S (Ali) :	-1.51
Solubility :	4.21 mg/ml ; 0.0307 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.93
Solubility :	0.16 mg/ml ; 0.00116 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 14318-66-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P272-P280-P301+P312+P330-P302+P352-P305+P351+P338-P333+P313-P337+P313-P501	UN#:	N/A
Hazard Statements:	H302-H317-H320	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14318-66-2 ]

* 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 [ 14318-66-2 ]

[ 14318-66-2 ] Synthesis Path-Downstream 1~18

1
[ 15799-79-8 ]
[ 14318-66-2 ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: A round-bottom flask was chargedwith N,N-dialkyl aniline dissolved in toluene solution, under N2 condition. TBHP was added drop wise and reaction was stirred for 2 min. Triethylamine was added thereafter, and then the contents of the reaction were stirred for 3 h at 110 C under inert N2 condition. The reaction mixture was washed 2-3 times with H2O and ethyl acetate. The upper organic layer was separated and dried over sodium sulphate and then subjected to rotavapour. The crude mixture was purified by column chromatography on silica gel (60-120).

Reference： [1]Journal of Chemical Sciences,2016,vol. 128,p. 1469 - 1473
[2]Tetrahedron Letters,1982,vol. 23,p. 1553 - 1556
[3]Tetrahedron Letters,1982,vol. 23,p. 1553 - 1556

2
[ 141-82-2 ]
[ 14318-66-2 ]
[ 74798-86-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 225 - 229
[2]Liebigs Annalen der Chemie,1990,p. 531 - 539

3
[ 14318-66-2 ]
[ 105-53-3 ]
[ 74798-86-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 225 - 229

4
[ 14318-66-2 ]
[ 248282-13-5 ]
4-hydroxy-5-methoxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid (3-methoxy-phenyl)-methyl-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In toluene for 6h; Heating;

Reference： [1]Jönsson, Stig; Andersson, Gunnar; Fex, Tomas; Fristedt, Tomas; Hedlund, Gunnar; Jansson, Karl; Abramo, Lisbeth; Fritzson, Ingela; Pekarski, Olga; Runström, Anna; Sandin, Helena; Thuvesson, Ingela; Björk, Anders [Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088]

5
[ 14318-66-2 ]
[ 7699-21-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / NaHCO₃ / CH₂Cl₂; H₂O / Ambient temperature 2: 6 percent / NaHCO₃ / acetonitrile; H₂O / Irradiation

Reference： [1]Hamada; Okuno; Ohmori; et al. [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 1, p. 128 - 136]

6
[ 13061-96-6 ]
[ 536-90-3 ]
[ 15799-79-8 ]
[ 14318-66-2 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 1677 - 1680

7
[ 121-39-1 ]
[ 14318-66-2 ]
C₁₉H₂₃NO₄ [ No CAS ]
C₁₉H₂₃NO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2464 - 2467

8
[ 62005-48-5 ]
[ 14318-66-2 ]
N-(2-((3-methoxyphenyl)(methyl)amino)ethyl)acetamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 704 - 707
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 7902 - 7916

9
[ 55854-46-1 ]
[ 14318-66-2 ]
[ 1396244-97-5 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a solution of 3-methoxy-/V-methylaniline (137 mg, 1 mmol) in CH2CI2 (3 ml) was added NaOH 50% (1 ml) under stirring followed by tetrabutyl ammonium hydrogen sulphate (51 mg, 0.15 mmol). After few minutes, 5-bromothiophene-2-sulfonyl chloride (262 mg, 1 mmol) was added to the reaction mixture. The solution was stirred at rt for 5 h, then water (10 ml) was added to quench the reaction followed by ethyl acetate (10 ml). The aqueous layer was extracted twice with ethyl acetate. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The product was purified on silica gel (/7-hexane/ethyl acetate 8 : 2) and afforded the desired compound as yellowish oil (277 mg, 77%); IR (cm 1) : 3101, 2938, 2835, 1734, 1602, 1354; *H NMR (CD3COCD3) : 3.27 (s, 3H), 3.77 (s, 3H), 6.78 - 6.81 (m, 2H), 6.90 - 6.92 (m, 1 H), 7.26 - 7.30 (m, 2H), 7.31 (d, J = 4.1 Hz, 1 H); 13C NMR (CD3COCD3) : 38.7, 55.8, 113.5, 114.2, 119.3, 120.1, 130.5, 132.2, 134.3, 138.9, 143.2, 161.0.
77%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; at 20℃; for 5h;	To a stirred solution of 3-methoxy-N-methylaniline (137mg, 1mmol) in CH2Cl2 (3mL) was added NaOH 50% (1mL) followed by n-tetrabutyl ammonium hydrogen sulfate (51mg, 0.15mmol). After few minutes, 5-bromothiophene-2-sulfonyl chloride (262mg, 1mmol) was added to the reaction mixture. The solution was stirred at room temperature for 5h. Water (10mL) was added to quench the reaction followed by EtOAc (10mL). The aqueous layer was extracted twice with EtOAc (2×15mL). The organic layer was dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The product was purified on silica gel (hexanes/EtOAc 8:2) to afford the desired compound as yellow oil (277mg, 77%). IR (neat): 3101, 2938, 2835, 1734, 1602, 1354cm-1. 1H NMR (CD3COCD3) delta 3.27 (s, 3H), 3.77 (s, 3H), 6.78-6.81 (m, 2H), 6.90-6.92 (m, 1H), 7.26-7.30 (m, 2H), 7.31 (d, J=4.1Hz, 1H); 13C NMR (CD3COCD3) delta 38.7, 55.8, 113.5, 114.2, 119.3, 120.1, 130.5, 132.2, 134.3, 138.9, 143.2, 161.0; LC-MS (ESI): 361.07, 362.90 [M+H]+.

Reference： [1]Patent: WO2012/117097,2012,A1 .Location in patent: Page/Page column 74
[2]European Journal of Medicinal Chemistry,2014,vol. 83,p. 317 - 337

10
[ 124-38-9 ]
[ 14318-66-2 ]
[ 15799-79-8 ]
[ 14924-70-0 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2127 - 2131

11
[ 64-18-6 ]
[ 14318-66-2 ]
[ 15799-79-8 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7879 - 7883

12
[ 64-18-6 ]
[ 536-90-3 ]
[ 15799-79-8 ]
[ 14318-66-2 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 14033 - 14036

13
[ 124-38-9 ]
[ 14318-66-2 ]
[ 15799-79-8 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 12186 - 12190
Angew. Chem.,2014,vol. 126,p. 12382 - 12386,5

14
[ 89539-54-8 ]
[ 14318-66-2 ]
C₂₁H₂₁NO₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6444 - 6454

15
[ 89539-54-8 ]
[ 14318-66-2 ]
5-hydroxy-2-(((3-methoxyphenyl)(methyl)amino)methyl)-4H-pyran-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6444 - 6454

16
[ 139-45-7 ]
[ 14318-66-2 ]
3-methoxy-N-methyl-N-propylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tris(2,4-pentanedionato)ruthenium(III); hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 130℃; for 18h; Autoclave;

Reference： [1]Adam, Rosa; Cabrero-Antonino, Jose R.; Junge, Kathrin; Jackstell, Ralf; Beller, Matthias [Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11049 - 11053][Angew. Chem., 2016, vol. 128, # 37, p. 11215 - 11219,5]

17
[ 538-23-8 ]
[ 14318-66-2 ]
3-methoxy-N-methyl-N-octylaniline [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11049 - 11053
Angew. Chem.,2016,vol. 128,p. 11215 - 11219,5

18
[ 14318-66-2 ]
[ 92221-89-1 ]
N-(3-methoxyphenyl)-N-methyl-[1,2,4]triazol[4,3-a]quinazolin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: <1,2,4>triazolo<4,3-a>quinazolin-5-one With sodium (S)-2-((S)-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoate; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; Stage #2: 3-methoxy-N-methylaniline In 1-methyl-pyrrolidin-2-one at 20 - 55℃;	9 Example 9. N-(3-methoxyphenyl)-N-methyl-[1,2,4]triazolo[4,3-a]quinazolin-5-amine To a mixture of [1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one (50 mg, 0.269 mmol) and DBU (0.061 mL, 0.403 mmol) in NMP (1 mL) was added BOP (143 mg, 0.322 mmol) at RT. The mixture was stirred for 10 min at RT. Then, 3-methoxy-N-methylaniline (47.9 mg, 0.349 mmol) was added to the mixture at RT, and the stirring was continued for 3h at RT and then overnight at 55 °C. The reaction mixture was purified by prep-LCMS (acidic condition) to afford crude product, which was purified by column chromatography (Si-column, hexane : AcOEt = 100 : 0 - 0 : 100, then MeOH) to afford the desired product: 1 H-NMR (DMSO-d6) δ 9.62 (s, 1H), 8.32 - 8.25 (m, 1H), 7.78 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 7.37 - 7.20 (m, 3H), 6.93 (t, J = 2.3 Hz, 1H), 6.82 (m, 2H), 3.71 (s, 3H), 3.54 (s, 3H). LCMS(m/z) 306.1 [M+H]+.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC; CARNA BIOSCIENCES, INC. - WO2021/130638, 2021, A1 Location in patent: Paragraph 1087

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H201	Explosive; mass explosion hazard
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 14318-66-2 ] {[proInfo.proName]}

Quality Control of [ 14318-66-2 ]

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Calculated chemistry of [ 14318-66-2 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 14318-66-2 ]

[ 14318-66-2 ] Synthesis Path-Downstream 1~18

Precautionary Statements-General

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Physical hazards

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