[ CAS No. 4073-98-7 ]

Name: 4073-98-7|4,4-Methylenebis(2,6-dimethylaniline)|97%
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Quality Control of [ 4073-98-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4073-98-7 ]

SDS Specification

Alternatived Products of [ 4073-98-7 ]

Product Details of [ 4073-98-7 ]

CAS No. :	4073-98-7	MDL No. :	MFCD00058680
Formula :	C₁₇H₂₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OMHOXRVODFQGCA-UHFFFAOYSA-N
M.W :	254.37	Pubchem ID :	77690
Synonyms :

Calculated chemistry of [ 4073-98-7 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.29
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	2.0
Molar Refractivity :	84.57
TPSA :	52.04 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	3.94
Log Po/w (WLOGP) :	3.69
Log Po/w (MLOGP) :	3.7
Log Po/w (SILICOS-IT) :	4.41
Consensus Log Po/w :	3.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.23
Solubility :	0.0148 mg/ml ; 0.0000583 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.73
Solubility :	0.00471 mg/ml ; 0.0000185 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.16
Solubility :	0.000178 mg/ml ; 0.0000007 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.79

Safety of [ 4073-98-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4073-98-7 ]

* 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 [ 4073-98-7 ]
Downstream synthetic route of [ 4073-98-7 ]

[ 4073-98-7 ] Synthesis Path-Upstream 1~14

1
[ 67129-08-2 ]
[ 288-13-1 ]
[ 4073-98-7 ]
[ 1131-01-7 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326

2
[ 50-00-0 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: With hydrogenchloride In water at 70℃; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 2 h; Stage #3: With sodium hydroxide In diethyl ether; water	To a solution of 2,6-dimethylaniline (10.00 g, 0.083 mol) and formaldehyde (4.03 g, 0.054 mol, 0.65 eq. ) was added dilute hydrochloric acid (2.2 ml, 0.1 M). The biphasic solution was stirred at 70 °C overnight. The dark reddish solution was left to cool to ambient temperature and diluted with dichloromethane (15 ml). The minimum amount of concentrated hydrochloric acid (2 ml) was introduced and the solution stirred at room temperature for 2 hours before being filtered. The white salt collected was washed thoroughly with dichloromethane and air-dried. The salt was suspended in diethyl ether (70 ml) and stirred with an aqueous solution of saturated sodium hydroxide until the dissolution of the solid. The aqueous phase was extracted with diethyl ether (2 x 70 ml) and the combined organic phases dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2a as an orange solid (8.97 g, 86percent).

Reference： [1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 4, p. 528 - 535
[2] Patent: WO2005/118605, 2005, A1, . Location in patent: Page/Page column 107
[3] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326
[4] Monatshefte fuer Chemie, 1898, vol. 19, p. 641
[5] Journal of Materials Chemistry, 1999, vol. 9, # 7, p. 1425 - 1429

3
[ 67-68-5 ]
[ 87-62-7 ]
[ 4073-98-7 ]
[ 120578-20-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 38, p. 9742 - 9745

4
[ 5293-94-7 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1420 - 1426

5
[ 71893-15-7 ]
[ 4073-98-7 ]
[ 67-64-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1420 - 1426

6
[ 67129-08-2 ]
[ 288-13-1 ]
[ 4073-98-7 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326

7
[ 67-68-5 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 38, p. 9742 - 9745

8
[ 71893-15-7 ]
[ 87-62-7 ]
[ 4073-98-7 ]
[ 67-64-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1420 - 1426

9
[ 110-88-3 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 38, p. 9742 - 9745

10
[ 288-13-1 ]
[ 50-00-0 ]
[ 87-62-7 ]
[ 4073-98-7 ]
[ 125709-82-2 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326

11
[ 415686-54-3 ]
[ 4073-98-7 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 1154

12
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 1154

13
[ 67129-08-2 ]
[ 288-13-1 ]
[ 4073-98-7 ]
[ 1131-01-7 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326

14
[ 7647-01-0 ]
[ 50-00-0 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1] Monatshefte fuer Chemie, 1898, vol. 19, p. 641

[ 4073-98-7 ] Synthesis Path-Downstream 1~58

1
[ 415686-54-3 ]
[ 4073-98-7 ]

Reference： [1]Journal of the Chemical Society,1949,p. 1154

2
[ 4073-98-7 ]
[ 108-24-7 ]
[ 125709-83-3 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1989,vol. 98,p. 319 - 326
[2]Journal of the Chemical Society,1949,p. 1154

3
[ 4073-98-7 ]
[ 62-53-3 ]
4,4',4''-Triamino-3,5,3',5'-tetramethyl-tritylium [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1898,vol. 19,p. 641

4
[ 50-00-0 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		To a solution of 2,6-dimethylaniline (10.00 g, 0.083 mol) and formaldehyde (4.03 g, 0.054 mol, 0.65 eq. ) was added dilute hydrochloric acid (2.2 ml, 0.1 M). The biphasic solution was stirred at 70 °C overnight. The dark reddish solution was left to cool to ambient temperature and diluted with dichloromethane (15 ml). The minimum amount of concentrated hydrochloric acid (2 ml) was introduced and the solution stirred at room temperature for 2 hours before being filtered. The white salt collected was washed thoroughly with dichloromethane and air-dried. The salt was suspended in diethyl ether (70 ml) and stirred with an aqueous solution of saturated sodium hydroxide until the dissolution of the solid. The aqueous phase was extracted with diethyl ether (2 x 70 ml) and the combined organic phases dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 2a as an orange solid (8.97 g, 86percent).

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 528 - 535
[2]Patent: WO2005/118605,2005,A1 .Location in patent: Page/Page column 107
[3]Bulletin des Societes Chimiques Belges,1989,vol. 98,p. 319 - 326
[4]Monatshefte fur Chemie,1898,vol. 19,p. 641
[5]Journal of Materials Chemistry,1999,vol. 9,p. 1425 - 1429

5
[ 4073-98-7 ]
[ 636-21-5 ]
[ 95-53-4 ]
4,4',4''-triamino-3,5,3',3''-tetramethyl-tritylium; chloride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1936,vol. 58,p. 1427

6
[ 288-13-1 ]
[ 50-00-0 ]
[ 87-62-7 ]
[ 4073-98-7 ]
[ 125709-82-2 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1989,vol. 98,p. 319 - 326

7
[ 71893-15-7 ]
[ 4073-98-7 ]
[ 67-64-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1420 - 1426

8
[ 67129-08-2 ]
[ 288-13-1 ]
[ 4073-98-7 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1989,vol. 98,p. 319 - 326

9
[ 67129-08-2 ]
[ 288-13-1 ]
[ 4073-98-7 ]
[ 1131-01-7 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1989,vol. 98,p. 319 - 326

10
[ 5293-94-7 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1420 - 1426

11
[ 71893-15-7 ]
[ 87-62-7 ]
[ 4073-98-7 ]
[ 67-64-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1420 - 1426

13
[ 124-38-9 ]
[ 4073-98-7 ]
[ 1472-83-9 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 3940 - 3946

14
[ 3739-94-4 ]
[ 4073-98-7 ]
[ 43078-60-0 ]
[(CH₃)2C₅NH₂NHCOC₅NH₃CONHC₆H₂(CH₃)2]2CH₂ [ No CAS ]

Reference： [1]Chemical Communications,1999,p. 2069 - 2070

15
[ 4073-98-7 ]
4,4'-diamino-3,5,3',5'-tetramethyl-2,2'-dinitrodiphenylmethane [ No CAS ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1425 - 1429

16
[ 7647-01-0 ]
[ 50-00-0 ]
[ 87-62-7 ]
[ 4073-98-7 ]

Reference： [1]Monatshefte fur Chemie,1898,vol. 19,p. 641

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE VI A suitable reaction vessel containing 0.55 mol of 40percent aqueous dimethylamine, 1.17 mols of acetic acid, 100 ml of methanol, and 0.55 mol of 37percent aqueous formaldehyde was allowed to warm to room temperature while adding 0.5 mol of 2,6-dimethylaniline. The reaction mixture was then heated, maintained at 67-81° C. for about three hours, cooled, and worked up to provide a crude product which was determined by GC analysis to contain 2,2',6,6'tetramethyl-4,4'-methylenebisaniline and 2,6-dimethyl-4-dimethylaminomethylaniline in an area percent ratio of 1.7/1.0, as well as a small amount of 2,6-dimethyl-4-methoxymethylaniline.
		EXAMPLE 1 In a reaction vessel was placed 2 gms (0.01 mole) of 2,6-dimethylaniline hydrochloride and 30 gms of diethyl carbonate. The stirred mixture was heated to 124° C. at which time 15 ml dimethylsulfoxide was added. The suspension turned to a clear purple solution following which a crystalline precipitate formed. The diethyl carbonate was distilled out under vacuum at 80° C. and then aqueous caustic was added in an amount which made the mixture alkaline. The mixture was then extracted with 40 ml of toluene. The toluene extract was water washed and then the toluene was distilled out leaving a residue. This residue was distilled using a Kugel-rohr distillation set-up. The fraction removed at about 170° C. was crystallized from isporopanol yielding 4,4'-methylenebis-(2,6-dimethylaniline), mp 119-120° C.

18
[ 4073-98-7 ]
[ 87-62-7 ]
2.6-dimethyl-aniline hydrochloride [ No CAS ]
4,4',4''-triamino-3,5,3',5',3'',5''-hexamethyl-tritylium; chloride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1936,vol. 58,p. 1427

19
[ 4073-98-7 ]
[ 376368-24-0 ]
polymer; monomers: 5-dodecyloxy-2-hydroxyterephthaldehyde; bis(4-amino-3,5-dimethylphenyl)methane [ No CAS ]

Reference： [1]Chemistry Letters,2001,p. 916 - 917

20
[ 1121-60-4 ]
[ 4073-98-7 ]
4,4'-methylene-N,N'-(2-pyridinylmethylene)-bis(2,6-dimethylanil) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	formic acid; In ethanol; at 45℃;	To a suspension of 2a (0.50 g, 1.97 mmol) in absolute ethanol (2 ml) was added 2- pyridinecarboxaldehyde (0.56 ml, 5.91 mmol, 3 eq. ) and one drop of formic acid. The mixture was stirred at 45 °C overnight. On cooling to room temperature the suspension was filtered, washed with cold ethanol and dried under reduced pressure to afford 17 as a yellow solid (0.28 g, 18percent). Compound 17: ES mass spectrum, m/z 433 [M+H]+; 1H NMR (CDCl3), delta 2.12 (s, 12H, CH3), 3.77 (s, 2H, CH2), 6.88 (s, 4H, Ar-H), 7.2-7.4 (m, 2H, Py-H), 7.7-7.8 (m, 2H, Py- H), 8.1-8.3 (m, 4H, Py-H, HC=N), 8.6-8.7 (m, 2H, Py-H) ; 13C NMR (CDCl3, 1H gated decoupled), delta 18.4 (s, CH3), 40.9 (s, CH2), 121.2 (s, Ar), 125.2 (s, Ar), 127.0 (s, Ar), 128.7 (s, Ar), 136.7 (s, Ar), 137.1 (s, Ar), 148.3 (s, Ar), 149.6 (s, Ar), 154.6 (s, Ar), 163.4 (s, C=N). In addition, a single crystal X-ray diffraction study of 17 has confirmed the structural type.

Reference： [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 4244 - 4247
[2]Journal of Organometallic Chemistry,2005,vol. 690,p. 1739 - 1749
[3]Patent: WO2005/118605,2005,A1 .Location in patent: Page/Page column 125-126

21
[ 91-02-1 ]
[ 4073-98-7 ]
4,4'-methylene-N,N'-(phenyl-2-pyridinylmethlene)-bis(2,6-dimethyl-anil) [ No CAS ]