4,4'-Methylenebis(2,6-dimethylaniline) supplier

Name
4,4'-Methylenebis(2,6-dimethylaniline)
EINECS 223-786-9
CAS No. 4073-98-7
Article Data12
CAS DataBase
Density 1.066 g/cm³
Solubility 27.02mg/L at 20℃
Melting Point 121-123 °C(lit.)
Formula C₁₇H₂₂N₂
Boiling Point 424.9 °C at 760 mmHg
Molecular Weight 254.375
Flash Point 252.5 °C
Transport Information
Appearance Off white powder
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms 2,6-Xylidine,4,4'-methylenedi- (8CI);3,3',5,5'-Tetramethyl-4,4'-diaminodiphenylmethane;4,4'-Methylenebis(2,6-dimethylaniline);4,4'-Methylenebis(2,6-xylidine);4,4'-Methylenedi-2,6-xylidine;Kayabond C 200;Kayabond C 200S;
PSA 52.04000
LogP 4.83780

Synthetic route

: 5293-94-7
bis(chloromethyl)mercury

: 87-62-7
2,6-dimethylaniline

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 20h;	99%

: 50-00-0
formaldehyd

: 87-62-7
2,6-dimethylaniline

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
With hydrogenchloride In water at 95 - 100℃; for 6.16667h;	87%
Stage #1: formaldehyd; 2,6-dimethylaniline With hydrogenchloride In water at 70℃; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 2h; Stage #3: With sodium hydroxide In diethyl ether; water	86%
hydrogenchloride In water for 14h; Heating;	60%
With hydrogenchloride Entsteht in Form seines salzsauren Salzes;
With hydrogenchloride at 65 - 70℃; for 6h; Condensation;

: 71893-15-7
C4H7ClHgO

A: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

B: 67-64-1
acetone

Conditions

Conditions	Yield
With 2,6-dimethylaniline at 20℃; for 30h;	A 74% B 86%

: 71893-15-7
C4H7ClHgO

: 87-62-7
2,6-dimethylaniline

A: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

B: 67-64-1
acetone

Conditions

Conditions	Yield
at 20℃; for 0.5h;	A 74% B 860 %

...Expand

: 288-13-1
NH-pyrazole

: 50-00-0
formaldehyd

: 87-62-7
2,6-dimethylaniline

A: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

B: 125709-82-2
1-(N-2,6-dimethylaniline)-1-(1N-pyrazol)-methane

Conditions

Conditions	Yield
In water; benzene for 14h; Heating;	A 30% B 60%

...Expand

: 67129-08-2
Metazachlor

A: 288-13-1
NH-pyrazole

B: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
hydrogenchloride In water for 8h; Heating;	A 59% B 35%

: 67-68-5
dimethyl sulfoxide

: 87-62-7
2,6-dimethylaniline

A: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

B: 120578-20-3
4-amino-3,5-dimethylphenyl methyl sulphide

Conditions

Conditions	Yield
With ammonium iodide In water at 140℃; for 16h; Reagent/catalyst; Sealed tube; regioselective reaction;	A 52% B 42%

...Expand

: 67-68-5
dimethyl sulfoxide

: 87-62-7
2,6-dimethylaniline

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
With ammonium iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water at 140℃; for 16h; Mechanism; Sealed tube; regioselective reaction;	48%

: 67129-08-2
Metazachlor

A: 288-13-1
NH-pyrazole

B: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

C: 1131-01-7
2-chloro-N-(2,6-dimethylphenyl)acetamide

Conditions

Conditions	Yield
hydrogenchloride In water for 5h; Product distribution; Mechanism; Heating; variation of catalyst concentration, reaction time;	A 47% B 21% C 12%

...Expand

: 110-88-3
1,3,5-Trioxan

: 87-62-7
2,6-dimethylaniline

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
With ammonium iodide In water at 140℃; for 16h; Mechanism; Sealed tube; regioselective reaction;	21%

: 415686-54-3
bis-(4-formylamino-3,5-dimethyl-phenyl)-methane

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
With calcium hydroxide; sodium hydroxide

: 7647-01-0
hydrogenchloride

: 50-00-0
formaldehyd

: 87-62-7
2,6-dimethylaniline

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

...Expand

: 87-62-7
2,6-dimethylaniline

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid / 250 °C / 2206520 Torr 2: sodium hydroxide; calcium hydroxide View Scheme

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 90-02-8
salicylaldehyde

: 685509-02-8
[(HOC6H4-o-C(H)=N-2,6-(CH3)2C6H2)2-4-CH2]

Conditions

Conditions	Yield
toluene-4-sulfonic acid In methanol for 12h; Heating / reflux;	95%

: 24623-65-2
3-tert-butyl-2-hydroxybenzaldehyde

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 937721-13-6
[(HO-(3-tert-butyl)C6H3-o-C(H)=N-2,6-(methyl)2C6H2)2-4-CH2]

Conditions

Conditions	Yield
toluene-4-sulfonic acid In methanol for 12h; Heating / reflux;	95%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 1236010-37-9
1,1'-{methylenebis[(3,5-dimethyl-1,4-phenylene)iminomethyl]}bis(2-naphthol)

Conditions

Conditions	Yield
With formic acid In methanol Reflux;	95%

: 24424-99-5
di-tert-butyl dicarbonate

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 1472-83-9
2,2',6,6'-Tetramethyl-4,4'-methylendiphenylisocyanat

Conditions

Conditions	Yield
With dmap In acetonitrile at 25℃; for 0.166667h;	93%

: 37942-07-7
3,5-di-tert-butyl-2-hydroxybenzaldehyde

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 6,6'-{methylenebis[(3,5-dimethyl-1,4-phenylene)iminomethyl]}-bis(2,4-di-tert-butylphenol)

Conditions

Conditions	Yield
With formic acid In methanol Reflux;	93%
In methanol

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 870284-63-2
deuterated 4,4'-methylene-di-2,6-xylidine

Conditions

Conditions	Yield
With water-d2; 1 % platinum on carbon; 1% Pd/C Selcat Q6 at 180℃; for 24h; Product distribution / selectivity;	93%
With water-d2; platinum on carbon at 180℃; for 24h; Product distribution / selectivity;	82%
With water-d2; platinum on carbon; palladium 10% on activated carbon at 180℃; for 24h; Product distribution / selectivity;	63%

: 24623-65-2
3-tert-butyl-2-hydroxybenzaldehyde

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 6,6'-{methylenebis[(3,5-dimethyl-1,4-phenylene)iminomethyl]}-bis(2-tert-butylphenol)

Conditions

Conditions	Yield
With formic acid In methanol Reflux;	93%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 376368-24-0
5-dodecyloxy-2-hydroxyterephthaldehyde

polymer; monomers: 5-dodecyloxy-2-hydroxyterephthaldehyde; bis(4-amino-3,5-dimethylphenyl)methane: polymer; monomers: 5-dodecyloxy-2-hydroxyterephthaldehyde; bis(4-amino-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With lithium chloride In 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 24h;	92%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 90-02-8
salicylaldehyde

: 2,2'-{methylenebis[(3,5-dimethyl-1,4-phenylene)iminomethyl]}-diphenol

Conditions

Conditions	Yield
With formic acid In methanol Reflux;	91%
In methanol at 20℃; for 0.0833333h;	45.4%

: 1129-30-2
2,6-Diacetylpyridine

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: C35H36N4O2

Conditions

Conditions	Yield
In ethanol at 20℃; for 96h;	91%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 108-24-7
acetic anhydride

: 125709-83-3
4,4'-methylenebis-(N-acetyl-2,6-dimethylbenzenamine)

Conditions

Conditions	Yield
In benzene for 2h; Heating;	85%

: 5470-96-2
quinoline 2-carbaldehyde

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 849661-11-6
C37H32N4

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	82%

: 124-38-9
carbon dioxide

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 1472-83-9
2,2',6,6'-Tetramethyl-4,4'-methylendiphenylisocyanat

Conditions

Conditions	Yield
With tributylphosphine; di-isopropyl azodicarboxylate In dichloromethane at -78 - 20℃; under 760 Torr;	81%

: 1121-60-4
pyridine-2-carbaldehyde

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 4,4'-methylene-N,N'-(2-pyridinylmethylene)-bis(2,6-dimethylanil)

Conditions

Conditions	Yield
In methanol at 20℃; for 24h;	81%
With toluene-4-sulfonic acid In ethanol at 20℃; for 48h;	63.3%
formic acid In ethanol at 45℃;	18%

: 1121-60-4
pyridine-2-carbaldehyde

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 500697-36-9
CH2(C6H2(CH3)2NCHC5H4N)2

Conditions

Conditions	Yield
Stage #1: 4,4'-methylenebis(2,6-dimethylaniline) In methanol for 0.0833333h; Molecular sieve 3Å; Stage #2: pyridine-2-carbaldehyde In methanol at 20℃; for 24h;	81%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 134296-07-4
6-formyl-2,2'-bipyridine

: bis{((6-pyridin-2-yl)pyridin-2-ylmethyleneamino)-3,5-dimethylphenyl}methane

Conditions

Conditions	Yield
formic acid In ethanol for 24h; Heating / reflux;	71%

: 91-02-1
phenyl(pyridin-2-yl)methanone

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 4,4'-methylene-N,N'-(phenyl-2-pyridinylmethlene)-bis(2,6-dimethyl-anil)

Conditions

Conditions	Yield
With tetraethoxy orthosilicate; sulfuric acid at 150℃; for 10h;	65%

: C22H15NO

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: C61H48N4

Conditions

Conditions	Yield
Stage #1: 4,4'-methylenebis(2,6-dimethylaniline) With 1,4-diaza-bicyclo[2.2.2]octane; titanium tetrachloride In toluene for 2h; Stage #2: C22H15NO In toluene at 140℃; for 36h;	63%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 82-86-0
acenaphthene quinone

: C46H46N4

Conditions

Conditions	Yield
sulfuric acid Heating;	62%

: 950-81-2
4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 1296869-07-2
CH2[C6H2(CH3)2NCHC3N2(CH3)2(C6H5)O]2

Conditions

Conditions	Yield
With formic acid In methanol for 4h; Reflux; Inert atmosphere;	46.3%

: 4073-98-7
4,4'-methylenebis(2,6-dimethylaniline)

: 53566-95-3
4,4'-diformyltriphenylamine

polyazomethine, by polycondensation, Tg(DSC) = 196 deg C; monomer(s): 4,4'-diformyltriphenylamine, bis(4-amino-3,5-dimethylphenyl)methane: polyazomethine, by polycondensation, Tg(DSC) = 196 deg C; monomer(s): 4,4'-diformyltriphenylamine, bis(4-amino-3,5-dimethylphenyl)methane

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; toluene-4-sulfonic acid at 160℃; for 6h;	40%

4,4'-Methylenebis(2,6-dimethylaniline) Specification

The Benzenamine,4,4'-methylenebis[2,6-dimethyl-, with CAS registry number 4073-98-7, belongs to the following product categories: (1)Industrial/Fine Chemicals; (2)Amines; (3)Miscellaneous; (4)Amine Monomers; (5)Monomers; (6)Primary Amines. It has the systematic name of 4,4'-methanediylbis(2,6-dimethylaniline). What's more, its EINECS is 223-786-9.

Physical properties of Benzenamine,4,4'-methylenebis[2,6-dimethyl-: (1)ACD/LogP: 3.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.35; (4)ACD/LogD (pH 7.4): 3.48; (5)ACD/BCF (pH 5.5): 191.87; (6)ACD/BCF (pH 7.4): 260.24; (7)ACD/KOC (pH 5.5): 1372.8; (8)ACD/KOC (pH 7.4): 1862.01; (9)#H bond acceptors: 2; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 6.48 Å²; (13)Index of Refraction: 1.615; (14)Molar Refractivity: 83.33 cm³; (15)Molar Volume: 238.4 cm³; (16)Polarizability: 33.03×10^-24cm³; (17)Surface Tension: 45.8 dyne/cm; (18)Density: 1.066 g/cm³; (19)Flash Point: 252.5 °C; (20)Enthalpy of Vaporization: 67.95 kJ/mol; (21)Boiling Point: 424.9 °C at 760 mmHg; (22)Vapour Pressure: 1.99E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,6-dimethyl-aniline and formaldehyde. This reaction will need reagent hydrochloric acid.

When you are using this chemical, please be cautious about it as the following:
The Benzenamine,4,4'-methylenebis[2,6-dimethyl- irritates to eyes, respiratory system and skin. And this chemical is harmful by inhalation, in contact with skin and if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Nc1c(cc(cc1C)Cc2cc(c(N)c(c2)C)C)C
(2)InChI: InChI=1/C17H22N2/c1-10-5-14(6-11(2)16(10)18)9-15-7-12(3)17(19)13(4)8-15/h5-8H,9,18-19H2,1-4H3
(3)InChIKey: OMHOXRVODFQGCA-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C17H22N2/c1-10-5-14(6-11(2)16(10)18)9-15-7-12(3)17(19)13(4)8-15/h5-8H,9,18-19H2,1-4H3
(5)Std. InChIKey: OMHOXRVODFQGCA-UHFFFAOYSA-N

Product Name

4,4'-Methylenebis(2,6-dimethylaniline)

Synthetic route

4,4'-Methylenebis(2,6-dimethylaniline) Specification

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