1,4-Benzenediamine,2,3,5,6-tetramethyl- supplier

Name
2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE
EINECS 221-457-4
CAS No. 3102-87-2
Article Data9
CAS DataBase
Density 1.032 g/cm³
Solubility
Melting Point 150-155 °C(lit.)
Formula C₁₀H₁₆N₂
Boiling Point 310.6 °C at 760 mmHg
Molecular Weight 164.25
Flash Point 167.8 °C
Transport Information
Appearance beige fine crystalline powder
Safety 26-36-22
Risk Codes 36/37/38-40
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms p-Phenylenediamine,2,3,5,6-tetramethyl- (6CI,7CI,8CI);1,4-Diamino-2,3,5,6-tetramethylbenzene;2,3,5,6-Tetramethyl-1,4-benzenediamine;2,3,5,6-Tetramethyl-1,4-phenylenediamine;2,3,5,6-Tetramethyl-p-phenylenediamine;2,3,5,6-Tetramethylphenylenediamine;DAD(H);Diaminodurene;Diaminodurol;Durenediamine;NSC 158251;
PSA 52.04000
LogP 3.24700

Synthetic route

: 5465-13-4
dinitrodurene

: 3102-87-2
tetramethyl-p-phenylenediamine

Conditions

Conditions	Yield
With ethanol; nickel at 60℃; Hydrogenation;
With ethanol; nickel under 110326 Torr; Hydrogenation;
With nickel; hydrazine hydrate In ethanol at 60 - 70℃;

: 13171-61-4
2,3,5,6-tetramethyl-4-amino-1-nitrobenzene

: 3102-87-2
tetramethyl-p-phenylenediamine

Conditions

Conditions	Yield
With ammonium sulfide at 135℃;

eso-dinitro-durol: eso-dinitro-durol

: 3102-87-2
tetramethyl-p-phenylenediamine

Conditions

Conditions	Yield
With acetic acid; zinc

eso-dinitro-durol: eso-dinitro-durol

A: 3102-87-2
tetramethyl-p-phenylenediamine

B: 13171-61-4
2,3,5,6-tetramethyl-4-amino-1-nitrobenzene

Conditions

Conditions	Yield
With ammonium sulfide at 130℃;

: 5465-13-4
dinitrodurene

A: 3102-87-2
tetramethyl-p-phenylenediamine

B tellurium: tellurium

Conditions

Conditions	Yield
With disodium telluride In 1,4-dioxane; water at 50℃; for 7h; twice amount of reducing agent; Yield given;

: 3102-87-2
tetramethyl-p-phenylenediamine

: 81-30-1
1,4,5,8-naphthalenetetracarboxylic dianhydride

: 13821-25-5
2,7-diaminobenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

Conditions

Conditions	Yield
With NH-pyrazole at 110℃; for 17h;	95%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 128-69-8
perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

: 1454647-98-3
2,9-bis-(4-amino-2,3,5,6-tetramethylphenyl)anthra[2,1,9-def;6,5,10-d′e′f ′]diisoquinolin-1,3,8,10-tetraone

Conditions

Conditions	Yield
With NH-pyrazole at 140℃; for 4h;	95%

: 933-00-6
p-methylbenzenesulfenyl chloride

: 3102-87-2
tetramethyl-p-phenylenediamine

: 2,3,5,6-tetramethyl-N,N′-bis(4-methylphenylsulfanyl)cyclohexa-2,5-diene-1,4-diimine

Conditions

Conditions	Yield
With pyridine at 0 - 20℃; for 1h;	95%

: 75-77-4
chloro-trimethyl-silane

: 3102-87-2
tetramethyl-p-phenylenediamine

: N,N'-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-phenylenediamine

Conditions

Conditions	Yield
Stage #1: tetramethyl-p-phenylenediamine With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 16h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h;	91%

: 75-09-2
dichloromethane

: 172481-11-7
trans,mer-[Ti(t-butylimide)Cl2(pyridine)3]

: 3102-87-2
tetramethyl-p-phenylenediamine

: [Ti(pyridine)3Cl2(1,4-NC6Me4NH2)]*0.4CH2Cl2

Conditions

Conditions	Yield
In dichloromethane byproducts: tBuNH2; (Ar); for 2 h at room temp.; evapd., layered with hexane at room temp. from CH2Cl2 soln.;	91%

...Expand

: 3102-87-2
tetramethyl-p-phenylenediamine

: 81-30-1
1,4,5,8-naphthalenetetracarboxylic dianhydride

: N,N'-bis(4-amino-2,3,5,6-tetramethylphenyl)naphthalene-1,4,5,8-dicarboxyimide

Conditions

Conditions	Yield
In N,N-dimethyl acetamide at 135℃; for 12h;	90%
With N,N-dimethyl acetamide at 135℃; for 12h;	90%

: 1121-60-4
pyridine-2-carbaldehyde

: 3102-87-2
tetramethyl-p-phenylenediamine

: 1056633-12-5
N,N'-bis((pyridin-2-yl)methylene)-2,3,5,6-tetramethylbenzene-1,4-diamine

Conditions

Conditions	Yield
With formic acid In ethanol at 20℃;	90%
In ethanol at 70℃;	90%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 4755-77-5
Ethyl oxalyl chloride

: 1326681-00-8
Et2H2Me4Meppba

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Reflux;	90%
In tetrahydrofuran at 0℃; for 1h; Reflux;	90%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 100-52-7
benzaldehyde

: C17H20N2

Conditions

Conditions	Yield
In tetrahydrofuran at 70℃; for 6h; Inert atmosphere; Schlenk technique;	90%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 23801-15-2
(E)-N-(3-(dimethylamino)-2-(naphthalen-1-yl)allylidene)-N-methylmethanaminium perchlorate

: C44H36N4

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	90%

: 3102-87-2
tetramethyl-p-phenylenediamine

: C50H30O8

: C70H58N4O6

Conditions

Conditions	Yield
In N,N-dimethyl acetamide at 20 - 165℃; for 48h; Inert atmosphere;	89%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 7089-34-1
((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate

: C36H32N4

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	87%

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 3102-87-2
tetramethyl-p-phenylenediamine

: C24H24N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	86%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 2-(3,5-dimethylpyridinium-1-yl)-1-dimethylamino-3-(dimethyliminium)prop-1-ene bisperchlorate

: C38H40N6(2+)*2ClO4(1-)

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	86%

: 3102-87-2
tetramethyl-p-phenylenediamine

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

: 1240390-15-1
(Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-18a-dihydronaphthalen-2(3H)-one

Conditions

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

: 3102-87-2
tetramethyl-p-phenylenediamine

: 98-59-9
p-toluenesulfonyl chloride

: 407609-46-5
N,N-ditosyl-2,3,5,6-tetramethyl-1,4-phenylenediamine

Conditions

Conditions	Yield
With triethylamine In diethyl ether	84%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one

: C52H64N6

Conditions

Conditions	Yield
Stage #1: tetramethyl-p-phenylenediamine; 1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one With toluene-4-sulfonic acid In toluene at 80℃; for 12h; Stage #2: In toluene for 120h; Solvent; Time; Reflux; Dean-Stark;	84%

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

: 3102-87-2
tetramethyl-p-phenylenediamine

: N1,N4-bis((6-bromopyridin-2-yl)methyl)-2,3,5,6-tetramethylbenzene-1,4-diamine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 70℃; for 12h; Inert atmosphere;	83.2%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 1,1,5,5-tetramethyl-3-(1-isoquinolinio)-1,5-diazapentadienium bis(perchlorate)

: C42H36N6(2+)*2ClO4(1-)

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	82%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 1,1,5,5-tetramethyl-3-(4-ethylpyridinium)-1,5-diazapentadienium bis(perchlorate)

: C38H40N6(2+)*2ClO4(1-)

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	81%

: 1,1,5,5-tetramethyl-3-(1-quinolinio)-1,5-diazapentadienium bis(perchlorate)

: 3102-87-2
tetramethyl-p-phenylenediamine

: C42H36N6(2+)*2ClO4(1-)

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	80%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 431-03-8
dimethylglyoxal

: 1206533-48-3
C24H34N4

Conditions

Conditions	Yield
With sulfuric acid In benzene for 3h; Inert atmosphere; Reflux;	77%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 1,1,5,5-tetramethyl-3-(1-pyridinio)-1,5-diazapentadienium bis(perchlorate)

: C34H32N6(2+)*2ClO4(1-)

Conditions

Conditions	Yield
With acetic acid In acetonitrile for 15h; Reflux;	77%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 259880-39-2
2,10-bis(1-hexylheptyl)furo[3′,4′:4,5]pyreno-[2,1,10-def:7,8,9-d′e′f ′]diisoquinoline-1,3,5,7,9,11(2H,10H)-hexone

: 1442460-40-3
N,N''-Bis(1-hexylheptyl)-N'-(4-amino-2,3,5,6-tetramethylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexacarboxylic-2,3,8,9-bis-(dicarboximide)-11,12-dicarboximide

Conditions

Conditions	Yield
With quinoline at 160℃; for 12h;	76%

: 75-44-5
phosgene

: 3102-87-2
tetramethyl-p-phenylenediamine

: 719-61-9
tetramethylphenylene-1,4-diisocyanate

Conditions

Conditions	Yield
In various solvent(s) for 0.5h; Condensation; Heating;	75%

: 868961-34-6
oxo-(2,4,6-trimethylphenylamino)acetyl chloride

: 3102-87-2
tetramethyl-p-phenylenediamine

: 1071505-62-8
C32H38N4O4

Conditions

Conditions	Yield
In tetrahydrofuran	75%

: 3102-87-2
tetramethyl-p-phenylenediamine

: 24801-88-5
3-(triethoxypropyl) isocyanate

: 1,4-bis{N'-[3-(triethoxysilyl)propyl]ureido}-2,3,5,6-tetramethylbenzene

Conditions

Conditions	Yield
In ethanol	73%

: 245423-02-3
2-(mesitylimino)acenaphthylene-1-one

: 3102-87-2
tetramethyl-p-phenylenediamine

: C52H46Br4N4Ni2

Conditions

Conditions	Yield
With nickel dibromide In acetic acid at 20℃; for 144h; Heating / reflux;	73%

: 1122-62-9
2-acetylpyridine

: 3102-87-2
tetramethyl-p-phenylenediamine

: N,N'-bis(1-(pyridin-2-yl)ethylidene)-2,3,5,6-tetramethylbenzene-1,4-diamine

Conditions

Conditions	Yield
With formic acid In butan-1-ol at 90℃;	73%

: 12093-10-6
ferrocenecarboxaldehyde

: 3102-87-2
tetramethyl-p-phenylenediamine

: C32H32Fe2N2

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene reflux, 16 h; filtrn., evapn. in vac., washed (ethanol, petroleum ether), elem. anal.;	72%

1,4-Benzenediamine,2,3,5,6-tetramethyl- Specification

The CAS register number of 1,4-Benzenediamine,2,3,5,6-tetramethyl- is 3102-87-2. It also can be called as Diaminodurene and the IUPAC name about this chemical is 2,3,5,6-tetramethylbenzene-1,4-diamine. The molecular formula about this chemical is C₁₀H₁₆N₂ and the molecular weight is 164.25. It belongs to the following product categories which include Fluorenes, etc. (reagent for high-performance polymer research); Functional Materials; Reagent for High-Performance Polymer Research and so on.

Physical properties about 1,4-Benzenediamine,2,3,5,6-tetramethyl- are: (1)ACD/LogP: 1.16; (2)ACD/LogD (pH 5.5): 0.45; (3)ACD/LogD (pH 7.4): 1.13; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 4.24; (6)ACD/KOC (pH 5.5): 20.08; (7)ACD/KOC (pH 7.4): 96.46; (8)#H bond acceptors: 2; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 6.48Å²; (12)Index of Refraction: 1.594; (13)Molar Refractivity: 54.02 cm³; (14)Molar Volume: 159 cm³; (15)Polarizability: 21.41x10^-24cm³; (16)Surface Tension: 43.9 dyne/cm; (17)Enthalpy of Vaporization: 55.14 kJ/mol; (18)Boiling Point: 310.6 °C at 760 mmHg; (19)Vapour Pressure: 0.000595 mmHg at 25°C.

Uses of 1,4-Benzenediamine,2,3,5,6-tetramethyl-: it can be used to produce 1,4-bis-(2,5-dimethylpyrrol-1-yl)-2,3,5,6-tetramethylbenzene with hexane-2,5-dione at heating. This reaction will need reagent conc. HCl and solvent ethanol with reaction time of 1 hours. The yield is about 62%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is limited evidence of a carcinogenic effect. When you are using it, please wear suitable protective clothing and do not breathe dust. In case of 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(c(c(c(c1C)C)N)C)C
(2)InChI: InChI=1/C10H16N2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h11-12H2,1-4H3
(3)InChIKey: WCZNKVPCIFMXEQ-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C10H16N2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h11-12H2,1-4H3
(5)Std. InChIKey: WCZNKVPCIFMXEQ-UHFFFAOYSA-N

Product Name

2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE

Synthetic route

1,4-Benzenediamine,2,3,5,6-tetramethyl- Specification

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