3102-87-2

Basic information

• Product Name: 2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE
• Synonyms: DIAMINO DURENE;DURENE DIAMINE;2,3,5,6-TETRAMETHYL-P-PHENYLENEDIAMINE;2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE;3,6-DIAMINODURENE;3,6-DIAMINODUROL;3,6-DIAMINO-1,2,4,5-TETRAMETHYLBENZENE;1,4-Benzenediamine, 2,3,5,6-tetramethyl-
• CAS NO: 3102-87-2
• Molecular Formula: C₁₀H₁₆N₂
• Molecular Weight: 164.25
• EINECS: 221-457-4
• Product Categories: Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;pharmaceutical intermediates;4-mpd whatsapp;8618031153937 ada@tuskwei.com;Medical research
• Mol File: 3102-87-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 150-155 °C(lit.)
• Boiling Point: 281.73°C (rough estimate)
• Flash Point: 167.8 °C
• Appearance: beige fine crystalline powder
• Density: 1.0244 (rough estimate)
• Vapor Pressure: 0.000595mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 6.11±0.10(Predicted)
• BRN: 2208743
• CAS DataBase Reference: 2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE(3102-87-2)
• EPA Substance Registry System: 2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE(3102-87-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-36-22
• WGK Germany: 3
• RTECS: CZ1599700
• Hazardous Substances Data: 3102-87-2(Hazardous Substances Data)

Usage

Chemical Properties

beige fine crystalline powder

Uses

Monomer used in the preparation of polyimide coatings for electronic applications-IC passivation, dielectric for multichip modules, and as a stress relief layer in sensor applications.

InChI:InChI=1/C10H16N2/c1-5-6(2)10(12)8(4)7(3)9(5)11/h11-12H2,1-4H3

Synthetic route

dinitrodurene (5465-13-4) → tetramethyl-p-phenylenediamine (3102-87-2)

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

2,3,5,6-tetramethyl-4-amino-1-nitrobenzene (13171-61-4) → tetramethyl-p-phenylenediamine (3102-87-2)

Conditions	Yield
With ammonium sulfide at 135℃;

eso-dinitro-durol → tetramethyl-p-phenylenediamine (3102-87-2)

Conditions	Yield
With acetic acid; zinc

eso-dinitro-durol → tetramethyl-p-phenylenediamine (3102-87-2) + 2,3,5,6-tetramethyl-4-amino-1-nitrobenzene (13171-61-4)

Conditions	Yield
With ammonium sulfide at 130℃;

dinitrodurene (5465-13-4) → tetramethyl-p-phenylenediamine (3102-87-2) + tellurium

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

tetramethyl-p-phenylenediamine (3102-87-2) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → 2,7-diaminobenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (13821-25-5)

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

tetramethyl-p-phenylenediamine (3102-87-2) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → 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 (1454647-98-3)

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

p-methylbenzenesulfenyl chloride (933-00-6) + tetramethyl-p-phenylenediamine (3102-87-2) → 2,3,5,6-tetramethyl-N,N′-bis(4-methylphenylsulfanyl)cyclohexa-2,5-diene-1,4-diimine

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

chloro-trimethyl-silane (75-77-4) + tetramethyl-p-phenylenediamine (3102-87-2) → N,N'-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-phenylenediamine

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%

dichloromethane (75-09-2) + trans,mer-[Ti(t-butylimide)Cl2(pyridine)3] (172481-11-7) + tetramethyl-p-phenylenediamine (3102-87-2) → [Ti(pyridine)3Cl2(1,4-NC6Me4NH2)]*0.4CH2Cl2

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

tetramethyl-p-phenylenediamine (3102-87-2) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → N,N'-bis(4-amino-2,3,5,6-tetramethylphenyl)naphthalene-1,4,5,8-dicarboxyimide

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

pyridine-2-carbaldehyde (1121-60-4) + tetramethyl-p-phenylenediamine (3102-87-2) → N,N'-bis((pyridin-2-yl)methylene)-2,3,5,6-tetramethylbenzene-1,4-diamine (1056633-12-5)

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

tetramethyl-p-phenylenediamine (3102-87-2) + Ethyl oxalyl chloride (4755-77-5) → Et2H2Me4Meppba (1326681-00-8)

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

tetramethyl-p-phenylenediamine (3102-87-2) + benzaldehyde (100-52-7) → C17H20N2

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

tetramethyl-p-phenylenediamine (3102-87-2) + (E)-N-(3-(dimethylamino)-2-(naphthalen-1-yl)allylidene)-N-methylmethanaminium perchlorate (23801-15-2) → C44H36N4

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

tetramethyl-p-phenylenediamine (3102-87-2) + C50H30O8 → C70H58N4O6

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

tetramethyl-p-phenylenediamine (3102-87-2) + ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate (7089-34-1) → C36H32N4

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

2,3-dihydroxybenzaldehyde (24677-78-9) + tetramethyl-p-phenylenediamine (3102-87-2) → C24H24N2O4

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

tetramethyl-p-phenylenediamine (3102-87-2) + 2-(3,5-dimethylpyridinium-1-yl)-1-dimethylamino-3-(dimethyliminium)prop-1-ene bisperchlorate → C38H40N6(2+)*2ClO4(1-)

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

tetramethyl-p-phenylenediamine (3102-87-2) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → (Z)-1-[(4-amino-2,3,5,6-tetramethylphenylamino)methylene]-18a-dihydronaphthalen-2(3H)-one (1240390-15-1)

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

tetramethyl-p-phenylenediamine (3102-87-2) + p-toluenesulfonyl chloride (98-59-9) → N,N-ditosyl-2,3,5,6-tetramethyl-1,4-phenylenediamine (407609-46-5)

Conditions	Yield
With triethylamine In diethyl ether	84%

tetramethyl-p-phenylenediamine (3102-87-2) + 1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one → C52H64N6

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%

6-bromo-2-pyridinecarbaldehyde (34160-40-2) + tetramethyl-p-phenylenediamine (3102-87-2) → N1,N4-bis((6-bromopyridin-2-yl)methyl)-2,3,5,6-tetramethylbenzene-1,4-diamine

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

tetramethyl-p-phenylenediamine (3102-87-2) + 1,1,5,5-tetramethyl-3-(1-isoquinolinio)-1,5-diazapentadienium bis(perchlorate) → C42H36N6(2+)*2ClO4(1-)

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

tetramethyl-p-phenylenediamine (3102-87-2) + 1,1,5,5-tetramethyl-3-(4-ethylpyridinium)-1,5-diazapentadienium bis(perchlorate) → C38H40N6(2+)*2ClO4(1-)

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

1,1,5,5-tetramethyl-3-(1-quinolinio)-1,5-diazapentadienium bis(perchlorate) + tetramethyl-p-phenylenediamine (3102-87-2) → C42H36N6(2+)*2ClO4(1-)

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

tetramethyl-p-phenylenediamine (3102-87-2) + dimethylglyoxal (431-03-8) → C24H34N4 (1206533-48-3)

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

tetramethyl-p-phenylenediamine (3102-87-2) + 1,1,5,5-tetramethyl-3-(1-pyridinio)-1,5-diazapentadienium bis(perchlorate) → C34H32N6(2+)*2ClO4(1-)

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

tetramethyl-p-phenylenediamine (3102-87-2) + 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 (259880-39-2) → 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 (1442460-40-3)

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

phosgene (75-44-5) + tetramethyl-p-phenylenediamine (3102-87-2) → tetramethylphenylene-1,4-diisocyanate (719-61-9)

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

oxo-(2,4,6-trimethylphenylamino)acetyl chloride (868961-34-6) + tetramethyl-p-phenylenediamine (3102-87-2) → C32H38N4O4 (1071505-62-8)

Conditions	Yield
In tetrahydrofuran	75%

tetramethyl-p-phenylenediamine (3102-87-2) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 1,4-bis{N'-[3-(triethoxysilyl)propyl]ureido}-2,3,5,6-tetramethylbenzene

Conditions	Yield
In ethanol	73%

2-(mesitylimino)acenaphthylene-1-one (245423-02-3) + tetramethyl-p-phenylenediamine (3102-87-2) → C52H46Br4N4Ni2

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

2-acetylpyridine (1122-62-9) + tetramethyl-p-phenylenediamine (3102-87-2) → N,N'-bis(1-(pyridin-2-yl)ethylidene)-2,3,5,6-tetramethylbenzene-1,4-diamine

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

ferrocenecarboxaldehyde (12093-10-6) + tetramethyl-p-phenylenediamine (3102-87-2) → C32H32Fe2N2

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

Upstream product

• 5465-13-4 dinitrodurene 
• 13171-61-4 2,3,5,6-tetramethyl-4-amino-1-nitrobenzene 

Downstream Products

• 66907-63-9 N,N,N',N'-Tetramethyl-3,6-diaminodurene 
• 132588-50-2 N,N'-bis(1',1'-dimethylprop-2'-ynyl)-2,3,4,5-tetramethylbenzene-1,4-diamine 
• 407609-46-5 N,N-ditosyl-2,3,5,6-tetramethyl-1,4-phenylenediamine 
• 29815-58-5 tetramethyl-[1,4]benzoquinone-diimine 
• 719-61-9 tetramethylphenylene-1,4-diisocyanate 
• 136814-87-4 1,4-bis-(2,5-dimethylpyrrol-1-yl)-2,3,5,6-tetramethylbenzene 
• 66608-45-5 2,3,5,6-Tetramethyl-N,N'-bis-(N-diethoxyphosphoryl-thiocarbamoyl)-1,4-phenylendiamin 
• 13908-70-8 1-(2-Chloro-ethyl)-3-{4-[3-(2-chloro-ethyl)-ureido]-2,3,5,6-tetramethyl-phenyl}-urea 
• 19835-87-1 N,N'-(tetramethyl-p-phenylene)-bis-benzenesulfonamide 
• 66258-29-5 N,N'-Diacetyl-1,4-diamino-2,3,5,6-tetramethylbenzen 
• 527-17-3 Duroquinone 
• 858242-04-3 2,3,5,6,N,N'-hexamethyl-p-phenylenediamine 
• 858498-27-8 N-(2-cyano-ethyl)-N,N'-(tetramethyl-p-phenylene)-bis-benzenesulfonamide 
• 855231-24-2 cis-N,N'-dibenzyl-N,N'-(tetramethyl-p-phenylene)-bis-benzenesulfonamide 

Relevant articles and documents

Activated sterically strained C=N bond in N-Arylsulfonyl-p-quinonemono-and diimines: IX. Synthesis and reactions of N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine

N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine as the other N-arylsulfonyl-1,4-benzoquinonimines with an activated C=N bond reacts along 1,2-addition path with alcohols and sodium azide and along 1,2-addition-elimination path with aromatic amines. The higher activity of the C=N bond in the N-arylsulfonyl-1,4-benzoquinonimines is not due to the electronic character of the substituent attached to the ring (Cl, CH3) but to steric influence resulting in increase in the bond angle C=N-S.

REDUCTION OF AROMATIC NITRO COMPOUNDS WITH SODIUM TELLURIDE

Sodium telluride, prepared by heating tellurium with Rongalite in aqueous sodium hydroxide, easily reduces aromatic nitro compounds to the corresponding amines in good yields.The reduction can be carried out using a catalytic amount of tellurium, since sodium telluride is readily regenerated in the presence of excess Rongalite.