536-46-9

Basic information

• Product Name: N,N-DIMETHYL-P-PHENYLENEDIAMINE MONOHYDROCHLORIDE
• Synonyms: 1,4-Amino-N,N-dimethylaniline,dihydrochloride;1,4-Benzenediamine,N,N-dimethyl-,dihydrochloride;4-benzenediamine,n,n-dimethyl-dihydrochloride;dimethyl-p-phenylenediaminehydrochloride;N,N-Dimethyl-p-phenylenediami;n,n-dimethyl-p-phenylenediamindihydrochloride;usafek-7423;N,N-DIMETHYL-P-PHENYLENEDIAMINE MONOHYDROCHLORIDE
• CAS NO: 536-46-9
• Molecular Formula: C₈H₁₄N₂*2Cl
• Molecular Weight: 209.12
• EINECS: 218-146-0
• Product Categories: Intermediates of Dyes and Pigments;API intermediates
• Mol File: 536-46-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 222 °C (dec.)(lit.)
• Boiling Point: 262 °C at 760 mmHg
• Flash Point: 88.6 °C
• Appearance: White to beige to gray/Powder
• Density: 0.94g/cm3
• Vapor Pressure: 0.0112mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: 2000g/l
• Water Solubility: Soluble in water
• Merck: 14,3254
• BRN: 3913463
• CAS DataBase Reference: N,N-DIMETHYL-P-PHENYLENEDIAMINE MONOHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-P-PHENYLENEDIAMINE MONOHYDROCHLORIDE(536-46-9)
• EPA Substance Registry System: N,N-DIMETHYL-P-PHENYLENEDIAMINE MONOHYDROCHLORIDE(536-46-9)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-43
• Safety Statements: 36/37-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: ST1750000
• F: 3-8-9
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 536-46-9(Hazardous Substances Data)

Usage

Chemical Properties

white to beige to grey powder

Uses

It is a stain used in microscopy. N,N-Dimethyl-p-phenylenediamine dihydrochloride is also suitable for use in the peroxidase test. It is a compound that is normally used to measure the antioxidant potential.

InChI:InChI=1/C8H12N2.2ClH/c1-10(2)8-5-3-7(9)4-6-8;;/h3-6H,9H2,1-2H3;2*1H

Synthetic route

N,N-dimethylammonium chloride (506-59-2) + 4-chlorobenzonitrile (100-00-5) → 4-dimethylaminophenylamine dihydrochloride (536-46-9)

Conditions	Yield
With water; sodium hydroxide In toluene at 20 - 40℃; for 2h; Temperature; Heating;	97.3%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 7-formyl-4-methyl-3-methylthio-2,2-dioxo-1-phenyl-1H-thieno<3,4-c><1,2>thiazine (220966-77-8) → 4-methyl-3-methylthio-7-(4-N,N-dimethylaminoanilinomethylidene)-2,2-dioxo-1-phenyl-1H-thieno<3,4-c><1,2>thiazine

Conditions	Yield
With potassium hydroxide In ethanol for 4h;	92%

methanol (67-56-1) + Pt(4,7-diphenylphenanthroline)(4-ethynylbenzaldehyde(-1H))2 * methanol + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → Pt(4,7-diphenylphenanthroline)[C2C6H4-p-(CH=N-C6H4NMe2)]2* 2(methanol)

Conditions	Yield
With (C2H5)3N; ZnCl2 In methanol; dichloromethane (Ar); stirred for 40 h at room temp.; washed (MeOH, EtOH, Et2O), recrystd. (MeOH/CH2Cl2), washed (MeOH, Et2O),dried (vac.); elem. anal.;	90%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 1-(4-methoxyphenyl)ethanone (100-06-1) → (E)-4-((1-(4-methoxyphenyl)ethylidene)amino)-N,N-dimethylaniline (130597-95-4)

Conditions	Yield
With potassium carbonate In dichloromethane; water; toluene at 160℃; Dean-Stark;	89%

3-methoxyphenyl bromide (2398-37-0) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → 4-(N,N-dimethylamino)-3’-methoxydiphenylamine (178400-99-2)

Conditions	Yield
With potassium hydroxide; bis(tri-t-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 1h; Product distribution / selectivity;	88%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9, 13829-06-6) → N,N,N',N'-tetramethylguanidino-N",N"-dimethyl-p-phenylenediamine (20815-34-3)

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 21h; Schlenk technique; Inert atmosphere;	87%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 1,1'-carbonyldiimidazole (530-62-1) + ethylhydrazine carboxylate (4114-31-2) → 1-ethoxycarbonyl-4-(4'-dimethylaminophenyl)semicarbazide (112667-72-8)

Conditions	Yield
Stage #1: 1,1'-carbonyldiimidazole; ethylhydrazine carboxylate In N,N-dimethyl-formamide at 20℃; for 3h; Stage #2: 4-dimethylaminophenylamine dihydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;	81.6%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + salicylaldehyde (90-02-8) → 2-((4-(N,N-dimethylamino)aniline)formimidoyl)phenol (959-74-0)

Conditions	Yield
With potassium hydroxide In methanol at 25℃; for 3h; Heating;	78%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 3,4,5-tris(hexadecyloxy)benzoic acid chloride (851168-12-2) → C63H112N2O4

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	76%
Stage #1: 4-dimethylaminophenylamine dihydrochloride; 3,4,5-tris(hexadecyloxy)benzoic acid chloride With triethylamine In dichloromethane Stage #2: Reflux;

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 1-naphthylcyanamide (41279-57-6) → N-Cyano-N'-(4'-dimethylaminophenyl)-1,4-naphthoquinone di-imine (124646-94-2)

Conditions	Yield
With sodium hydroxide; ammonium peroxydisulfate In water at 5℃; for 0.5h;	72%
With sodium hydroxide; ammonium peroxydisulfate In water at 5℃; for 0.5h;	72%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + methyl 1-(4-acetoxy-2-methylphenyl)-6-(formyl)-1,4-dihydro-4-oxonicotinate (92394-83-7) → methyl 1-(4-acetoxy-2-methylphenyl)-4-oxo-6-(4-dimethylaminophenyl)iminomethyne-1,4-dihydropyridine-3-carboxylate

Conditions	Yield
With triethylamine In dichloromethane Ambient temperature;	70.7%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 2-(1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (117506-45-3) → 4-methylene>-1,4-dihydro-3-methyl-1-phenyl-5H-pyrazol-5-one

Conditions	Yield
With sodium hydrogencarbonate In methanol 1.) reflux, 15 min; 2.) reflux, 1 h;	64%

Boc-Glu(OBzl)-OH (13574-13-5) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N-Boc-L-Glu-(OBzl)-adma (222736-47-2)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature;	64%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + (1,3-dioxoindan-2-ylidene)propanedinitrile (16954-74-8) → 2-methylene>-1,3-indandione

Conditions	Yield
With sodium hydrogencarbonate In methanol 1.) reflux, 15 min; 2.) reflux, 1 h;	63%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 3,4,5-tris(dodecanyloxy)benzoyl chloride (117241-33-5) → C51H88N2O4

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	58%
Stage #1: 4-dimethylaminophenylamine dihydrochloride; 3,4,5-tris(dodecanyloxy)benzoyl chloride With triethylamine In dichloromethane Stage #2: Reflux;

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-Acetyl-2-methylphenyl morpholine-4-carboxylate (65851-36-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 8h;	57%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 3,4,5-tri(tetradecyloxy)-benzoyl chloride (853055-43-3) → C57H100N2O4

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	56%
Stage #1: 4-dimethylaminophenylamine dihydrochloride; 3,4,5-tris(tetradecyloxy)benzoyl chloride With triethylamine In dichloromethane Stage #2: Reflux;

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid (61172-66-5) + 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride (25952-53-8) → N-(4-dimethylaminophenyl)-α-[(1,1-dimethylethoxycarbonyl)amino]-4-pentynamide (254979-43-6)

Conditions	Yield
With benzotriazol-1-ol; triethylamine In dichloromethane at 23℃; for 16h;	56%

1,5-dichloropentan-3-one (3592-25-4) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → 1-(4-dimethylamino-phenyl)-4-piperidone (370885-30-6)

Conditions	Yield
With sodium carbonate In methanol for 1.5h; Heating;	55%

2-chloro-1,3-dimethyl-4,5-dihydro-1H-imidazolium chloride + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N,N'-dimethylethyleneguanidino-N",N"-dimethyl-p-phenylene-diamine

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 5h;	55%

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 3,3'-(3,6-dioxaoctamethylene)bis(5-hydroxy-6-methoxy-4(3H)-quinazolinone) (120622-48-2) → 3,3'-(3,6-dioxaoctamethylene)bis<8-(4-N,N-dimethylaminophenylimino)-6-methoxy-4,5-quinazolinedione> (120622-50-6)

Conditions	Yield
With sodium carbonate; silver(I) chloride In ethanol; water for 4.5h;	53%

1,5-dibromo-pentane (111-24-0) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N,N-dimethyl-4-(piperidin-1-yl)aniline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 8h;	52%

carbodiimide (151-51-9) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N,N-dimethyl-p-guanidinoaniline hydrochloride

Conditions	Yield
Stage #1: carbodiimide; 4-dimethylaminophenylamine dihydrochloride In ethanol for 30h; Reflux; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; ethanol Schlenk technique; Inert atmosphere;	50%

2-(naphthalen-1-yl)malononitrile (5518-09-2) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → 4-(4-dimethylaminophenylimino)-1,4-dihydronaphthylidenemalononitrile (110930-61-5)

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III) In water for 0.166667h; Ambient temperature;	46%
In water for 0.166667h; Product distribution; Ambient temperature; various oxidizing agents and various yield;

4-dimethylaminophenylamine dihydrochloride (536-46-9) + 3,4,5-tri(octyloxy)benzoyl chloride (157980-11-5) → C39H64N2O4

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	46%
Stage #1: 4-dimethylaminophenylamine dihydrochloride; 3,4,5-tri(octyloxy)benzoyl chloride With triethylamine In dichloromethane Stage #2: Reflux;

1,4-dibromo-butane (110-52-1) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N,N-dimethyl-4-(pyrrolidin-1-yl)aniline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 8h;	21%

pyridine (110-86-1) + (Z)-1,2,3,4-tetraphenyl-2-butene-1,4-dione (7510-34-1, 10496-80-7, 6313-26-4) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N,N-dimethyl-4-tetraphenylpyrrol-1-yl-aniline (2405-95-0)

4-pyrone (108-97-4) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → 1-(4-dimethylamino-phenyl)-1H-pyridin-4-one (105974-06-9)

Conditions	Yield
With water und Behandeln des Reaktionsprodukts mit wss.Ammoniak;

methanol (67-56-1) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → N,N,N',N'-tetramethyl-para-phenylenediamine (100-22-1)

Conditions	Yield
at 150℃;

2,5-Dimethylphenol (95-87-4) + 4-dimethylaminophenylamine dihydrochloride (536-46-9) → 2,5-dimethyl-[1,4]benzoquinone-mono-(4-dimethylamino-phenylimine) (57239-95-9)

Conditions	Yield
With ethanol; sodium carbonate; silver(I) chloride

Upstream product

• 506-59-2 N,N-dimethylammonium chloride 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 100-22-1 N,N,N',N'-tetramethyl-para-phenylenediamine 
• 57239-95-9 2,5-dimethyl-[1,4]benzoquinone-mono-(4-dimethylamino-phenylimine) 
• 108063-18-9 N'-(6-chloro-2-methyl-[4]quinolyl)-N,N-dimethyl-p-phenylenediamine 
• 109979-49-9 N'-(2,8-dimethyl-[4]quinolyl)-N,N-dimethyl-p-phenylenediamine 
• 109980-03-2 N'-(6-methoxy-2-methyl-[4]quinolyl)-N,N-dimethyl-p-phenylenediamine 
• 52887-14-6 (2,4-dinitro-phenyl)-acetic acid-(4-dimethylamino-anilide) 
• 7512-47-2 chloro-[1,4]-benzoquinone-4-(4-dimethylamino-phenylimine) 
• 26060-34-4 thioformic acid-(4-dimethylamino-anilide) 
• 5469-91-0 2-(4-dimethylamino-phenylimino)-1-phenyl-ethanone 
• 5775-53-1 N,N-diethyl-N',N'-dimethyl-p-phenylenediamine 
• 91091-11-1 (4-dimethylamino-phenylimino)-malononitrile 
• 96732-07-9 cyano-(4-dimethylamino-phenylimino)-acetic acid ethyl ester 
• 57842-97-4 N,N-dimethyl-p-phenylenediamine,radical ion[1+]; bromide 
• 31772-03-9 4-nitro-benzoic acid-(4-dimethylamino-anilide) 

Relevant articles and documents

Preparation method of N, N-dimethyl p-phenylenediamine hydrochloride

The invention relates to the technical field of organic synthesis, and particularly relates to a preparation method of N, N-dimethyl p-phenylenediamine hydrochloride, which comprises the following steps: (1) dissolving p-nitrochlorobenzene in toluene to obtain a solution A; (2) dissolving dimethylamine hydrochloride in water, and adding the solution A; (3) under stirring, dropwise adding a sodiumhydroxide aqueous solution into the solution, heating, dropwise adding the sodium hydroxide aqueous solution, and carrying out heat preservation reaction; (4) standing, separating phases, adding a catalyst into a toluene layer, and carrying out hydrogenation reduction; (5) filtering and separating the catalyst; introducing hydrogen chloride gas into the toluene layer to obtain N, N-dimethyl p-phenylenediamine hydrochlorideprecipitate; (6) centrifuging to obtain the N, N-dimethyl p-phenylenediamine hydrochloride. In the process, dimethylamine hydrochloride is added with sodium hydroxide to release dimethylamine and react in time, so that the process is mild, efficient and safe; the three wastes are less.