87-62-7

Basic information

• Product Name: 2,6-Dimethylaniline
• Synonyms: 2,6-Xylidine, 2-Amino-m-xylene;2,6-two Methyl aniline;2.6-DiMethylan;2,6-Dimethylaniline Solution, 100ppm;2,6-Dimethylaniline (Lidocaine RCA);2,6-dimethyl-benzenamin;2,6-Dimethylbenzenamine;2,6-dimethyl-Benzenamine
• CAS NO: 87-62-7
• Molecular Formula: C8H11N
• Molecular Weight: 121.18
• EINECS: 201-758-7
• Product Categories: Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Intermediates;Aromatic Amine;Aniline;Anilines, Aromatic Amines and Nitro Compounds;Organics;Amines;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C8;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 87-62-7.mol
• Article Data: 162

Chemical Properties

• Melting Point: 10-12 °C(lit.)
• Boiling Point: 216 °C
• Flash Point: 196 °F
• Appearance: Clear yellow to red-brown/Liquid
• Density: 0.984 g/mL at 25 °C(lit.)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.560(lit.)
• Storage Temp.: Refrigerator
• Solubility: 13g/l
• PKA: 3.89(at 25℃)
• Explosive Limit: 1.3-6.9%(V)
• Water Solubility: 7.5 g/L (20 ºC)
• Merck: 14,10084
• BRN: 636332
• CAS DataBase Reference: 2,6-Dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethylaniline(87-62-7)
• EPA Substance Registry System: 2,6-Dimethylaniline(87-62-7)

Safety Data

• Hazard Codes: Xn,N,T
• Statements: 20/21/22-37/38-40-51/53
• Safety Statements: 23-25-36/37-61
• RIDADR: UN 1711 6.1/PG 2
• WGK Germany: 2
• RTECS: ZE9275000
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 87-62-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 87-62-7 differently. You can refer to the following data:
1. Bupivacaine (B689560) impurity.
2. 2,6-Dimethylaniline is used in pharmaceuticals, as dye intermediates and in organic synthesis. It is also used in the production of antioxidants, agricultural, pharmaceutical, rubber chemicals and other target organic molecules.

Definition

ChEBI: A primary arylamine that is aniline in which the hydrogens at the 2- and 6-positions are replaced by methyl groups. It is used in the production of some anasthetics and other chemicals. It is a drug metabolite of lidocaine (local anasthetic).

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 7464, 1970 DOI: 10.1021/ja00728a038The Journal of Organic Chemistry, 37, p. 3570, 1972

General Description

A liquid. Toxic by ingestion, inhalation and skin absorption. Slightly soluble in water. Used in pharmaceuticals, as dye intermediates and organic syntheses.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

2,6-Dimethylaniline reacts with strong oxidizing agents [Handling Chemicals Safely 1980 p. 964]. Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

May be fatal if inhaled, swallowed or absorbed through skin. Vapor or mist irritating to the eyes, mucous membranes and upper respiratory tract; causes skin irritation. Absorption into body leads to the formation of methemoglobin which, in sufficient concentration, may cause cyanosis. Onset may be delayed 2-4 hours or longer. Exposure can cause nausea, dizziness, headache, damage to the eyes, and blood effects.

Fire Hazard

Special Hazards of Combustion Products: Container explosion may occur under fire conditions. Emits toxic fumes under fire conditions.

Safety Profile

Suspected carcinogen. Moderately toxic by ingestion. Mutation data reported. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx. See also other xylidme entries.

Purification Methods

Convert vic-xylidine to a derivative (see below) which, after recrystallisation, is decomposed with alkali to give the free base. Dry it over KOH and fractionally distil. The acetyl derivative has m 177o, the benzoyl derivative has m 168o, and the picrate has m 180o. [Beilstein 12 H 1107, 12 IV 2521.]

InChI:InChI=1/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3

Synthetic route

2,6-dimethylnitrobenzene (81-20-9) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 3h;	100%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;	100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 10h;	100%

2,6-dimethylphenylazide (26334-20-3) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With sodium hydrogen telluride In diethyl ether; ethanol for 0.25h; Ambient temperature;	100%
With aluminium(III) iodide In benzene for 0.166667h; Reduction; Heating;	90%
With diphosphorus tetraiodide In benzene for 11h; Heating;	40%

N-methyl-2,6-dimethylaniline (767-71-5) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine In acetonitrile at -78℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;	100%

4-amino-3,5-dimethyl-benzoic acid methyl ester (3095-48-5) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With sodium hydroxide In water at 60 - 130℃; under 4560.31 Torr; for 3.5h; Temperature;	99.1%

2-(2,6-dimethylphenyl)-4,5,6,7-tetrafluoroisoindoline-1,3-dione → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With ethylenediamine In ethanol at 65℃; for 14h;	99%

2,6-dimethyl-1-chlorobenzene (6781-98-2) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;	98%
With C28H30Cl5N3Pd; ammonia; lithium isopropoxide; sodium t-butanolate In 1,4-dioxane at 100℃; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	91%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;	89%

3,5-dimethyl-4-aminobenzoic acid ethyl ester (3095-47-4) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With potassium hydroxide In water at 60 - 125℃; under 2280.15 Torr; for 3h;	97.5%

1,2-dimethoxybenzene (91-16-7) + N-(2,6-diimethylphenyl)benzamide (18109-39-2) → 3,4-dimethoxybenzophenone (4038-14-6) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
Stage #1: N-(2,6-diimethylphenyl)benzamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; for 0.166667h; Inert atmosphere; Stage #2: 1,2-dimethoxybenzene In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In ethanol for 2h; Inert atmosphere; Reflux; chemoselective reaction;	A 97% B 90%

2.6-dimethylphenol (576-26-1) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With 2,6-dimethylcyclohexanone; ammonium hydroxide; 5%-palladium/activated carbon at 180℃; for 5h; Concentration; Temperature;	95.62%
With ammonia; hydrogen In 1,4-dioxane at 230℃; under 760.051 Torr;	86.56%
With ammonia

2,6-dimethylphenyl diethyl phosphate (39604-15-4) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With potassium; potassium amide In diethyl ether; ammonia at -78℃; 1.0-1.2 h;	95%

2,6-dimethylbenzene boronic acid (100379-00-8) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 12h;	92%
With potassium carbonate; ammonium hydroxide In methanol at 60℃; for 13h;	87%
With copper(ll) sulfate pentahydrate; ammonia; sodium hydroxide In water at 20℃; under 760.051 Torr; for 4h;	58%
Multi-step reaction with 2 steps 1: potassium hydrogenfluoride / methanol; water / 0.5 h / 0 °C 2: ammonium hydroxide; copper(ll) sulfate pentahydrate; sodium hydroxide / water / 24 h / 25 °C View Scheme

2-Bromo-m-xylene (576-22-7) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 15h; Inert atmosphere;	88%
With magnesium In diethyl ether Ambient temperature;	79%
With [N,N'-bis(5-sulfonatosalicylidene)-1,2-diaminoethane]copper disodium salt; ammonia; sodium hydroxide In water at 120℃; for 12h; sealed tube;	64%
With C24H32N2*ClCu; ammonia; potassium carbonate In 1-methyl-pyrrolidin-2-one; methanol at 120℃; under 5171.62 Torr; for 48h; Inert atmosphere;	7%
With ammonium hydroxide; sodium hydroxide In water

N'-(2,6-methyl-phenyl)-N,N-dimethyl-formamidine → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In methanol; water at 20℃; under 3620.04 Torr; for 60h; Hydrogenolysis;	86%

N-methyl-N-allylamine (627-37-2) + N-(2,6-dimethylphenyl)benzimidamide (16239-27-3) → 1,4-dimethyl-2-phenyl-4,5-dihydro-1H-imidazole + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With bis(trimethylsilyl)amide yttrium(III) In neat (no solvent) at 100℃; for 120h; Inert atmosphere;	A 86% B n/a

N'-(2,6-dimethyl-phenyl)-N,N-dibenzyl-formamidine → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In methanol; water under 3620.04 Torr; Ambient temperature;	83%
With hydrogen; palladium on activated charcoal; palladium hydroxide - carbon In methanol; water at 20℃; under 3620.04 Torr; for 64h; Hydrogenolysis;	83%

5-chloropentano-2',6'-xylidide (77470-78-1) + diethylamine (109-89-7) → 5-(diethylamino)pentano-2',6'-xylidide (77470-82-7) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With sodium iodide In ethanol for 48h; Heating;	A 82% B n/a

2,6-dimethyl-N-methylene benzamine (35203-02-2) → N-methyl-2,6-dimethylaniline (767-71-5) + N,N,2,6-tetramethylaniline (769-06-2) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Heating;	A 81% B 3% C 10%

(E)-3-Phenyl-acrylic acid 1-(2,6-dimethyl-phenylcarbamoyl)-1-methyl-2-oxo-propyl ester (105887-12-5) → N-(2,6-dimethylphenyl) 2-acetyl 2-hydroxypropanamide (105915-43-3) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride In tetrahydrofuran for 24h; Heating;	A 80% B n/a

2,6-dimethylbenzene boronic acid (100379-00-8) → 2.6-dimethylphenol (576-26-1) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With ammonium hydroxide; potassium nitrate In water at 20℃; for 2h; Electrochemical reaction; chemoselective reaction;	A n/a B 73%
With ammonium hydroxide; potassium nitrate In water at 20℃; for 4h; Electrochemical reaction; chemoselective reaction;	A 70% B n/a

2-(2,6-bismethylphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With O-Methylhydroxylamin; n-butyllithium In tetrahydrofuran; hexane at -78 - 60℃; for 24h; Inert atmosphere; Cooling with acetone-dry ice; stereospecific reaction;	71%

2-methyl-6-(thiomethoxymethyl)-aniline → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
	66%

2,6-dimethylcyclohexanone (2816-57-1) → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 15h; Schlenk technique;	63%
With urea In water; 1,3,5-trimethyl-benzene at 150℃; under 760.051 Torr; for 24h; Schlenk technique; Inert atmosphere;	37 %Chromat.

4-chlorobutyro-2',6'-xylidide (77470-76-9) + diethylamine (109-89-7) → N-(2,6-dimethylphenylcarbamoylpropyl)diethylamine (21236-53-3) + 1-(2,6-dimethylphenyl)pyrrolidin-2-one (77470-81-6) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
In toluene for 2h; Heating;	A 31% B 60% C n/a

3-Methoxy-pyridine-2-carboxylic acid (2,6-dimethyl-phenyl)-amide (160938-51-2) → 2,6-dimethylaniline (87-62-7) + 3-Methoxy-1,4,5,6-tetrahydro-pyridine-2-carboxylic acid (2,6-dimethyl-phenyl)-amide

Conditions	Yield
With water In methanol at 25℃; electrochemical reduction;	A 60% B 5%

η6-2,6-dimethylaniline-η5-cyclopentadienyliron hexafluorophosphate → 2,6-dimethylaniline (87-62-7)

Conditions	Yield
Sample heated for 1.0 h at 200-220°C and 1 torr.;	60%

N1,N2-bis(2,6-dimethylphenyl)ethane-1,2-diimine (49673-43-0) + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 15h;	A 58% B n/a

m-xylene (108-38-3) → 3,5-dimethylaminoaniline (108-69-0) + 2,4-Xylidine (95-68-1) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 25℃; for 1h;	A 2% B 58% C 15%
With hydrogenchloride; aluminium trichloride; sodium azide In various solvent(s) at 20℃;
With sodium azide; trifluorormethanesulfonic acid at 20℃; Ultrasonic irradiation;
Stage #1: m-xylene With sulfuric acid; hydroxylamine hydrochloride In acetonitrile at 25℃; for 0.166667h; Stage #2: With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 25℃; Inert atmosphere; Sealed tube; Overall yield = 60 percent; Overall yield = 72 mg;

N-methyl-N-allylamine (627-37-2) + C49H53N6OY → 1,4-dimethyl-2-phenyl-4,5-dihydro-1H-imidazole + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
In neat (no solvent) at 100℃; for 120h;	A 57% B n/a

Acetic acid 1-(2,6-dimethyl-phenylcarbamoyl)-1-methyl-2-oxo-propyl ester (105887-10-3) → N,N'-di (2,6-dimethylphenyl) urea (25348-08-7) + N-(2,6-dimethylphenyl) 2-acetyl 2-hydroxypropanamide (105915-43-3) + 2,3-Dimethyl-5-oxo-2,5-dihydro-furan-2-carboxylic acid (2,6-dimethyl-phenyl)-amide (105915-44-4) + 2,6-dimethylaniline (87-62-7)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride In tetrahydrofuran for 4h; Heating;	A n/a B 50% C 40% D n/a

formic acid (64-18-6) + 2,6-dimethylaniline (87-62-7) → 2,6-dimethylformanilide (607-92-1)

Conditions	Yield
In toluene Reflux;	100%
In toluene Reflux;	100%
In toluene Reflux;	100%

2,4,6-trinitrochlorobenzene (88-88-0) + 2,6-dimethylaniline (87-62-7) → (2,6-dimethyl-phenyl)-picryl-amine

Conditions	Yield
In acetonitrile at 25℃;	100%

Carbonylbis(isocyaniddichlorid) (26551-87-1) + 2,6-dimethylaniline (87-62-7) → 4,6-Dichlor-5-(2,6-dimethylphenyl)-1,3,5-triazin-2(5H)-on (84384-14-5)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 0.75h;	100%

2,6-dimethylaniline (87-62-7) + Acetic formic anhydride (2258-42-6) → 2,6-dimethylformanilide (607-92-1)

Conditions	Yield
In tetrahydrofuran at -20℃; for 0.25h;	100%
In tetrahydrofuran at 20℃;
In dichloromethane at 20℃; for 2h;

2,6-dimethylaniline (87-62-7) + Trimethylacetic acid (75-98-9) → 2,2-dimethyl-N-(2,6-dimethylphenyl)propionamide (39627-97-9)

Conditions	Yield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;	100%

1,2-dibromo-4,5-dimethylbenzene (24932-48-7) + 2,6-dimethylaniline (87-62-7) → N,N'-bis(2,6-dimethylphenyl)-4,5-dimethyl-o-phenylenediamine

Conditions	Yield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene	100%
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 14h;	75%

di-tert-butyl dicarbonate (24424-99-5) + 2,6-dimethylaniline (87-62-7) → N-tert-butoxycarbonyl-2,6-dimethylaniline

Conditions	Yield
With indium(III) bromide at 30 - 35℃; for 0.5h;	100%
In ethanol at 30℃; for 48h;	99%
copper(II) bis(tetrafluoroborate) at 30 - 33℃; for 0.5h;	98%
With choline chloride; urea at 50℃; Green chemistry;	90%
In tetrahydrofuran; water for 0.5h;	111 mg

2,4-dinitrophenyl 2,4,6-trinitrophenyl ether (5950-87-8) + 2,6-dimethylaniline (87-62-7) → (2,6-dimethyl-phenyl)-picryl-amine

Conditions	Yield
In acetonitrile at 25℃;	100%
In acetonitrile at 25℃; Equilibrium constant; Kinetics; Further Variations:; title comp. concentration;

2-chloroacetylisocyanate (4461-30-7) + 2,6-dimethylaniline (87-62-7) → C11H13ClN2O2

Conditions	Yield
In dichloromethane at 20℃;	100%
In dichloromethane at 20℃;

2,6-dimethylaniline (87-62-7) → 3-(2,6-dimethyl phenyl carbamoyl)-5-acetoxymethyl isoxazole (130403-23-5)

Conditions	Yield
With triethylamine; trichlorophosphate In tetrahydrofuran	100%
With triethylamine; trichlorophosphate In tetrahydrofuran	100%

2,4,6-trinitrophenyl phenyl ether (6973-40-6) + 2,6-dimethylaniline (87-62-7) → (2,6-dimethyl-phenyl)-picryl-amine

Conditions	Yield
In acetonitrile at 25℃; Kinetics;	100%

1-(4-nitrophenoxy)-2,4,6-trinitrobenzene (10242-31-6) + 2,6-dimethylaniline (87-62-7) → (2,6-dimethyl-phenyl)-picryl-amine

Conditions	Yield
In acetonitrile at 25℃; Kinetics; Concentration;	100%

2-nitrophenyl 2,4,6-trinitrophenyl ether (10242-30-5) + 2,6-dimethylaniline (87-62-7) → (2,6-dimethyl-phenyl)-picryl-amine

Conditions	Yield
In acetonitrile at 25℃; Kinetics; Concentration;	100%

2,6-dinitrophenyl 2,4,6-trinitrophenyl ether (103612-93-7) + 2,6-dimethylaniline (87-62-7) → (2,6-dimethyl-phenyl)-picryl-amine

Conditions	Yield
In acetonitrile at 25℃; Kinetics; Concentration;	100%

phenylacetylene (536-74-3) + 2,6-dimethylaniline (87-62-7) → 2,6-dimethyl-N-(1-phenylethylidene)benzenamine (75472-72-9, 75472-77-4, 10228-84-9)

Conditions	Yield
With C30H36FeP2*2Au(1+)*Cl(1-)*C32H12BF24(1-) In (2)H8-toluene at 120℃; for 6h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; Glovebox;	100%
With silver tetrafluoroborate; {(2,6-bis(1-isopropyl-2,3-dihydro-1H-imidazole-2-thione)pyridine)12Cu8}(PF6)8 In acetonitrile at 70℃; for 2h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; regioselective reaction;	99%
With silver tetrafluoroborate; C57H72Au4I4N12O4 In [D3]acetonitrile at 70℃; for 6h; Reagent/catalyst; Inert atmosphere;	93%

[RuVI(5,10,15,20-tetrakis(4-methylphenyl)porphyrinato(2-))O2] (138735-96-3) + 2,6-dimethylaniline (87-62-7) → [Ru(IV)(ttp)(NQu)(OH)] (1237762-58-1)

Conditions	Yield
Stage #1: [RuVI(5,10,15,20-tetrakis(4-methylphenyl)porphyrinato(2-))O2]; 2,6-dimethylaniline In ethanol for 8h; Stage #2: With water In dichloromethane for 0.5h;	100%

[Ru(VI)(O)2(5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinate)] (138735-97-4) + 2,6-dimethylaniline (87-62-7) → [Ru(IV)(4-OMe-ttp)(NQu)(OH)] (1237762-71-8)

Conditions	Yield
Stage #1: [Ru(VI)(O)2(5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinate)]; 2,6-dimethylaniline In ethanol for 8h; Stage #2: With water In dichloromethane for 0.5h;	100%

[Ru(VI)(meso-tetrakis(p-chlorophenyl)porphyrinato)O2] (138735-98-5) + 2,6-dimethylaniline (87-62-7) → [Ru(IV)(4-Cl-ttp)(NQu)(OH)] (1237762-72-9)

Conditions	Yield
Stage #1: [Ru(VI)(meso-tetrakis(p-chlorophenyl)porphyrinato)O2]; 2,6-dimethylaniline In ethanol for 8h; Stage #2: With water In dichloromethane for 0.5h;	100%

salicylaldehyde (90-02-8) + 2,6-dimethylaniline (87-62-7) → 2-(((2,6-dimethylphenyl)imino)methyl)phenol (54220-52-9)

Conditions	Yield
In ethanol at 80℃; for 2h; Inert atmosphere;	100%
With magnesium sulfate In toluene for 4h; Inert atmosphere; Reflux;	98%
In isopropyl alcohol at 80℃; for 24h; Inert atmosphere;

5-Nitrosalicylaldehyde (97-51-8) + 2,6-dimethylaniline (87-62-7) → 2-[(2,6-dimethylphenylimino)methyl]-4-nitrophenol (339991-46-7)

Conditions	Yield
In ethanol at 80℃; for 2h; Inert atmosphere;	100%
In isopropyl alcohol at 80℃; for 24h; Inert atmosphere;

(NCNdipp)3Lu3(μ2-Me)3(μ3-Me)(μ3-CH2) + 2,6-dimethylaniline (87-62-7) → (PhC(NC6H3iPr2-2,6)2)3Lu3(μ2-Me)3(μ3-Me)(μ-η1:η3-NC6H3Me2-2,6)

Conditions	Yield
In toluene at 20℃; for 48h;	100%

(NCNdipp)3Y3(μ2-Me)3(μ3-Me)(μ3-CH2) + 2,6-dimethylaniline (87-62-7) → (PhC(NC6H3iPr2-2,6)2)3Y3(μ2-Me)3(μ3-Me)(μ-η1:η3-NC6H3Me2-2,6)

Conditions	Yield
In toluene at 20℃; for 48h;	100%

benzoyl chloride (98-88-4) + 2,6-dimethylaniline (87-62-7) → N-(2,6-diimethylphenyl)benzamide (18109-39-2)

Conditions	Yield
With triethylamine In toluene Heating;	99%
With triethylamine In acetone at 20℃; Cooling with ice;	93%
With triethylamine In dichloromethane for 48h; Reflux;	67%

2-Bromoacetyl bromide (598-21-0) + 2,6-dimethylaniline (87-62-7) → 2-bromo-N-(2,6-dimethyl-phenyl)-acetamide (32433-61-7)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0℃; for 1h;	99%
With sodium carbonate In water pH=9 - 10;	99%
With triethylamine In chloroform at -10℃; for 2.25h;	88%

2,6-dimethylaniline (87-62-7) + methyl iodide (74-88-4) → N-methyl-2,6-dimethylaniline (767-71-5)

Conditions	Yield
	99%
Stage #1: 2,6-dimethylaniline With n-butyllithium In hexane at -20 - 20℃; for 3h; Inert atmosphere; Stage #2: methyl iodide In diethyl ether at -20 - 20℃; Inert atmosphere;	94%
Stage #1: 2,6-dimethylaniline With n-butyllithium In hexane at -20 - 20℃; for 3h; Inert atmosphere; Stage #2: methyl iodide In diethyl ether at -20 - 20℃; Inert atmosphere;	85%

2,6-dimethylaniline (87-62-7) → 2,6-dimethyl-N-sulfinyl-benzenamine (17420-02-9, 52867-02-4)

Conditions	Yield
With thionyl chloride In benzene for 16h; Reflux;	99%
With thionyl chloride
With thionyl chloride In benzene Heating;
Multistep reaction;
With thionyl chloride In toluene Reflux;

Upstream product

• 4919-40-8 4-amino-3,5-dimethylbenzoic acid 
• 64289-45-8 3-amino-2,4-dimethylbenzoic acid 
• 56-23-5 tetrachloromethane 
• 5152-79-4 acetic acid-(N-chloro-2,6-dimethyl-anilide) 
• 94-36-0 dibenzoyl peroxide 
• 26334-20-3 2,6-dimethylphenylazide 
• 18201-61-1 N-(2,6-dimethylphenyl)anthranilic acid 
• 576-22-7 2-Bromo-m-xylene 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 
• 39604-15-4 2,6-dimethylphenyl diethyl phosphate 
• 105887-10-3 Acetic acid 1-(2,6-dimethyl-phenylcarbamoyl)-1-methyl-2-oxo-propyl ester 
• 49673-43-0 N¹,N²-bis(2,6-dimethylphenyl)ethane-1,2-diimine 
• 613-73-0 1,2-phenylenediacetonitrile 
• 77470-76-9 4-chlorobutyro-2',6'-xylidide 

Downstream Products

• 22442-56-4 2,6-dimethyl-4-tricyanovinylaniline 
• 108954-75-2 2-Cyano-3-(2,6-dimethyl-phenylamino)-but-2-enedinitrile 
• 124143-91-5 2,6-dimethyl-N-(2-pyrrolidino-ethyl)-aniline 
• 109366-40-7 2,6-dimethyl-N-(2-morpholino-ethyl)-aniline 
• 52793-02-9 N-(2,6-dimethylphenyl)-3-oxobutanamide 
• 84951-65-5 Nicotinsaeure-(2,6-dimethyl-anilid) 
• 68280-05-7 N-(2,6-dimethylphenyl)pyridine-4-carboxamide 
• 68873-22-3 N-(2,6-dimethylphenyl)furan-2-carboxamide 
• 136341-01-0 N-(2,6-dimethyphenyl)thiophene-2-carboxamide 
• 100718-36-3 4-(2,6-dimethyl-phenylcarbamoyl)-3-methyl-crotonic acid 
• 60277-11-4 1-[N-(2,6-dimethyl-phenyl)-glycyl]-pyrrolidine 
• 92698-91-4 1-[N-(2,6-dimethyl-phenyl)-glycyl]-piperidine 
• 119569-81-2 2,6-dimethyl-N-[2-(piperidin-1-yl)ethyl]aniline 
• 20730-99-8 N-(2,6-dimethylphenyl)phthalimide 

Relevant articles and documents

Substitution of OH with NH2 in calix[4]arenes: An approach to the synthesis of aminocalixarenes

From p-t-butylcalix[4]arene bis(diethylphosphate) ester (1), monodehydroxymonoamino-p-t-butylcalix[4]arene (3) and diamino-p-t-butyl-calix[4]arene (4) were synthesized in liquid ammonia-co-solvent in the presence of KNH2. This is the first successful example for the substitution of the OH group with the NH2 group.

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Pd nanoparticles/graphene quantum dot supported on chitosan as a new catalyst for the reduction of nitroarenes to arylamines

A new heterogeneous catalyst was obtained by growing graphene quantum dots on chitosan and subsequent immobilization of Pd nanoparticles. The catalyst after characterization was used in the reduction of nitroarenes to the corresponding amines by NaBH4 as a weak reducing agent of nitro compounds. The catalyst exhibited excellent catalytic activity and selectivity under mild reaction conditions in water as a green solvent during 1?h. Additionally, the catalyst can be reused for five consecutive runs without any significant decrease in its activity and selectivity.