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108-69-0 Usage

Chemical Properties

clear yellow-brown to brown liquid

Uses

3,5-Dimethylaniline is the reagent commonly useful in the manufacture of dyes. It undergoes polymerization in the presence of cerium(IV) sulfate as an oxidant. 3,5-Dimethylaniline was used in the synthesis of chiral packing materials for high performance liquid chromatography.

General Description

Dark brown liquid.

Air & Water Reactions

3,5-Dimethylaniline may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

3,5-Dimethylaniline ignites on contact with fuming nitric acid . 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.

Fire Hazard

3,5-Dimethylaniline is combustible.

Safety Profile

Suspected carcinogen. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also other xylidine entries.

Purification Methods

Convert sym-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 it. The acetyl derivative has m 144o, the benzoyl derivative has m 136o and the picrate has m 209o (from H2O, EtOH or 10% AcOH). [Beilstein 12 H 1131, 12 IV 2561.]

Check Digit Verification of cas no

The CAS Registry Mumber 108-69-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 108-69:
(5*1)+(4*0)+(3*8)+(2*6)+(1*9)=50
50 % 10 = 0
So 108-69-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-6-4-3-5-8(9)7(6)2/h3-5H,9H2,1-2H3

108-69-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A10570)  3,5-Dimethylaniline, 97+%   

  • 108-69-0

  • 100g

  • 480.0CNY

  • Detail
  • Alfa Aesar

  • (A10570)  3,5-Dimethylaniline, 97+%   

  • 108-69-0

  • 500g

  • 1620.0CNY

  • Detail

108-69-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,5-Dimethylaniline

1.2 Other means of identification

Product number -
Other names 3,5-Xylidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-69-0 SDS

108-69-0Synthetic route

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;100%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;91%
With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 24h;86%
With diethylenetriaminopentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide In water at 100℃; for 6h;74%
Stage #1: 5-bromo-1,3-xylene With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;
74%
5-nitro-m-xylene
99-12-7

5-nitro-m-xylene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With borane-ammonia complex In methanol; water at 49.84℃; for 0.166667h; Catalytic behavior;99%
With sodium tetrahydroborate In water at 60℃; for 0.0166667h;96%
Stage #1: 5-nitro-m-xylene With Cu(OH)x impregnated on Fe3O4 In water for 0.0833333h; Green chemistry;
Stage #2: With sodium tetrahydroborate In water at 55 - 60℃; for 0.116667h; Green chemistry;
95%
3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;99%
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid; ammonia In water; dimethyl sulfoxide at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;95%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere;92%
1-chloro-3,5-dimethylbenzene
556-97-8

1-chloro-3,5-dimethylbenzene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;99%
Multi-step reaction with 2 steps
1.1: sulfuric acid; nitric acid / 30 °C / Cooling with ice
2.1: palladium on activated charcoal / ethanol / 0.5 h / 50 °C / Autoclave
2.2: 0.83 h / 65 °C / 2250.23 Torr / Autoclave
View Scheme
N-hydroxy-3,5-dimethylbenzamide
62034-72-4

N-hydroxy-3,5-dimethylbenzamide

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 4h; Lossen Rearrangement;97%
3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With palladium/alumina; ammonia; hydrogen In toluene at 250℃; under 2250.23 Torr; Temperature; Pressure; Solvent;95%
With 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;71%
With ammonia at 350℃; under 117681 - 183877 Torr;
With aluminum oxide; nitrogen; ammonia; hydrogen at 450℃; under 147102 Torr;
3,5-dimethyl-cyclohexanone oxime
101252-04-4

3,5-dimethyl-cyclohexanone oxime

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With Pd(OH)x/LDH In N,N-dimethyl acetamide at 130℃; for 11h; Schlenk technique; Inert atmosphere;91%
5-[(3,5-dimethylphenyl)imino]-5H-5γ4-dibenzo[b,d]thiophene-5-oxide

5-[(3,5-dimethylphenyl)imino]-5H-5γ4-dibenzo[b,d]thiophene-5-oxide

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 100℃; Sealed tube;88%
1,2,3,4-tetrahydroisoquinoline
635-46-1

1,2,3,4-tetrahydroisoquinoline

5-nitro-m-xylene
99-12-7

5-nitro-m-xylene

A

quinoline
91-22-5

quinoline

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 73%
B 76%
5-nitro-m-xylene
99-12-7

5-nitro-m-xylene

2-methyl indoline
6872-06-6

2-methyl indoline

A

2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 74%
B 76%
3,5-dimethylcyclohexanone
2320-30-1

3,5-dimethylcyclohexanone

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 15h; Schlenk technique;71%
ethanol
64-17-5

ethanol

5-nitro-m-xylene
99-12-7

5-nitro-m-xylene

A

2,5,7-trimethylquinoline
102871-67-0

2,5,7-trimethylquinoline

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With platinum-loaded TiO2 at 30℃; for 5h; UV-irradiation;A 68%
B 16%
2,4-Xylenol
105-67-9

2,4-Xylenol

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
Stage #1: 2,4-Xylenol With Nonafluorobutanesulfonyl fluoride; tris(trimethylsilyl)amine; potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 5h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 0.0833333h; pH=3 - 4;
67%
5-methoxyindoline
21857-45-4

5-methoxyindoline

5-nitro-m-xylene
99-12-7

5-nitro-m-xylene

A

5-methoxylindole
1006-94-6

5-methoxylindole

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 62%
B 61%
m-xylene
108-38-3

m-xylene

A

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

B

2,4-Xylidine
95-68-1

2,4-Xylidine

C

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

Conditions
ConditionsYield
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;
3,5-dimethylbenzoic acid
499-06-9

3,5-dimethylbenzoic acid

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With hydrogenchloride; PPA; hydroxylamine
3,5-dimethylbenzamide
5692-35-3

3,5-dimethylbenzamide

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With alkaline sodium hypobromite
2-amino-4,6-dimethylbenzene-1,3-dicarbonitrile
10272-10-3

2-amino-4,6-dimethylbenzene-1,3-dicarbonitrile

A

2-amino-4,6-dimethyl benzamide
875241-52-4

2-amino-4,6-dimethyl benzamide

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With sulfuric acid
3,5-dimethyl-cyclohex-2-enone oxime
67543-92-4

3,5-dimethyl-cyclohex-2-enone oxime

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With hydrogenchloride at 170℃;
3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

A

bis-(3,5-dimethylphenyl)-amine
5369-25-5

bis-(3,5-dimethylphenyl)-amine

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With ammonium chloride at 350℃; under 36775.4 Torr;
5-nitro-m-xylene

5-nitro-m-xylene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride
With iron; acetic acid
With hydrogenchloride; tin
ammonia
7664-41-7

ammonia

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
at 350℃; under 117681 Torr;
ammonium chloride

ammonium chloride

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

A

bis-(3,5-dimethylphenyl)-amine
5369-25-5

bis-(3,5-dimethylphenyl)-amine

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
at 350℃; under 36775.4 - 44130.5 Torr;
3,5-dimethylbenzamide
5692-35-3

3,5-dimethylbenzamide

alkaline hypobromite

alkaline hypobromite

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

1,2,3-triethylbenzene
42205-08-3

1,2,3-triethylbenzene

bis-(3,5-dimethyl-cyclohex-2-enylidene)-hydrazine
83186-90-7

bis-(3,5-dimethyl-cyclohex-2-enylidene)-hydrazine

palladium/charcoal

palladium/charcoal

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

hydrogenchloride
7647-01-0

hydrogenchloride

4-(3,5-dimethyl-phenylazo)-3,5-dimethyl-aniline
91536-77-5

4-(3,5-dimethyl-phenylazo)-3,5-dimethyl-aniline

tin

tin

A

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

B

2.5-diamino-m-xylene

2.5-diamino-m-xylene

[Pd((CH3)2C6H3NH2)4](2+)*2CF3COCHCOCF3(1-)=[Pd((CH3)2C6H3NH2)4](CF3COCHCOCF3)2

[Pd((CH3)2C6H3NH2)4](2+)*2CF3COCHCOCF3(1-)=[Pd((CH3)2C6H3NH2)4](CF3COCHCOCF3)2

[Pd(CF3COCHCOCF3)((CH3)2C6H3NH2)2](1+)*CF3COCHCOCF3(1-)=[Pd(CF3COCHCOCF3)((CH3)2C6H3NH2)2](CF3COCHCOCF3)

[Pd(CF3COCHCOCF3)((CH3)2C6H3NH2)2](1+)*CF3COCHCOCF3(1-)=[Pd(CF3COCHCOCF3)((CH3)2C6H3NH2)2](CF3COCHCOCF3)

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
In chloroform-d1 not isolated; detected by NMR;
(E)-cyclooct-2-en-1-yl (3,5-dimethylphenyl)carbamate

(E)-cyclooct-2-en-1-yl (3,5-dimethylphenyl)carbamate

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With 3,6-dimethyl-1,2,4,5-tetrazine; formic acid In acetonitrile at 20℃; for 1h; Reagent/catalyst; Solvent;
With 3,6-dimethyl-1,2,4,5-tetrazine; formic acid In acetonitrile at 20℃; for 1h; Reagent/catalyst; Solvent;
3,6-dimethyl-1,2,4,5-tetrazine
1558-23-2

3,6-dimethyl-1,2,4,5-tetrazine

C17H23NO2

C17H23NO2

A

C12H18N2
86997-05-9

C12H18N2

B

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With pyridine In acetonitrile at 20℃; for 1h; Reagent/catalyst;
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(3,5-dimethylphenyl)-4-methyl-benzenesulfonamide
114097-28-8

N-(3,5-dimethylphenyl)-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With silica gel at 20℃;95%
With triethylamine In dichloromethane at 0 - 20℃;82%
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Trimethylacetic acid
75-98-9

Trimethylacetic acid

N-(3,5-dimethylphenyl)pivalamide
86489-67-0

N-(3,5-dimethylphenyl)pivalamide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl (Z)-N-(3,5-dimethylphenyl)aminofumarate
92952-51-7

dimethyl (Z)-N-(3,5-dimethylphenyl)aminofumarate

Conditions
ConditionsYield
at 20℃; for 0.133333h; Michael addition;100%
In diethyl ether at 0℃;75%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3,5-dimethyl-N-(4-methoxybenzylidene)aniline
199435-31-9

3,5-dimethyl-N-(4-methoxybenzylidene)aniline

Conditions
ConditionsYield
at 20℃;100%
With acetic acid In methanol at 20℃;
Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

2-(3,5-dimethylphenylamino)-2-oxoacetic acidethyl ester
333441-77-3

2-(3,5-dimethylphenylamino)-2-oxoacetic acidethyl ester

Conditions
ConditionsYield
With pyridine at 20℃; for 1.5h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 0 - 20℃;68%
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3-(3,5-dimethyl-phenylamino)-propionamide
857070-85-0

3-(3,5-dimethyl-phenylamino)-propionamide

Conditions
ConditionsYield
With ammonia In methanol at 80℃;100%
2-(2-tert-butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid
864460-87-7

2-(2-tert-butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 12h;100%
{4-[6-formyl-1-(3-hydroxy-6-methylpyridin-2-ylmethyl)-1H-benzoimidazol-2-ylamino]piperidin-1-yl}acetic acid ethyl ester
1009646-49-4

{4-[6-formyl-1-(3-hydroxy-6-methylpyridin-2-ylmethyl)-1H-benzoimidazol-2-ylamino]piperidin-1-yl}acetic acid ethyl ester

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

{4-[6-[(3,5-dimethylphenylamino)methyl]-1-(3-hydroxy-6-methylpyridin-2-ylmethyl)-1H-benzoimidazol-2-ylamino]piperidin-1-yl}acetic acid ethyl ester
1009646-54-1

{4-[6-[(3,5-dimethylphenylamino)methyl]-1-(3-hydroxy-6-methylpyridin-2-ylmethyl)-1H-benzoimidazol-2-ylamino]piperidin-1-yl}acetic acid ethyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In acetonitrile at 20℃; for 12h;100%
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

N,N'-di(3,5-dimethylphenyl)benzene-1,2-diamine
1068437-89-7

N,N'-di(3,5-dimethylphenyl)benzene-1,2-diamine

Conditions
ConditionsYield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene100%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere;100 %Chromat.
β-(1-naphthyl)nitroethylene
37630-26-5, 4735-49-3

β-(1-naphthyl)nitroethylene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C20H20N2O2
1268482-47-8

C20H20N2O2

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
1-nitro-2-(2-nitrovinyl)benzene
5670-66-6, 5670-67-7, 3156-39-6

1-nitro-2-(2-nitrovinyl)benzene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C16H17N3O4
1268482-40-1

C16H17N3O4

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C16H18N2O2
1266995-18-9

C16H18N2O2

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
3-nitro-β-nitrostyrene
882-26-8

3-nitro-β-nitrostyrene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3,5-dimethyl-N-[2-nitro-1-(3-nitro-phenyl)-ethyl]-aniline
108836-94-8

3,5-dimethyl-N-[2-nitro-1-(3-nitro-phenyl)-ethyl]-aniline

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
1-chloro-4-(2-nitrovinyl)benzene
706-07-0

1-chloro-4-(2-nitrovinyl)benzene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C16H17ClN2O2
1268482-45-6

C16H17ClN2O2

Conditions
ConditionsYield
at 20℃; for 0.1h; Michael addition; neat (no solvent);100%
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl (Z)-N-(3,5-dimethylphenyl)aminofumarate
1349802-62-5

diethyl (Z)-N-(3,5-dimethylphenyl)aminofumarate

Conditions
ConditionsYield
at 20℃; for 0.15h; Michael addition;100%
benzaldehyde
100-52-7

benzaldehyde

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3,5-dimethyl-N-benzylideneaniline
91000-43-0

3,5-dimethyl-N-benzylideneaniline

Conditions
ConditionsYield
at 20℃;100%
In methanol99%
In ethanol for 3h; Reflux;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3,5-dimethyl-N-(4-methylbenzylidene)aniline
107399-20-2

3,5-dimethyl-N-(4-methylbenzylidene)aniline

Conditions
ConditionsYield
at 20℃;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3,5-dimethyl-N-(4-chlorobenzylidene)aniline
180569-73-7

3,5-dimethyl-N-(4-chlorobenzylidene)aniline

Conditions
ConditionsYield
at 20℃;100%
In neat (no solvent) at 20℃; for 0.5h; Schlenk technique; Molecular sieve; Inert atmosphere;
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

3,5-dimethyl-N-(4-bromobenzylidene)aniline
348601-49-0

3,5-dimethyl-N-(4-bromobenzylidene)aniline

Conditions
ConditionsYield
at 20℃;100%
Isophthalaldehyde
626-19-7

Isophthalaldehyde

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C24H26N2

C24H26N2

Conditions
ConditionsYield
at 20℃;100%
2-bromo-butyryl bromide
26074-52-2

2-bromo-butyryl bromide

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

2-bromo-N-(3,5-dimethylphenyl)butanamide

2-bromo-N-(3,5-dimethylphenyl)butanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
3-Hydroxy-3-methylbutyric acid
625-08-1

3-Hydroxy-3-methylbutyric acid

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

C13H19NO2

C13H19NO2

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 14h;100%
acetic anhydride
108-24-7

acetic anhydride

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

N-acetyl-3,5-dimethylaniline
2050-45-5

N-acetyl-3,5-dimethylaniline

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;99%
Stage #1: acetic anhydride; 3,5-dimethylaminoaniline In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #2: With sodium hydroxide In tetrahydrofuran; water pH=12 - 14; Cooling with ice;
99%
Stage #1: acetic anhydride; 3,5-dimethylaminoaniline In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: With sodium hydroxide In tetrahydrofuran; water pH=12 - 14; Cooling with ice;
99%
3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

acetyl chloride
75-36-5

acetyl chloride

N-acetyl-3,5-dimethylaniline
2050-45-5

N-acetyl-3,5-dimethylaniline

Conditions
ConditionsYield
With triethylamine In dichloromethane at 201℃; for 1h;99%
Stage #1: 3,5-dimethylaminoaniline With potassium carbonate In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: acetyl chloride for 2h; Inert atmosphere;
99%
With potassium carbonate In dichloromethane at 20℃; for 2.5h; Cooling with ice;98.8%
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide
131179-77-6

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;99%
With boric acid In toluene for 18h; Heating;95%
With pyridine; FI-750-M; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 60℃; for 0.75h; Sealed tube;86%
2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate
2009-81-6

2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3-(3,5-dimethylphenylamino)-2-(dimethylphenyliminomethyl)propenal hydrogenperchlorate

3-(3,5-dimethylphenylamino)-2-(dimethylphenyliminomethyl)propenal hydrogenperchlorate

Conditions
ConditionsYield
With perchloric acid In ethanol at 105℃; for 1.5h;99%
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

(S)-tert-butyl 2-((3,5-dimethylphenyl)carbamoyl)pyrrolidine-1-carboxylate
137496-70-9

(S)-tert-butyl 2-((3,5-dimethylphenyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With chloroformic acid ethyl ester; triethylamine In dichloromethane at 20℃; for 1h;99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h;85%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 12h; Ambient temperature;65%
para-chlorotoluene
106-43-4

para-chlorotoluene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

3,5-dimethyl-N-p-tolylbenzenamine
34160-16-2

3,5-dimethyl-N-p-tolylbenzenamine

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1.5h; Inert atmosphere;99%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; potassium hydroxide; sodium t-butanolate In water at 110℃; for 22h; Buchwald-Hartwig amination; Inert atmosphere; chemoselective reaction;95%
With sodium t-butanolate; [Na2PdCl4]; dicyclohexyl-(9-ethyl-9H-fluoren-9-yl)phosphane*HBF4 In toluene at 120℃; for 12h; Buchwald-Hartwig coupling reaction;
With sodium t-butanolate; palladium diacetate; dicyclohexyl(9-ethyl-9H-fluorene-9-yl)-phosphine·HBF4 In toluene at 120℃; for 12h; Product distribution / selectivity; Buchwald-Hartwig Amination;

108-69-0Relevant articles and documents

-

Haller,Adams,Wherry

, p. 1842 (1920)

-

First example of using a ionic liquid in electrophilic amination of arenes. Amination of methylbenzenes with the system NaN3-AlCl 3-HCl

Borodkin,Elanov,Shubin

, p. 1541 - 1542 (2004)

-

Coordination or Oxidative Addition? Activation of N-H with [Tp′Rh(PMe3)]

Yuwen, Jing,Brennessel, William W.,Jones, William D.

, p. 557 - 566 (2019)

A thermal reaction of amines, anilines, and amides with Tp′Rh(PMe3)(CH3)H (1, Tp′ = tris(3,5-dimethyl-pyrazolyl)borate) is described in this report. No N-H bond cleavage was observed for reactions between ammonia or unsubstituted aliphatic amines with the reactive fragment [Tp′Rh(PMe3)]. Instead, amine coordination products (κ2-Tp′)Rh(PMe3)(NHR1R2) (R1 = H, R2 = H, nPr, iPr, octyl; R1 = R2 = Et; R1, R2: pyrrolidine) were observed, and the crystal structure of (κ2-Tp′)Rh(PMe3)(NH2iPr) is reported. No coordination products were observed when 1 was reacted with 1,1,1,3,3,3-hexafluoropropan-2-amine, anilines, and amides. Instead, the oxidative addition products (κ3-Tp′)Rh(PMe3)(NHR)H (R = CH(CF3)2, C6H5, 3,5-dimethylbenzyl, C6F5, C(O)CH3, C(O)CF3) were observed. Both RhI-N coordination products (κ2-Tp′)Rh(PMe3)(NH2CH2CF3) and RhIII N-H addition products (κ3-Tp′)Rh(PMe3)(NHCH2CF3)H were generated when 1 was reacted with 2,2,2-trifluoroethylamine. Coordination products dissociate ammonia and amines in benzene much faster than oxidative addition products eliminate anilines and amides. The relative metal-nitrogen bond energies were studied using established kinetic techniques. Analysis of the relationship between the relative M-N bond strengths and N-H bond strengths showed a linear correlation with a slope = RM-N/N-H of 0.91 (10), indicating that the Rh-N bond strength varies in direct proportion to the N-H bond strength.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.

, p. 2895 - 2906 (2021/02/27)

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko

supporting information, p. 1530 - 1534 (2021/03/08)

The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

-

Paragraph 0111-0119, (2021/05/29)

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

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