Product Name

  • Name

    3,5-Dimethylaniline

  • EINECS 203-607-0
  • CAS No. 108-69-0
  • Article Data71
  • CAS DataBase
  • Density 0.972 g/cm3
  • Solubility <0.1 g/100 mL at 19 °C in water
  • Melting Point 7-9 °C
  • Formula C8H11N
  • Boiling Point 218.5 °C at 760 mmHg
  • Molecular Weight 121.182
  • Flash Point 93.3 °C
  • Transport Information UN 1711 6.1/PG 2
  • Appearance clear yellow-brown to brown liquid
  • Safety 28-36/37-45-61-28A
  • Risk Codes 23/24/25-33-51/53
  • Molecular Structure Molecular Structure of 108-69-0 (3,5-Dimethylaniline)
  • Hazard Symbols ToxicT,DangerousN
  • Synonyms 3,5-Dimethylbenzeneamine;3,5-Xylidine;3,5-Dimethy Iani line;3,5-Dimethyl aniline;Product Name: 3,5-dimethylaniline;3,5-Xylidene;3,5-Xylylamine;5-Amino-1,3-xylene;3, 5-Dimethylbenzeneamine;benzenamine, 3,5-dimethyl-;1-Amino-3,5-dimethylbenzene;5-Amino-1,3-dimethylbenzene;Benzene, 1-amino-3,5-dimethyl-;3,5-Xylidine;3, 5-Xylylamine;3,5-Dimethylphenylamine;3,5-Dimethylbenzenamine;
  • PSA 26.02000
  • LogP 2.46680

Synthetic 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;

3,5-Dimethylaniline Chemical Properties

Molecular Formula:C8H11N
Molar mass:121.17964g/mol
Structure:
              
Synonyms :3,5-Xylidene;3,5-Dimethylbenzenamine;Benzenamine, 3,5-dimethyl-;5-Amino-1,3-xylene;3,5-Xylylamine;5-Amino-m-xylene;m-Xylidine
Density:0.975 g/cm                         
Flash Point:93.3 °C             
Boiling Point:218.5 °C at 760 mmHg         
Index of Refraction:1.559        
Vapour Pressure:0.126 mmHg at 25°C   
Melting point:7-9°C
Solubility: Not dissolve in water
Water solubility:<0.1 g/100 mL at 19°C

3,5-Dimethylaniline Uses

3,5-Dimethylaniline(108-69-0) is used for production of pesticides, dyes, and other chemicals.

3,5-Dimethylaniline Toxicity Data With Reference

1.   

mmo-sat 1 mg/plate

   EMMUEG    Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1.
2.   

orl-rat LD50:707 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB214-270 .
3.   

orl-mus LD50:421 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB214-270 .
4.   Carcinogenicity:3,5-Dimethylaniline(108-69-0)- Not listed as a carcinogen by  NTP, IARC,ACGIH, or CA Prop 65. 
Other: See actual entry in RTECS for complete information.

3,5-Dimethylaniline Consensus Reports

Reported in EPA TSCA Inventory.

3,5-Dimethylaniline Safety Profile

Suspected carcinogen. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also XYLIDINE; 2,3-XYLIDINE; 2,4-XYLIDINE; 2,5-XYLIDINE; 2,6-XYLIDINE; 3,4-XYLIDINE; 2,4-XYLIDINE HYDROCHLORIDE; 2,5-XYLIDINE HYDROCHLORIDE.
Hazard Codes:T,N
Risk Statements:
23:  Toxic by inhalation
24:  Toxic in contact with skin
25:  Toxic if swallowed
33:  Danger of cumulative effects
51:  Toxic to aquatic organisms
53:  May cause long-term adverse effects in the aquatic environment
28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 
37:  Wear suitable gloves
39:  Wear eye/face protection
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
61:  Avoid release to the environment. Refer to special instructions safety data sheet

3,5-Dimethylaniline Standards and Recommendations

DFG MAK: (all isomers except 2,4-xylidene) Confirmed Animal Carcinogen with Unknown Relevance to Humans

3,5-Dimethylaniline Specification

Stability and Reactivity of 3,5-Dimethylaniline(108-69-0):
Conditions to Avoid:Incompatible materials, light, exposure to air, excess heat. 
Chemical Stability:Stable under normal pressures and temperatures. Darkens on exposure to light and air.
Incompatibilities with Other Materials: Excess heat, chloroformates, acids, acid chlorides,acid anhydrides,halogens,coatings, plastics, rubber, hypochlorite.
Hazardous Decomposition Products: carbon dioxide,nitrogen oxides,Carbon monoxide.
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