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88-05-1

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88-05-1 Usage

Chemical Properties

clear yellow to brown liquid. Insoluble in water, soluble in organic solvents such as ethanol and ether.

Uses

2,4,6-Trimethylaniline is useful for the preparation of Grubbs' catalyst. It is used as a precursor to dyes. It undergoes condensation reaction with glyoxal to prepare glyoxal-bis(mesitylimine). It is also involved in the preparation of 1,3-diketimines ligands by condensation with 1,3-diketones. Further, it is used for the production of Acid Blue 129 dye, which is useful in histochemistry studies. In addition to this, it serves as a building block to various bulky ligands.

Preparation

2,4,6-Trimethylaniline is prepared by selective mononitration of mesitylene, avoiding oxidation of the methyl groups.Mix sulfuric acid and nitric acid into mixed acid, nitrify with mesitylene at atmospheric pressure below 10°C for 4 hours, stand for stratification, and let off the waste acid. The obtained 2,4,6-trimethylnitrobenzene, iron powder, hydrochloric acid and water were prepared in a ratio of 1:3.74:0.9:2.22 (mol ratio) for reduction reaction at 100-105°C for 8h. Crude 2,4,6-Trimethylaniline was then distilled off from the reduced material and purified by distillation.

General Description

2,4,6-Trimethylaniline is a clear liquid. easily turns light brown when exposed to air and light. It is an intermediate for dyes, organic pigments and pesticides.

Reactivity Profile

2,4,6-Trimethylaniline 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

2,4,6-Trimethylaniline is moderately toxic orally. It is also considered highly toxic by unspecified routes. It is a skin and eye irritant. Suspect occupational carcinogen. (Non-Specific -- Aromatic Amines) The danger of acute poisoning is represented by methemoglobinemia leading to adverse effects on the red cells. A number of the amines may act as skin sensitizers.

Fire Hazard

When heated to decomposition, 2,4,6-Trimethylaniline emits toxic fumes of nitrogen oxides. Avoid decomposing heat.

Safety Profile

Poison by inhalation. Moderately toxic by ingestion. A skin and severe eye irritant. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

Used on small scale in organic synthesis.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Check Digit Verification of cas no

The CAS Registry Mumber 88-05-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 88-05:
(4*8)+(3*8)+(2*0)+(1*5)=61
61 % 10 = 1
So 88-05-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H13N/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,10H2,1-3H3

88-05-1 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A13049)  2,4,6-Trimethylaniline, 98%   

  • 88-05-1

  • 100g

  • 306.0CNY

  • Detail
  • Alfa Aesar

  • (A13049)  2,4,6-Trimethylaniline, 98%   

  • 88-05-1

  • 500g

  • 1296.0CNY

  • Detail
  • Alfa Aesar

  • (A13049)  2,4,6-Trimethylaniline, 98%   

  • 88-05-1

  • 2500g

  • 5834.0CNY

  • Detail

88-05-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4,6-Trimethylaniline

1.2 Other means of identification

Product number -
Other names Benzenamine, 2,4,6-trimethyl-

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:88-05-1 SDS

88-05-1Synthetic route

1-Benzyl-1,4-dihydronicotinamide
952-92-1

1-Benzyl-1,4-dihydronicotinamide

A

1-benzyl-3-carbamoylpyridinium ion
16183-83-8

1-benzyl-3-carbamoylpyridinium ion

B

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
In acetonitrile at 25℃; Kinetics;A 100%
B 85%
N-methyl-2,4,6-trimethylaniline
13021-14-2

N-methyl-2,4,6-trimethylaniline

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
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%
nitromesitylene
603-71-4

nitromesitylene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran for 12h;99%
With titanium tetrachloride; di-isobutyl telluride In dichloromethane for 0.5h; Ambient temperature;98%
With hydrogen In tetrahydrofuran; water at 120℃; under 37503.8 Torr; for 24h; chemoselective reaction;96%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
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;99%
With copper(l) iodide; sodium azide; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere;72%
Stage #1: 2,4,6-trimethylphenyl bromide With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With 3-tert-butyl-3-phenyloxaziridine In tetrahydrofuran; toluene at -45℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Reagent/catalyst; Inert atmosphere;
31%
2,4,6-Trimethylacetophenone
1667-01-2

2,4,6-Trimethylacetophenone

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;96%
With ethanol; hydroxylamine hydrochloride at 160℃; und Erhitzen mit Salzsaeure im Druckrohr;
anti-2,2',4,4',6,6'-Hexamethylazobenzene
20488-59-9

anti-2,2',4,4',6,6'-Hexamethylazobenzene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With sodium dithionite In methanol; dichloromethane; water for 3h; Heating;96%
nitromesitylene
603-71-4

nitromesitylene

A

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

B

tellurium

tellurium

Conditions
ConditionsYield
With disodium telluride In 1,4-dioxane; water at 50℃; for 2h;A 95%
B n/a
N,N-dibenzyl-2,4,6-trimethylaniline
137129-03-4

N,N-dibenzyl-2,4,6-trimethylaniline

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;95%
carbon monoxide
201230-82-2

carbon monoxide

nitromesitylene
603-71-4

nitromesitylene

A

mesityl isocyanate
2958-62-5

mesityl isocyanate

B

1,3-bis(2,4,6-trimethylphenyl)urea
6095-81-4

1,3-bis(2,4,6-trimethylphenyl)urea

C

anti-2,2',4,4',6,6'-Hexamethylazobenzene
20488-59-9

anti-2,2',4,4',6,6'-Hexamethylazobenzene

D

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
Vanadium (III) chloride-(tris-tetrahydrofuran); (Bu4N) In various solvent(s) at 120℃; for 0.5h; Product distribution; further catalysts, other reaction times;A 94%
B n/a
C n/a
D n/a
Vanadium (III) chloride-(tris-tetrahydrofuran); (Bu4N) In various solvent(s) at 120℃; for 0.5h;A 94%
B n/a
C n/a
D n/a
2,3,5,6-tetrafluoro-4-(2,4,6-trimethylphenylazo)pyridine
86249-71-0

2,3,5,6-tetrafluoro-4-(2,4,6-trimethylphenylazo)pyridine

A

2,3,5,6-tetrafluoropyridin-4-amine
1682-20-8

2,3,5,6-tetrafluoropyridin-4-amine

B

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With sodium disulfite; hydrogen iodide for 1h; Heating;A 31%
B 93%
10-Methyl-4a,9,9a,10-tetrahydro-acridine

10-Methyl-4a,9,9a,10-tetrahydro-acridine

A

acridinium

acridinium

B

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
In acetonitrile at 25℃; Kinetics;A 93%
B 78%
mesitylboronic acid
5980-97-2

mesitylboronic acid

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 12h;92%
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In 1,2-dichloro-ethane at 25℃; for 48h; Inert atmosphere;42%
1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With tert-butyl N-tosyloxycarbamate at 20℃; for 36h; Solvent; Reagent/catalyst; Temperature; Concentration; chemoselective reaction;89%
With 16-crown-6; 1-aminoquinolinium perchlorate In trifluoroacetic acid for 4h; Irradiation;80%
With hydrogenchloride; aluminium trichloride; sodium azide In various solvent(s) at 20℃;76%
N-(diphenyl methylene)-2,4,6-trimethylaniline
67565-93-9

N-(diphenyl methylene)-2,4,6-trimethylaniline

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
Acid hydrolysis;87%
2,4,6-trimethylphenyl p-toluenesulfonate
356031-47-5

2,4,6-trimethylphenyl p-toluenesulfonate

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
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 50℃; for 24h; Inert atmosphere;86%
(2,4,6-trimethyl-phenyl)-carbamic acid tert-butyl ester
56700-69-7

(2,4,6-trimethyl-phenyl)-carbamic acid tert-butyl ester

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With methanol; oxalyl dichloride at 20℃; for 2h;83%
1-fluoro-2,4,6-trimethylbenzene
392-69-8

1-fluoro-2,4,6-trimethylbenzene

potassium enolate of acetone
128190-66-9, 25088-58-8

potassium enolate of acetone

A

1-(2,4,6-trimethylphenyl)-2-propanone
42797-68-2

1-(2,4,6-trimethylphenyl)-2-propanone

B

1-(2,4,6-Trimethylphenyl)-2-propanol
27645-30-3

1-(2,4,6-Trimethylphenyl)-2-propanol

C

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

D

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With ammonia; potassium amide at -33℃; Product distribution; Rate constant;A 2.8%
B 5.6%
C 11.7%
D 80%
With ammonia; potassium amide at -33℃;A 1.8 % Chromat.
B 3.1 % Chromat.
C 18.2 % Chromat.
D 77 % Chromat.
With ammonia; potassium amide at -33℃;A 2.8 % Chromat.
B 5.6 % Chromat.
C 11.7 % Chromat.
D 80 % Chromat.
dimesityl-1,3-tetraphenylcyclodigermazane
122422-41-7

dimesityl-1,3-tetraphenylcyclodigermazane

3,5-di-tert-butyl-o-benzoquinone
3383-21-9

3,5-di-tert-butyl-o-benzoquinone

A

2,2-diphenyl(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolane
110577-23-6

2,2-diphenyl(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolane

B

ditertiobutyl-2,4 (trimethyl-2,4,6 phenylimino)-6 cyclohexadiene-2,4 one-1
112079-83-1

ditertiobutyl-2,4 (trimethyl-2,4,6 phenylimino)-6 cyclohexadiene-2,4 one-1

C

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
In benzene-d6 inert atmosphere (Ar or N2); 100°C, 12 h; not isolated; (1)H-NMR;A n/a
B <1
C 80%
(C6H5)2ClGeNHC6H2(CH3)3
122422-42-8

(C6H5)2ClGeNHC6H2(CH3)3

3,5-di-tert-butyl-o-benzoquinone
3383-21-9

3,5-di-tert-butyl-o-benzoquinone

A

2,2-diphenyl(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolane
110577-23-6

2,2-diphenyl(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolane

B

ditertiobutyl-2,4 (trimethyl-2,4,6 phenylimino)-6 cyclohexadiene-2,4 one-1
112079-83-1

ditertiobutyl-2,4 (trimethyl-2,4,6 phenylimino)-6 cyclohexadiene-2,4 one-1

C

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene-d6 byproducts: DBU*HCl; inert atmosphere (Ar or N2); 20°C, 17 h; (1)H-NMR; evapn., pentane addn., filtn.;A 67%
B <1
C 80%
2-bromomesitylene
1667-04-5

2-bromomesitylene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate at 100 - 110℃; for 12h;72%
mesitylenecarboxylic acid
480-63-7

mesitylenecarboxylic acid

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
Stage #1: mesitylenecarboxylic acid With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; for 0.06h; Schmidt Reaction; Flow reactor;
Stage #2: With water In methanol; chloroform at 20℃; Schmidt Reaction; Flow reactor;
71%
2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

A

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

B

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
ConditionsYield
With sodium amide In diethyl ether; ammonia for 2h; Irradiation;A 70%
B 6%
With sodium amide In diethyl ether; ammonia for 2h; Product distribution; Irradiation; variation of reaction conditions;A 70%
B 6%
N-(tert-butoxycarbonyl)-O-(mesitylsulfonyl)hydroxylamine
36016-39-4

N-(tert-butoxycarbonyl)-O-(mesitylsulfonyl)hydroxylamine

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0℃; for 25h; regioselective reaction;70%
With Rh2(esp)2; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0 - 20℃; for 25h; Inert atmosphere;70%
18-crown-6 ether
17455-13-9

18-crown-6 ether

potassium graphite

potassium graphite

C52H58Br2N8Ni2

C52H58Br2N8Ni2

A

C12H24O6*2C17H19N3(1-)*K(1+)*Ni(1+)

C12H24O6*2C17H19N3(1-)*K(1+)*Ni(1+)

B

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
In benzene at 20℃; for 12h; Inert atmosphere;A 70%
B n/a
iodomesitylene
4028-63-1

iodomesitylene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Sealed tube;60%
cyclohexa-1,4-diene
1165952-92-0

cyclohexa-1,4-diene

A

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
In acetonitrile at 25℃; Kinetics;A 26%
B 60%
2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

C28H33MnN5O4

C28H33MnN5O4

A

3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol
6390-69-8

3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol

B

[MnIII(3,4,8,9-tetrahydro-3,3,6,6,9-hexamethyl-1H-1,4,8,11-benzotetraazocyclotridecane-2,5,7,10-(6H,11H)-tetrone)]-

[MnIII(3,4,8,9-tetrahydro-3,3,6,6,9-hexamethyl-1H-1,4,8,11-benzotetraazocyclotridecane-2,5,7,10-(6H,11H)-tetrone)]-

C

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
In acetonitrile at 20℃; Inert atmosphere;A 25%
B n/a
C 56%
N,N'-bis(2,4,6-trimethylphenyl)ethanediimine
56222-36-7

N,N'-bis(2,4,6-trimethylphenyl)ethanediimine

1,2-phenylenediacetonitrile
613-73-0

1,2-phenylenediacetonitrile

A

naphthalene-1,4-dicarbonitrile
3029-30-9

naphthalene-1,4-dicarbonitrile

B

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 15h;A 54%
B n/a
azidotri-2,4,6-trimethylphenylgermane
124862-47-1

azidotri-2,4,6-trimethylphenylgermane

A

diethoxybis(2,4,6-trimethylphenyl)germane
124862-49-3

diethoxybis(2,4,6-trimethylphenyl)germane

B

Ge(C6H2(CH3)3)2NHCH2(C6H2(CH3)2)
124862-48-2

Ge(C6H2(CH3)3)2NHCH2(C6H2(CH3)2)

C

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With ethanol In ethanol; cyclohexaneA 14%
B 50%
C 11%
mesitylenesulfonylhydroxylamine
36016-40-7

mesitylenesulfonylhydroxylamine

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0℃; for 0.5h; regioselective reaction;49%
With Rh2(esp)2 In 2,2,2-trifluoroethanol at 0℃; for 0.5h; Inert atmosphere;49%
phthalic anhydride
85-44-9

phthalic anhydride

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

1-(N-phthalimido)-2,4,6-trimethylbenzene
93315-97-0

1-(N-phthalimido)-2,4,6-trimethylbenzene

Conditions
ConditionsYield
With acetic acid at 150℃; for 2h; Inert atmosphere;100%
With acetic acid at 140℃; for 12h;90%
With 1H-imidazole at 140℃; for 3h; Inert atmosphere; Schlenk technique;22%
acetic anhydride
108-24-7

acetic anhydride

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-mesitylacetamide
5096-21-9

N-mesitylacetamide

Conditions
ConditionsYield
at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique;100%
With sulfonic acid-functionalized hyper-cross-linked poly(2-naphthol) In neat (no solvent) at 25℃; for 0.166667h; Green chemistry; chemoselective reaction;93%
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium chloride In neat (no solvent) at 20℃; for 0.216667h; Milling; Green chemistry;90%
Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester
79354-30-6

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester

Conditions
ConditionsYield
With pyridine at 20℃; for 1.5h; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;97%
In tetrahydrofuran at 70℃; for 1h;96%
p-Toluic acid
99-94-5

p-Toluic acid

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-(2,4,6-trimethylphenyl)-4-methylbenzamide
86489-65-8

N-(2,4,6-trimethylphenyl)-4-methylbenzamide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
triphenylbismuth(V) diacetate
28899-97-0

triphenylbismuth(V) diacetate

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-mesitylaniline
23592-67-8

N-mesitylaniline

Conditions
ConditionsYield
With copper(II) dipivaloate In dichloromethane for 0.0833333h; Product distribution; Ambient temperature; other BiV reagents; copper-catalyzed phenylation of amines by BiV reagents;100%
copper In dichloromethane for 24h; Ambient temperature;92%
With copper(II) dipivaloate In dichloromethane for 0.0833333h; Ambient temperature;100 % Chromat.
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

(2,4,6-trimethyl-phenyl)-carbamic acid tert-butyl ester
56700-69-7

(2,4,6-trimethyl-phenyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With indium(III) bromide at 30 - 35℃; for 0.5h;100%
Stage #1: 2,4,6-trimethylaniline With triethylamine In tetrahydrofuran; water at 20℃; for 0.0833333h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 6h;
100%
In tetrahydrofuran for 168h; Heating;98%
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride

trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride

5,6-dihydro-2-trifluoromethyl-N-(2,4,6-trimethyl)phenyl-1,4-dioxin-3-carboxamide

5,6-dihydro-2-trifluoromethyl-N-(2,4,6-trimethyl)phenyl-1,4-dioxin-3-carboxamide

Conditions
ConditionsYield
Stage #1: trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride With pyridine; polystyrene-bound 4-hydroxy-3-nitrobenzophenone In dichloromethane at 20℃; for 24h; Acylation;
Stage #2: 2,4,6-trimethylaniline With triethylamine In acetonitrile for 14h; Acylation; Heating;
100%
phenylacetylene
536-74-3

phenylacetylene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-(1-phenylethylidene)-2,4,6-trimethylaniline
75472-71-8, 17432-52-9

N-(1-phenylethylidene)-2,4,6-trimethylaniline

Conditions
ConditionsYield
With [Zn2Cp*3]+[B(3,5-(CF3)2C6H3)4]- at 20℃; for 72h; Reagent/catalyst; Inert atmosphere; Schlenk technique; regioselective reaction;100%
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 1h; Inert atmosphere; regioselective reaction;100%
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%
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

(Z)-4-[2,4,6-Tris-(bis-trimethylsilanyl-methyl)-phenylamino]-pent-3-en-2-one
926625-25-4

(Z)-4-[2,4,6-Tris-(bis-trimethylsilanyl-methyl)-phenylamino]-pent-3-en-2-one

C41H78N2Si6
926625-28-7

C41H78N2Si6

Conditions
ConditionsYield
With titanium tetrachloride In toluene for 16h; Heating;100%
With titanium tetrachloride In toluene for 16h; Heating;94%
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

N1,N2-bis(2,4,6-trimethylphenyl)-1,2-benzenediamine
852414-57-4

N1,N2-bis(2,4,6-trimethylphenyl)-1,2-benzenediamine

Conditions
ConditionsYield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene100%
With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate; sodium t-butanolate In toluene at 60 - 135℃; Inert atmosphere;87%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene for 12h; Heating;86%
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

2,4,6-trimethylaniline hydrochloric acid salt
6334-11-8

2,4,6-trimethylaniline hydrochloric acid salt

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0 - 20℃; for 0.5h;100%
3-nitrophenyl isothiocyanate
3529-82-6

3-nitrophenyl isothiocyanate

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

1-(mesityl)-3-(3-nitrophenyl)thiourea
851886-25-4

1-(mesityl)-3-(3-nitrophenyl)thiourea

Conditions
ConditionsYield
In methanol at 20℃; for 2h;100%
In methanol at 20℃; for 2h;
2-(2,3,4,5-tetramethylcyclopentadienyl)-benzaldehyde

2-(2,3,4,5-tetramethylcyclopentadienyl)-benzaldehyde

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-(2,4,6-trimethylphenyl)amine

N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-(2,4,6-trimethylphenyl)amine

Conditions
ConditionsYield
acetic acid In ethanol at 20℃;100%
2-bromoisobutyric acid bromide
20769-85-1

2-bromoisobutyric acid bromide

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

2-bromo-N-mesityl-2-methylpropanamide
101263-21-2

2-bromo-N-mesityl-2-methylpropanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;94%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N,N'-dimesitylformamidine
75105-48-5

N,N'-dimesitylformamidine

Conditions
ConditionsYield
With acetic acid In neat (no solvent) at 160℃; for 3h;100%
With acetic acid In neat (no solvent) at 120 - 160℃; for 4h;98%
With acetic acid at 90 - 120℃; for 4 - 6h; Product distribution / selectivity;92%
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-(1-(cyclohexyl)ethylidene)-2,4,6-trimethylaniline

N-(1-(cyclohexyl)ethylidene)-2,4,6-trimethylaniline

Conditions
ConditionsYield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 8h; Inert atmosphere; regioselective reaction;100%
With AuC34H47N(1+)*B(C6F5)4(1-)=(AuC34H47N)(B(C6F5)4) In benzyl methyl ether; benzene-d6 at 90℃; for 24h; Inert atmosphere;82 %Spectr.
(C4HN(adamantyl)Me2(2,6-diisopropylphenyl))AuCl; potassium tetrakis(pentafluorophenyl)borate In benzyl methyl ether; benzene-d6 at 90℃; for 24h; Product distribution / selectivity; Inert atmosphere;82 %Spectr.
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

2,4,6-trimethyl-N-(1-(p-tolyl)ethylidene)aniline
1227637-88-8

2,4,6-trimethyl-N-(1-(p-tolyl)ethylidene)aniline

Conditions
ConditionsYield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 1h; Inert atmosphere; regioselective reaction;100%
With silver tetrafluoroborate; {(2,6-bis(1-isopropyl-2,3-dihydro-1H-imidazole-2-thione)pyridine)12Cu8}(PF6)8 In acetonitrile at 70℃; Reagent/catalyst; Schlenk technique; Inert atmosphere; regioselective reaction;98%
With silver tetrafluoroborate; [1-(3,3-dimethyl-2-oxobutyl)-4-benzyl-1,2,4-triazol-5-ylidene]AuCl; acetonitrile at 90℃; for 12h; regioselective reaction;93 %Chromat.
4-bromo-1-ethynylbenzene
766-96-1

4-bromo-1-ethynylbenzene

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-[1-(4-bromophenyl)ethylidene]-2,4,6-trimethylaniline
1318024-67-7

N-[1-(4-bromophenyl)ethylidene]-2,4,6-trimethylaniline

Conditions
ConditionsYield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 0.5h; Inert atmosphere; regioselective reaction;100%
With decamethyldizincocene; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In benzene-d6 at 20℃; for 21.66h; regioselective reaction;95 %Spectr.
With (η1,η5)bis(pentamethylcyclopentadienyl)zinc; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In benzene-d6 at 60℃; for 0.5h; Inert atmosphere; regioselective reaction;
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

4-ethynyl-N,N-dimethylaniline
17573-94-3

4-ethynyl-N,N-dimethylaniline

N-[1-(4-(dimethylamino)phenyl)ethylidene]-2,4,6-trimethylaniline
1318024-68-8

N-[1-(4-(dimethylamino)phenyl)ethylidene]-2,4,6-trimethylaniline

Conditions
ConditionsYield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 2h; Inert atmosphere; regioselective reaction;100%
With decamethyldizincocene; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In benzene-d6 at 20℃; for 21.75h; regioselective reaction;96 %Spectr.
With bis(pentamethylcyclopentadienyl)dizinc; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In benzene-d6 at 20℃; for 21.75h; Inert atmosphere; regioselective reaction;
3-hydroxy-1(3H)-isobenzofuranone
16859-59-9

3-hydroxy-1(3H)-isobenzofuranone

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

3-(2,4,6-trimethylphenylamino)phthalide
1332980-69-4

3-(2,4,6-trimethylphenylamino)phthalide

Conditions
ConditionsYield
In isopropyl alcohol Reflux;100%
C20H23NO2

C20H23NO2

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

C29H34N2O
1349188-96-0

C29H34N2O

Conditions
ConditionsYield
With acetic acid In toluene100%
C17H26FeO2Si2
1400792-42-8

C17H26FeO2Si2

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

C26H37FeNOSi2
1400792-54-2

C26H37FeNOSi2

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 125℃; for 4.5h; Inert atmosphere; Schlenk technique;100%
n-octyne
629-05-0

n-octyne

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

2,4,6-trimethyl-N-(octan-2-ylidene)aniline
914388-61-7

2,4,6-trimethyl-N-(octan-2-ylidene)aniline

Conditions
ConditionsYield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 2h; Inert atmosphere; regioselective reaction;100%
With C33H49Cl2N2PPd; silver trifluoromethanesulfonate In acetonitrile at 80℃; for 25h; Inert atmosphere; Schlenk technique;59%
With silver hexafluoroantimonate; C25H28Au2Br2N4 In neat (no solvent) at 40℃; for 4h; Inert atmosphere; Schlenk technique;76 %Spectr.
With (η1,η5)bis(pentamethylcyclopentadienyl)zinc; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In benzene-d6 at 20℃; for 4h; Inert atmosphere; regioselective reaction;
chloroform
67-66-3

chloroform

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

2-mesityl isocyanide
57116-96-8

2-mesityl isocyanide

Conditions
ConditionsYield
Stage #1: 2,4,6-trimethylaniline With 15-crown-5; sodium hydride In benzene at 40 - 50℃; for 0.25h;
Stage #2: chloroform In benzene at 40℃; for 1h;
100%
With benzyltriethylammonium chloride; sodium hydroxide In dichloromethane; water for 22h;53%
2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

N-(1-(4-methoxyphenyl)ethylidene)-2,4,6-trimethylaniline
1609074-94-3

N-(1-(4-methoxyphenyl)ethylidene)-2,4,6-trimethylaniline

Conditions
ConditionsYield
With C18H5AlF36O4Zn In benzene-d6 at 60℃; for 6h; Inert atmosphere; regioselective reaction;100%
With silver hexafluoroantimonate; AuBr(8-Mes) In acetonitrile at 90℃; for 14h; Schlenk technique; Sealed tube;98%
With (THT)Au(P(C3H7)2CB11Cl11) In neat (no solvent) at 50℃; for 24h; Catalytic behavior;93%
6-(2,6-diisopropoxyphenyl)-2-pyridinecarboxaldehyde

6-(2,6-diisopropoxyphenyl)-2-pyridinecarboxaldehyde

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

C27H32N2O2

C27H32N2O2

Conditions
ConditionsYield
In methanol at 20℃; for 12h;100%
With air In ethanol at 20℃; for 4h;
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-ferrocenylmethylidene-2,4,6-trimethylaniline

N-ferrocenylmethylidene-2,4,6-trimethylaniline

Conditions
ConditionsYield
In chloroform soln. of Fe-complex and ligand in CHCl3 was heated under reflux, cooled to room temp.; solvent was evapd., dried under vac.; elem. anal.;99.62%
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark;90%
In chloroform refluxing (6 h); removal of solvent, trituration with hexane;82%
In ethanol boiling;
In toluene for 8h; Inert atmosphere; Reflux; Molecular sieve;

88-05-1Relevant articles and documents

Solvent Effects in the Electrophilic Amination of Mesitylene with the System NaN3-AlCl3-HCl

Borodkin,Popov,Pokrovskii,Shubin

, p. 747 - 749 (2003)

-

A Metal-Free Direct Arene C?H Amination

Wang, Tao,Hoffmann, Marvin,Dreuw, Andreas,Hasagi?, Edina,Hu, Chao,Stein, Philipp M.,Witzel, Sina,Shi, Hongwei,Yang, Yangyang,Rudolph, Matthias,Stuck, Fabian,Rominger, Frank,Kerscher, Marion,Comba, Peter,Hashmi, A. Stephen K.

supporting information, p. 2783 - 2795 (2021/04/05)

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

Transformation of Formazanate at Nickel(II) Centers to Give a Singly Reduced Nickel Complex with Azoiminate Radical Ligands and Its Reactivity toward Dioxygen

Ar, Deniz,Kilpatrick, Alexander F. R.,Cula, Beatrice,Herwig, Christian,Limberg, Christian

, p. 13844 - 13853 (2021/05/04)

The heteroleptic (formazanato)nickel bromide complex LNi(μ-Br)2NiL [LH = Mes-NH-N═C(p-tol)-N═N-Mes] has been prepared by deprotonation of LH with NaH followed by reaction with NiBr2(dme). Treatment of this complex with KC8led to transformation of the formazanate into azoiminate ligands via N-N bond cleavage and the simultaneous release of aniline. At the same time, the potentially resulting intermediate complex L′2Ni [L′ = HN═C(p-tol)-N═N-Mes] was reduced by one additional electron, which is delocalized across the π system and the metal center. The resulting reduced complex [L′2Ni]K(18-c-6) has aS=1/2ground state and a square-planar structure. It reacts with dioxygen via one-electron oxidation to give the complex L′2Ni, and the formation of superoxide was detected spectroscopically. If oxidizable substrates are present during this process, these are oxygenated/oxidized. Triphenylphosphine is converted to phosphine oxide, and hydrogen atoms are abstracted from TEMPO-H and phenols. In the case of cyclohexene, autoxidations are triggered, leading to the typical radical-chain-derived products of cyclohexene.

Iron-Catalyzed Alkyne Carboamination via an Isolable Iron Imide Complex

Richards, Corey A.,Rath, Nigam P.,Neely, Jamie M.

supporting information, p. 2945 - 2950 (2021/09/07)

Transition metal imide-mediated C-N bond formation is a powerful strategy for the introduction of nitrogen into organic compounds. We have discovered that the reaction ofN-mesityl(β-diketiminato)iron imide complextBuLFeNMes (tBuL = 3,5-bis(2,6-diisopropylphenylimino)-2,2,6,6-tetramethylheptyl and Mes = 2,4,6-trimethylphenyl) with a terminal alkyne substrate gives a β-alkynyl enamine product by a novel alkyne carboamination process. Stoichiometric experiments revealed a catalyst deactivation pathway involving generation of the acetylide complex,tBuLFeCCPh, and mesityl amine (MesNH2) from the acetylene complex,tBuLFe(HCCPh), and mesityl azide (MesN3). This reactivity is suppressed in the presence of coordinating additive 4-tert-butylpyridine (tBuPy), likely through formation of the four-coordinate complextBuLFe(HCCPh)(tBuPy). These insights were instrumental in identifying reaction conditions that allow for turnover of the iron catalyst.

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