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609-72-3

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609-72-3 Usage

Chemical Properties

clear colorless to amber liquid

Uses

N,N-Dimethyl-o-toluidine may be employed as starting reagent for the synthesis of roseoflavin.

General Description

A clear colorless liquid with an aromatic odor. Less dense than water and insoluble in water. Hence floats on water. May be toxic by skin absorption and inhalation. Flash point near 180°F. May release toxic vapors when burned.

Reactivity Profile

N,N,2-Trimethylbenzenamine 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. generates hydrogen, a flammable gas, in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Check Digit Verification of cas no

The CAS Registry Mumber 609-72-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 9 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 609-72:
(5*6)+(4*0)+(3*9)+(2*7)+(1*2)=73
73 % 10 = 3
So 609-72-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H13N/c1-8-6-4-5-7-9(8)10(2)3/h4-7H,1-3H3

609-72-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N-Dimethyl-o-toluidine

1.2 Other means of identification

Product number -
Other names N,N,2-Trimethylbenzenamine

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:609-72-3 SDS

609-72-3Synthetic route

carbon dioxide
124-38-9

carbon dioxide

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Autoclave; Green chemistry;99%
With dimanganese decacarbonyl; phenylsilane; C29H33N2P In acetonitrile at 100℃; under 750.075 Torr; for 15h;85%
With sodium tetrahydroborate In 1,4-dioxane at 100℃; under 7500.75 Torr; for 24h; Autoclave; Green chemistry;85%
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

o-toluidine
95-53-4

o-toluidine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With 0.72KNaX-BS zeolite at 150℃; for 1h; Reagent/catalyst;99%
formaldehyd
50-00-0

formaldehyd

o-toluidine
95-53-4

o-toluidine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With Zr(BH4)2Cl2(dabco)2; zirconium(IV) chloride In methanol; water at 20℃; for 0.1h;95%
With N-methylpyrrolidine zinc borohydride; sulfuric acid In tetrahydrofuran; water at 0 - 10℃; for 0.25h;90%
With sodium cyanoborohydride; acetic acid In tetrahydrofuran at 23 - 50℃; for 18h; Inert atmosphere;65%
formic acid
64-18-6

formic acid

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With hydrogen In toluene at 140℃; under 30003 Torr; for 3h; chemoselective reaction;94%
2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 7,9-bis(2,6-diisopropylphenyl)-7H-acenaphtho[1,2-d]imidazol-9-ium chloride; potassium tert-butylate In water; toluene at 35℃; for 24h; Glovebox; Sealed tube; Inert atmosphere;90%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 65℃; for 24h; Inert atmosphere;89%
2-methylchlorobenzene
95-49-8

2-methylchlorobenzene

dimethyl amine
124-40-3

dimethyl amine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran; toluene at 65℃; Buchwald-Hartwig amination; Inert atmosphere; Sealed vial;83%
carbon dioxide
124-38-9

carbon dioxide

o-toluidine
95-53-4

o-toluidine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With diphenylsilane; C21H41N3NiP2 In acetonitrile at 120℃; under 2052.14 Torr; for 24h; Autoclave;83%
With hydrogen In hexane at 140℃; under 15001.5 - 45004.5 Torr; for 7h; Autoclave; Green chemistry;96 %Chromat.
With diphenylsilane; caesium carbonate In acetonitrile at 80℃;14 %Spectr.
methanol
67-56-1

methanol

o-toluidine
95-53-4

o-toluidine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With C15H29IrN4(2+)*2I(1-) at 120℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube;82%
With hydrogenchloride at 200 - 220℃;
With aluminum oxide at 350 - 400℃;
With aluminum oxide at 360℃;
With TiO2 supported nano-Pd(0.8) catalyst In water at 20℃; for 15h; Inert atmosphere; Irradiation; Green chemistry;87 %Chromat.
N,N-dimethyl-N-(2'-methylphenyl)amine N-oxide
6852-47-7

N,N-dimethyl-N-(2'-methylphenyl)amine N-oxide

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With palladium on activated charcoal; tetrabutylammomium bromide; water; sodium hydroxide; silicon at 100℃; for 6h;81%
o-toluidine
95-53-4

o-toluidine

methyl iodide
74-88-4

methyl iodide

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
Stage #1: o-toluidine With tetra-(n-butyl)ammonium iodide; potassium hydroxide In water; benzene at 20℃; for 0.166667h;
Stage #2: methyl iodide In water; benzene at 90℃; for 24h;
77%
Behandeln des entstandenen Trimethyl-o-tolyl-ammonuimjodids mit Silberoxyd und Destillation;
With potassium fluoride at 180℃;
formaldehyd
50-00-0

formaldehyd

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With sodium carbonate In water; dimethyl sulfoxide at 130℃; for 15h; Schlenk technique; Sealed tube; Green chemistry;70%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

N,N-dimethyl O-(2,4,6-trimethylphenyl-sulfonyl) hydroxylamine
67530-30-7

N,N-dimethyl O-(2,4,6-trimethylphenyl-sulfonyl) hydroxylamine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 20℃; for 2h;60%
methanol
67-56-1

methanol

o-toluidine
95-53-4

o-toluidine

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

Conditions
ConditionsYield
With copper(I) oxide; hydrogenchloride; titanium(IV) oxide In water for 6h; UV-irradiation;A 6%
B 58%
With aluminum oxide at 350 - 400℃;
methanol
67-56-1

methanol

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

Conditions
ConditionsYield
With Cu-PMO (copper-doped porous metal oxide) for 6h; Supercritical conditions;A 43%
B 57%
methanol
67-56-1

methanol

N-benzylidene-2-methylaniline
5877-55-4, 34143-86-7

N-benzylidene-2-methylaniline

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

methanol
67-56-1

methanol

o-toluidine hydrochloride
636-21-5

o-toluidine hydrochloride

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
at 230℃;
methanol
67-56-1

methanol

2-methylanilinium bromide
16518-48-2

2-methylanilinium bromide

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

tri-N-methyl-o-toluidinium; bromide

tri-N-methyl-o-toluidinium; bromide

Conditions
ConditionsYield
at 120 - 130℃;
o-tolylazanediyl-bis-acetic acid
30243-45-9

o-tolylazanediyl-bis-acetic acid

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With sulfuric acid; iron(II) sulfate
sodium ethanolate
141-52-6

sodium ethanolate

tri-N-methyl-o-toluidinium; nitrate

tri-N-methyl-o-toluidinium; nitrate

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

Conditions
ConditionsYield
at 220 - 230℃; im Druckrohr;
at 220 - 230℃;
phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

N-methyl-2,6-dimethylaniline
767-71-5

N-methyl-2,6-dimethylaniline

C

N,N,2,6-tetramethylaniline
769-06-2

N,N,2,6-tetramethylaniline

D

Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

Conditions
ConditionsYield
at 220 - 230℃; im geschlossenen Rohr;
N,N-dimethyl-o-toluidine; perbromide

N,N-dimethyl-o-toluidine; perbromide

acetone
67-64-1

acetone

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

dimethyl sulfate
77-78-1

dimethyl sulfate

o-toluidine
95-53-4

o-toluidine

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With sodium hydrogencarbonate
at 140℃;
methanol
67-56-1

methanol

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

Conditions
ConditionsYield
With aluminum oxide at 350 - 400℃;
N-allyl-N,N-dimethyl-o-toluidinium bromide
80573-81-5

N-allyl-N,N-dimethyl-o-toluidinium bromide

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

N-allyl-N-methyl-o-toluidine
80573-83-7

N-allyl-N-methyl-o-toluidine

C

4-allyl-2-methyl-N,N-dimethylaniline
80573-85-9

4-allyl-2-methyl-N,N-dimethylaniline

D

3-allyl-2-dimethylaminotoluene
80573-84-8

3-allyl-2-dimethylaminotoluene

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; glycerol at 140℃; Product distribution; Mechanism; rearrangaments of anilinium compounds between var. conditions;A 25 % Chromat.
B 5 % Chromat.
C 1 % Chromat.
D 18 % Chromat.
With sodium hydrogencarbonate In water; glycerol at 140℃;A 25 % Chromat.
B 5 % Chromat.
C 1 % Chromat.
D 18 % Chromat.
methyl benzyl(phenyl)phosphinate
26086-06-6

methyl benzyl(phenyl)phosphinate

o-toluidine
95-53-4

o-toluidine

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

(±)-benzyl(phenyl)phosphinic acid
7282-98-6

(±)-benzyl(phenyl)phosphinic acid

C

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

Conditions
ConditionsYield
With hydrogenchloride 1.) 200-210 deg C, 10 min, 2.) dichloromethane; Yield given. Multistep reaction. Yields of byproduct given;
(N,N-dimethylaniline)tricarbonylchromium
12109-10-3

(N,N-dimethylaniline)tricarbonylchromium

methyl iodide
74-88-4

methyl iodide

A

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

B

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

C

Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

Conditions
ConditionsYield
Yield given. Multistep reaction;
methanol
67-56-1

methanol

aniline
62-53-3

aniline

A

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

B

N-methyl-p-toluidine
623-08-5

N-methyl-p-toluidine

C

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

D

N-methylaniline
100-61-8

N-methylaniline

E

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

F

Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

Conditions
ConditionsYield
With monoaluminum phosphate at 425℃; Product distribution; other catalyst, var. temp., var.molar ratio of educts;A 7.0 % Chromat.
B 8.5 % Chromat.
C 18.3 % Chromat.
D 31.2 % Chromat.
E 5.1 % Chromat.
F 10.0 % Chromat.
diethyl ether
60-29-7

diethyl ether

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-(dimethylamino)benzyllithium
64308-58-3

2-(dimethylamino)benzyllithium

Conditions
ConditionsYield
With n-butyllithium In hexane100%
With n-butyllithium In hexane
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

N-methyl-N-(2-methylphenyl)aminoacetonitrile
1048332-11-1

N-methyl-N-(2-methylphenyl)aminoacetonitrile

Conditions
ConditionsYield
With tert.-butylhydroperoxide; [(bpy)AuCl2]Cl In methanol; decane at 20℃; for 5h; regioselective reaction;95%
With amine functionalized Zr(IV) metal-organic framework (UiO-66-NH2) through covalent hooking of EOSIN-Y In methanol at 20℃; for 4h;84%
With tert.-butylhydroperoxide; iron(II) chloride In methanol; decane at 20℃; Inert atmosphere;76%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-methyl-4-bromo-N,N-dimethylaniline
50638-49-8

2-methyl-4-bromo-N,N-dimethylaniline

Conditions
ConditionsYield
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.166667h;92%
With bromine; acetic acid
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 23 °C / Inert atmosphere
2.1: dibromo sulfoxide / tetrahydrofuran / 4 h / -78 °C / Inert atmosphere
2.2: 0.75 h / -78 - 23 °C / Inert atmosphere
View Scheme
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

2-methyl-N,N,N-trimethylbenzeneaminium trifluoromethanesulfonate

2-methyl-N,N,N-trimethylbenzeneaminium trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane at 20℃;91%
In diethyl ether at 0 - 20℃;67%
In dichloromethane at 20℃; for 4h;
In dichloromethane at 20℃; Inert atmosphere;
Dimethyldisulphide
624-92-0

Dimethyldisulphide

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-[(methylthio)methyl]-N,N-dimethylbenzenamine
591214-24-3

2-[(methylthio)methyl]-N,N-dimethylbenzenamine

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-o-toluidine With n-butyllithium In diethyl ether at 20 - 35℃;
Stage #2: Dimethyldisulphide In diethyl ether at 0 - 20℃;
90%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

N,N-dimethyl-N-(2'-methylphenyl)amine N-oxide
6852-47-7

N,N-dimethyl-N-(2'-methylphenyl)amine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 80℃; under 760.051 Torr; for 4.5h;89%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 23℃; for 1h; Inert atmosphere;68%
With peracetic acid
With dihydrogen peroxide
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

C24H30N2O5S

C24H30N2O5S

C33H43N3O5S

C33H43N3O5S

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; sodium acetate In N,N-dimethyl-formamide at 20℃; for 16h; Irradiation; Inert atmosphere; diastereoselective reaction;89%
allylbenzene
300-57-2

allylbenzene

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

C18H23N

C18H23N

Conditions
ConditionsYield
With C32H53N2OScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 80℃; for 12h; Inert atmosphere;89%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

1-methyl-4,6-diphenyl-2(1H)-pyrimidinone
21418-80-4

1-methyl-4,6-diphenyl-2(1H)-pyrimidinone

3-Methyl-4-[(methyl-o-tolyl-amino)-methyl]-4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one
119638-83-4

3-Methyl-4-[(methyl-o-tolyl-amino)-methyl]-4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one

Conditions
ConditionsYield
In benzene for 15h; Ambient temperature; Irradiation;88%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

C10H12N2S

C10H12N2S

Conditions
ConditionsYield
With oxygen In tetrahydrofuran at 20℃; for 4h; Irradiation; chemoselective reaction;87%
With oxygen; Nitrogen dioxide; trifluoroacetic acid In acetonitrile at 15℃; for 3h;49%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

N,N'-bis(2,6-diisopropylphenyl)carbodiimide
2162-74-5

N,N'-bis(2,6-diisopropylphenyl)carbodiimide

C34H47N3

C34H47N3

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-o-toluidine With n-butyllithium In tetrahydrofuran at -30℃; for 10h; Inert atmosphere;
Stage #2: N,N'-bis(2,6-diisopropylphenyl)carbodiimide In tetrahydrofuran at -30 - 20℃; Inert atmosphere;
87%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-(dimethylamino)-α-(trimethylsilyl)toluene
102615-56-5

2-(dimethylamino)-α-(trimethylsilyl)toluene

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-o-toluidine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate In hexane; n-heptane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In hexane; n-heptane at 0℃; for 1h; Inert atmosphere;
86%
Stage #1: N,N-dimethyl-o-toluidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere;
Stage #2: With 2,2,6,6-tetramethyl-piperidine; potassium tert-butylate In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #3: chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
84%
Stage #1: N,N-dimethyl-o-toluidine With n-butyllithium In tetrahydrofuran at -78℃; for 0.0833333h;
Stage #2: With 2,2,6,6-tetramethyl-piperidine; potassium tert-butylate In tetrahydrofuran at -78℃; for 0.25h;
Stage #3: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 0.5h; regioselective reaction;
phenyl isocyanate
1197040-29-1

phenyl isocyanate

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

C16H16N2

C16H16N2

Conditions
ConditionsYield
With N-hydroxyphthalimide In acetonitrile at 20℃; for 12h; Irradiation; Inert atmosphere;86%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

2-{(diphenylphosphino)methyl}-N,N-dimethylaniline
75637-65-9

2-{(diphenylphosphino)methyl}-N,N-dimethylaniline

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-o-toluidine With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; for 3h;
Stage #2: chloro-diphenylphosphine In diethyl ether; hexane at -4 - 20℃; for 2h;
85%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

(2-deuteriomethylphenyl)dimethylamine
64065-24-3

(2-deuteriomethylphenyl)dimethylamine

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-o-toluidine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: With d(4)-methanol In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction;
83%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

benzyl bromide
100-39-0

benzyl bromide

N,N-dimethyl-2-phenethylaniline
23667-03-0

N,N-dimethyl-2-phenethylaniline

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-o-toluidine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium tert-butylate In hexane; n-heptane at 0℃; for 0.25h; Inert atmosphere;
Stage #2: benzyl bromide In hexane; n-heptane at 0℃; for 1h; Inert atmosphere;
83%
benzoyl cyanide
613-90-1

benzoyl cyanide

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

N-methyl-N-(2-methylphenyl)aminoacetonitrile
1048332-11-1

N-methyl-N-(2-methylphenyl)aminoacetonitrile

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; oxygen In methanol for 14h; Reflux;83%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-N,N-Dimethylaminonaphthalene
2436-85-3

2-N,N-Dimethylaminonaphthalene

1-(4-(dimethylamino)-3-methylphenyl)-N,N-dimethylnaphthalen-2-amine

1-(4-(dimethylamino)-3-methylphenyl)-N,N-dimethylnaphthalen-2-amine

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V) at 20℃; for 4h; Electrochemical reaction;83%
(2,4,6-trimethylphenyl)(phenyl)iodonium tosylate

(2,4,6-trimethylphenyl)(phenyl)iodonium tosylate

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

N-methyl-N-(2-methylphenyl)aniline
6590-44-9

N-methyl-N-(2-methylphenyl)aniline

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 110℃; for 16h; Inert atmosphere;82%
N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 0 - 25℃; for 8h; N-dealkylation;81%
Multi-step reaction with 2 steps
2: bei der Verseifung
View Scheme

609-72-3Relevant articles and documents

-

Hill et al.

, p. 1579,1582 (1951)

-

Preparation method of N-alkylated derivative of primary amine compound

-

Paragraph 0021; 0039, (2021/07/09)

The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

Chao, Jianbin,Guo, Zhiqiang,Pang, Tengfei,Wei, Xuehong,Xi, Chanjuan,Yan, Leilei

supporting information, p. 7534 - 7538 (2021/10/12)

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

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