6-Ethyl-o-toluidine supplier | CasNO.24549-06-2

Name
6-Ethyl-o-toluidine
EINECS 246-309-6
CAS No. 24549-06-2
Article Data7
CAS DataBase
Density 0.96 g/cm³
Solubility
Melting Point -33 °C
Formula C₉H₁₃N
Boiling Point 228.3 °C at 760 mmHg
Molecular Weight 135.209
Flash Point 89.4 °C
Transport Information UN 2810
Appearance Liquid
Safety 24/25-23
Risk Codes 22-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms o-Toluidine,6-ethyl- (7CI,8CI);(2-Ethyl-6-methylphenyl)amine;2-Ethyl-6-methylaniline;2-Ethyl-6-methylbenzenamine;2-Methyl-6-ethylaniline;6-Ethyl-2-methylaniline;
PSA 26.02000
LogP 2.72080

Synthetic route

: 1616514-62-5
tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate

: 108-24-7
acetic anhydride

A: 24549-06-2
6-ethyl-o-toluidine

B: N-(2-ethyl-6-methyl-4-((4-nitrophenyl)amino)phenyl)acetamide

C: 1616514-83-0
1-(2-ethyl-6-methylphenyl)-2-(4-nitrophenyl)diazene

D: 1616514-70-5
3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine

E: 100-01-6
4-nitro-aniline

Conditions

Conditions	Yield
Stage #1: tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate With hydrogenchloride In ethanol; water at 20℃; for 2h; Inert atmosphere; Reflux; Stage #2: acetic anhydride	A 11% B 3% C 26% D 3% E 20%
Stage #1: tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; Stage #2: acetic anhydride Overall yield = 52 %; regioselective reaction;	A 11% B 3% C 26% D 3% E 20%

...Expand

: 1616514-65-8
tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate

A: 455-14-1
4-trifluoromethylphenylamine

B: 24549-06-2
6-ethyl-o-toluidine

C: 1616514-73-8
3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine

D: 1616514-79-4
3-ethyl-5-methyl-N1-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine

E: 1616514-85-2
1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 2h; Inert atmosphere; Reflux;	A 10% B 6% C 10% D 18% E 12%
With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; Overall yield = 50 %; regioselective reaction;	A 10% B 6% C 10% D 18% E 12%

...Expand

: 102878-74-0
2-methyl-6-ethylnitrobenzene

: 24549-06-2
6-ethyl-o-toluidine

Conditions

Conditions	Yield
With sodium hydroxide; sodium dithionite

: 74-85-1
ethene

: 95-53-4
o-toluidine

: 24549-06-2
6-ethyl-o-toluidine

: 620-14-4
1-Methyl-3-ethylbenzene

: 24549-06-2
6-ethyl-o-toluidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid 2: Na2S2O4; aq.-ethanolic NaOH View Scheme

: 636-98-6
p-nitrobenzene iodide

: 1639128-65-6
N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine

A: 24549-06-2
6-ethyl-o-toluidine

B: 1616514-70-5
3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine

C: 100-01-6
4-nitro-aniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,10-Phenanthroline; caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 2 h / 20 °C / Inert atmosphere; Reflux View Scheme

...Expand

: 455-13-0
4-Iodobenzotrifluoride

: 1639128-65-6
N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine

A: 455-14-1
4-trifluoromethylphenylamine

B: 24549-06-2
6-ethyl-o-toluidine

C: 1616514-73-8
3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine

D: 1616514-85-2
1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,10-Phenanthroline; caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 2 h / 20 °C / Inert atmosphere; Reflux View Scheme

...Expand

: 24549-06-2
6-ethyl-o-toluidine

: 70598-49-1
4-bromo-2-ethyl-6-methylbenzenamine

Conditions

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃;	100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.166667h;	100%
With sulfuric acid; dihydrogen peroxide; boric acid; potassium bromide In water at 20℃; for 3h;	78%

: 25726-04-9
phenylglyoxylyl chloride

: 24549-06-2
6-ethyl-o-toluidine

: 1266932-87-9
C17H17NO2

Conditions

Conditions	Yield
With triethylamine In toluene	100%

: 24549-06-2
6-ethyl-o-toluidine

: 1349188-26-6
C21H33NO2

: 1349188-63-1
C30H44N2O

Conditions

Conditions	Yield
With acetic acid In toluene	100%

: 24549-06-2
6-ethyl-o-toluidine

: 5704-66-5
pyruvoyl chloride

: 1267003-21-3
C12H15NO2

Conditions

Conditions	Yield
With triethylamine In toluene	100%

: 2586-62-1
1-bromo-2-methylnaphtalene

: 24549-06-2
6-ethyl-o-toluidine

: N-(2-ethyl-6-methylphenyl)-2-methylnaphthale N-1-amine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); trineopentyl phosphine; sodium t-butanolate In toluene at 80℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere;	100%

: 24549-06-2
6-ethyl-o-toluidine

: 79-04-9
chloroacetyl chloride

: 86763-47-5
2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1-methylethoxy)methyl]acetamide

Conditions

Conditions	Yield
Stage #1: 6-ethyl-o-toluidine With Methoxyacetone; toluene-4-sulfonic acid In toluene at 88℃; for 10h; Stage #2: With hydrogen at 50℃; under 56255.6 Torr; for 4.5h; Autoclave; Inert atmosphere; Stage #3: chloroacetyl chloride With sodium carbonate In water; toluene at 25℃; for 0.5h; Reagent/catalyst;	98.6%

: 5878-19-3
Methoxyacetone

: 24549-06-2
6-ethyl-o-toluidine

: 51219-00-2, 118604-69-6, 118604-70-9
2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)aniline

Conditions

Conditions	Yield
With phosphoric acid; palladium on activated charcoal; hydrogen In toluene at 70℃; under 11251.1 Torr; for 0.5h; Autoclave;	98%

: 2749-70-4
bis(benzyloxy)methane

: 24549-06-2
6-ethyl-o-toluidine

: 2-methyl-6-ethyl-N-(benzyloxymethyl)aniline

Conditions

Conditions	Yield
In chlorobenzene at 125 - 132℃; for 11h;	97.6%

: 2568-89-0
diisopropoxymethane

: 24549-06-2
6-ethyl-o-toluidine

: 2-methyl-6-ethyl-N-(isopropoxymethyl)aniline

Conditions

Conditions	Yield
In chlorobenzene at 130 - 132℃; for 13h;	97.2%

: 13353-03-2
bis-methoxymethoxy-methane

: 24549-06-2
6-ethyl-o-toluidine

: 2-methyl-6-ethyl-N-(methoxymethoxymethyl)aniline

Conditions

Conditions	Yield
In benzene at 75 - 80℃; for 18h;	97.2%

: 24549-06-2
6-ethyl-o-toluidine

: 598-21-0
2-Bromoacetyl bromide

: 70529-06-5
2-bromo-N-(2'-ethyl-6'-methylphenyl)acetamide

Conditions

Conditions	Yield
With triethylamine at 0℃; for 1h; Inert atmosphere;	97%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h; bromoacetylation;
With sodium carbonate In water for 0.5h; pH=8 - 9;

: 24549-06-2
6-ethyl-o-toluidine

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: N-(2-ethyl-6-methylphenyl)-4-nitrobenzenesulfonamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2.5h;	97%
With pyridine In dichloromethane at -10 - 25℃; for 18h; Solvent; Reagent/catalyst; Cooling with ice;	92.9%
With pyridine In dichloromethane at -10 - 25℃; for 18h; Solvent; Reagent/catalyst; Cooling with ice;	92.9%

: 67-56-1
methanol

: 51594-55-9
(R)-(-)-epichlorohydrin

: 24549-06-2
6-ethyl-o-toluidine

: 1578258-67-9
(R)-1-((2-ethyl-6-methylphenyl)amino)-3-methoxypropan-2-ol

Conditions

Conditions	Yield
Stage #1: methanol; (R)-(-)-epichlorohydrin; 6-ethyl-o-toluidine at 70℃; for 6h; Reflux; Stage #2: With potassium hydroxide at 10 - 30℃; for 8h;	96%

...Expand

: 505-84-0
dipropoxymethane

: 24549-06-2
6-ethyl-o-toluidine

: 2-methyl-6-ethyl-N-(propoxymethyl)aniline

Conditions

Conditions	Yield
In toluene at 105 - 110℃; for 12h;	95.2%

: 5878-19-3
Methoxyacetone

: 24549-06-2
6-ethyl-o-toluidine

: 118604-70-9
(S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methylaniline

Conditions

Conditions	Yield
With hydrogen at 80℃; under 37503.8 Torr; for 3h; Pressure; Reagent/catalyst; Autoclave;	95%

: 24549-06-2
6-ethyl-o-toluidine

: 98-59-9
p-toluenesulfonyl chloride

: 135518-57-9
N-(2-ethyl-6-methylphenyl)-4-methylbenzenesulfonamide

Conditions

Conditions	Yield
With pyridine Heating / reflux;	93%

: 24549-06-2
6-ethyl-o-toluidine

: 199620-14-9, 13007-92-6
chromium(0) hexacarbonyl

: 93596-66-8
(6-ethyl-2-methylaniline)tricarbonylchromium

Conditions

Conditions	Yield
With tetrahydrofuran In tetrahydrofuran; dibutyl ether under N2, educts heated under reflux in n-Bu2O/THF for 22 h in the dark, cooled; filtered through Kieselguhr, evapd. in vac., rinsed with petroleum ether, dissolved in acetone, refiltered, pptd. by addn. of light petroleum, recrystd. from acetone/light petroleum; elem. anal.;	93%

: 24549-06-2
6-ethyl-o-toluidine

: 2258-42-6
Acetic formic anhydride

: 312488-22-5
C10H13NO

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;	93%

: 24549-06-2
6-ethyl-o-toluidine

: 110-16-7
maleic acid

: 56746-13-5
N-(2-ethyl-6-methylphenyl)-maleimide

Conditions

Conditions	Yield
With sodium acetate In ice-water; di-isopropyl ether	92.9%

: 18610-33-8
(E)-4-chloropent-2-ene

: 24549-06-2
6-ethyl-o-toluidine

: 2-methyl-6-ethyl-4-(1-methyl-2-butenyl)aniline

Conditions

Conditions	Yield
at 170℃;	92%
at 170℃; for 2h;	86%

: 7073-94-1
1-bromo-2-isopropylbenzene

: 24549-06-2
6-ethyl-o-toluidine

: 2-ethyl-N-(2-isopropylphenyl)-6-methylaniline

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); trineopentyl phosphine; sodium t-butanolate In toluene at 80℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere;	91%

: 24549-06-2
6-ethyl-o-toluidine

: 76-03-9
trichloroacetic acid

: 113260-60-9
2,2,2-Trichloro-N-(2-ethyl-6-methyl-phenyl)-acetamide

Conditions

Conditions	Yield
With phosphorus trichloride at 110℃; for 0.5h;	90%

: 24549-06-2
6-ethyl-o-toluidine

: C27H20ClNO4S

: C36H32N2O4S

Conditions

Conditions	Yield
In ethylene glycol at 120℃; for 18h;	89.88%

: 18610-33-8
(E)-4-chloropent-2-ene

: 24549-06-2
6-ethyl-o-toluidine

: N-(1-methyl-2-butenyl)-2-methyl-6-ethylaniline

Conditions

Conditions	Yield
With triethylamine for 4h; Heating;	89%
Product distribution; various anilines and α-chloroalkenes;

: 26423-64-3
3,4-dichloro-2-pentene

: 24549-06-2
6-ethyl-o-toluidine

: 4-(2-chloro-1-methyl-2-butenyl)-2,6-methyethylaniline

Conditions

Conditions	Yield
at 170℃;	89%

: 24549-06-2
6-ethyl-o-toluidine

: 536-74-3
phenylacetylene

: (2-Ethyl-6-methyl-phenyl)-[1-phenyl-eth-(E)-ylidene]-amine

Conditions

Conditions	Yield
With tetrafluoroboric acid diethyl ether; dodecacarbonyl-triangulo-triruthenium at 100℃; for 12h; Addition; Hydroamination;	89%

: 24549-06-2
6-ethyl-o-toluidine

: 431-03-8
dimethylglyoxal

: bis[N,N'-(2-ethyl-6-methylphenyl)imino]-1,2-dimethylethane

Conditions

Conditions	Yield
With formic acid In methanol for 24h; Friedel-Crafts Acylation; Reflux;	89%

: 24549-06-2
6-ethyl-o-toluidine

: 126-81-8
dimedone

: 105-07-7
4-cyanobenzaldehyde

: C33H36N2O2

Conditions

Conditions	Yield
With saponin immobilized on magnetite nanoparticles doped with copper ions In water at 20℃; for 0.416667h;	89%

...Expand

: 24549-06-2
6-ethyl-o-toluidine

: 2170-03-8
itaconic acid anhydride

: 126404-36-2
N-(2-Ethyl-6-methyl-phenyl)-2-methylene-succinamic acid

Conditions

Conditions	Yield
In benzene for 0.5h; Ambient temperature;	87%

: 1657-49-4, 1657-50-7, 4714-23-2, 130059-92-6, 130059-96-0
1-chloro-4-styrylbenzene

: 24549-06-2
6-ethyl-o-toluidine

: N-(2-ethyl-6-methylphenyl)-4-styrylbenzenamine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium; sodium t-butanolate; tricyclohexylphosphine In o-xylene at 120℃; for 5h; Inert atmosphere;	86%

6-Ethyl-o-toluidine Chemical Properties

Molecular Structure of 6-Ethyl-o-toluidine (CAS NO.24549-06-2):

IUPAC Name: 2-ethyl-6-methylaniline
Empirical Formula: C₉H₁₃N
Molecular Weight: 135.2062
H bond acceptors: 1
H bond donors: 2
#Freely Rotating Bonds: 2
Polar Surface Area: 3.24 Å²
Index of Refraction: 1.55
Molar Refractivity: 44.86 cm³
Molar Volume: 140.8 cm³
Surface Tension: 37 dyne/cm
Density: 0.96 g/cm³
Flash Point: 89.4 °C
Enthalpy of Vaporization: 46.49 kJ/mol
Boiling Point: 228.3 °C at 760 mmHg
Vapour Pressure: 0.0741 mmHg at 25°C
Index of Refraction: 1.55
EINECS: 246-309-6
Melting Point: -25 °C
Sensitive: Air & Light Sensitive
BRN: 2079468
Product Categories: Intermediates of Dyes and Pigments
Synonyms of 6-Ethyl-o-toluidine (CAS NO.24549-06-2): 2-Ethyl-6-methylaniline ; Benzenamine, 2-ethyl-6-methyl- ; 2-Amino-3-ethyltoluene ; 2-Methyl-6-ethylaniline ; 3-Ethyl-2-aminotoluene ; 6-Ethyl-2-toluidine ; 6-Ethyl-o-toluidine
Product Categories: Intermediates of Dyes and Pigments

6-Ethyl-o-toluidine Production

6-Ethyl-o-toluidine 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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

6-Ethyl-o-toluidine Toxicity Data With Reference

1.		mmo-sat 8300 nmol/plate		MUREAV Mutation Research. 211 (1988),279.
2.		orl-rat LD50:885 mg/kg		FAATDF Fundamental and Applied Toxicology. 3 (1983),285.

6-Ethyl-o-toluidine Consensus Reports

Reported in EPA TSCA Inventory.

6-Ethyl-o-toluidine Safety Profile

Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Safety information of 6-Ethyl-o-toluidine (CAS NO.24549-06-2):
Hazard Codes: Xn
Risk Statements:
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:
24/25: Avoid contact with skin and eyes
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
RIDADR: 2810
WGK Germany: 2
RTECS: BY5600000
F: 8-23
HS Code: 29214980

6-Ethyl-o-toluidine Specification

6-Ethyl-o-toluidine (CAS NO.24549-06-2) is a light yellow liquid, used as an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR Product Data Sheet.

Product Name

6-Ethyl-o-toluidine

Synthetic route

6-Ethyl-o-toluidine Chemical Properties

6-Ethyl-o-toluidine Production

6-Ethyl-o-toluidine Toxicity Data With Reference

6-Ethyl-o-toluidine Consensus Reports

6-Ethyl-o-toluidine Safety Profile

6-Ethyl-o-toluidine Specification

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