2-Ethylaniline supplier | CasNO.578-54-1

Name
2-Ethylaniline
EINECS 209-424-2
CAS No. 578-54-1
Article Data100
CAS DataBase
Density 0.973 g/cm³
Solubility insoluble in water
Melting Point -44 °C
Formula C₈H₁₁N
Boiling Point 212.3 °C at 760 mmHg
Molecular Weight 121.182
Flash Point 87.9 °C
Transport Information UN 2273 6.1/PG 3
Appearance clear yellow to red-brownish liquid
Safety 36/37/39-45
Risk Codes 36/37/38-33-23/24/25
Molecular Structure
Hazard Symbols T
Synonyms Aniline,o-ethyl- (8CI);2-Ethylaniline;2-Ethylbenzenamine;2-Ethylphenylamine;NSC62014;o-Aminoethylbenzene;o-Ethylaniline;
PSA 26.02000
LogP 2.41240

Synthetic route

: 1821-38-1
N-methyl ortho-ethylaniline

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
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%

: 612-22-6
2-nitro(ethylbenzene)

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With hydrogen In methanol at 20℃; under 750.075 Torr; for 1h; chemoselective reaction;	99.6%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃;	98%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;	98%

: 35774-47-1
1-azido-2-ethylbenzene

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With iron In water at 20℃; Inert atmosphere;	90%

: 612-22-6
2-nitro(ethylbenzene)

A: 578-54-1
ortho-ethylaniline

B: 64287-80-5
Bis(2-ethylphenyl)diazene 1-oxide

Conditions

Conditions	Yield
With ammonium chloride; zinc In water at 80℃; for 24h; Catalytic behavior; Inert atmosphere;	A 8% B 84%

: 74-84-0
ethane

: 62-53-3
aniline

A: 578-54-1
ortho-ethylaniline

B: 589-16-2
4-aminoethylbenzene

Conditions

Conditions	Yield
In gaseous matrix at 80℃; Irradiation;	A 82% B 18 % Spectr.
In gaseous matrix at 80℃; Irradiation;	A 82 % Spectr. B n/a

...Expand

: 155690-08-7
2-p-Tolyl-3H,4H-2λ4-benzo[c][1,2]thiazine 2-oxide

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With disodium hydrogenphosphate; sodium amalgam In tetrahydrofuran; methanol for 18h; Ambient temperature;	81%

: 89-96-3
1-chloro-2-ethylbenzene

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate at 100 - 110℃; for 12h;	79%

: 1973-22-4
1-bromo-2-ethylbenzene

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With ammonium sulfate; (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(tri-ortho-tolylphosphine)palladium(0); sodium t-butanolate In 1,4-dioxane at 100℃; for 8h; Inert atmosphere; Glovebox;	76%

: 52670-38-9
2-ethynylaniline

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With [Fe(nacnac)dippCH2SiMe3]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 20℃; for 0.5h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;	74%
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;	42%

: 109-72-8, 29786-93-4
n-butyllithium

: 35774-47-1
1-azido-2-ethylbenzene

A: 578-54-1
ortho-ethylaniline

B: 204926-79-4
N-butyl-2-ethylphenylamine

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 3h;	A 69% B 8%

...Expand

: 848170-57-0
2-ethylphenyl tosylate

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
Stage #1: 2-ethylphenyl tosylate With [(k2-P,N-di(1-adamantyl)-2-morpholinophenylphosphine)Pd(Ph)Cl]; sodium t-butanolate In 1,4-dioxane Inert atmosphere; Glovebox; Stage #2: With ammonia In 1,4-dioxane at 24℃; Inert atmosphere; Glovebox;	66%

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 612-22-6
2-nitro(ethylbenzene)

A: 91-22-5
quinoline

B: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 58% B 62%

...Expand

: 34557-54-5
methane

: 62-53-3
aniline

A: 578-54-1
ortho-ethylaniline

B: 589-16-2
4-aminoethylbenzene

Conditions

Conditions	Yield
In gaseous matrix at 80℃; Irradiation;	A 57% B 43 % Spectr.

...Expand

: 153856-89-4
7-amino-1,2,3,4-tetrahydroquinoline

: 612-22-6
2-nitro(ethylbenzene)

A: 580-19-8
quinolin-7-ylamine

B: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 51% B 54%

...Expand

: 120-15-0
6-methoxy-1,2,3,4-tetrahydroquinoline

: 612-22-6
2-nitro(ethylbenzene)

A: 5263-87-6
6-methoxy quinoline

B: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 48% B 52%

...Expand

: 577-59-3
2-acetylnitrobenzene

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With formic acid; triethylamine; palladium on activated charcoal at 100℃;	51%
Stage #1: 2-acetylnitrobenzene With hydrazine hydrate at 135℃; for 3h; Stage #2: With potassium hydroxide at 135℃; for 24h;	33%

: 100-41-4
ethylbenzene

A: 578-54-1
ortho-ethylaniline

B: 587-02-0
m-ethylaniline

C: 589-16-2
4-aminoethylbenzene

Conditions

Conditions	Yield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 25℃; for 4h;	A 47% B 8% C 34%
With 1-aminoquinolinium perchlorate In trifluoroacetic acid for 4h; Irradiation;	A 29% B 20% C 32%
With 18-crown-6 ether; 1-aminoquinolinium perchlorate In trifluoroacetic acid for 4h; Irradiation;	A 29% B 22% C 31%

...Expand

: 120-72-9
indole

A: 578-54-1
ortho-ethylaniline

B: 1678-91-7
ethyl-cyclohexane

C: 100-41-4
ethylbenzene

D: 95-53-4
o-toluidine

Conditions

Conditions	Yield
With hydrogen sulfide; hydrogen; MoOxNy at 326.85℃; under 68255.5 Torr; Product distribution; Further Variations:; Catalysts; hydrodenitrogenation;	A 45.2% B 15.9% C 6.2% D 9.3%

...Expand

: 612-22-6
2-nitro(ethylbenzene)

A: 578-54-1
ortho-ethylaniline

B: 16433-80-0
1-ethyl-2-nitrosobenzene

C: 64287-80-5
Bis(2-ethylphenyl)diazene 1-oxide

Conditions

Conditions	Yield
With ammonium chloride; zinc In water at 80℃; for 3.33333h; Catalytic behavior; Inert atmosphere;	A 45% B 24% C 19%

...Expand

: 14936-94-8
ethyl cation

: 62-53-3
aniline

A: 578-54-1
ortho-ethylaniline

B: 589-16-2
4-aminoethylbenzene

C N-alkylation product(s): N-alkylation product(s)

Conditions

Conditions	Yield
Product distribution; reactions with other charged electrophiles;	A 44% B 34% C n/a

...Expand

: 34557-54-5
methane

: 62-53-3
aniline

A: 578-54-1
ortho-ethylaniline

B: 587-02-0
m-ethylaniline

C: 589-16-2
4-aminoethylbenzene

Conditions

Conditions	Yield
In gaseous matrix at 80℃; Irradiation;	A 63 % Spectr. B 2% C 35%
With oxygen; trimethylamine at 80℃; Product distribution; Irradiation;

...Expand

: 612-22-6
2-nitro(ethylbenzene)

A: 578-54-1
ortho-ethylaniline

B: 16433-80-0
1-ethyl-2-nitrosobenzene

C: 61653-34-7
1,2-bis(2-ethylphenyl)diazene

D: 64287-80-5
Bis(2-ethylphenyl)diazene 1-oxide

Conditions

Conditions	Yield
With ammonium chloride; zinc In water at 80℃; for 3.33333h; Catalytic behavior; Inert atmosphere;	A 32% B 32% C 7% D 24%

...Expand

: 77-77-0
Divinyl sulfone

: 612-22-6
2-nitro(ethylbenzene)

A: 578-54-1
ortho-ethylaniline

B: 1219600-77-7
4-(2-ethylphenyl)-thiomorpholine 1,1-dioxide

Conditions

Conditions	Yield
With indium; acetic acid In methanol for 24h; aza-Michael type 1,4-addition reaction; Inert atmosphere; Reflux;	A 24% B 12%

...Expand

: 97-93-8
triethylaluminum

: 98-95-3
nitrobenzene

A: 578-54-1
ortho-ethylaniline

B: 103-69-5
N-ethyl-N-phenylamine

C: 62-53-3
aniline

D: 589-16-2
4-aminoethylbenzene

Conditions

Conditions	Yield
In hexane for 0.5h; Ambient temperature; Further byproducts given;	A 9.1% B 13.7% C 15.4% D 5%

...Expand

: 120-72-9
indole

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With nickel; decalin at 225℃; under 19000 Torr; Hydrogenation;

: 496-15-1
1-indoline

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With nickel; decalin at 225℃; under 19000 Torr; Hydrogenation;

: 623-81-4
diethyl sulphite

: 62-53-3
aniline

A: 578-54-1
ortho-ethylaniline

B: 91-66-7
N,N-diethylaniline

...Expand

: 74-85-1
ethene

: 62-53-3
aniline

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
With aniline; aluminium anilide at 300 - 350℃; under 110326 - 147102 Torr;

: 74-85-1
ethene

: 108-90-7
chlorobenzene

A: 578-54-1
ortho-ethylaniline

B: 587-02-0
m-ethylaniline

Conditions

Conditions	Yield
With aluminium trichloride at 80℃; under 3677.5 Torr; Hydrogenation.und Erhitzen der bei 190-195grad siedenden Anteile des nach dem Behandeln mit wss.Natriumcarbonat-Loesung erhaltenen Reaktonsprodukts mit wss.Ammoniak und Kupfer(I)-oxid auf 225grad;
With aluminium trichloride at 80℃; under 3677.5 Torr; und Erhitzen der bei 190-195grad siedenden Anteile des nach dem Behandeln mit wss.Natriumcarbonat-Loesung erhaltenen Reaktionsprodukts mit wss.Ammoniak und Kupfer(I)-oxid auf 225grad;

...Expand

: 578-54-1
ortho-ethylaniline

: 75-36-5
acetyl chloride

: 33098-65-6
2-acetamido-1-ethylbenzene

Conditions

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane at 0℃; Reflux;	58%
With triethylamine In chloroform at 0℃; for 1h;
With triethylamine at 0 - 28℃; for 3h;

: 578-54-1
ortho-ethylaniline

: 35774-47-1
1-azido-2-ethylbenzene

Conditions

Conditions	Yield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 1h;	100%
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 1h;	75%
With hydrogenchloride; sodium azide; sodium nitrite In water
Stage #1: ortho-ethylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 2h;

: 7677-24-9
trimethylsilyl cyanide

: 578-54-1
ortho-ethylaniline

: 100-52-7
benzaldehyde

: 2-[N-(2-ethylanilino)]-2-phenylacetonitrile

Conditions

Conditions	Yield
With azaphosphatrane salt on Merrifield resin In acetonitrile at 20℃; for 15h; Strecker coupling;	99%

...Expand

: 108-86-1
bromobenzene

: 578-54-1
ortho-ethylaniline

: 51488-25-6
2-ethyl-N-phenylaniline

Conditions

Conditions	Yield
With sodium t-butanolate at 110℃; for 18h;	99%
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; 2,6-bis(diphenylphosphino)pyridine In N,N-dimethyl acetamide at 135℃; for 6h; Catalytic behavior; Buchwald-Hartwig Coupling; Inert atmosphere;	80%
With C22H26Cl2NPPd; sodium t-butanolate In toluene at 110℃; for 22h; Time; Inert atmosphere;

: 696-63-9
4-Methoxybenzenethiol

: 578-54-1
ortho-ethylaniline

: 2-ethyl-4-(4-methoxyphenylthio)aniline

Conditions

Conditions	Yield
With di-tert-butyl peroxide; iodine at 120℃; for 24h; Inert atmosphere; Sealed tube;	99%

: 578-54-1
ortho-ethylaniline

: 106-45-6
para-thiocresol

: 2-ethyl-4-(p-tolylthio)aniline

Conditions

Conditions	Yield
With di-tert-butyl peroxide; iodine at 120℃; for 24h; Inert atmosphere; Sealed tube;	99%
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine; oxygen In acetonitrile at 60℃; for 24h; Schlenk technique; Green chemistry;	88%

: 578-54-1
ortho-ethylaniline

: 598-21-0
2-Bromoacetyl bromide

: 895854-04-3
2-bromo-N-(2'-ethylphenyl)acetamide

Conditions

Conditions	Yield
With sodium carbonate In water pH=9 - 10;	99%
With triethylamine at 0℃; for 1h; Inert atmosphere;	86%
With sodium carbonate In water for 0.5h; pH=9 - 10;

: 578-54-1
ortho-ethylaniline

: (2-ethylphenyl)hydrazine hydrochloride

Conditions

Conditions	Yield
Stage #1: ortho-ethylaniline With calcium nitrite In water at 32℃; Acidic conditions; Flow reactor; Stage #2: With lithium bisulfite In water at 70 - 90℃; Stage #3: With hydrogenchloride In water at 120℃;	98.4%

: 578-54-1
ortho-ethylaniline

: 2,4-dibromo-6-ethylaniline

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 0 - 5℃; Schlenk technique; Inert atmosphere;	98%
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane for 0.5h; Ambient temperature;	92%

: 578-54-1
ortho-ethylaniline

: 3282-30-2
pivaloyl chloride

: 174781-73-8
N-(2-ethylphenyl)pivalamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 18h;	98%
With triethylamine In dichloromethane at 0 - 25℃;	88%
With potassium hydrogencarbonate In water	87%

: 696-59-3
cis,trans-2,5-dimethoxytetrahydrofuran

: 578-54-1
ortho-ethylaniline

: 299426-84-9
1-(2-ethylphenyl)-1H-pyrrole

Conditions

Conditions	Yield
With nanosulfated titania In neat (no solvent) at 120℃; for 0.416667h;	98%
With acetic acid	73%
With acetic acid Clauson-Kaas Synthesis; Reflux;

: 578-54-1
ortho-ethylaniline

: 576-83-0
2,4,6-trimethylphenyl bromide

2,4,6-trimethylphenyl-2'-ethyldiphenylamine: 2,4,6-trimethylphenyl-2'-ethyldiphenylamine

Conditions

Conditions	Yield
With sodium t-butanolate; [(η3-cinnamyl)PdCl((t-Bu)2PN=P(i-BuNCH2CH2)3N)] In toluene at 80℃; for 16h; Buchwald-Hartwig amination;	98%

: 578-54-1
ortho-ethylaniline

Conditions

Conditions	Yield
Stage #1: ortho-ethylaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 0 - 20℃; for 8h;	98%

2-Ethylaniline Consensus Reports

Reported in EPA TSCA Inventory.

2-Ethylaniline Standards and Recommendations

DOT Classification: 6.1; Label: KEEP AWAY FROM FOOD

2-Ethylaniline Specification

The Benzenamine, 2-ethyl-, with the CAS registry number 578-54-1, is also known as 2-Ethylbenzenamine. It belongs to the product categories of Amines; C8; Nitrogen Compounds. Its EINECS number is 209-424-2. This chemical's molecular formula is C₈H₁₁N and molecular weight is 121.18. What's more, its systematic name is 2-ethylaniline. It is an important pesticides, dyes and pharmaceutical intermediates, which is also a key synthetic intermediate of new pesticides. Its storage temperature is -20°C.

Physical properties of Benzenamine, 2-ethyl- are: (1)ACD/LogP: 1.93; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.9; (4)ACD/LogD (pH 7.4): 1.93; (5)ACD/BCF (pH 5.5): 16.01; (6)ACD/BCF (pH 7.4): 17.16; (7)ACD/KOC (pH 5.5): 248.38; (8)ACD/KOC (pH 7.4): 266.23; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.02 Å²; (13)Index of Refraction: 1.556; (14)Molar Refractivity: 40.03 cm³; (15)Molar Volume: 124.5 cm³; (16)Polarizability: 15.87×10^-24cm³; (17)Surface Tension: 38.2 dyne/cm; (18)Density: 0.973 g/cm³; (19)Flash Point: 87.9 °C; (20)Enthalpy of Vaporization: 44.86 kJ/mol; (21)Boiling Point: 212.3 °C at 760 mmHg; (22)Vapour Pressure: 0.174 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-ethyl-2-nitro-benzene at the temperature of 40 °C. This reaction will need reagent H₂ and solvent ethanol. This reaction will also need catalyst 1% Pd in AV-17-8-Pd. The yield is about 98%.

Benzenamine, 2-ethyl- can be prepared by 1-ethyl-2-nitro-benzene at the temperature of 40 °C

Uses of Benzenamine, 2-ethyl-: it can be used to produce 2-(2-ethyl-phenylamino)-isophthalic acid by heating. It will need reagent N-ethylmorpholine and solvents benzene, various solvent(s) with the reaction time of 1 hour. This reaction will also need catalyst CuCl. The yield is about 65%.

Benzenamine, 2-ethyl- can be used to produce 2-(2-ethyl-phenylamino)-isophthalic acid by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. It has the danger of cumulative effects. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: CCc1ccccc1N
(2)Std. InChI: InChI=1S/C8H11N/c1-2-7-5-3-4-6-8(7)9/h3-6H,2,9H2,1H3
(3)Std. InChIKey: MLPVBIWIRCKMJV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	750mg/kg (750mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
rat	LD50	oral	1260mg/kg (1260mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS BLOOD: CHANGES IN SPLEEN	Toxicology and Applied Pharmacology. Vol. 22, Pg. 153, 1972.

Product Name

2-Ethylaniline

Synthetic route

2-Ethylaniline Consensus Reports

2-Ethylaniline Standards and Recommendations

2-Ethylaniline Specification

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