148-87-8

Basic information

• Product Name: 3-Ethylanilinopropiononitrile
• Synonyms: 3-(ethylphenylamino)-propanenitrile;3-ethylanilinopropiononitrile;3-(N-Ethylanilino)propiononitrile;3-(N-ETHYL-N-PHENYLAMINO)PROPIONITRILE;(2-cyanoethyl)ethylaniline;3-(Ethylanilino)propanenitrile;3-(ethylphenylamino)-propanenitril;3-(Ethylphenylamino)propionitrile
• CAS NO: 148-87-8
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24
• EINECS: 205-728-4
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 148-87-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 137-140°C 4mm
• Flash Point: 132.8 °C
• Appearance: /
• Density: 1,03 g/cm3
• Vapor Pressure: 0.000547mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• PKA: 5.27±0.50(Predicted)
• CAS DataBase Reference: 3-Ethylanilinopropiononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethylanilinopropiononitrile(148-87-8)
• EPA Substance Registry System: 3-Ethylanilinopropiononitrile(148-87-8)

Safety Data

• Safety Statements: 24/25
• RTECS: BY0100000
• Hazardous Substances Data: 148-87-8(Hazardous Substances Data)

Usage

Description

3-Ethylanilinopropiononitrile, also known as 3-(Ethylphenylamino)propanenitrile, is an organic compound that serves as a crucial reagent in the chemical industry. It is characterized by its ability to be used in the synthesis of various dyes, particularly mono-azo dyes, which are essential for coloring nylon and polyester fibers. 3-Ethylanilinopropiononitrile is known for its versatility and effectiveness in producing vibrant and long-lasting colors in the textile industry.

Uses

Used in Textile Industry:
3-Ethylanilinopropiononitrile is used as a reagent for the synthesis of mono-azo dyes for nylon and polyester fibers. It plays a vital role in the production of these dyes, which are essential for imparting color and enhancing the visual appeal of textiles.
Used in Plastics Industry:
In the plastics industry, 3-Ethylanilinopropiononitrile is utilized as a reagent in the synthesis of dyes for coloring plastics. Its application in this industry helps to produce plastics with a wide range of colors, catering to the diverse aesthetic requirements of various products.
Used in Synthesis of Disperse Orange 37 (D493490):
3-Ethylanilinopropiononitrile is specifically used in the synthesis of Disperse Orange 37 (D493490), a prominent mono-azo dye. This dye is widely used in the coloring of synthetic fibers, such as nylon and polyester, and is known for its excellent colorfastness and brightness. The use of 3-Ethylanilinopropiononitrile in the synthesis of Disperse Orange 37 contributes to the overall quality and performance of the dye in the textile and plastics industries.

InChI:InChI=1/C11H14N2/c1-2-13(10-6-9-12)11-7-4-3-5-8-11/h3-5,7-8H,2,6,10H2,1H3

Synthetic route

3-diethylaminopropionitrile (5351-04-2) + N-ethyl-N-phenylamine (103-69-5) → N-ethyl-N-(2-cyanoethyl)aniline (148-87-8)

N-ethyl-N-phenylamine (103-69-5) + acrylonitrile (107-13-1) → N-ethyl-N-(2-cyanoethyl)aniline (148-87-8)

anthranilic acid nitrile (1885-29-6) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2-{4-[(2-Cyano-ethyl)-ethyl-amino]-phenylazo}-benzonitrile (52547-43-0)

Conditions	Yield
Stage #1: anthranilic acid nitrile With sulfuric acid; nitrosyl sulphuric acid In water at 0 - 20℃; for 2h; Stage #2: N-ethyl-N-(2-cyanoethyl)aniline With sulfuric acid In water at 0℃; for 1h;	99%

C6H2Br2N3O2(1+)*HO4S(1-) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-[[4-[(2,6-dibromo-4-nitrophenyl)azo]phenyl]ethylamino]propanenitrile (55281-26-0)

Conditions	Yield
With hydrogenchloride; sulfuric acid In water at 10℃; for 1.83333h; Green chemistry;	97.3%

3-nitro-aniline (99-09-2) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → C17H17N5O2

Conditions	Yield
Stage #1: 3-nitro-aniline With hydrogenchloride In water for 0.333333h; Stage #2: With sodium nitrite In water at 10℃; for 1h; Stage #3: N-ethyl-N-(2-cyanoethyl)aniline With sulfuric acid In water at 10℃; for 3h;	97.18%

2-nitro-aniline (88-74-4) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 4-N-Aethyl-N-(2-cyano)aethylamino-2'-nitroazobenzol (52301-71-0)

Conditions	Yield
Stage #1: 2-nitro-aniline With hydrogenchloride In water for 0.5h; Stage #2: With sodium nitrite In water at 10℃; for 1h; Stage #3: N-ethyl-N-(2-cyanoethyl)aniline In water at 5 - 10℃; for 1.5h;	96.33%

N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → N-(3-aminopropyl)-N-ethylaniline (53606-48-7)

Conditions	Yield
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave;	91%
Hydrogenation;

ethenetetracarbonitrile (670-54-2) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → p-tricyanovinyl-N-ethyl-N-(β-cyanoethyl)aniline (81430-43-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20 - 25℃; for 0.25h; Sonication;	73%

benzo[c]isothiazol-3-ylamine (2400-12-6) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-{Ethyl-[4-(7-nitro-benzo[c]isothiazol-3-ylazo)-phenyl]-amino}-propionitrile

Conditions	Yield
With sodium hydroxide; nitrosylsulfuric acid; sulfuric acid; nitric acid; acetic acid Product distribution; multistep reaction; reactions of 3-amino-2,1-benzothiazole and 3-aminoindazole with nitrozonium hydrogen sulfate and HNO3 in conc. H2SO4; formation of diazonium ions; nitration followed by diazotation; diazo coupling products;	68%
With sodium hydroxide; nitrosylsulfuric acid; sulfuric acid; nitric acid; acetic acid 1.) 0-5 deg C, 2 h, 2.) 20 deg C, 3.5 h, 3.) H2O, pH 3-3.5; Yield given. Multistep reaction;

4-methoxy-2-nitroaniline (96-96-8) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-(ethyl(4-((4-methoxy-2-nitrophenyl)diazenyl)phenyl)amino)propanenitrile

Conditions	Yield
With hydrogenchloride; sodium nitrite In methanol; water	48%

methyl p-toluene sulfonate (80-48-8) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → N-ethyl-N-(2-cyano-ethyl)-N-methyl-anilinium; toluene-4-sulfonate

N-methyl-N-phenylformamide (93-61-8) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → N-ethyl-N-cyanoethyl-4-aminobenzaldehyde (27914-15-4)

Conditions	Yield
With trichlorophosphate

N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → N-ethyl-N-phenyl-β-aminopropionic acid (3334-57-4)

Conditions	Yield
With potassium hydroxide
With sulfuric acid at 140℃;

N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → N-ethyl-N-phenyl-β-alanine amide (43151-55-9)

Conditions	Yield
With sulfuric acid anschliessend Eintragen des Reaktionsgemisches in Wasser;

2-amino-6-(2-hydroxyethoxy)benzothiazole (73532-98-6) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-(Ethyl-{4-[6-(2-hydroxy-ethoxy)-benzothiazol-2-ylazo]-phenyl}-amino)-propionitrile (89787-45-1)

Conditions	Yield
With hydrogenchloride; sulfuric acid; sodium nitrite 1.) H2O, o deg C, 1 h; 2.) H2O, 10 deg C, 1 h; Yield given. Multistep reaction;

2-cyano-4-nitrobenzenediazonium hydrogen sulphate + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2'-cyano-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene (16889-10-4)

Conditions	Yield
In sulfuric acid; acetic acid at 0℃; for 1.5h;

5-Nitro-1H-indazole-3-diazonium; dihydrogen phosphate + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-{Ethyl-[4-(5-nitro-1H-indazol-3-ylazo)-phenyl]-amino}-propionitrile (76486-30-1)

Conditions	Yield
In sulfuric acid at 0℃; for 1.5h;

5-nitrobenzo[c]-1,2-thiazole-3-diazonium hydrogensulfate + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-{Ethyl-[4-(5-nitro-benzo[c]isothiazol-3-ylazo)-phenyl]-amino}-propionitrile (76486-28-7)

Conditions	Yield
In sulfuric acid; acetic acid at 0℃; for 1.5h;

2-Cyano-4-nitro-naphthalene-1-diazonium; hydrogen sulfate + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 1-{4-[(2-Cyano-ethyl)-ethyl-amino]-phenylazo}-4-nitro-naphthalene-2-carbonitrile (76486-13-0)

Conditions	Yield
In sulfuric acid; acetic acid at 0℃; for 1.5h; Yield given;

5-Nitro-1H-benzo[g]indazole-3-diazonium; dihydrogen phosphate + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-{Ethyl-[4-(5-nitro-1H-benzo[g]indazol-3-ylazo)-phenyl]-amino}-propionitrile (76486-22-1)

Conditions	Yield
In sulfuric acid at 0℃; for 1.5h; Yield given;

5-Nitro-2-thia-1-aza-cyclopenta[a]naphthalene-3-diazonium; hydrogen sulfate + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-{Ethyl-[4-(5-nitro-2-thia-1-aza-cyclopenta[a]naphthalen-3-ylazo)-phenyl]-amino}-propionitrile (76486-19-6)

Conditions	Yield
In sulfuric acid; acetic acid at 0℃; for 1.5h; Yield given;

5-Amino-3-nitromethyl-1-phenyl-pyrazol-4-carbonsaeuremethylester (86737-41-9) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 5-(p--phenylazo)-3-nitromethyl-1-phenyl-pyrazol-4-carbonsaeuremethylester (86737-58-8)

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite 1) glacial acetic acid, 10 deg , 10 min, 2) glacial acetic acid; Yield given. Multistep reaction;

4-methylthiazol-2-ylamine (1603-91-4) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-{Ethyl-[4-(4-methyl-thiazol-2-ylazo)-phenyl]-amino}-propionitrile

Conditions	Yield
With hydrogenchloride; sodium carbonate; sodium nitrite 1.) from 0 to 5 deg C, 1 h, 2.) from 0 to 5 deg C, 3 h; Multistep reaction;

4-nitro-aniline (100-01-6) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 3-[N-ethyl-4-(4-nitrophenylazo)phenylamino]propionitrile (31482-56-1)

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;

2-Chloro-4-nitroaniline (121-87-9) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2'-chloro-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene (40880-51-1)

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;
Stage #1: 2-Chloro-4-nitroaniline With nitrosylsulfuric acid; sulfuric acid at 10℃; for 5.5h; Stage #2: N-ethyl-N-(2-cyanoethyl)aniline With aminosulfonic acid at 5 - 10℃; for 8h;

2-methoxy-4-nitrophenylamine (97-52-9) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2'-methoxy-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;

5-nitroanthranilonitrile (17420-30-3) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2'-cyano-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene (16889-10-4)

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;
Stage #1: 5-nitroanthranilonitrile With naphthalene-1,5-disulfonate In ethyl acetate at 50℃; for 0.166667h; Stage #2: With tert.-butylnitrite In ethyl acetate at 25℃; for 0.333333h; Stage #3: N-ethyl-N-(2-cyanoethyl)aniline With hydrogenchloride In water at 0 - 5℃; for 0.266667h;

4-nitro-2,6-dichloroaniline (99-30-9) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2',6'-dichloro-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene (13301-61-6)

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;
Stage #1: 4-nitro-2,6-dichloroaniline With naphthalene-1,5-disulfonate In ethyl acetate at 50℃; for 0.166667h; Stage #2: With tert.-butylnitrite In ethyl acetate at 25℃; for 0.333333h; Stage #3: N-ethyl-N-(2-cyanoethyl)aniline With hydrogenchloride In water at 0 - 5℃; for 0.166667h;

1-amino-2-cyano-4-nitro-6-chlorobenzene (20352-84-5) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2'-chloro-6'-cyano-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;

1-amino-2,6-dicyano-4-nitrobenzene (20033-48-1) + N-ethyl-N-(2-cyanoethyl)aniline (148-87-8) → 2',6'-dicyano-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene (26309-21-7)

Conditions	Yield
With sulfuric acid; sodium acetate; acetic acid; sodium nitrite 1.) 10 deg C, 2.) 5 deg C, overnight; Yield given. Multistep reaction;

Upstream product

• 5351-04-2 3-diethylaminopropionitrile 
• 103-69-5 N-ethyl-N-phenylamine 
• 107-13-1 acrylonitrile 

Downstream Products

• 27914-15-4 N-ethyl-N-cyanoethyl-4-aminobenzaldehyde 
• 3334-57-4 N-ethyl-N-phenyl-β-aminopropionic acid 
• 43151-55-9 N-ethyl-N-phenyl-β-alanine amide 
• 53606-48-7 N-(3-aminopropyl)-N-ethylaniline 
• 89787-45-1 3-(Ethyl-{4-[6-(2-hydroxy-ethoxy)-benzothiazol-2-ylazo]-phenyl}-amino)-propionitrile 
• 16889-10-4 2'-cyano-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene 
• 76486-30-1 3-{Ethyl-[4-(5-nitro-1H-indazol-3-ylazo)-phenyl]-amino}-propionitrile 
• 76486-28-7 3-{Ethyl-[4-(5-nitro-benzo[c]isothiazol-3-ylazo)-phenyl]-amino}-propionitrile 
• 76486-13-0 1-{4-[(2-Cyano-ethyl)-ethyl-amino]-phenylazo}-4-nitro-naphthalene-2-carbonitrile 
• 76486-22-1 3-{Ethyl-[4-(5-nitro-1H-benzo[g]indazol-3-ylazo)-phenyl]-amino}-propionitrile 
• 76486-19-6 3-{Ethyl-[4-(5-nitro-2-thia-1-aza-cyclopenta[a]naphthalen-3-ylazo)-phenyl]-amino}-propionitrile 
• 86737-58-8 5-(p--phenylazo)-3-nitromethyl-1-phenyl-pyrazol-4-carbonsaeuremethylester 
• 31482-56-1 3-[N-ethyl-4-(4-nitrophenylazo)phenylamino]propionitrile 
• 40880-51-1 2'-chloro-4'-nitro-4-(N-β-cyanoethyl-N-ethyl)amino-1,1'-azobenzene 

Relevant articles and documents

A high efficiency energy-saving environmental protection N - ethyl N - cyanoethyl aniline preparation method (by machine translation)

The invention is efficient energy-saving environmental protection N - ethyl N - cyanoethyl aniline preparation method, comprises a medium-pressure synthesis, and in the reaction, the addition reaction of the rectification and distillation, medium pressure in the synthesis, the alcohol, aniline and 1st catalyst into the medium-pressure in a reaction kettle, 1st catalyst by phosphorus oxychloride and copper-chromium according to weight ratio of 5:1 - 2 is mixed, after the reaction the crude product obtained after N - ethyl aniline rectification; in addition reaction, the N - ethyl aniline with catalyst third thin eyeball and 2nd input addition reaction kettle, 2nd catalyst is zinc chloride and copper-chromium according to weight ratio of 6:2 by mixing, reaction to the end of the N - ethyl N - cyanoethyl aniline crude distillation after. The invention further improves the N - ethyl N - cyanoethyl aniline reaction selectivity of; the other in reducing energy use and shorten the reaction time of the N - ethyl N - at the same time improve the selectivity of the cyanoethyl aniline. (by machine translation)

Assessment and use of two silicon carbide multi-well plates for library synthesis and proteolytic digests using microwave heating

The use of two silicon carbide plates is reported for the preparation of three libraries of organic molecules using microwave heating. In addition, a preliminary study has been carried out, showing that one of the plates can also be used in a proteomics setting. Both the 24-position and 48-position plates heated evenly when irradiated with microwave energy. The 48-position plate was used to prepare a library of N-aryl functionalized β-amino esters via an aza-Michael reaction between anilines and Michael acceptors. The 24-position plate was used to prepare a library of biaryls via a Suzuki coupling methodology and a library of 1,4-dihydropyridines via a Hantzsch synthesis. The 48-position plate was also used to perform the proteolytic digestion of insulin chain B by trypsin. The Royal Society of Chemistry 2009.