104-75-6

Hazards Identification

Pictogram(s):

Signal:

Danger

GHS Hazard Statements:

H226 (97.78%): Flammable liquid and vapor [Warning Flammable liquids]
H302 (99.97%): Harmful if swallowed [Warning Acute toxicity, oral]
H311 (23.33%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H312 (72.37%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (25.88%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H330 (91.92%): Fatal if inhaled [Danger Acute toxicity, inhalation]
H412 (17.44%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes:

P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Hazard Classes and Categories:

Flam. Liq. 3 (97.78%)
Acute Tox. 4 (99.97%)
Acute Tox. 3 (23.33%)
Acute Tox. 4 (72.37%)
Skin Corr. 1B (100%)
Eye Dam. 1 (25.88%)
Acute Tox. 2 (91.92%)
Aquatic Chronic 3 (17.44%)
Flammable liquids - Category 3
Skin corrosion/irritation - Category 1
Serious eye damage/eye irritation - Category 1
Hazardous to the aquatic environment (Acute) - Category 3
Hazardous to the aquatic environment (Long-term) - Category 3
Corrosives, Flammable - 2nd degree

Hazards Summary:

A severe eye and moderate to severe skin irritant; [RTECS] Highly irritating to skin and eyes; [CAMEO] A severe skin and eye irritant, with second-degree burns possible after a few minutes contact; High vapor concentrations cause respiratory tract and lung irritation, and may cause corneal edema; [CHRIS] A severe skin and mucous membrane irritant; [NTP] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Highly toxic by inhalation; Toxic by ingestion and skin absorption; [Sigma-Aldrich MSDS] See N-Ethyl cyclohexylamine.

Usage

Uses

Used in Organic Syntheses:
2-Ethylhexylamine is used as an intermediate in organic syntheses for the production of a wide range of chemicals.
Used in Pharmaceutical and Chemical Production:
2-Ethylhexylamine is utilized in the manufacturing of pharmaceuticals and other chemicals, playing a crucial role in the development of various medical and industrial products.
Used as a Beam Material and Surface Active Agent:
2-Ethylhexylamine serves as a beam material and surface active agent, contributing to its versatility in different applications.
Used in Synthesis of Aliphatic Amines:
2-Ethylhexylamine is involved in the synthesis of aliphatic amines, which are essential building blocks for various chemical products.
Used in Detergent, Rubber Chemical, and Oil Additive Synthesis:
The compound is employed in the synthesis of detergents, rubber chemicals, oil additives, and insecticides, highlighting its importance in the chemical industry.
Used in Agricultural Chemicals:
2-Ethylhexylamine is used as an intermediate to manufacture agricultural chemicals, contributing to its role in the agricultural sector.
Used in Surfactants, Polymerization Auxiliaries, and Plastic Additives:
2-Ethylhexylamine is also used in the production of surfactants, polymerization auxiliaries, and plastic additives, further expanding its applications across various industries.
Used in Dyes, Insecticides, Flotation Agents, and Corrosion Inhibitors:
2-Ethylhexylamine finds use in the synthesis of dyes, insecticides, flotation agents, and corrosion inhibitors, showcasing its diverse applications.
Used in Paint Additives, Detergents, Fuel Additives, and Lubricant Additives:
The compound is also utilized in the production of paint additives, detergents, fuel additives, and lubricant additives, demonstrating its widespread use in the chemical industry.
Used in Novel 2-Ethylhexylamine Salt Anionic Monoazo Dyes:
Novel 2-Ethylhexylamine salt anionic monoazo dyes are very useful for dyeing solvents, printing inks, or polymeric film-forming materials, highlighting its importance in the dye and ink industries.

Reference

www.chemicalland21.com/industrialchem/organic/2-ETHYLHEXYLAMINE.htm? Loeffler, Hermann, and R. Dyllick-Brenzinger. "2-ethylhexylamine salts of anionic monoazo dyes." US, US 4668774 A. 1987.

Air & Water Reactions

Flammable. Soluble in water. Sensitive to prolonged exposure to air.

Reactivity Profile

2-Ethylhexylamine reacts with oxidizing materials . 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.

Hazard

Moderate fire risk. Toxic by ingestion and inhalation.

Health Hazard

INHALATION: High concentration of vapor will produce irritation of the respiratory tract and the lungs. Prolonged exposure may cause systemic effects. EYES: Contact with liquid may result in severe eye irritation. Exposure to concentrated vapor may result in corneal edema. SKIN: Contact with liquid may result in severe skin irritation, burns and possible skin absorption. INGESTION: May cause systemic poisoning.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion, inhalation, and skin contact. Corrosive. A severe skin and eye irritant.Flammable liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

InChI:InChI=1/C8H19N/c1-3-5-6-8(4-2)7-9/h8H,3-7,9H2,1-2H3/p+1/t8-/m0/s1

Synthetic route

2-Ethylhexyl alcohol (104-76-7) → 2-Ethylhexylamine (104-75-6)

Conditions	Yield
With sodium azide; triphenylphosphine In dichloromethane; N,N-dimethyl-formamide at 90℃; for 5h; Substitution; Mitsunobu reaction; Staudinger reaction;	92%
With Ru(CO)ClH(oxydi-2,1-phenylene)bis(diphenylphosphine)(triphenylphosphine); ammonia In toluene at 170℃; for 48h; Autoclave; Glovebox; Inert atmosphere;	77 %Spectr.

2-ethylhexenal (645-62-5) → 2-Ethylhexylamine (104-75-6)

Conditions	Yield
With ammonia; hydrogen; nickel at 140℃;

2-ethyl-N-(2-ethylhexyl)-1-hexanamine (106-20-7) → 2-Ethylhexylamine (104-75-6)

Conditions	Yield
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); ammonia; water In tert-Amyl alcohol; tert-butyl methyl ether at 170℃; for 16h; pressure tube; Inert atmosphere;	70 %Chromat.

2-ethyl-hexanal oxime (34612-83-4) → 2-Ethylhexylamine (104-75-6)

Conditions	Yield
Stage #1: 2-ethyl-hexanal oxime With hydrogenchloride; zinc In ethanol; water at 20℃; for 0.25h; Stage #2: With ammonia; sodium hydroxide In ethanol; water at 20℃; for 0.25h;	5.513 g

d,l-2-ethylhexanal (123-05-7) → 2-Ethylhexylamine (104-75-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride / ethanol / 0.67 h / 20 °C 2.1: hydrogenchloride; zinc / ethanol; water / 0.25 h / 20 °C 2.2: 0.25 h / 20 °C View Scheme

2-Ethylhexyl alcohol (104-76-7) → 2-Ethylhexylamine (104-75-6) + 2-ethyl-N-(2-ethylhexyl)-1-hexanamine (106-20-7)

Conditions	Yield
With chlorocyclopentadienylbis(triphenylphosphine)ruthenium(II); urea; diphenylphosphinopropane In diethylene glycol dimethyl ether at 160℃; for 12h; Autoclave; Inert atmosphere;

maleic anhydride (108-31-6) + 2-Ethylhexylamine (104-75-6) → N-(2-ethylhexyl)maleimide (48149-71-9)

Conditions	Yield
Stage #1: maleic anhydride; 2-Ethylhexylamine In toluene at 80℃; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide In toluene at 80℃; for 2.5h;	100%
With chloroform Erwaermen des Reaktionsprodukts mit Natriumacetat und Acetanhydrid;

2-Ethylhexylamine (104-75-6) + methanesulfonyl chloride (124-63-0) → N-(2-ethyl-hexyl)-methanesulfonamide (362665-05-2)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%

2-Ethylhexylamine (104-75-6) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → 2,9-bis(2-ethylhexyl)anthra[2,1,9-def:6,5,10-d',e',f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (82531-03-1)

Conditions	Yield
With 1H-imidazole; zinc diacetate at 160℃; for 5h; Inert atmosphere;	99%
With 1H-imidazole	98%
In N,N-dimethyl-formamide for 8h; Inert atmosphere; Reflux;	97%

2-Ethylhexylamine (104-75-6) + N-(2,6-diisopropylphenyl)-1,6-dichloro-7,12-di-(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxy monoimide monoanhydride → N-(2,6-diisopropylphenyl)-N′-(2-ethyl-1hexyl)-1,6-dichloro-7,12-di(4-tert-butylphenoxy)perylene-3,4,9,10-tetracarboxy bisimide

Conditions	Yield
In toluene for 16h; Reflux;	99%

2-Ethylhexylamine (104-75-6) + diglycolyl chloride (21062-20-4) → 2,2’-oxybis(N-(2-ethylhexyl)acetamide)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	99%

2-Ethylhexylamine (104-75-6) + N-butyl-N-(chloro(dibutylamino)methylene)butan-1-aminium chloride (81363-13-5) → N,N,N',N'-tetra-(n-butyl)-N''-(2-ethylhexyl)guanidine (1283075-93-3)

Conditions	Yield
With triethylamine In acetonitrile	98%

2-Ethylhexylamine (104-75-6) + 4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) → 6-bromo-2-(2-ethylhexyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (1193092-32-8)

Conditions	Yield
In ethanol for 24h; Reflux;	98%
In ethanol at 110℃; Inert atmosphere;	95.01%
In ethanol for 4h; Reflux;	85%

carbon disulfide (75-15-0) + 2-Ethylhexylamine (104-75-6) → 2-ethyl-1-hexyl isothiocyanate (21663-56-9)

Conditions	Yield
Stage #1: carbon disulfide; 2-Ethylhexylamine With potassium carbonate In water at 20℃; for 1h; Inert atmosphere; Stage #2: With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water at 0℃; for 0.5h; Inert atmosphere; Stage #3: With sodium hydroxide In dichloromethane; water pH=11; Inert atmosphere;	98%
With dicyclohexyl-carbodiimide In dichloromethane at -10 - 20℃; for 18h; Inert atmosphere;	81%

2-Ethylhexylamine (104-75-6) + 3-phenyl-1-(2-thioxobenzo[d]oxazol-3(2H)-yl)propan-1-one (312313-34-1) → N-(2-ethylhexyl)-3-phenylpropanamide (551910-81-7)

Conditions	Yield
With triethylamine; benzoic acid In 1-methyl-pyrrolidin-2-one at 20℃; for 1h;	98%

2-Ethylhexylamine (104-75-6) + 5-chloro-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde (87867-73-0) → 5-((2-ethylhexyl)amino)-3-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.166667h; Microwave irradiation; Sealed tube; chemoselective reaction;	98%

2-Ethylhexylamine (104-75-6) + C15H13ClN4O4S → C23H31N5O4S

Conditions	Yield
With triethylamine In 1,4-dioxane at 25℃; for 1.25h;	98%
With triethylamine In chloroform at 20℃; for 0.166667h; Cooling with ice;	28.4 g

2-Ethylhexylamine (104-75-6) + N-(2,6-diisopropylphenyl)-1,6-dichloro-7,12-di-(4-methoxyphenoxy)perylene-3,4,9,10-tetracarboxy monoimide monoanhydride → N-(2,6-diisopropylphenyl)-1,6-dichloro-7,12-di-(4-methoxyphenoxy)perylene-3,4,9,10-tetracarboxy monoimide monoanhydride

Conditions	Yield
In toluene for 16h; Reflux;	98%

2-Ethylhexylamine (104-75-6) + chloroacetyl chloride (79-04-9) → 2-Chloro-N-(2-ethyl-hexyl)-acetamide (32461-85-1)

Conditions	Yield
With sodium hydroxide In dichloromethane for 0.25h;	97%
With TEA In dichloromethane at 20℃; for 3h;

2-Ethylhexylamine (104-75-6) + 2,3-diacetyl succinic acid dimethyl ester (74536-45-1) → 1-(2-Ethyl-hexyl)-2,5-dimethyl-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester (181262-97-5)

Conditions	Yield
With acetic acid for 24h; Ambient temperature;	97%

2-Ethylhexylamine (104-75-6) + epichlorohydrin (106-89-8) → 3,3'-(2-ethylhexylazanediyl)bis(1-chloropropan-2-ol)

Conditions	Yield
In methanol at 20℃; for 12h;	97%

2-Ethylhexylamine (104-75-6) + 2,3,4,2',3',4',6'-hepta-O-benzoyl-6-O-trifluoromethylsulfonyl-α,α-trehalose → 2,3,4,2',3',4',6'-hepta-O-benzoyl-6-O-deoxy-6-[(2-ethylhexyl)amino]-α,α-trehalose

Conditions	Yield
In dichloromethane at 20℃; for 20h;	96%

2-Ethylhexylamine (104-75-6) + isatoic anhydride (118-48-9) → N-(2-ethylhexyl)-2-aminobenzamide (556062-39-6)

Conditions	Yield
In water; N,N-dimethyl-formamide; toluene	96%

2-Ethylhexylamine (104-75-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-82-9)

Conditions	Yield
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 140℃; for 24h; Inert atmosphere; Stage #2: With thionyl chloride at 140℃; for 3h; Inert atmosphere;	96%
In acetic acid Inert atmosphere; Reflux; Schlenk technique;
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 140℃; for 24h; Stage #2: With thionyl chloride for 3h; Reflux;	6.20 g
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene Reflux; Stage #2: With thionyl chloride for 4h; Reflux;

2-Ethylhexylamine (104-75-6) + [silver(I)(acetonitrile)](bis(trifluoromethanesulfonyl)imide) (1334406-90-4, 1357467-59-4) → [Ag(2-EtHexAm)2][Tf2N]

Conditions	Yield
In acetonitrile at 20℃; for 1h;	96%

2-Ethylhexylamine (104-75-6) + 3-methoxy-4-bromo-1,8-naphthalic anhydride → N-(2-ethylhexyl)-3-methoxy-4-bromo-1,8-naphthalimide

Conditions	Yield
In ethanol for 4h; Reflux; Inert atmosphere;	96%

2-Ethylhexylamine (104-75-6) + 25,27-bis[(3-isothiocyanatopropyl)oxy]calix[4]arene-crown-6 (252357-81-6) → 25,27-bis[(3-(N'-(2-ethylhexyl)thioureido)propyl)oxy]calix[4]arene-crown-6

Conditions	Yield
In dichloromethane at 20℃; for 10h; Addition;	95%

2-Ethylhexylamine (104-75-6) + D,L-lactide (95-96-5) → N-(2-ethyl-hexyl)-lactamide (100535-55-5)

Conditions	Yield
at 20℃; under 760.051 Torr; for 96h;	95%

2-Ethylhexylamine (104-75-6) + p-toluenesulfonyl chloride (98-59-9) → N-(2-ethylhexyl)-4-methylbenzenesulfonamide

Conditions	Yield
With pyridine at 0 - 20℃;	95%
With triethylamine In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane at 0 - 25℃;

methanol (67-56-1) + 2-Ethylhexylamine (104-75-6) → 1,3-bis(2-ethylhexyl)urea

Conditions	Yield
With Ru-MACHO-BH In toluene at 140℃; for 24h; Autoclave; Inert atmosphere;	95%

2-Ethylhexylamine (104-75-6) + (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2) → exo-N-2-ethylhexylnorbornene dicarboximide

Conditions	Yield
In toluene at 115℃; for 17h;	95%

2-Ethylhexylamine (104-75-6) + 4-nitrophenyl azide (1516-60-5) → 1-(2-ethylhexyl)-5-methyl-1,2,3-triazole

Conditions	Yield
With acetic acid In toluene at 55℃; for 18h;	95%

2-Ethylhexylamine (104-75-6) + cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → 2-(2-ethylhexyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions	Yield
In N,N-dimethyl-formamide for 24h; Molecular sieve; Reflux;	94.9%

pyridine-4-carbaldehyde (872-85-5) + 2-Ethylhexylamine (104-75-6) → C14H22N2

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 80℃; for 8h;	94.5%
With toluene-4-sulfonic acid In ethanol for 8h; Reflux;	94.5%
With toluene-4-sulfonic acid In ethanol at 80℃; for 8h;	94.5%

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + 2-Ethylhexylamine (104-75-6) → 2,2'-dithiobis (88848-47-9)

Conditions	Yield
In 1,4-dioxane for 2h; Ambient temperature;	94.1%

2-Ethylhexylamine (104-75-6) + N,N,N′,N′-tetraethylchloroformamidinium chloride (70976-93-1) → N''-(2-ethylhexyl)-N,N,N',N'-tetraethylguanidine (1283075-91-1)

Conditions	Yield
With triethylamine In acetonitrile	94%

Upstream product

• 645-62-5 2-ethylhexenal 
• 104-76-7 2-Ethylhexyl alcohol 
• 106-20-7 2-ethyl-N-(2-ethylhexyl)-1-hexanamine 
• 123-05-7 d,l-2-ethylhexanal 
• 34612-83-4 2-ethyl-hexanal oxime 

Downstream Products

• 48149-71-9 N-(2-ethylhexyl)maleimide 
• 20392-34-1 3-(isocyanatomethyl)heptane 
• 20308-52-5 dichloro-acetic acid-(2-ethyl-hexylamide) 
• 5443-76-5 (2-ethyl-hexyl)-amidophosphoric acid dimethyl ester 
• 63765-90-2 (2-ethyl-hexyl)-(β-nitro-isobutyl)-amine 
• 101449-86-9 N-(2-ethyl-hexyl)-mandelamide 
• 86888-13-3 N,N'-bis-(2-ethyl-hexyl)-ethylenediamine 
• 28567-53-5 N-((Ξ)-2-ethyl-hexyl)-D-gluconamide 
• 113-48-4 (+/-)-2-(2-ethyl-hexyl)-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-isoindole-1,3-dione 
• 22573-93-9 alexidine 
• 67205-48-5 2,4,5-Trichloro-6-(2-ethyl-hexylamino)-isophthalonitrile 
• 37801-30-2 (2-Ethyl-hexyl)-carbamic acid 3-ethylsulfanylcarbonylamino-phenyl ester 
• 71416-38-1 Cyclohex-1-ene-1,2-dicarboxylic acid 1-[(4-chloro-2-fluoro-phenyl)-amide] 2-[(2-ethyl-hexyl)-amide] 
• 71416-55-2 Cyclohex-1-ene-1,2-dicarboxylic acid 1-[(4-bromo-2-fluoro-phenyl)-amide] 2-[(2-ethyl-hexyl)-amide] 

Relevant academic research and scientific papers

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A process for preparing an amine by catalytic reaction of an olefin with ammonia or a primary or secondary amine by contacting a mixture of the reactants in a reactor at 200° to 400° C. and an elevated pressure up to 700 bar in the presence of a catalyst consisting essentially of an X-ray amorphous (non-crystalline) mesoporous catalyst, some of which may have a microporous non-crystalline content. The catalyst has the composition where Q is at least one of the trivalent elements aluminum, boron, chromium, iron or gallium, and M is at least one of the tetravalent elements silicon, titanium or germanium. The molar ratio of a:b is from 0.5:1 to 1000:1 and the molar ratio of c:b is from 0 to 2:1. As prepared and used in the process, this non-crystalline catalyst has a specific BET surface area of from 200 to 1000 m2 /g.

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