104-75-6

Basic information

• Product Name: 2-Ethylhexylamine
• Synonyms: 2-ethyl-hexylamin;3-Octylamine;Armeen L8D;beta-Ethylhexylamine;Ethylhexylamine;Hexylamine, 2-ethyl-;1-AMINO-2-ETHYLHEXANE;2H
• CAS NO: 104-75-6
• Molecular Formula: C₈H₁₉N
• Molecular Weight: 129.24
• EINECS: 203-233-8
• Product Categories: Industrial/Fine Chemicals;Butoctamide;Amines;C8;Nitrogen Compounds;pharmaceutical
• Mol File: 104-75-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: -76 °C
• Boiling Point: 169 °C(lit.)
• Flash Point: 126 °F
• Appearance: Clear colorless/Liquid
• Density: 0.789 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: Flammables area
• Solubility: 1.6g/l
• PKA: 10.75±0.10(Predicted)
• Explosive Limit: 1.6-7.7%(V)
• Water Solubility: 2.5 g/L (20 ºC)
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1209249
• CAS DataBase Reference: 2-Ethylhexylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylhexylamine(104-75-6)
• EPA Substance Registry System: 2-Ethylhexylamine(104-75-6)

Safety Data

• Hazard Codes: T,C
• Statements: 10-21/22-23-34
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2276 3/PG 3
• WGK Germany: 2
• RTECS: MQ5250000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 104-75-6(Hazardous Substances Data)

Usage

Description

2-Ethylhexylamine is used as an intermediate to manufacture agricultural chemicals, rubber chemicals, pharmaceuticals, surfactants, polymerization auxiliaries, plastic additives, dyes, insecticides, flotation agents, corrosion inhibitors, paint additives, detergents, fuel additives, and lubricant additives1. Novel 2-Ethylhexylamine salt anionic monoazo dyes are very useful for dyeing solvents, printing inks or polymeric film-forming materials2.

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.

Chemical Properties

Different sources of media describe the Chemical Properties of 104-75-6 differently. You can refer to the following data:
1. colourless liquid
2. 2-Ethylhexylamine is a corrosive liquid.

Uses

Different sources of media describe the Uses of 104-75-6 differently. You can refer to the following data:
1. 2-Ethylhexylamine is used in organic syntheses.
2. 2-Ethylhexylamine is used to make pharmaceuticals and other chemicals. It is used as beam material and surface active agent. It also involves in synthesis of aliphatic amines.
3. Synthesis of detergents, rubber chemicals, oil additives, and insecticides.

General Description

A water-white liquid with a fishlike odor. Less dense than water. Flash point 140°F. Extremely irritating to skin and eyes. Vapors heavier than air. Used to make pharmaceuticals and other chemicals.

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

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

Downstream Products

• 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 
• 3687-16-9 triamin 
• 6204-28-0 {[(2-ethylhexyl)imino]bis(methylene)}bisphosphonic acid 
• 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] 
• 10576-05-3 2-ethylhexylidene 2-ethylhexyl amine 
• 137795-70-1 (R)-4-Benzyloxycarbonylamino-4-(2-ethyl-hexylcarbamoyl)-butyric acid benzyl ester 

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