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104-76-7

Basic Information
CAS No.: 104-76-7
Name: 2-Ethylhexanol
Article Data: 177
Molecular Structure:
Molecular Structure of 104-76-7 (2-Ethylhexanol)
Formula: C8H18O
Molecular Weight: 130.23
Synonyms: 2-Ethyl-1-hexanol;2-Ethyl-1-hexyl alcohol;2-Ethylhexylalcohol;Conol 10WS;Ethylhexanol;G 301;NSC 9300;
EINECS: 203-234-3
Density: 0.821 g/cm3
Melting Point: -76 °C(lit.)
Boiling Point: 184.6 °C at 760 mmHg
Flash Point: 77.2 °C
Solubility: Water Solubility :1 g/L (20 °C)
Appearance: colourless liquid
Hazard Symbols: HarmfulXn; IrritantXi
Risk Codes: 37/38-41-36-21
Safety: 26-36/37/39
PSA: 20.23000
LogP: 2.19510
Synthetic route
100528-70-9

2-(2-ethylhexyloxy)-tetrahydro-2H-pyran

104-76-7

2-Ethylhexyl alcohol

Conditions
ConditionsYield
With methanol at 20℃; for 0.5h;98%
With methanol at 20℃; for 0.916667h;94%
645-62-5

2-ethylhexenal

104-76-7

2-Ethylhexyl alcohol

Conditions
ConditionsYield
With hydrogen at 110℃; under 18751.9 Torr; for 28h; Inert atmosphere;96%
With Ni/γ-Al2O3 catalyst at 180℃; under 15001.5 Torr; for 1.33333h; Catalytic behavior; Pressure; Temperature; Time;93.8%
With sodium butanolate at 310℃; unter Druck;
149-57-5

2-Ethylhexanoic acid

104-76-7

2-Ethylhexyl alcohol

Conditions
ConditionsYield
With sodium hydroxide; samarium diiodide; water In tetrahydrofuran for 0.00277778h; Ambient temperature;94%
With sodium hydroxide; samarium diiodide In tetrahydrofuran; water for 0.00333333h; Ambient temperature;94%
With nonan-1-al; samarium diiodide; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; potassium hydroxide at 20℃; for 0.133333h; Reduction;93 % Chromat.
123-05-7

d,l-2-ethylhexanal

104-76-7

2-Ethylhexyl alcohol

Conditions
ConditionsYield
With hydrogenchloride; Raney(R) nickel 2800; isopropyl alcohol In water for 0.5h; Heating;90%
With sodium tetrahydroborate; tetrabutylammomium bromide In benzene at 20 - 25℃; for 1h;85%
With Zr(BH4)2Cl2(dabco)2 In water for 0.5h; Heating;85%
71-36-3

butan-1-ol

104-76-7

2-Ethylhexyl alcohol

Conditions
ConditionsYield
With potassium hydroxide; dichloro(pentamethylcyclopentadienyl) iridium; 1,7-Octadiene In para-xylene at 120℃; for 4h; Guerbet reaction;83%
With calcium carbide at 275℃; for 6h; Autoclave;32.6%
With dicarbonyl(η4-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)(iodine)ruthenium[1,3 -dimethylimidazolium]; p-benzoquinone; sodium hydroxide at 150℃; for 4h; Reagent/catalyst; Schlenk technique; Inert atmosphere;32.9%
645-62-5

2-ethylhexenal

A

123-05-7

d,l-2-ethylhexanal

B

104-76-7

2-Ethylhexyl alcohol

Conditions
ConditionsYield
With Ni/γ-Al2O3 catalyst under 7500.75 Torr;A 80.1%
B 19.9%
With methanol; nickel boride; diborane for 0.5h; Ambient temperature;A 51.2%
B 40.9%
With Pd0078Co5790B42.02; hydrogen In ethanol at 99.84℃; under 7500.75 Torr; for 4h; Autoclave;
With hydrogen; palladium In ethanol at 99.84℃; under 7500.75 Torr; for 4h; Autoclave;
With butan-1-ol at 180℃; under 11103.3 Torr; for 4h; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere;
36653-82-4

1-Hexadecanol

5466-77-3

2-propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

A

104-76-7

2-Ethylhexyl alcohol

B

125628-87-7

n-hexadecyl 4-methoxycinnamate

Conditions
ConditionsYield
With aluminium trichloride 1.) 90 deg C, 50 h, 2.) reflux, 26 h;A n/a
B 75%
123-72-8

butyraldehyde

A

123-05-7

d,l-2-ethylhexanal

B

104-76-7

2-Ethylhexyl alcohol

C

645-62-5

2-ethylhexenal

D

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen at 180℃; under 30003 Torr; for 10h; Catalytic behavior; Autoclave; Inert atmosphere; Green chemistry; Overall yield = 97.7 %;A 73%
B 1.1%
C 2%
D 4.5%
With hydrogen at 180℃; under 30003 Torr; for 10h; Catalytic behavior; Autoclave; Inert atmosphere; Green chemistry; Overall yield = 91.7 %;A 54.6%
B 0.2%
C 27.3%
D 2.3%
With hydrogen at 180℃; under 30003 Torr; for 10h; Catalytic behavior; Autoclave; Inert atmosphere; Green chemistry; Overall yield = 100 %;A 33%
B 1.6%
C 36.7%
D 1.6%
With hydrogen; zeolite NaX; platinum at 150℃; Product distribution; further catalysts; further temperature;
18908-66-2

2-ethylhexyl bromide

123-31-9

hydroquinone

A

104-76-7

2-Ethylhexyl alcohol

B

110126-93-7

1,4-bis((2-ethylhexyl)oxy)benzene

Conditions
ConditionsYield
With ethanol; potassium hydroxide In methanol for 18h; Reflux;A n/a
B 64%
123-72-8

butyraldehyde

A

104-76-7

2-Ethylhexyl alcohol

B

645-62-5

2-ethylhexenal

C

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen at 180℃; under 30003 Torr; for 10h; Catalytic behavior; Reagent/catalyst; Autoclave; Inert atmosphere; Green chemistry; Overall yield = 100 %;A n/a
B 22.8%
C 58.1%
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Specification

The CAS registry number of 2-Ethylhexanol is 104-76-7. Its EINECS registry number is 203-234-3. The IUPAC name is 2-ethylhexan-1-ol. In addition, the molecular formula is C8H18O and the molecular weight is 130.23. It is also called 1-hexanol, 2-ethyl-. What's more, it is a kind of colourless liquid that is nearly insoluble in water but soluble in most organic solvents. And it belongs to the class of Industrial/Fine Chemicals. Besides, it should be stored in sealed container, and put in a cool and dry place. The storage place must stay away from oxidant, the fire, water source and heat source

Physical properties about this chemical are: (1)ACD/LogP: 2.82; (2)ACD/LogD (pH 5.5): 2.82; (3)ACD/LogD (pH 7.4): 2.82; (4)ACD/BCF (pH 5.5): 81.41; (5)ACD/BCF (pH 7.4): 81.41; (6)ACD/KOC (pH 5.5): 811.45; (7)ACD/KOC (pH 7.4): 811.45; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 9.23 Å2; (12)Index of Refraction: 1.426; (13)Molar Refractivity: 40.6 cm3; (14)Molar Volume: 158.4 cm3; (15)Polarizability: 16.09 ×10-24cm3; (16)Surface Tension: 28 dyne/cm; (17)Density: 0.821 g/cm3; (18)Flash Point: 77.2 °C; (19)Enthalpy of Vaporization: 48.98 kJ/mol; (20)Boiling Point: 184.6 °C at 760 mmHg; (21)Vapour Pressure: 0.207 mmHg at 25°C.

Preparation of 2-Ethylhexanol: it is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde. The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully-integrated facility. The equation is as follows:

2-Ethylhexanol is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde

Uses of 2-Ethylhexanol: It is commonly used as a low volatility solvent. And it is used in the production of plasticizers, defoaming agents, dispersants, antioxidants and oil additives. In addition, it can be used to get 3-bromomethyl-heptane. This reaction will need reagent 48percent aq. HBr, catalyst aliquat 336 and solvent chlorobenzene. The reaction time is 14 hours at reaction temperature of 100 °C. The yield is about 98.8%.

2-Ethylhexanol can be used to get 3-bromomethyl-heptane

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating respiratory system. And it is harmful in contact with skin. Moreover, it has risk of serious damage to eyes. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: OCC(CC)CCCC
(2)InChI: InChI=1/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3
(3)InChIKey: YIWUKEYIRIRTPP-UHFFFAOYAU

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 1860mg/kg (1860mg/kg)   Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974.
mouse LD50 intraperitoneal 759mg/kg (759mg/kg)   Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974.
mouse LD50 oral 2500mg/kg (2500mg/kg)   Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974.
mouse LD50 parenteral 1670mg/kg (1670mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 775, 1979.
rabbit LD50 oral 1180mg/kg (1180mg/kg)   Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. Vol. 20, Pg. 575, 1974.
rabbit LD50 skin 1970mg/kg (1970mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 61, 1974.
rat LC inhalation > 2000ppm/6H (2000ppm)   Kodak Company Reports. Vol. 21MAY1971,
rat LD50 intraperitoneal 500mg/kg (500mg/kg)   Hydrometallurgy. Vol. 3, Pg. 201, 1978.
rat LD50 oral 3730mg/kg (3730mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Industrial Hygiene Association Journal. Vol. 34, Pg. 493, 1973.
rat LD50 parenteral 4600mg/kg (4600mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 775, 1979.
rat LD50 skin > 3gm/kg (3000mg/kg)   National Technical Information Service. Vol. OTS0524344,
rat LD50 subcutaneous 650mg/kg (650mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 61, 1974.