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111-76-2

Basic Information
CAS No.: 111-76-2
Name: Ethanol,2-butoxy-
Molecular Structure:
Molecular Structure of 111-76-2 (Ethanol,2-butoxy-)
Formula: C6H14O2
Molecular Weight: 118.18
Synonyms: 2-Butoxy-1-ethanol;2-n-Butoxyethanol;3-Oxa-1-heptanol;Bikanol B 1;Buchiseru;Butyl Cellosolve;Butyl Cellu-Sol;Butyl Glysolv;Butyl Oxitol;Butyl glycol;Butyl icinol;Butyl monoether glycol;C4E1;Chimec NR;DB solvent;Dowanol EB;EGBE;Eastman EB;Ektasolve EB;Ethylene glycol butyl ether;Ethylene glycolmono-n-butyl ether;Ethylene glycol monobutyl ether;Ethylene glycol n-butylether;2-Butoxyethanol;
EINECS: 203-905-0
Density: 0.901 g/cm3
Melting Point: -70 °C
Boiling Point: 167.7 °C at 760 mmHg
Flash Point: 60 °C
Solubility: miscible with water
Appearance: clear colourless to light yellow liquid
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/38
Safety: 36/37-46
Transport Information: UN 2369
PSA: 29.46000
LogP: 0.79540
Synthetic route
74-85-1

ethene

71-36-3

butan-1-ol

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With dihydrogen peroxide Green chemistry;98.5%
75-21-8

oxirane

71-36-3

butan-1-ol

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With aluminum tri-n-butoxide; acetic acid at 170℃; for 24h; Reagent/catalyst; Autoclave;97.75%
With MCM-41-500 ° C catalyst at 100℃; for 4h; Reagent/catalyst; Temperature; Autoclave; High pressure;86.8%
In dodecane at 100℃; Kinetics;
75-21-8

oxirane

71-36-3

butan-1-ol

A

111-76-2

2-Butoxyethanol

B

112-34-5

Diethylene glycol monobutyl ether

Conditions
ConditionsYield
With potassium aluminum sulfate at 170℃; for 24h; Reagent/catalyst; Autoclave;A 93.1%
B 6.63%
111-34-2

-butyl vinyl ether

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
Stage #1: -butyl vinyl ether With borane-ammonia complex In tetrahydrofuran at 90℃; for 3h;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 3h;
59%
96-49-1

[1,3]-dioxolan-2-one

2372-45-4

sodium butanolate

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With benzene at 100℃;
96-49-1

[1,3]-dioxolan-2-one

71-36-3

butan-1-ol

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With dimethyl sulfate at 130℃;
71808-63-4

1,1-bis-(2-methoxy-ethoxy)-butane

A

111-76-2

2-Butoxyethanol

B

13343-98-1

1-(2-methoxy-ethoxy)-butane

Conditions
ConditionsYield
With nickel at 200 - 240℃; under 51485.6 - 77228.3 Torr; Hydrogenation;
10228-54-3

Methyl butoxyacetate

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With ethanol; copper oxide-chromium oxide at 200℃; under 147102 Torr; Hydrogenation;
10397-22-5

butyl butoxyacetate

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With copper-chromium-iron at 280℃; under 95616 Torr; Hydrogenation;
107-21-1

ethylene glycol

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With sodium und anschliessenden Erhitzen mit 1-Brom-butan;
109-69-3

n-Butyl chloride

107-21-1

ethylene glycol

A

111-76-2

2-Butoxyethanol

B

112-48-1

1,2-dibutoxyethane

Conditions
ConditionsYield
(i) DMSO, NaOH, (ii) /BRN= 1730909/; Multistep reaction;
3390-13-4

2-propyl-1,3-dioxolane

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction;
In ethylene glycol
With hydrogen; 0.6 wt % palladium on alumina at 210℃; under 16274.9 Torr; Product distribution / selectivity;
3390-13-4

2-propyl-1,3-dioxolane

A

111-76-2

2-Butoxyethanol

B

107-21-1

ethylene glycol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
110-80-5

2-ethoxy-ethanol

869-01-2

1-butyl-1-nitrosourea

A

628-81-9

butyl ethyl ether

B

111-76-2

2-Butoxyethanol

C

4413-13-2

1-(2-Ethoxyethoxy)butan

D

77078-19-4

ethylene glycol sec-butyl ethyl ether

Conditions
ConditionsYield
With potassium carbonate Ambient temperature; Further byproducts given;A 2.7 % Chromat.
B 1.8 % Chromat.
C 83.2 % Chromat.
D 11.6 % Chromat.
With sodium hydrogencarbonate for 24h; Ambient temperature; Further byproducts given;A 1.3 % Chromat.
B 2.9 % Chromat.
C 81.9 % Chromat.
D 12.6 % Chromat.
110-80-5

2-ethoxy-ethanol

869-01-2

1-butyl-1-nitrosourea

A

111-76-2

2-Butoxyethanol

B

629-14-1

monoethylene glycol diethyl ether

C

4413-13-2

1-(2-Ethoxyethoxy)butan

D

77078-19-4

ethylene glycol sec-butyl ethyl ether

Conditions
ConditionsYield
With sodium hydrogencarbonate for 24h; Ambient temperature; Further byproducts given;A 2.9 % Chromat.
B 0.9 % Chromat.
C 81.9 % Chromat.
D 12.6 % Chromat.
10397-22-5

butyl butoxyacetate

Cu-Cr-Fe-catalyst

Cu-Cr-Fe-catalyst

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
at 280℃; under 95616 Torr; Anfangsdruck.Hydrogenation;
542-69-8

1-iodo-butane

monosodium compound of ethylene glycol

monosodium compound of ethylene glycol

111-76-2

2-Butoxyethanol

formaldehyde-<2-butyloxy-ethylacetal>

formaldehyde-<2-butyloxy-ethylacetal>

A

111-76-2

2-Butoxyethanol

B

13343-98-1

1-(2-methoxy-ethoxy)-butane

Conditions
ConditionsYield
With nickel at 200 - 240℃; under 51485.6 - 77228.3 Torr; Hydrogenation;
109-86-4

2-methoxy-ethanol

869-01-2

1-butyl-1-nitrosourea

A

110-71-4

1,2-dimethoxyethane

B

628-28-4

butyl methyl ether

C

111-76-2

2-Butoxyethanol

D

7795-91-7

2-(1-Methylpropoxy)ethanol

E

13343-98-1

1-(2-methoxy-ethoxy)-butane

F

2-(2-Methoxyethoxy)butan

G

butenes, butanols, sBuOMe

butenes, butanols, sBuOMe

Conditions
ConditionsYield
With potassium carbonate for 0.0833333h; Product distribution; Mechanism; Ambient temperature; further reagent: NaHCO3, further reactions with EtOCH2CH2OH, MeOH-oxirane, -oxetane, -tetrahydrofuran;A 0.5 % Chromat.
B 2.9 % Chromat.
C 7.2 % Chromat.
D 0.5 % Chromat.
E 74.4 % Chromat.
F 14.2 % Chromat.
G n/a
75-21-8

oxirane

71-36-3

butan-1-ol

A

111-76-2

2-Butoxyethanol

B

112-34-5

Diethylene glycol monobutyl ether

C

143-22-6

triethyleneglycol monobutyl ether

Conditions
ConditionsYield
2,4,6-trimethyl-pyridine at 160℃; under 2311.54 - 3345.86 Torr; for 2.5h; Product distribution / selectivity; Inert atmosphere;
sodium butanolate at 140℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;A 20.16 %Chromat.
B 9.07 %Chromat.
C 6.10 %Chromat.
catalyst of invention (Sb2O3, copper acetate, hydrogen peroxide; calcined) at 140℃; under 30003 Torr; for 24 - 120h; Product distribution / selectivity;A 76 - 77 %Chromat.
B 13 - 14 %Chromat.
C 9 %Chromat.
2568-90-3

di-n-butyloxymethane

111-76-2

2-Butoxyethanol

Ru3 (CO)12

Ru3 (CO)12

HCCo(CO)9

HCCo(CO)9

109-87-5

Dimethoxymethane

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With carbon monoxide; hydrogen In butan-1-ol
71-36-3

butan-1-ol

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With hydrogen; paraformaldehyde
139-66-2

diphenyl sulfide

71-36-3

butan-1-ol

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With hydrogen; paraformaldehyde
112-60-7

Tetraethylene glycol

107-21-1

ethylene glycol

123-72-8

butyraldehyde

111-46-6

diethylene glycol

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

A

3390-13-4

2-propyl-1,3-dioxolane

B

111-76-2

2-Butoxyethanol

C

112-34-5

Diethylene glycol monobutyl ether

D

143-22-6

triethyleneglycol monobutyl ether

E

1559-34-8

tetraethylene glycol monobutyl ether

F

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h;
107-21-1

ethylene glycol

123-72-8

butyraldehyde

A

111-76-2

2-Butoxyethanol

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h; Product distribution / selectivity; Inert atmosphere;A 88.7 %Chromat.
B 7.2 %Chromat.
With hydrogen; 5%-palladium/activated carbon at 200℃; under 25877.6 Torr; for 1h; Autoclave;
With palladium 10% on activated carbon; hydrogen at 180℃; under 51755.2 Torr; for 2h; Temperature; Concentration;A 88.7 %Chromat.
B 7.2 %Chromat.
107-21-1

ethylene glycol

123-72-8

butyraldehyde

A

111-76-2

2-Butoxyethanol

B

112-48-1

1,2-dibutoxyethane

C

71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h; Product distribution / selectivity; Inert atmosphere;A 79.7 %Chromat.
B 7.7 %Chromat.
C 7.5 %Chromat.
With palladium 10% on activated carbon; hydrogen at 180℃; under 51755.2 Torr; for 2h;A 79.7 %Chromat.
B 7.7 %Chromat.
C 7.5 %Chromat.
107-21-1

ethylene glycol

123-72-8

butyraldehyde

111-76-2

2-Butoxyethanol

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon at 180℃; under 25858.1 Torr; for 3h; Product distribution / selectivity; Inert atmosphere;85.5 %Chromat.
With palladium 10% on activated carbon; hydrogen at 180℃; under 26252.6 Torr; for 3h;85.5 %Chromat.
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    MSDS/COA Download

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  • 2-Butoxyethanol 111-76-2CAS NO.: 111-76-2

  • Casno:

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    2-Butoxyethanol 111-76-2CAS NO.: 111-76-2

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  • 1-butoxyethanol CAS NO.111-76-2

  • Casno:

    111-76-2

    1-butoxyethanol CAS NO.111-76-2

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Consensus Reports

Reported in EPA TSCA Inventory. Glycol ethers are on the Community Right-To-Know List.

Standards and Recommendations

OSHA PEL: TWA 25 ppm (skin)
ACGIH TLV: 20 ppm (skin); Confirmed Animal Carcinogen.
DFG MAK: 20 ppm (98 mg/m3)
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Analytical Methods

For occupational chemical analysis use NIOSH: Alcohols IV, 1403.

Specification

The 2-Butoxyethanol is an organic solvent with the formula BuOC2H4OH (Bu = CH3CH2CH2CH2). It belongs to the product categories of Ethylene Glycols & Monofunctional Ethylene Glycols; Monofunctional Ethylene Glycols. Its EINECS registry number is 203-905-0. With the CAS registry number 111-76-2, its IUPAC name is called 2-butoxyethanol. This chemical's classification codes are Human Data; Mutation Data; Reproductive Effect; Skin / Eye Irritant; Tumor Data. It is a colorless liquid with a sweet, ether-like odour. 

Physical properties about 2-Butoxyethanol are: (1)ACD/LogP: 0.80; (2)ACD/LogD (pH 5.5): 0.8; (3)ACD/LogD (pH 7.4): 0.8; (4)ACD/BCF (pH 5.5): 2.37; (5)ACD/BCF (pH 7.4): 2.37; (6)ACD/KOC (pH 5.5): 64.62; (7)ACD/KOC (pH 7.4): 64.62; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.418; (12)Molar Refractivity: 33.12 cm3; (13)Molar Volume: 131.4 cm3; (14)Surface Tension: 29.8 dyne/cm; (15)Density: 0.899 g/cm3; (16)Flash Point: 60 °C; (17)Enthalpy of Vaporization: 47.06 kJ/mol; (18)Boiling Point: 167.7 °C at 760 mmHg; (19)Vapour Pressure: 0.552 mmHg at 25°C.

Preparation of 2-Butoxyethanol: 2-Butoxyethanol is produced by monoethoxylation of butanol. In 2006, the total European production of all butyl glycol ethers amounted to 181 kilotons per annum (kt/a), approximately 50% (90 kt/a) of which was 2-butoxyethanol. World production is estimated to be 200 to 500 kt/a, of which 75% is for paints and coatings.

C2H4O + BuOH → BuOC2H4OH

Uses of 2-Butoxyethanol: 2-Butoxyethanol is a solvent in paints and surface coatings, as well as cleaning products and inks. Other products that contain 2-butoxyethanol include acrylic resin formulations, asphalt release agents, firefighting foam, leather protectors, oil spill dispersants, degreaser applications, and photographic strip solutions. Other products containing 2-butoxyethanol as a primary ingredient include some whiteboard cleaners, liquid soaps, cosmetics, dry cleaning solutions, lacquers, varnishes, herbicides, and latex paints. It is the main ingredient of many home, commercial and industrial cleaning solutions.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCOCCO
(2)InChI: InChI=1S/C6H14O2/c1-2-3-5-8-6-4-7/h7H,2-6H2,1H3
(3)InChIKey: POAOYUHQDCAZBD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC inhalation > 633ppm/1H (633ppm)   National Technical Information Service. Vol. OTS0572613,
guinea pig LD50 oral 1200mg/kg (1200mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
guinea pig LD50 skin 230uL/kg (0.23mL/kg)   Toxicology and Applied Pharmacology. Vol. 7, Pg. 559, 1965.
human TCLo inhalation 100ppm (100ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 50, 1974.
human TCLo inhalation 195ppm/8H (195ppm) GASTROINTESTINAL: NAUSEA OR VOMITING AMA Archives of Industrial Health. Vol. 14, Pg. 114, 1956.
mammal (species unspecified) LD50 unreported 1500mg/kg (1500mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse LC50 inhalation 700ppm/7H (700ppm) BEHAVIORAL: ANALGESIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

KIDNEY, URETER, AND BLADDER: HEMATURIA
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 157, 1943.
mouse LD50 intraperitoneal 536mg/kg (536mg/kg)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 2, 1961.
mouse LD50 intravenous 1130mg/kg (1130mg/kg)   AMA Archives of Industrial Health. Vol. 14, Pg. 114, 1956.
mouse LD50 oral 1230mg/kg (1230mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
AMA Archives of Industrial Health. Vol. 14, Pg. 114, 1956.
mouse LD50 unreported 1050mg/kg (1050mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(11), Pg. 7, 1976.
mouse LDLo subcutaneous 500mg/kg (500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 42, Pg. 355, 1931.
rabbit LD50 intraperitoneal 220mg/kg (220mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 67, 1982.
rabbit LD50 intravenous 252mg/kg (252mg/kg)   AMA Archives of Industrial Health. Vol. 14, Pg. 114, 1956.
rabbit LD50 oral 300mg/kg (300mg/kg)   Yakkyoku. Pharmacy. Vol. 32, Pg. 1241, 1981.
rabbit LD50 skin 220mg/kg (220mg/kg)   Dow Chemical Company Reports. Vol. MSD-46,
rat LC50 inhalation 450ppm/4H (450ppm) BEHAVIORAL: ATAXIA Toxicology and Applied Pharmacology. Vol. 68, Pg. 405, 1983.
rat LD50 intraperitoneal 220mg/kg (220mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 67, 1982.
rat LD50 intravenous 307mg/kg (307mg/kg)   AMA Archives of Industrial Health. Vol. 14, Pg. 114, 1956.
rat LD50 oral 470mg/kg (470mg/kg)   Dow Chemical Company Reports. Vol. MSD-46,
rat LD50 unreported 917mg/kg (917mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(11), Pg. 7, 1976.
women TDLo oral 7813uL/kg (7.813mL/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Human Toxicology. Vol. 8, Pg. 243, 1989.
women TDLo oral 600mg/kg (600mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Human Toxicology. Vol. 7, Pg. 187, 1988.