Product Name

  • Name

    2-(2-HEXYLOXYETHOXY)ETHANOL

  • EINECS 203-988-3
  • CAS No. 112-59-4
  • Article Data6
  • CAS DataBase
  • Density 0.933 g/cm3
  • Solubility Soluble in water.
  • Melting Point ?40 ºC(lit.)
  • Formula C10H22 O3
  • Boiling Point 260 ºC at 760 mmHg
  • Molecular Weight 190.283
  • Flash Point 140 ºC
  • Transport Information
  • Appearance
  • Safety Moderately toxic by skin contact route. Mildly toxic by ingestion. An eye and severe skin irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also GLYCOL ETHERS.
  • Risk Codes 21-41
  • Molecular Structure Molecular Structure of 112-59-4 (2-(2-HEXYLOXYETHOXY)ETHANOL)
  • Hazard Symbols HarmfulXn
  • Synonyms 2-[2-(Hexyloxy)ethoxy]ethanol;3,6-Dioxa-1-dodecanol; DEGHE; Diethylene glycol hexyl ether; Diethylene glycolmonohexyl ether; HEDG; Hexyl Carbitol; Kyowanol HX 20; NSC 403666; Ucar FilmerEHC; n-Hexoxyethoxyethanol
  • PSA 38.69000
  • LogP 1.59220

Synthetic route

1-bromo-hexane
111-25-1

1-bromo-hexane

diethylene glycol
111-46-6

diethylene glycol

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane at 100 - 105℃;68%
With sodium hydride
oxirane
75-21-8

oxirane

2-hexyloxyethanol
112-25-4

2-hexyloxyethanol

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With borontrifluoride acetic acid
oxirane
75-21-8

oxirane

hexan-1-ol
111-27-3

hexan-1-ol

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 50℃;
1-bromo-hexane
111-25-1

1-bromo-hexane

sodium diethylene glycolate

sodium diethylene glycolate

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With diethylene glycol at 200℃;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate
187748-60-3

2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate

Conditions
ConditionsYield
Stage #1: diethylene glycol monohexyl ether; p-toluenesulfonyl chloride With dmap In dichloromethane at 20℃; for 0.166667h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 3.25h;
100%
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;92%
With pyridine In dichloromethane at 20℃; for 3h;71%
With dmap; triethylamine In dichloromethane for 3h;
2-chloromethyl-3-chloroprop-1-ene
1871-57-4

2-chloromethyl-3-chloroprop-1-ene

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

C24H48O6

C24H48O6

Conditions
ConditionsYield
Stage #1: diethylene glycol monohexyl ether With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-chloromethyl-3-chloroprop-1-ene In tetrahydrofuran; mineral oil at 65℃; for 5.5h; Inert atmosphere;
88%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1,2-Diiodobenzene
615-42-9

1,2-Diiodobenzene

1,2-bis-(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

1,2-bis-(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 72h; Inert atmosphere;85%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 72h; Inert atmosphere;85%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1-[2-(2-chloroethoxy)ethoxy]hexane
72510-64-6

1-[2-(2-chloroethoxy)ethoxy]hexane

Conditions
ConditionsYield
With pyridine; thionyl chloride In toluene at -5 - 100℃; for 2h;84%
With pyridine; thionyl chloride
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1,3-Diiodobenzene
626-00-6

1,3-Diiodobenzene

1,3-bis(2-(2-hexylethoxy)ethoxy)benzene

1,3-bis(2-(2-hexylethoxy)ethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Reflux; Inert atmosphere;82%
iodobenzene
591-50-4

iodobenzene

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

(2-(2-(hexyloxy)ethoxy)ethoxy)benzene
928346-61-6

(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 24h; Inert atmosphere;77%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 24h; Inert atmosphere;77%
1-bromo-hexane
111-25-1

1-bromo-hexane

diethylene glycol
111-46-6

diethylene glycol

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane at 100 - 105℃;68%
With sodium hydride
oxirane
75-21-8

oxirane

2-hexyloxyethanol
112-25-4

2-hexyloxyethanol

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With borontrifluoride acetic acid
oxirane
75-21-8

oxirane

hexan-1-ol
111-27-3

hexan-1-ol

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 50℃;
1-bromo-hexane
111-25-1

1-bromo-hexane

sodium diethylene glycolate

sodium diethylene glycolate

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Conditions
ConditionsYield
With diethylene glycol at 200℃;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate
187748-60-3

2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate

Conditions
ConditionsYield
Stage #1: diethylene glycol monohexyl ether; p-toluenesulfonyl chloride With dmap In dichloromethane at 20℃; for 0.166667h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 3.25h;
100%
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;92%
With pyridine In dichloromethane at 20℃; for 3h;71%
With dmap; triethylamine In dichloromethane for 3h;
2-chloromethyl-3-chloroprop-1-ene
1871-57-4

2-chloromethyl-3-chloroprop-1-ene

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

C24H48O6

C24H48O6

Conditions
ConditionsYield
Stage #1: diethylene glycol monohexyl ether With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-chloromethyl-3-chloroprop-1-ene In tetrahydrofuran; mineral oil at 65℃; for 5.5h; Inert atmosphere;
88%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1,2-Diiodobenzene
615-42-9

1,2-Diiodobenzene

1,2-bis-(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

1,2-bis-(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 72h; Inert atmosphere;85%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 72h; Inert atmosphere;85%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1-[2-(2-chloroethoxy)ethoxy]hexane
72510-64-6

1-[2-(2-chloroethoxy)ethoxy]hexane

Conditions
ConditionsYield
With pyridine; thionyl chloride In toluene at -5 - 100℃; for 2h;84%
With pyridine; thionyl chloride
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1,3-Diiodobenzene
626-00-6

1,3-Diiodobenzene

1,3-bis(2-(2-hexylethoxy)ethoxy)benzene

1,3-bis(2-(2-hexylethoxy)ethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 20h; Reflux; Inert atmosphere;82%
iodobenzene
591-50-4

iodobenzene

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

(2-(2-(hexyloxy)ethoxy)ethoxy)benzene
928346-61-6

(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 24h; Inert atmosphere;77%
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 24h; Inert atmosphere;77%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

hexafluoropropene-diethylamine adduct
309-88-6

hexafluoropropene-diethylamine adduct

A

N,N-diethyl 2,3,3,3-tetrafluoropropionamide

N,N-diethyl 2,3,3,3-tetrafluoropropionamide

B

1-[2-(2-Fluoro-ethoxy)-ethoxy]-hexane

1-[2-(2-Fluoro-ethoxy)-ethoxy]-hexane

C

2,3,3,3-Tetrafluoro-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester

2,3,3,3-Tetrafluoro-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester

Conditions
ConditionsYield
In dichloromethane for 3h; Ambient temperature;A n/a
B 70%
C 15%
In dichloromethane for 3h; Ambient temperature;A n/a
B 70%
C 15%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

2-methyl-2-octyldodecanoic acid

2-methyl-2-octyldodecanoic acid

C31H62O4

C31H62O4

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 18h; Dean-Stark; Reflux;70%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1-Iodonaphthalene
90-14-2

1-Iodonaphthalene

1-(2-(2-(hexyloxy)ethoxy)ethoxy)naphthalene

1-(2-(2-(hexyloxy)ethoxy)ethoxy)naphthalene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere;67%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

(5,10,15,20-tetraphenylporphinato)dichlorophosphorus(V) chloride

(5,10,15,20-tetraphenylporphinato)dichlorophosphorus(V) chloride

di(3,6-dioxadodecyloxo)tetraphenylporphyrinatophosphorus(V) chloride

di(3,6-dioxadodecyloxo)tetraphenylporphyrinatophosphorus(V) chloride

Conditions
ConditionsYield
With pyridine In acetonitrile for 24h; Reflux;66%
With pyridine In acetonitrile for 24h; Reflux;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

4-tolyl iodide
624-31-7

4-tolyl iodide

1-(2-(2-(hexyloxy)ethoxy)ethoxy)-4-methylbenzene

1-(2-(2-(hexyloxy)ethoxy)ethoxy)-4-methylbenzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere;63%
1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

C13H21Cl2N3O3
928346-63-8

C13H21Cl2N3O3

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate at 20 - 50℃; for 20h; Product distribution / selectivity;60%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

3,4-dimethyliodobenzene
31599-61-8

3,4-dimethyliodobenzene

4-(2-(2-(hexyloxy)ethoxy)ethoxy)-1,2-dimethylbenzene

4-(2-(2-(hexyloxy)ethoxy)ethoxy)-1,2-dimethylbenzene

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere;60%
1,2,3,4-tetra-O-acetyl-D-xylopyranose
62446-93-9

1,2,3,4-tetra-O-acetyl-D-xylopyranose

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

triacetylhexyl bis(oxyethyl)-α-D-xyloside

triacetylhexyl bis(oxyethyl)-α-D-xyloside

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 0℃; for 24h; Molecular sieve;54%
With tin(IV) chloride Helferich Method; stereoselective reaction;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

chloranil
118-75-2

chloranil

A

2,3,5-trichloro-[6-(2-(2-hexyloxy)ethoxy)ethoxy]cyclohexa-2,5-diene-1,4-dione

2,3,5-trichloro-[6-(2-(2-hexyloxy)ethoxy)ethoxy]cyclohexa-2,5-diene-1,4-dione

B

C26H42Cl2O8

C26H42Cl2O8

C

C26H42Cl2O8

C26H42Cl2O8

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;A 38%
B 4%
C 17%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

2-(2-(2-(hexyloxy)ethoxy)ethoxy)-3-chloro-1,4-naphthoquinone

2-(2-(2-(hexyloxy)ethoxy)ethoxy)-3-chloro-1,4-naphthoquinone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 12h;25%
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

C64H86O43

C64H86O43

C72H104O44

C72H104O44

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 45℃; for 5h; glycosidation;22%
oxirane
75-21-8

oxirane

diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

2-[2-(2-hexyloxy-ethoxy)-ethoxy]-ethanol
25961-89-1

2-[2-(2-hexyloxy-ethoxy)-ethoxy]-ethanol

Conditions
ConditionsYield
With borontrifluoride acetic acid
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Tetraethylene glycol monohexyl ether
39619-69-7

Tetraethylene glycol monohexyl ether

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride Erhitzen des Reaktionsprodukts mit Natrium-diaethylenglykolat in Diaethylenglykol auf 130grad;
Multi-step reaction with 2 steps
1: pyridine; thionyl chloride
2: diethylene glycol
View Scheme
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

acrylonitrile
107-13-1

acrylonitrile

3-[2-(2-hexyloxy-ethoxy)-ethoxy]-propionitrile
102236-85-1

3-[2-(2-hexyloxy-ethoxy)-ethoxy]-propionitrile

Conditions
ConditionsYield
With potassium hydroxide
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

diclofop
40843-25-2

diclofop

2-[4-(2,4-Dichloro-phenoxy)-phenoxy]-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester
65634-01-7

2-[4-(2,4-Dichloro-phenoxy)-phenoxy]-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester

Conditions
ConditionsYield
(i) SOCl2, toluene, (ii) /BRN= 1743959/, Et3N; Multistep reaction;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

4-(4-chlorophenoxy)-α-phenoxy-propionic acid chloride

4-(4-chlorophenoxy)-α-phenoxy-propionic acid chloride

2-[4-(4-Chloro-phenoxy)-phenoxy]-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester
65634-00-6

2-[4-(4-Chloro-phenoxy)-phenoxy]-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester

Conditions
ConditionsYield
With triethylamine In toluene
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

epichlorohydrin
106-89-8

epichlorohydrin

2-[2-(2-Hexyloxy-ethoxy)-ethoxymethyl]-oxirane
120439-33-0

2-[2-(2-Hexyloxy-ethoxy)-ethoxymethyl]-oxirane

Conditions
ConditionsYield
With sodium hydroxide at 70 - 90℃;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C42H70O35*C10H22O3

C42H70O35*C10H22O3

Conditions
ConditionsYield
In water at 80℃; for 24h;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

Methacryloyl chloride
920-46-7

Methacryloyl chloride

C14H26O4
183317-57-9

C14H26O4

Conditions
ConditionsYield
With triethylamine In benzene at 20℃;
diethylene glycol monohexyl ether
112-59-4

diethylene glycol monohexyl ether

1,3-bis<2-(n-hexyloxyethoxy)ethoxy>propane-2-ol

1,3-bis<2-(n-hexyloxyethoxy)ethoxy>propane-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50percent aq. NaOH / 70 - 90 °C
2: 50percent aq. NaOH / 1 h / 70 - 80 °C
View Scheme

Diethyleneglycolmonohexylether Chemical Properties

SYNONYMS Diethylene glycol hexyl ether; 2-((2-Hexyloxy)ethoxy)ethanol; 
Diethylene glycol mono(n-hexyl) ether; Hexol carbitol; Diethylene glycol monohexyl ether; n-Hexoxyethoxyethanol; Diethyleneglycolmonohexylether; 2-((2-Hexyloxy)ethoxy)ethanol; 2-(2-(hexyloxy)ethoxy)ethanol; 
EINECS NO.:203-988-3
FORMULA:CH3(CH2)5OCH2CH2OH
MOL WT:146.23
PHYSICAL STATE:clear liquid
MELTING POINT:-40 °C
BOILING POINT:260 °C
SPECIFIC GRAVITY:0.93 - 0.94
FLASH POINT:141°C
REFRACTIVE INDEX:1.435
SOLUBILITY IN WATER:1.7 (g/100g)

Diethyleneglycolmonohexylether,it is sable under ordinary conditions.

Diethyleneglycolmonohexylether Toxicity Data With Reference

1.   

skn-rbt 10 mg/24H open MLD

   AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 4 (1951),119.
2.   

skn-rbt 500 mg/24H SEV

   JPETAB    Journal of Pharmacology and Experimental Therapeutics. 82 (1944),377.
3.   

skn-rbt 500 mg open MLD

   UCDS**    Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 11/3 ,1971.
4.   

eye-rbt 5 mg MOD

   UCDS**    Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 11/3 ,1971.
5.   

orl-rat LD50:4920 mg/kg

   AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 4 (1951),119.
6.   

skn-rbt LD50:1500 mg/kg

   AMIHBC    AMA Archives of Industrial Hygiene and Occupational Medicine. 4 (1951),119.

Diethyleneglycolmonohexylether Consensus Reports

n-HEXYL CARBITOL is reported in PA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.

Diethyleneglycolmonohexylether Safety Profile

Moderately toxic by skin contact route. Mildly toxic by ingestion. An eye and severe skin irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also GLYCOL ETHERS.

Diethyleneglycolmonohexylether's Risk Statements:21:Harmful in contact with skin;41:Risk of serious damage to eyes   
Diethyleneglycolmonohexylether's Safety Statements:26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;36/37:Wear suitable protective clothing and gloves;46:If swallowed, seek medical advice immediately and show this container or label;24/25:Avoid contact with skin and eyes
Hazard Codes:Xn
WGK Germany:1

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