112-59-4

Basic information

• Product Name: 2-(2-HEXYLOXYETHOXY)ETHANOL
• Synonyms: C6E2;DI(ETHYLENE GLYCOL) HEXYL ETHER;DIETHYLENE GLYCOL MONO-N-HEXYL ETHER;HEXYLDIGLYCOL;2-(2-N-HEXYLOXYETHOXY)ETHANOL;2-(2-HEXYLOXYETHOXY)ETHANOL;2-(HEXYLOXYETHOXY)ETHANOL;N-HEXYL CARBITOL
• CAS NO: 112-59-4
• Molecular Formula: C₁₀H₂₂O₃
• Molecular Weight: 190.28
• EINECS: 203-988-3
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols
• Mol File: 112-59-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: −40 °C(lit.)
• Boiling Point: 261-265 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.935 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00182mmHg at 25°C
• Refractive Index: n20/D 1.4381(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 17g/l
• PKA: 14.37±0.10(Predicted)
• Explosive Limit: 1.1-6.3%(V)
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• BRN: 1743959
• CAS DataBase Reference: 2-(2-HEXYLOXYETHOXY)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-HEXYLOXYETHOXY)ETHANOL(112-59-4)
• EPA Substance Registry System: 2-(2-HEXYLOXYETHOXY)ETHANOL(112-59-4)

Safety Data

• Hazard Codes: Xn
• Statements: 21-41-38
• Safety Statements: 26-36/37-46-36/37/39
• WGK Germany: 1
• RTECS: KL2625000
• TSCA: Yes
• Hazardous Substances Data: 112-59-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Used as a solvent for coatings and degreasing.

General Description

Water-white liquid.

Air & Water Reactions

Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid.

Reactivity Profile

Ethers, such as 2-(2-HEXYLOXYETHOXY)ETHANOL can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Health Hazard

Exposure can cause irritation of eyes, nose and throat.

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H22O3/c1-2-3-4-5-7-12-9-10-13-8-6-11/h11H,2-10H2,1H3

Synthetic route

1-bromo-hexane (111-25-1) + diethylene glycol (111-46-6) → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 100 - 105℃;	68%
With sodium hydride

oxirane (75-21-8) + 2-hexyloxyethanol (112-25-4) → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With borontrifluoride acetic acid

oxirane (75-21-8) + hexan-1-ol (111-27-3) → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With boron trifluoride diethyl etherate at 50℃;

1-bromo-hexane (111-25-1) + sodium diethylene glycolate → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With diethylene glycol at 200℃;

diethylene glycol monohexyl ether (112-59-4) + p-toluenesulfonyl chloride (98-59-9) → 2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate (187748-60-3)

Conditions	Yield
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) + diethylene glycol monohexyl ether (112-59-4) → C24H48O6

Conditions	Yield
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) + 1,2-Diiodobenzene (615-42-9) → 1,2-bis-(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

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

Conditions	Yield
With pyridine; thionyl chloride In toluene at -5 - 100℃; for 2h;	84%
With pyridine; thionyl chloride

diethylene glycol monohexyl ether (112-59-4) + 1,3-Diiodobenzene (626-00-6) → 1,3-bis(2-(2-hexylethoxy)ethoxy)benzene

Conditions	Yield
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) + diethylene glycol monohexyl ether (112-59-4) → (2-(2-(hexyloxy)ethoxy)ethoxy)benzene (928346-61-6)

Conditions	Yield
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) + diethylene glycol (111-46-6) → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 100 - 105℃;	68%
With sodium hydride

oxirane (75-21-8) + 2-hexyloxyethanol (112-25-4) → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With borontrifluoride acetic acid

oxirane (75-21-8) + hexan-1-ol (111-27-3) → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With boron trifluoride diethyl etherate at 50℃;

1-bromo-hexane (111-25-1) + sodium diethylene glycolate → diethylene glycol monohexyl ether (112-59-4)

Conditions	Yield
With diethylene glycol at 200℃;

diethylene glycol monohexyl ether (112-59-4) + p-toluenesulfonyl chloride (98-59-9) → 2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate (187748-60-3)

Conditions	Yield
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) + diethylene glycol monohexyl ether (112-59-4) → C24H48O6

Conditions	Yield
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) + 1,2-Diiodobenzene (615-42-9) → 1,2-bis-(2-(2-(hexyloxy)ethoxy)ethoxy)benzene

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

Conditions	Yield
With pyridine; thionyl chloride In toluene at -5 - 100℃; for 2h;	84%
With pyridine; thionyl chloride

diethylene glycol monohexyl ether (112-59-4) + 1,3-Diiodobenzene (626-00-6) → 1,3-bis(2-(2-hexylethoxy)ethoxy)benzene

Conditions	Yield
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) + diethylene glycol monohexyl ether (112-59-4) → (2-(2-(hexyloxy)ethoxy)ethoxy)benzene (928346-61-6)

Conditions	Yield
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) + hexafluoropropene-diethylamine adduct (309-88-6) → N,N-diethyl 2,3,3,3-tetrafluoropropionamide + 1-[2-(2-Fluoro-ethoxy)-ethoxy]-hexane + 2,3,3,3-Tetrafluoro-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester

Conditions	Yield
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) + 2-methyl-2-octyldodecanoic acid → C31H62O4

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Dean-Stark; Reflux;	70%

diethylene glycol monohexyl ether (112-59-4) + 1-Iodonaphthalene (90-14-2) → 1-(2-(2-(hexyloxy)ethoxy)ethoxy)naphthalene

Conditions	Yield
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) + (5,10,15,20-tetraphenylporphinato)dichlorophosphorus(V) chloride → di(3,6-dioxadodecyloxo)tetraphenylporphyrinatophosphorus(V) chloride

Conditions	Yield
With pyridine In acetonitrile for 24h; Reflux;	66%
With pyridine In acetonitrile for 24h; Reflux;

diethylene glycol monohexyl ether (112-59-4) + 4-tolyl iodide (624-31-7) → 1-(2-(2-(hexyloxy)ethoxy)ethoxy)-4-methylbenzene

Conditions	Yield
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) + diethylene glycol monohexyl ether (112-59-4) → C13H21Cl2N3O3 (928346-63-8)

Conditions	Yield
With potassium carbonate In ethyl acetate at 20 - 50℃; for 20h; Product distribution / selectivity;	60%

diethylene glycol monohexyl ether (112-59-4) + 3,4-dimethyliodobenzene (31599-61-8) → 4-(2-(2-(hexyloxy)ethoxy)ethoxy)-1,2-dimethylbenzene

Conditions	Yield
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) + diethylene glycol monohexyl ether (112-59-4) → triacetylhexyl bis(oxyethyl)-α-D-xyloside

Conditions	Yield
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) + chloranil (118-75-2) → 2,3,5-trichloro-[6-(2-(2-hexyloxy)ethoxy)ethoxy]cyclohexa-2,5-diene-1,4-dione + C26H42Cl2O8 + C26H42Cl2O8

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	A 38% B 4% C 17%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + diethylene glycol monohexyl ether (112-59-4) → 2-(2-(2-(hexyloxy)ethoxy)ethoxy)-3-chloro-1,4-naphthoquinone

Conditions	Yield
With potassium carbonate In acetonitrile for 12h;	25%

diethylene glycol monohexyl ether (112-59-4) + C64H86O43 → C72H104O44

Conditions	Yield
With tin(IV) chloride In dichloromethane at 45℃; for 5h; glycosidation;	22%

oxirane (75-21-8) + diethylene glycol monohexyl ether (112-59-4) → 2-[2-(2-hexyloxy-ethoxy)-ethoxy]-ethanol (25961-89-1)

Conditions	Yield
With borontrifluoride acetic acid

diethylene glycol monohexyl ether (112-59-4) → Tetraethylene glycol monohexyl ether (39619-69-7)

Conditions	Yield
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) + acrylonitrile (107-13-1) → 3-[2-(2-hexyloxy-ethoxy)-ethoxy]-propionitrile (102236-85-1)

Conditions	Yield
With potassium hydroxide

diethylene glycol monohexyl ether (112-59-4) + diclofop (40843-25-2) → 2-[4-(2,4-Dichloro-phenoxy)-phenoxy]-propionic acid 2-(2-hexyloxy-ethoxy)-ethyl ester (65634-01-7)

Conditions	Yield
(i) SOCl2, toluene, (ii) /BRN= 1743959/, Et3N; Multistep reaction;

diethylene glycol monohexyl ether (112-59-4) + 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)

Conditions	Yield
With triethylamine In toluene

diethylene glycol monohexyl ether (112-59-4) + epichlorohydrin (106-89-8) → 2-[2-(2-Hexyloxy-ethoxy)-ethoxymethyl]-oxirane (120439-33-0)

Conditions	Yield
With sodium hydroxide at 70 - 90℃;

diethylene glycol monohexyl ether (112-59-4) + β‐cyclodextrin (7585-39-9) → C42H70O35*C10H22O3

Conditions	Yield
In water at 80℃; for 24h;

diethylene glycol monohexyl ether (112-59-4) + Methacryloyl chloride (920-46-7) → C14H26O4 (183317-57-9)

Conditions	Yield
With triethylamine In benzene at 20℃;

diethylene glycol monohexyl ether (112-59-4) → 1,3-bis<2-(n-hexyloxyethoxy)ethoxy>propane-2-ol

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

Upstream product

• 75-21-8 oxirane 
• 112-25-4 2-hexyloxyethanol 
• 111-27-3 hexan-1-ol 
• 111-25-1 1-bromo-hexane 
• 111-46-6 diethylene glycol 

Downstream Products

• 25961-89-1 2-[2-(2-hexyloxy-ethoxy)-ethoxy]-ethanol 
• 187748-60-3 2-(2'-n-hexyloxyethoxy)ethyl p-toluenesulfonate 
• 928346-61-6 (2-(2-(hexyloxy)ethoxy)ethoxy)benzene 
• 105391-15-9 3,6-dioxadodecyloic acid 
• 65634-00-6 2-[4-(4-Chloro-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 
• 39619-69-7 Tetraethylene glycol monohexyl ether 

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