111-44-4

Basic information

• Product Name: 2,2'-Dichlorodiethyl ether
• Synonyms: 1,1’-oxybis(2-chloro-ethan;1-Chloro-2-(2-chloroethoxy)ethane;1-chloro-2-(2-chloro-ethoxy)-ethane;1-Chloro-2-(beta-Chloroethoxy)ethane;2,2’-dichloorethylether;2,2’-dichlor-diaethylaether;2,2’-dichlorethylether;2,2’-dicloroetiletere
• CAS NO: 111-44-4
• Molecular Formula: C₄H₈Cl₂O
• Molecular Weight: 143.01
• EINECS: 203-870-1
• Product Categories: Industrial/Fine Chemicals;Halogen compounds;A-BAlphabetic;Alpha Sort;B;BI - BZ;Volatiles/ Semivolatiles;Building Blocks;C2 to C8;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds;fine chemical;fine chemicals;Quinoxalines ,Quinazolines
• Mol File: 111-44-4.mol
• Article Data: 47

Chemical Properties

• Melting Point: −47 °C(lit.)
• Boiling Point: 65-67 °C15 mm Hg(lit.)
• Flash Point: 131 °F
• Appearance: colourless liquid
• Density: 1.22 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.4 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: 2-8°C
• Solubility: 0.01g/l
• Explosive Limit: 0.8%(V)
• Water Solubility: Slightly soluble. 1.72 g/100 mL
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,3066
• BRN: 605317
• CAS DataBase Reference: 2,2'-Dichlorodiethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Dichlorodiethyl ether(111-44-4)
• EPA Substance Registry System: 2,2'-Dichlorodiethyl ether(111-44-4)

Safety Data

• Hazard Codes: T+,T,F
• Statements: 10-26/27/28-40-39/23/24/25-23/24/25-11
• Safety Statements: 27-28-36/37-45-7/9-28A-16
• RIDADR: UN 1916 6.1/PG 2
• WGK Germany: 2
• RTECS: KN0875000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 111-44-4(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Fire Hazard

May form phosgene or hydrogen chloride in fires. There is danger of explosion when ethers are heated or exposed to flames or sparks. Ethers tend to form peroxides; when ethers containing peroxides are heated, they can detonate. May be ignited by heat, sparks, or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Decomposes in the presence of moisture to form hydrochloric acid. Emits toxic fumes when heated to decomposition. Reacts vigorously with oleum and chlorosulfonic acid. Ethers tend to form peroxides upon standing. Heating peroxide-containing ethers can cause detonation.

Air & Water Reactions

Flammable. Insoluble in water. Reacts slowly with water to form HCl. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154].

Environmental Fate

Biological. When 5 and 10 mg/L of bis(2-chloroethyl)ether were statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, complete degradation was observed after 7 days (Tabak et al., 1981).Chemical/Physical. Bis(2-chloroethyl)ether is subject to hydrolysis (Enfield and Yates, 1990; NIOSH, 1994). The hydrolysis rate constant for bis(2-chloroethyl)ether at pH 7 and 25°C was determined to be 2.6 × 10–5/hour, resulting in a half-life oEmits chlorinated acids when incinerated (Sittig, 1985).

Source

Bis(2-chloroethyl) ether does not occur naturally in the environment. In Canada, this compound enters the environment as a by-product from chlorination of waste streams containing ethylene, propylene (Environment Canada, 1993) or ethyl ether (quoted, Verschueren, 1983).

Incompatibilities

Contact with moisture caused decomposition producing hydrochloric acid. Can form peroxides. May form explosive mixture with air. Contact with strong oxidizers may cause fire and explosion hazard. Attacks some plastics, rubber, and coatings. Attacks metals in the presence of moisture

Health Hazard

BCEE is an acute toxic compound withcancer-causing properties. The toxic routesare inhalation, ingestion, and absorptionthrough the skin. Exposure to its vaporscaused irritation of the eyes, nose, and res piratory tracts in test animals. Exposure to aconcentration of 250 ppm in air for 4 hoursproved lethal to rats (ACGIH 1986). At alower concentration, it caused delayed deathfollowing damage to lungs. Other organsaffected to a lesser degree were the liver,kidneys, and brain.The irritant action of BCEE on the eyesvaried from mild to severe. In humans,contact of pure liquid can cause conjunctivalirritation and injury to the cornea. On theskin, its irritation effect is mild. However,on prolonged contact, the liquid may beabsorbed through the skin and manifest toxiceffectsIngestion of this compound in smallamounts may produce nausea and vomiting.An oral dose of 50–75 mL is expected to befatal to humansLC50 value, inhalation (rats): 330 mg (56ppm)/m3/4 hrLD50 value, oral (rats): 75 mg/kgLD50 value, skin (guinea pigs): 300 mg/kgLD50 value, skin (guinea pigs): 300 mg/kg.

General Description

A clear colorless liquid with a sweet pleasant or nauseating odor. Flash point 131°F. Denser than water and insoluble in water. Toxic by inhalation and skin absorption. Used in cleaning compounds, paints, textile finishing, and as a general solvent.

Safety Profile

A poison by ingestion, skin contact, and inhalation. A skin, eye, and mucous membrane irritant. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. Exposure to 1000 ppm for 30 to 60 minutes may result in death within days. The odor is easily detectable at 35 ppm whch causes only slight irritation. Flammable liquid when exposed to heat, flame, or oxidants. Dangerous explosion hazard; reacts vigorously with oleum, chlorosulfonic acid. Reacts with water or steam to evolve toxic and corrosive fumes. Can react vigorously with oxidizing materials. To fight fire, use water, foam, mist, fog, spray, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also ETHERS.

Reactivity Profile

2,2'-Dichlorodiethyl ether may form phosgene or hydrogen when heated to high temperature. Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154]. Mixing in equal molar portions with the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid and oleum [NFPA 1991].

Physical properties

Colorless to pale yellow volatile liquid with a pungent, fruity, chlorinated-like odor. The low odor and high odor threshold concentrations were 90.0 and 2,160 mg/m3, respectively (Ruth, 1986).

Potential Exposure

Dichloroethyl ether is used as a soil fumigant, an insecticide, and an acaricide; in the manufacture of paint, varnish, lacquer, soap, and finish removers. It is also used as a solvent for cellulose esters, naphthalenes, oils, fats, waxes, greases, pectin, tar, and gum; in dry cleaning and in textile scouring.

Uses

Bis(2-chloroethyl)ether (BCEE) is used as ascouring agent for textiles; as a dewaxingagent for lubricating oils; as a soil fumigant;as a solvent for resins, oils, and lacquers; andin organic synthesis.

Chemical Properties

Dichloroethyl ether is a clear, colorless liquid. Pungent, fruity odor. It is also described as having a chlorinated solvent-like odor.

Purification Methods

Wash the ether with conc H2SO4, then Na2CO3 solution, dry with anhydrous Na2CO3, and finally pass it through a 50cm column of activated alumina before distillation. Altern

Waste Disposal

A potential candidate for liquid injection incineration at a temperature range of 650 to 1600C and a residence time 0.1 to 2 seconds. Also, a potential candidate for rotary kiln incineration at a temperature range of 820 to 1600C and residence times of seconds for liquids and gases, and hours for solids. Also, a potential candidate for fluidized bed incineration at a temperature range of 450 to 980C and residence times of seconds for liquids and gases, and longer for solids. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

Chemical Reactivity

Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: V; Inhibitor of Polymerization: Not pertinent.

Uses

Reagent for organic synthesis; solvent. Has been used as a scouring agent for textiles; as soil fumigant.

Uses

Soil fumigant; acaricide.

Shipping

UN1916 2,20 -Dichlorodiethyl ether, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid

Health Hazard

2,2'-Dichlorodiethyl ether is very toxic; the probable oral lethal dose is 50-500 mg/kg, or between 1 teaspoonful and 1 ounce for a 150 pound person. It can be a central nervous system depressant in high concentrations. It is extremely irritating to the eyes, nose, and respiratory passages. It can penetrate the skin to cause serious and even fatal poisoning. Poisonous; may be fatal if inhaled, swallowed or absorbed through skin.

Synthetic route

2-(2-Chloroethoxy)ethanol (628-89-7) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 17h; Chlorination;	92%
With hydrogenchloride; sulfuric acid; zinc(II) chloride at 95℃;

diethylene glycol bischloroformate (106-75-2) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With hexabutylguanidinium chloride at 120℃; for 4h;	91%

diethylene glycol (111-46-6) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With thionyl chloride Reflux;	86%
With thionyl chloride at 110℃;	84%
With pyridine; thionyl chloride In benzene for 20h; Heating;	35%

1,4-oxathiane-4,4-dioxide (107-61-9) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With hydrogenchloride In water at 30℃; for 12h; Temperature;	81.3%

tert-butylhypochlorite (507-40-4) + ethene (74-85-1) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With 2-chloro-ethanol

2-chloroethyl nitrite (10288-17-2) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With sulfuryl dichloride at 165℃;

ethene (74-85-1) → 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With chlorine; 2-chloro-ethanol
With oxirane; chlorine
With oxirane; chlorine; 2-chloro-ethanol

tert-butylhypochlorite (507-40-4) + ethene (74-85-1) + 2-chloro-ethanol (107-07-3) → 3-oxa-1,5-dichloropentane (111-44-4)

2-chloro-ethanol (107-07-3) → 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With sulfuric acid Entfernen das entstehende Wasser;
With sulfuryl dichloride at 165℃;
With sulfuric acid at 200 - 250℃;

1,4-dioxane (123-91-1) → 1,11-dichloro-3,6,9-trioxaundecane (638-56-2) + 1,2-bis(2-chloroethoxy)ethane (112-26-5) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
With titanium tetrachloride 1.) 20 deg C, 2.) 160 deg C, 5 d; Yield given. Multistep reaction. Yields of byproduct given;

methanol (67-56-1) + ethene (74-85-1) → 2-chloroethyl methyl ether (627-42-9) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + 1,4-dichlorobutane (110-56-5)

Conditions	Yield
With hydrogenchloride at 5 - 10℃; under 45003.6 Torr; electrolysis;	A 47 % Chromat. B 31 % Chromat. C 17 % Chromat. D 6 % Chromat.

ethene (74-85-1) → 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + 1,4-dichlorobutane (110-56-5)

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 5 - 10℃; under 45003.6 Torr; electrolysis, further solvent methanol;	A 82 % Chromat. B 17 % Chromat. C 6 % Chromat.

ethene (74-85-1) → 2-chloroethyl methyl ether (627-42-9) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + 1,4-dichlorobutane (110-56-5)

Conditions	Yield
With hydrogenchloride In methanol at 5 - 10℃; under 45003.6 Torr; electrolysis, further solvent aq. acetonitrile;	A 47 % Chromat. B 31 % Chromat. C 17 % Chromat. D 6 % Chromat.

ethene (74-85-1) → 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + 2-chloro-ethanol (107-07-3)

Conditions	Yield
With hypochloric acid; chlorine In various solvent(s) at 25℃; for 0.00883333h; in tributyl phosphate, in a rotor-pulsation apparatus; Title compound not separated from byproducts;	A 11.9 % Spectr. B 14.4 % Spectr. C 42.1 % Spectr.
With hypochloric acid; chlorine In various solvent(s) at 25℃; for 0.00883333h; in tributyl phosphate, in a rotor pulsation apparatus; Title compound not separated from byproducts;	A 11.9 % Spectr. B 14.4 % Spectr. C 42.1 % Spectr.
With hypochloric acid; chlorine In various solvent(s) at 25℃; for 0.00883333h; Product distribution; dependence of yield of products on time of reaction in tributyl phosphate in a rotor-pulsation apparatus;	A 11.9 % Spectr. B 14.4 % Spectr. C 42.1 % Spectr.

sulfuric acid (7664-93-9) + 2-chloro-ethanol (107-07-3) → 3-oxa-1,5-dichloropentane (111-44-4)

sulfuryl dichloride (7791-25-5) + 2-chloro-ethanol (107-07-3) → sulfuric acid bis-(2-chloroethyl) ester (5411-48-3) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
at 165℃;

ethene (74-85-1) + chlorine (7782-50-5) + 2-chloro-ethanol (107-07-3) → 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
at 15 - 20℃; Kinetics; unter Lichtausschluss;

ethene (74-85-1) → 3-oxa-1,5-dichloropentane (111-44-4) + ethylene chloride and ethylene chlorohydrin

Conditions	Yield
With chlorine; sodium sulfate at 60℃;
With chlorine; sodium sulfate at 60℃;

ethene (74-85-1) → 3-oxa-1,5-dichloropentane (111-44-4) + ethylene chloride and ethylene glycol-bis-<2-chloro-ethyl ether >

Conditions	Yield
With 1,4-dioxane; polyethylene glycol chlorohydrin; chlorine; 2-chloro-ethanol at 25 - 35℃;
With 1,4-dioxane; chlorine at 20 - 25℃;
With polyethylene glycol mixture; chlorine

2-chloro-ethanol (107-07-3) → 1,4-dioxane (123-91-1) + 2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + 2-(2-Chloroethoxy)ethanol (628-89-7) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + HCl, water

Conditions	Yield
at 150℃; for 5h; Product distribution; Kinetics; Rate constant; dependence of the products of ECH decomposition on temperature in sealed tube at 115, 130, 140, 150, 160 deg C;

sulfuryl dichloride (7791-25-5) + 2-chloroethyl nitrite (10288-17-2) → chloroethyl chlorosulfate (13891-58-2) + sulfuric acid bis-(2-chloroethyl) ester (5411-48-3) + 3-oxa-1,5-dichloropentane (111-44-4)

ethene (74-85-1) + chlorine (7782-50-5) + 2-chloro-ethanone-(1) → 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
at 15 - 20℃; unter Lichtausschluss;

1,4-dioxane (123-91-1) + ethene (74-85-1) + chlorine (7782-50-5) → 1,2-bis(2-chloroethoxy)ethane (112-26-5) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
at 20 - 25℃; weniger als 1 Mol Chlor;
at 20 - 25℃; weniger als 1 Mol Chlor;

ethene (74-85-1) + water (7732-18-5) + chlorine (7782-50-5) → 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + 2-chloro-ethanol (107-07-3)

ethanol (64-17-5) + ethene (74-85-1) + chlorine (7782-50-5) → 2-chloroethyl ethyl ether (628-34-2) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4) + 2-chloro-ethanol (107-07-3)

sulfurous acid bis-(2-chloro-ethyl ester) (62516-55-6) → 3-oxa-1,5-dichloropentane (111-44-4) + SO2

1,3-DIOXOLANE (646-06-0) → bis(2-chloromethyl)ether (542-88-1) + 2-chloroethyl chloromethyl ether (1462-33-5) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
Stage #1: 1,3-DIOXOLANE With dichloromethane; tungsten(VI) chloride In Chloroform-D at 20℃; for 192h; Stage #2: With water In Chloroform-D at -20℃;

2-Methoxyethoxymethyl chloride (3970-21-6) → bis(2-chloromethyl)ether (542-88-1) + methylene chloride (74-87-3) + Dimethyl ether (115-10-6) + chloromethyl methyl ether (107-30-2) + 1,2-dichloro-ethane (107-06-2) + 3-oxa-1,5-dichloropentane (111-44-4)

Conditions	Yield
Stage #1: 2-Methoxyethoxymethyl chloride With dichloromethane; tungsten(VI) chloride In Chloroform-D at 20℃; for 12h; Stage #2: With water In Chloroform-D at -20℃;

3-oxa-1,5-dichloropentane (111-44-4) → 2,2'-diiodoethyl ether (34270-90-1)

Conditions	Yield
With sodium iodide In acetone for 120h; Heating / reflux;	100%
With sodium iodide In acetone for 72h; Heating;	81%
With sodium iodide In acetone for 72h; Reflux; Darkness;	81%

ditosylethylenediamine (4403-78-5) + 3-oxa-1,5-dichloropentane (111-44-4) → N,N',N'',N'''-tetrakis(tolyl-p-sulphonyl)-1,10-dioxa-4,7,13,16-tetra-azacyclo-octadecane (93274-33-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide 170 deg C, 5 h; cool, 12 h;	100%
With potassium carbonate In N,N-dimethyl-formamide for 5h; Heating;	78%
With potassium carbonate In N,N-dimethyl-formamide at 5 - 170℃; for 30h;	15%
With potassium carbonate In N,N-dimethyl-formamide at 170℃; for 12h;	14.3%
With potassium carbonate In N,N-dimethyl-formamide at 170℃; for 5h; Yield given;

3-oxa-1,5-dichloropentane (111-44-4) → bis-(2-chloro-ethyl)-ether ; compound with boron chloride

Conditions	Yield
With boron trichloride at -78 - 0℃;	100%

p-methoxybenzylnitrile (104-47-2) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile (3648-78-0)

Conditions	Yield
Stage #1: p-methoxybenzylnitrile With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.5h; Stage #2: 3-oxa-1,5-dichloropentane In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2.33333h;	100%
Stage #1: p-methoxybenzylnitrile With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 80 - 100℃; for 5h;	69%
With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice;	64%
With NaH In dimethyl sulfoxide

phenylacetonitrile (140-29-4) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-phenyltetrahydro-2H-pyran-4-carbonitrile (1202-81-9)

Conditions	Yield
With sodium hydride; sodium iodide In dimethyl sulfoxide; mineral oil at 20℃; for 12h; Inert atmosphere; Sealed tube;	99%
With sodium amide; toluene

3,5-dihydroxy-4-(phenylmethoxy)benzoic acid methyl ester (91925-82-5) + 3-oxa-1,5-dichloropentane (111-44-4) → methyl 4-O-benzyl-3,5-di-O-methoxymethylgallate (1034343-25-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;	99%

3,5-dimethyl-1H-pyrazole (67-51-6) + 3-oxa-1,5-dichloropentane (111-44-4) → 1,1'-(2,2'-oxybis(ethane-2,1-diyl))bis(3,5-dimethyl-1H-pyrazole) (85650-02-8)

Conditions	Yield
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 1h; Stage #2: 3-oxa-1,5-dichloropentane In dimethyl sulfoxide at 80℃; Further stages.;	98%

1,2-bis(t-butyloxycarbonyl)hydrazine (16466-61-8) + 3-oxa-1,5-dichloropentane (111-44-4) → 1,4,5-oxadiazepane-4,5-dicarboxylic acid di-tert-butyl ester (243973-69-5)

Conditions	Yield
Stage #1: 1,2-bis(t-butyloxycarbonyl)hydrazine With sodium hydride In N,N-dimethyl-formamide at -3 - 20℃; for 2.13333h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at -3 - 20℃; Temperature;	97.1%

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + 3-oxa-1,5-dichloropentane (111-44-4) → C16H38N2O5(2+)*2Cl(1-)

Conditions	Yield
In acetonitrile at 60℃; for 24h;	97%

4-methoxy-aniline (104-94-9) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(4-methoxyhenyl)morpholine nitric acid salt (955095-74-6)

Conditions	Yield
Stage #1: 4-methoxy-aniline; 3-oxa-1,5-dichloropentane With tetrabutylammomium bromide; sodium hydroxide for 8h; Heating; Stage #2: With nitric acid at 0 - 5℃; for 12h;	97%

4-bromo-phenol (106-41-2) + 3-oxa-1,5-dichloropentane (111-44-4) → C16H16Br2O3 (72659-52-0)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 90℃; for 24h;	96%

(4-fluoromethyl-phenyl)-acetonitrile (135420-00-7) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(4-fluorophenyl)tetrahydro-2H-pyran-4-carbonitrile (473706-10-4)

Conditions	Yield
With sodium hydride In diethyl ether; dimethyl sulfoxide at 5 - 30℃;	96%

1-methyl-1H-imidazole (616-47-7) + 3-oxa-1,5-dichloropentane (111-44-4) → 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]ethyl)-1H-imidazol-3-ium dichloride

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 3h;	96%
In acetonitrile at 100℃; for 48h; Inert atmosphere;	90%

1,3-dihydroxy-4-iodo-2-nitrobenzene (153843-74-4) + 3-oxa-1,5-dichloropentane (111-44-4) → 1-iodo-2,4-bis(methoxymethoxy)-3-nitrobenzene (1155368-39-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;	96%

carbon dioxide (124-38-9) + 3-oxa-1,5-dichloropentane (111-44-4) → Tetrahydro-4H-pyran-4-one (29943-42-8)

Conditions	Yield
With cesium iodide In ethanol; water at 90℃; under 8250.83 Torr; Temperature; Pressure;	95.9%

3-oxa-1,5-dichloropentane (111-44-4) + 2-hydroxynitrobenzene (88-75-5) → 1,5-bis(o-nitrophenoxy)-3-oxapentane (54533-65-2)

Conditions	Yield
With 15-crown-5; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 5h;	95%
With potassium carbonate In dimethyl sulfoxide at 130℃; for 6h;	85%
With potassium carbonate In N,N-dimethyl-formamide

ethylenediamine (107-15-3) + 3-oxa-1,5-dichloropentane (111-44-4) → 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1)

Conditions	Yield
With sodium carbonate In acetonitrile for 24h; Heating;	95%

3-Dimethylamino-1-propanol (3179-63-3) + 3-oxa-1,5-dichloropentane (111-44-4) → C14H34N2O3(2+)*2Cl(1-)

Conditions	Yield
In acetonitrile at 60℃; for 24h;	95%

2-Benzoyl-hydrazin-1-carbonsaeuremethylester (29430-29-3) + 3-oxa-1,5-dichloropentane (111-44-4) → N-methoxycarbonyl-N'-benzoyl[1,4,5]-oxadiazepane

Conditions	Yield
With sodium hydride In N,N-dimethyl acetamide; N,N-dimethyl-formamide at 0 - 20℃;	95%

2,4-diamino-6-(4-nitrophenyl)-1,3,5-triazine (29366-73-2) + 3-oxa-1,5-dichloropentane (111-44-4) → 4,4'-(6-(4-nitrophenyl)-1,3,5-triazine-2,4-diyl)dimorpholine

Conditions	Yield
Stage #1: 2,4-diamino-6-(4-nitrophenyl)-1,3,5-triazine With sodium hydride In N,N-dimethyl acetamide at 55 - 60℃; for 0.166667h; Inert atmosphere; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl acetamide for 4.5h; Reagent/catalyst; Temperature; Inert atmosphere;	94.6%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 65℃; Thermodynamic data; Solvent; Reagent/catalyst; Concentration; Temperature; Inert atmosphere; Green chemistry;	77%

para-tert-butylphenol (98-54-4) + 3-oxa-1,5-dichloropentane (111-44-4) → 1,5-Bis(4-t-butylphenoxy)-3-oxapentane (109879-29-0)

Conditions	Yield
With potassium hydroxide In butan-1-ol for 18h; Heating;	94%
With sodium hydroxide at 180 - 190℃;

ethyl 4,6-O-benzylidene-α-D-glucopyranoside (71676-29-4, 101833-22-1) + 3-oxa-1,5-dichloropentane (111-44-4) → ethyl 4,6-O-benzylidene-2,3-bis-O-[(2-chloroethoxy)ethyl]-α-D-glucopyranoside

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20℃; for 9h;	94%

3-oxa-1,5-dichloropentane (111-44-4) → 1,5-diazido-3-oxapentane (24345-74-2)

Conditions	Yield
With sodium azide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 90℃; for 48h;	93%
With sodium azide In N,N-dimethyl-formamide for 17h; Heating;	62.8%
With sodium azide; choline chloride In N,N-dimethyl-formamide at 95℃; Rate constant; var. phase transfer catalysts;
With sodium azide; cetyltributylphosphonium bromide; potassium iodide for 17h; Heating; Yield given;
With sodium azide; cetylpyridinium chloride; potassium iodide In water for 20h; Heating / reflux;

3-oxa-1,5-dichloropentane (111-44-4) → 2,2,2-trichloro-1-fluoroethyl 2-chloroethyl ether (109776-90-1)

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride; chlorine at 80℃; for 5h; Product distribution; other temperature, stainless-steel autoclave, other ratio of reagents;	93%
With sulfur tetrafluoride; hydrogen fluoride; chlorine at 80℃; for 5h; stainless-steel autoclave;	93%

3-oxa-1,5-dichloropentane (111-44-4) + C22H18F6N2O5 → C26H24F6N2O6

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Cycloaddition;	93%

endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2) + 3-oxa-1,5-dichloropentane (111-44-4) → 3-oxapentane-1,5-dioxy-endo-2',3'-dicarboxydiimidenorbornene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 22h; Gabriel Amine Synthesis;	64.5 g

N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) + 3-oxa-1,5-dichloropentane (111-44-4) → C22H24N2O7

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	92%

N,N-dimethyldecylamine (1120-24-7) + 3-oxa-1,5-dichloropentane (111-44-4) → diethyl ether-α,ω-didecyldimethylammonium chloride

Conditions	Yield
In acetonitrile for 24h; Menshutkin Reaction; Heating;	92%
With sodium carbonate In isopropyl alcohol at 55 - 83℃; for 8h;

3-oxa-1,5-dichloropentane (111-44-4) + 2-(4-phenylthiazol-2-yl)acetonitrile (41381-89-9) → 4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile (1314886-95-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice;	92%

Upstream product

• 111443-80-2 1-[2-(4-methylbenzoyl)butyl]azepanium chloride 
• 111442-25-2 8-[(dimethylamino)methyl]-7-hydroxy-2-methyl-3-phenyl-4H-chromen-4-one 
• 111441-88-4 Picembrin diacetate 
• 11144-18-6 Lipocaic 
• 1114-41-6 MURAMIC ACID 
• 111440-02-9 1-methyl-1-tridecylpiperazin-1-ium chloride 
• 111439-99-7 1-butyl-1-decylpiperazin-1-ium chloride 
• 111439-82-8 L-Arg-L-Arg-L-Cys-L-Ile-L-Cys-L-Thr-L-Thr-L-Arg-L-Thr-L-Cys-L-Arg-L-Phe-L-Pro-L-Tyr-L-Arg-L-Arg-L-Leu-Gly-L-Thr-L-Cys-L-Ile-L-Phe-L-Gln-L-Asn-L-Arg-L-Val-L-Tyr-L-Thr-L-Phe-L-Cys-L-Cys-OH 
• 111439-81-7 Formaldehyde, polymer with 4,4-(1-methylethylidene)bisphenol, reaction products with diethylenetriamine 
• 111439-76-0 Isobutylisopropyldimethoxysilane 
• 1114-39-2 1,1-diethylguanidine hydrochloride 
• 111438-94-9 6-NITROANTHANTHRENE 
• 1114384-60-9 (S)-1-(2-(trifluoroMethyl)phenyl)propanol 
• 1114-38-1 Butanamide, 2-ethyl- 

Downstream Products

• 130290-79-8 4-(Aminomethyl)tetrahydro-2H-pyran 
• 125552-89-8 4-BROMOMETHYLTETRAHYDROPYRAN 
• 121-54-0 Benzethonium chloride 
• 36141-82-9 diamfenetide 
• 65412-03-5 4-(2-AMINOETHYL)TETRAHYDROPYRAN 
• 14774-37-9 (TETRAHYDRO-2H-PYRAN-4-YL)METHANOL 
• 40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 
• 4319-49-7 N-Aminomorpholine 
• 5337-03-1 Tetrahydro-2H-pyran-4-carboxylic acid 
• 109-02-4 4-Methylmorpholine 
• 50675-18-8 Tetrahydropyran-4-carbaldehyde 

Recommend Products

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