Name: 2,2'-Dichlorodiethyl ether
SKU: 111-44-4

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Basic Information

Molecular Structure:
CAS No.:	111-44-4
Name:	2,2'-Dichlorodiethyl ether

Formula:	C₄H₈Cl₂O
Molecular Weight:	143.013
Synonyms:	Ether,bis(2-chloroethyl) (8CI);1,1'-Oxybis[2-chloroethane];1,5-Dichloro-3-oxapentane;1-Chloro-2-(b-chloroethoxy)ethane;2-(2-Chloroethoxy)ethyl chloride;2-Chloroethyl ether;Bis(2-chloroethyl)ether;Bis(b-chloroethyl) ether;Chlorex;Di(b-Chloroethyl) ether;Di-2-chloroethyl ether;Diethylene glycol dichloride;Oxygenmustard;sym-Dichloroethyl ether;b,b'-Dichlorodiethyl ether;
EINECS:	203-870-1
Density:	1.156 g/cm³
Melting Point:	-47 °C(lit.)
Boiling Point:	178.7 °C at 760 mmHg
Flash Point:	55 °C
Solubility:	Slightly soluble. 1.72 g/100 mL
Appearance:	colourless liquid
Hazard Symbols:	T,T+,F
Risk Codes:	10-26/27/28-40-39/23/24/25-23/24/25-11
Safety:	27-28-36/37-45-7/9-28A
Transport Information:	UN 1916 6.1/PG 2
PSA:	9.23000
LogP:	1.48060

Synthetic route

: 628-89-7
2-(2-Chloroethoxy)ethanol

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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℃;

: 106-75-2
diethylene glycol bischloroformate

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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

: 111-46-6
diethylene glycol

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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

: 107-61-9
1,4-oxathiane-4,4-dioxide

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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

: 507-40-4
tert-butylhypochlorite

: 74-85-1
ethene

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

Conditions	Yield
With 2-chloro-ethanol

: 10288-17-2
2-chloroethyl nitrite

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

Conditions	Yield
With sulfuryl dichloride at 165℃;

: 74-85-1
ethene

A: 107-06-2
1,2-dichloro-ethane

B: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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

: 507-40-4
tert-butylhypochlorite

: 74-85-1
ethene

: 107-07-3
2-chloro-ethanol

: 111-44-4
3-oxa-1,5-dichloropentane

...Expand

: 107-07-3
2-chloro-ethanol

: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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

: 123-91-1
1,4-dioxane

A: 638-56-2
1,11-dichloro-3,6,9-trioxaundecane

B: 112-26-5
1,2-bis(2-chloroethoxy)ethane

C: 111-44-4
3-oxa-1,5-dichloropentane

Conditions

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

...Expand

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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 (1975),p. 117.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. On Community Right-To-Know List. On EPA Extremely Hazardous Substances List.

Standards and Recommendations

OSHA PEL: TWA 5 ppm; STEL 10 ppm (skin)
ACGIH TLV: TWA 5 ppm; STEL 10 ppm (skin); Not Classifiable as a Human Carcinogen
DFG MAK: 10 ppm (59 mg/m³)
DOT Classification: 6.1; Label: Poison, Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: sym-Dichloroethyl Ether, 1004.

Specification

The CAS registry number of Dichloroethyl ether is 111-44-4. The IUPAC name is 1-chloro-2-(2-chloroethoxy)ethane. Its EINECS registry number is 203-870-1. In addition, the molecular formula is C₄H₈Cl₂O and the molecular weight is 143.01. It is a kind of colourless liquid and belongs to the classes of Industrial/Fine Chemicals; Halogen compounds; A-BAlphabetic; Alpha Sort; B; BI - BZ; Volatiles/Semivolatiles.

Physical properties about this chemical are: (1)ACD/LogP: 1.19; (2)ACD/LogD (pH 5.5): 1.19; (3)ACD/LogD (pH 7.4): 1.19 ; (4)#H bond acceptors: 1; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: Å²; (7)Index of Refraction: 1.431; (8)Molar Refractivity: 32.02 cm³; (9)Molar Volume: 123.6 cm³; (10)Polarizability: 12.69 ×10^-24cm³; (11)Surface Tension: 29.3 dyne/cm; (12)Density: 1.156 g/cm³; (13)Flash Point: 55 °C; (14)Enthalpy of Vaporization: 39.8 kJ/mol; (15)Boiling Point: 178.7 °C at 760 mmHg; (16)Vapour Pressure: 1.32 mmHg at 25°C.

Preparation of Dichloroethyl ether: it can be prepared by 2,2'-oxy-bis-ethanol. This reaction will need reagent SOCl₂ and pyridine and solvent benzene. The reaction time is 20 hours by heating. The yield is about 35%.

Uses of Dichloroethyl ether: it can be used as solvent of fat, oil, wax, rubber, tar, asphalt, resin and ethyl cellulose. And it is used in the preparation of coating, soil pesticides and dry lotion. In addition, it can be used in organic synthesis and gas chromatography fixed liquid. What's more, it can react with 2-amino-ethanol to get 2-morpholin-4-yl-ethanol. This reaction will need reagent Na₂CO₃ and solvent acetonitrile. The reaction time is 48 hours by heating. The yield is about 83%.

Dichloroethyl ether can react with 2-amino-ethanol to get 2-morpholin-4-yl-ethanol.

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable and has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. There is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing and gloves. If the clothing all contaminate it, you should take off the clothing immediately. If it contact with skin, you should wash immediately with plenty of soap-suds. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). After using it, keep container tightly closed and in a well-ventilated place.

You can still convert the following datas into molecular structure:
(1)SMILES: ClCCOCCCl
(2)InChI: InChI=1/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2
(3)InChIKey: ZNSMNVMLTJELDZ-UHFFFAOYAN

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LC50	inhalation	500ppm/1H (500ppm)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 541, 1986.
guinea pig	LD50	skin	300mg/kg (300mg/kg)		Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.
mammal (species unspecified)	LD50	oral	112mg/kg (112mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse	LC50	inhalation	650mg/m³/2H (650mg/m³)		"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 45, 1982.
mouse	LD50	oral	209mg/kg (209mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 163, 1992.
rabbit	LD50	oral	126mg/kg (126mg/kg)		"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2A, Pg. 2518, 1981.
rabbit	LD50	skin	90mg/kg (90mg/kg)		"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2A, Pg. 2518, 1981.
rat	LC50	inhalation	330mg/m³/4H (330mg/m³)		"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 45, 1982.
rat	LD50	oral	75mg/kg (75mg/kg)		Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.

111-44-4

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Consensus Reports

Standards and Recommendations

Analytical Methods

Specification