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2,2'-Dichlorodiethyl ether

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Name

2,2'-Dichlorodiethyl ether

EINECS 203-870-1
CAS No. 111-44-4 Density 1.156 g/cm3
PSA 9.23000 LogP 1.48060
Solubility Slightly soluble. 1.72 g/100 mL Melting Point -47 °C(lit.)
Formula C4H8Cl2O Boiling Point 178.7 °C at 760 mmHg
Molecular Weight 143.013 Flash Point 55 °C
Transport Information UN 1916 6.1/PG 2 Appearance colourless liquid
Safety 27-28-36/37-45-7/9-28A Risk Codes 10-26/27/28-40-39/23/24/25-23/24/25-11
Molecular Structure Molecular Structure of 111-44-4 (2,2'-Dichlorodiethyl ether) Hazard Symbols ToxicT,VeryT+,FlammableF
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;

Article Data 47

2,2'-Dichlorodiethyl ether Synthetic route

628-89-7

2-(2-Chloroethoxy)ethanol

111-44-4

3-oxa-1,5-dichloropentane

Conditions
ConditionsYield
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
ConditionsYield
With hexabutylguanidinium chloride at 120℃; for 4h;91%
111-46-6

diethylene glycol

111-44-4

3-oxa-1,5-dichloropentane

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With 2-chloro-ethanol
10288-17-2

2-chloroethyl nitrite

111-44-4

3-oxa-1,5-dichloropentane

Conditions
ConditionsYield
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
ConditionsYield
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

107-07-3

2-chloro-ethanol

111-44-4

3-oxa-1,5-dichloropentane

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

2,2'-Dichlorodiethyl ether 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.

2,2'-Dichlorodiethyl ether 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

2,2'-Dichlorodiethyl ether Analytical Methods

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

2,2'-Dichlorodiethyl ether 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%.

Dichloroethyl ether can be prepared by 2,2'-oxy-bis-ethanol

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.

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