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Chloromethyl ethyl ether

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Name

Chloromethyl ethyl ether

EINECS 221-687-5
CAS No. 3188-13-4 Density 0.987 g/cm3
PSA 9.23000 LogP 1.21920
Solubility N/A Melting Point -98oC
Formula C3H7ClO Boiling Point 82.999 °C at 760 mmHg
Molecular Weight 94.541 Flash Point 19.444 °C
Transport Information UN 2354 3/PG 2 Appearance clear colorless to pale yellow liquid
Safety 16-36/37-9-45-29 Risk Codes 11-20/21/22-36-40
Molecular Structure Molecular Structure of 3188-13-4 (Chloromethyl ethyl ether) Hazard Symbols FlammableF,HarmfulXn
Synonyms

Ether,chloromethyl ethyl (6CI,7CI,8CI);Chloromethoxyethane;Ethoxychloromethane;Ethoxymethyl chloride;Ethyl chloromethyl ether;

Article Data 37

Chloromethyl ethyl ether Synthetic route

462-95-3

formaldehyde diethyl acetal

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With benzoyl chloride; phosphotungstic acid at 60 - 65℃;78%
With acetyl chloride; zinc trifluoromethanesulfonate at 24 - 32℃; for 17h;
With sulfuric acid; acetyl chloride at 40℃; for 3h; Inert atmosphere;
With acetyl chloride; zinc dibromide In toluene at 20 - 45℃; for 4h;
50-00-0

formaldehyd

64-17-5

ethanol

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
(i) aq. HCl, (ii) /BRN= 1718733/, HCl; Multistep reaction;
50-00-0

formaldehyd

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride; ethanol
110-88-3

1,3,5-Trioxan

64-17-5

ethanol

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
54699-20-6

1-ethoxy-1-(ethylthio)methane

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With acetyl chloride at 45 - 55℃; for 144h;
64-17-5

ethanol

polyoxymethylene

polyoxymethylene

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
With hydrogenchloride
829-59-4

1-ethoxymethoxy-2,4-dichloro-benzene

7782-50-5

chlorine

A

35412-53-4

bis(2,4-dichlorophenoxy)methane

B

13543-09-4

2,4-dichlorophenoxymethyl chloride

C

120-83-2

2,4-dichlorophenol

D

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
at 200℃;
462-95-3

formaldehyde diethyl acetal

A

75-00-3

chloroethane

B

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
Stage #1: formaldehyde diethyl acetal With dichloromethane; tungsten(VI) chloride In Chloroform-D at 20℃; for 288h;
Stage #2: With water In Chloroform-D
462-95-3

formaldehyde diethyl acetal

75-36-5

acetyl chloride

3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With Zinc chloride
2034-22-2

2,4,5-tribromo-1H-imidazole

3188-13-4

ethyl chloromethyl ether

22927-65-7

2,4,5-tribromo-1-(ethoxymethyl)-1H-imidazole

Conditions
ConditionsYield
With triethylamine In benzene for 2h; Ambient temperature;100%
With sodium carbonate In N,N-dimethyl-formamide100%
With triethylamine In benzene Ambient temperature;100%

Chloromethyl ethyl ether Consensus Reports

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Chloromethyl ethyl ether Specification

The Chloromethyl ethyl ether, with the CAS registry number 3188-13-4, is also known as Ethoxymethyl chloride. It belongs to the product categories of Others; Protecting and Derivatizing Reagents; Protection and Derivatization. Its EINECS number is 221-687-5. This chemical's molecular formula is C3H7ClO and molecular weight is 94.54. What's more, its systematic name is (Chloromethoxy)ethane. This chemical should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. It is used in organic synthesis. It can be prepared by paraformaldehyde, ethanol and hydrogen chloride.

Physical properties of Chloromethyl ethyl ether are: (1)ACD/LogP: 0.69; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.69; (4)ACD/LogD (pH 7.4): 0.69; (5)ACD/BCF (pH 5.5): 1.97; (6)ACD/BCF (pH 7.4): 1.97; (7)ACD/KOC (pH 5.5): 56.54; (8)ACD/KOC (pH 7.4): 56.54; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.387; (14)Molar Refractivity: 22.542 cm3; (15)Molar Volume: 95.803 cm3; (16)Polarizability: 8.936×10-24cm3; (17)Surface Tension: 22.9 dyne/cm; (18)Density: 0.987 g/cm3; (19)Flash Point: 19.444 °C; (20)Enthalpy of Vaporization: 31.012 kJ/mol; (21)Boiling Point: 82.999 °C at 760 mmHg; (22)Vapour Pressure: 85.6 mmHg at 25°C.

Uses of Chloromethyl ethyl ether: it can be used to produce 2-ethoxy-1-phenyl-ethanol at the temperature of 0 °C. It will need reagents Li, 4,4'-di-tert-butylbiphenyl and solvent tetrahydrofuran. The yield is about 84%.

Chloromethyl ethyl ether can be used to produce 2-ethoxy-1-phenyl-ethanol at the temperature of 0 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is irritating to eyes and has a limited evidence of a carcinogenic effect. This chemical is harmful by inhalation, in contact with skin and if swallowed. You should keep the container in a well-ventilated place and not empty into drains. When using it, you need wear suitable protective clothing amd gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: ClCOCC
(2)Std. InChI: InChI=1S/C3H7ClO/c1-2-5-3-4/h2-3H2,1H3
(3)Std. InChIKey: FCYRSDMGOLYDHL-UHFFFAOYSA-N  

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