Product Name

  • Name

    Chloromethyl ethyl ether

  • EINECS 221-687-5
  • CAS No. 3188-13-4
  • Article Data37
  • CAS DataBase
  • Density 0.987 g/cm3
  • Solubility
  • 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;
  • PSA 9.23000
  • LogP 1.21920

Synthetic route

formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

ethyl chloromethyl ether
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;
formaldehyd
50-00-0

formaldehyd

ethanol
64-17-5

ethanol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

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

formaldehyd

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride; ethanol
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

ethanol
64-17-5

ethanol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
1-ethoxy-1-(ethylthio)methane
54699-20-6

1-ethoxy-1-(ethylthio)methane

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

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

ethanol

polyoxymethylene

polyoxymethylene

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
With hydrogenchloride
1-ethoxymethoxy-2,4-dichloro-benzene
829-59-4

1-ethoxymethoxy-2,4-dichloro-benzene

chlorine
7782-50-5

chlorine

A

bis(2,4-dichlorophenoxy)methane
35412-53-4

bis(2,4-dichlorophenoxy)methane

B

2,4-dichlorophenoxymethyl chloride
13543-09-4

2,4-dichlorophenoxymethyl chloride

C

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

D

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
at 200℃;
formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

A

chloroethane
75-00-3

chloroethane

B

ethyl chloromethyl ether
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
formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

acetyl chloride
75-36-5

acetyl chloride

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With Zinc chloride
2,4,5-tribromo-1H-imidazole
2034-22-2

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

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2,4,5-tribromo-1-(ethoxymethyl)-1H-imidazole
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%
(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol
72174-24-4, 53269-97-9

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

ethoxymethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

ethoxymethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

Conditions
ConditionsYield
With triethylamine In dichloromethane Condensation;100%
ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-bromo-4-(ethoxymethoxy)benzene
152565-23-6

1-bromo-4-(ethoxymethoxy)benzene

Conditions
ConditionsYield
Stage #1: 4-bromo-phenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.666667h;
Stage #2: ethyl chloromethyl ether In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.25h;
100%
3,5-dichloro-2-iodophenol
1028332-19-5

3,5-dichloro-2-iodophenol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene
1028332-20-8

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;100%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;90%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 22h;
2-hydroxy-3-bromobenzaldehyde
1829-34-1

2-hydroxy-3-bromobenzaldehyde

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C10H11BrO3
1138152-16-5

C10H11BrO3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3h;100%
C16H25O5PolSSi

C16H25O5PolSSi

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C19H31O6PolSSi

C19H31O6PolSSi

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 23℃; for 12h; Inert atmosphere; solid phase reaction;100%
5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
137571-73-4

5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C16H22O7
1201848-91-0

C16H22O7

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; Inert atmosphere;100%
formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

ethyl chloromethyl ether
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;
Stage #1: formaldehyde diethyl acetal With zinc(II) chloride at 15 - 25℃; for 0.216667h;
Stage #2: With acetyl chloride at 20 - 35℃; for 2h;
formaldehyd
50-00-0

formaldehyd

ethanol
64-17-5

ethanol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

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

formaldehyd

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride; ethanol
1,3,5-Trioxan
110-88-3

1,3,5-Trioxan

ethanol
64-17-5

ethanol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
1-ethoxy-1-(ethylthio)methane
54699-20-6

1-ethoxy-1-(ethylthio)methane

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

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

ethanol

polyoxymethylene

polyoxymethylene

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
With hydrogenchloride
1-ethoxymethoxy-2,4-dichloro-benzene
829-59-4

1-ethoxymethoxy-2,4-dichloro-benzene

chlorine
7782-50-5

chlorine

A

bis(2,4-dichlorophenoxy)methane
35412-53-4

bis(2,4-dichlorophenoxy)methane

B

2,4-dichlorophenoxymethyl chloride
13543-09-4

2,4-dichlorophenoxymethyl chloride

C

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

D

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
at 200℃;
formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

A

chloroethane
75-00-3

chloroethane

B

ethyl chloromethyl ether
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
formaldehyde diethyl acetal
462-95-3

formaldehyde diethyl acetal

acetyl chloride
75-36-5

acetyl chloride

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

Conditions
ConditionsYield
With Zinc chloride
2,4,5-tribromo-1H-imidazole
2034-22-2

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

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2,4,5-tribromo-1-(ethoxymethyl)-1H-imidazole
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%
(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol
72174-24-4, 53269-97-9

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

ethoxymethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

ethoxymethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

Conditions
ConditionsYield
With triethylamine In dichloromethane Condensation;100%
ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-bromo-4-(ethoxymethoxy)benzene
152565-23-6

1-bromo-4-(ethoxymethoxy)benzene

Conditions
ConditionsYield
Stage #1: 4-bromo-phenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.666667h;
Stage #2: ethyl chloromethyl ether In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.25h;
100%
3,5-dichloro-2-iodophenol
1028332-19-5

3,5-dichloro-2-iodophenol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene
1028332-20-8

1,5-dichloro-3-(ethoxymethoxy)-2-iodobenzene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;100%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;90%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 22h;
2-hydroxy-3-bromobenzaldehyde
1829-34-1

2-hydroxy-3-bromobenzaldehyde

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C10H11BrO3
1138152-16-5

C10H11BrO3

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3h;100%
C16H25O5PolSSi

C16H25O5PolSSi

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C19H31O6PolSSi

C19H31O6PolSSi

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 23℃; for 12h; Inert atmosphere; solid phase reaction;100%
5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
137571-73-4

5,7-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C16H22O7
1201848-91-0

C16H22O7

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; Inert atmosphere;100%
acide 2,4,6-trihydroxybenzoique
83-30-7

acide 2,4,6-trihydroxybenzoique

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C16H22O7
1201848-91-0

C16H22O7

Conditions
ConditionsYield
Stage #1: acide 2,4,6-trihydroxybenzoique With trifluoroacetic acid; trifluoroacetic anhydride In acetone at 23℃; for 12h;
Stage #2: ethyl chloromethyl ether With N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide In dichloromethane; acetone at 23℃; for 12h;
100%
2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2,4-bis(ethoxymethoxy)benzaldehyde
128837-29-6

2,4-bis(ethoxymethoxy)benzaldehyde

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h;99%
With potassium carbonate In acetone for 1.5h; Heating;4 g
ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid
147167-96-2

ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

(E)-3-(3,5-Di-tert-butyl-4-ethoxymethoxy-phenyl)-acrylic acid ethyl ester

(E)-3-(3,5-Di-tert-butyl-4-ethoxymethoxy-phenyl)-acrylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide99%
2-(dimethylamino)ethyl acetate
1421-89-2

2-(dimethylamino)ethyl acetate

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

(2-acetoxy-ethyl)-ethoxymethyl-dimethyl-ammonium; chloride

(2-acetoxy-ethyl)-ethoxymethyl-dimethyl-ammonium; chloride

Conditions
ConditionsYield
In hexane at 20℃; for 0.166667h; Menschutkin reaction;99%
In hexane at 20℃; Menschutkin reaction;
C26H36O4Si
1200831-59-9

C26H36O4Si

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C29H42O5Si
1200831-34-0

C29H42O5Si

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 12h; Inert atmosphere;99%
2-(trifluoromethyl)phenol
444-30-4

2-(trifluoromethyl)phenol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-(ethoxymethoxy)-2-(trifluoromethyl)benzene
1391830-45-7

1-(ethoxymethoxy)-2-(trifluoromethyl)benzene

Conditions
ConditionsYield
Stage #1: 2-(trifluoromethyl)phenol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: ethyl chloromethyl ether In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique;
99%
6-hydroxy-2-bromo-benzothiazole
808755-67-1

6-hydroxy-2-bromo-benzothiazole

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2-bromo-6-(ethoxymethoxy)benzo[d]thiazole
1427773-37-2

2-bromo-6-(ethoxymethoxy)benzo[d]thiazole

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide99%
2-bromoresorcinol
6751-75-3

2-bromoresorcinol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2-bromo-1,3-bis(ethoxymethoxy)benzene
1610702-02-7

2-bromo-1,3-bis(ethoxymethoxy)benzene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;99%
3-hydroxy-2-naphthoic acid methyl ester
883-99-8

3-hydroxy-2-naphthoic acid methyl ester

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C15H16O4
1621132-93-1

C15H16O4

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-naphthoic acid methyl ester With sodium hydride
Stage #2: ethyl chloromethyl ether
99%
Stage #1: 3-hydroxy-2-naphthoic acid methyl ester With sodium hydride In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: ethyl chloromethyl ether In tetrahydrofuran at 20℃;
C13H10BrClO2
943920-03-4

C13H10BrClO2

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C16H16BrClO3

C16H16BrClO3

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;99%
2,5-dimethoxyphenol
18113-18-3

2,5-dimethoxyphenol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2-(ethoxymethoxy)-1,4-dimethoxybenzene

2-(ethoxymethoxy)-1,4-dimethoxybenzene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In chloroform at 60℃; for 20h;99%
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-(ethoxymethoxy)-2-nitrobenzene

1-(ethoxymethoxy)-2-nitrobenzene

Conditions
ConditionsYield
Stage #1: 2-hydroxynitrobenzene With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: ethyl chloromethyl ether In tetrahydrofuran at 0℃; for 2h;
99%
methyl (E)-sinapate
42041-51-0

methyl (E)-sinapate

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

(E)-methyl 3-(4-(ethoxymethoxy)-3,5-dimethoxyphenyl)acrylate

(E)-methyl 3-(4-(ethoxymethoxy)-3,5-dimethoxyphenyl)acrylate

Conditions
ConditionsYield
Stage #1: methyl (E)-sinapate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: ethyl chloromethyl ether In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;
99%
4-(6-hydroxyhexyloxy)benzoic acid
83883-25-4

4-(6-hydroxyhexyloxy)benzoic acid

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

C16H24O5

C16H24O5

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 25℃;99%
methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate
37169-36-1

methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

(S)-methyl 3-(3,4-bis(ethoxymethoxy)phenyl)-2-((tertbutoxycarbonyl)amino)propanoate

(S)-methyl 3-(3,4-bis(ethoxymethoxy)phenyl)-2-((tertbutoxycarbonyl)amino)propanoate

Conditions
ConditionsYield
Stage #1: methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: ethyl chloromethyl ether at 0 - 40℃; for 15h; Inert atmosphere; Sealed tube;
99%
1-((2-(2-(pyrrolidin-1-yl)ethoxy)naphthalen-1-yl)methyl)naphthalen-2-ol

1-((2-(2-(pyrrolidin-1-yl)ethoxy)naphthalen-1-yl)methyl)naphthalen-2-ol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-(2-((1-((2-(ethoxymethoxy)naphthalen-1-yl)methyl)naphthalen-2-yl)oxy)ethyl)pyrrolidine

1-(2-((1-((2-(ethoxymethoxy)naphthalen-1-yl)methyl)naphthalen-2-yl)oxy)ethyl)pyrrolidine

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;99%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

4-(ethyloxymethoxy)benzaldehyde
128837-26-3

4-(ethyloxymethoxy)benzaldehyde

Conditions
ConditionsYield
Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate In acetone at 0℃; for 0.333333h;
Stage #2: ethyl chloromethyl ether With tetra-(n-butyl)ammonium iodide In acetone at 0 - 20℃; for 8h;
98%
With sodium hydroxide In dichloromethane; water for 16h; Substitution; Williamson reaction;96%
Stage #1: 4-hydroxy-benzaldehyde With triethylamine In acetone at 20℃; for 0.333333h;
Stage #2: ethyl chloromethyl ether With tetra-(n-butyl)ammonium iodide In acetone at 0 - 20℃; for 22h;
88%
vanillin
121-33-5

vanillin

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

4-Ethoxymethoxy-3-methoxybenzaldehyde
128837-27-4

4-Ethoxymethoxy-3-methoxybenzaldehyde

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 19h; Inert atmosphere;98%
With potassium carbonate In acetone for 1h; Heating;3.5 g
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;
cyclohexenone
930-68-7

cyclohexenone

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

1-ethoxymethyl-2-cyclohexen-1-ol

1-ethoxymethyl-2-cyclohexen-1-ol

Conditions
ConditionsYield
With lithium; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 0℃; for 0.75h; other aldehydes and ketones;98%
With lithium; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 0℃;98%
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at 0℃;98%
ethyl (S)-3-hydroxybutyrate
56816-01-4

ethyl (S)-3-hydroxybutyrate

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

(S)-ethyl 3-(ethoxymethoxy)butanoate
137645-28-4

(S)-ethyl 3-(ethoxymethoxy)butanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;98%
90%

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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