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3188-13-4

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3188-13-4 Usage

Chemical Properties

clear colorless to pale yellow liquid

Uses

Chloromethyl ethyl ether can be used to prepare:6-Benzyl-1-(ethoxymethyl)-5-iodopyrimidine-2,4(1H,3H)-dione, a key intermediate in the preparation of MKC-442 analog.Acylation catalyst for alcohols named 1,3-bis-[(R)-1-(2-naphthyl)ethyl]imidazoliumchloride by reacting with glyoxal-bis-[(R)-1-(2-naphthyl)ethyl]imine.

General Description

A colorless liquid. Slightly denser than water and insoluble in water. Flash point below 73°F. May be moderately toxic by ingestion, inhalation or skin absorption. Severely irritates skin, eyes and mucous membranes.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Chloromethyl ethyl ether tends to form unstable peroxides when exposed to oxygen or air. These products can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Forms salts with strong acids and addition complexes with Lewis acids. May react violently with strong oxidizing agents. I

Health Hazard

TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Check Digit Verification of cas no

The CAS Registry Mumber 3188-13-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,8 and 8 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3188-13:
(6*3)+(5*1)+(4*8)+(3*8)+(2*1)+(1*3)=84
84 % 10 = 4
So 3188-13-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H7ClO/c1-2-5-3-4/h2-3H2,1H3

3188-13-4 Well-known Company Product Price

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  • Aldrich

  • (142670)  Chloromethylethylether  95%

  • 3188-13-4

  • 142670-25G

  • 829.53CNY

  • Detail

3188-13-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name chloromethoxyethane

1.2 Other means of identification

Product number -
Other names Ethoxychloromethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3188-13-4 SDS

3188-13-4Synthetic 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%

3188-13-4Relevant articles and documents

PROCESS FOR PREPARING AN ALKOXYMETHYL ALKYNYL ETHER COMPOUND HAVING A TERMINAL TRIPLE BOND

-

Paragraph 0150; 0151; 0153-0157, (2021/06/26)

The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4):H-CtriplebondC(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and "a" represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H-CtriplebondC(CH2)aOH (1), wherein "a" is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.

Development of Acidic Imidazolium Ionic Liquids for Activation of Kraft Lignin by Controlled Oxidation: Comprehensive Evaluation and Practical Utility

Klapiszewski, ?ukasz,Szalaty, Tadeusz J.,Kurc, Beata,Stanisz, Ma?gorzata,Zawadzki, Bartosz,Skrzypczak, Andrzej,Jesionowski, Teofil

, p. 361 - 374 (2018/06/04)

A novel, eco-friendly method for the activation of lignin by controlled oxidation was studied. The results obtained for six acidic imidazolium ionic liquids containing the hydrogen sulfate anion were compared. The key goal of this research was to increase the content of carbonyl groups in the lignin structure because these may play the main role in the transport of protons and electrons in active materials for electrochemical applications. By means of a variety of analytical techniques (FTIR, 13C CP/MAS NMR, and X-ray photoelectron spectroscopy; selected reactions to determine the presence of carbonyl groups; SEM; zeta-potential analysis; thermogravimetric analysis/differential thermogravimetric analysis; and porous structure analysis), it was determined that the product obtained after treatment with 3-cyclohexyloxymethy-1-methylimidazolium hydrogen sulfate had favorable properties, in terms of the target application. Electrochemical tests proved that the obtained materials could be used as anodes in lithium batteries. The results show that the activation of lignin with ionic liquids can increase its capacity and maintain stability.

3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

Tang, Jing,Maddali, Kasthuraiah,Metifiot, Mathieu,Sham, Yuk Y.,Vince, Robert,Pommier, Yves,Wang, Zhengqiang

experimental part, p. 2282 - 2292 (2011/06/17)

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

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