52808-36-3

Basic information

• Product Name: 2-(2-Methoxyethoxy)ethyl chloride
• Synonyms: 1-chloro-2-(2-methoxyethoxy)ethane;2-(2-METHOXYETHOXY)ETHYL CHLORIDE;1-(2-Chloroethoxy)-2-methoxyethane;2-Chloroethyl 2-methoxyethyl ether;2-(2-chloroethoxy)ethyl methyl ether
• CAS NO: 52808-36-3
• Molecular Formula: C₅H₁₁ClO₂
• Molecular Weight: 138.59
• Mol File: 52808-36-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 156°Cat760mmHg
• Flash Point: 44.8°C
• Appearance: /
• Density: 1.025g/cm³
• Vapor Pressure: 3.8mmHg at 25°C
• Refractive Index: 1.41
• CAS DataBase Reference: 2-(2-Methoxyethoxy)ethyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Methoxyethoxy)ethyl chloride(52808-36-3)
• EPA Substance Registry System: 2-(2-Methoxyethoxy)ethyl chloride(52808-36-3)

Safety Data

• Hazardous Substances Data: 52808-36-3(Hazardous Substances Data)

Usage

Uses

1-Chloro-2-(2-methoxyethoxy)ethane is a useful reactant in organic synthesis.

InChI:InChI=1/C5H11ClO2/c1-7-4-5-8-3-2-6/h2-5H2,1H3

Synthetic route

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3)

Conditions	Yield
With pyridine; thionyl chloride In dichloromethane for 14h; Inert atmosphere; Reflux;	97%
With thionyl chloride In N,N-dimethyl-formamide at 28 - 60℃; for 3h;	95.2%
With pyridine; thionyl chloride In chloroform for 3h; Heating;	92%

toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester (50586-80-6) → 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3)

Conditions	Yield
With ammonium chloride In dimethyl sulfoxide at 80℃; for 5h;	51%
With ammonium chloride In dimethyl sulfoxide at 80℃; for 5h;	51%

sodium methylate (124-41-4) + 3-oxa-1,5-dichloropentane (111-44-4) → 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3)

3-oxa-1,5-dichloropentane (111-44-4) + sodium methylate<1 mol> → 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3)

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → 3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]benzoic acid methyl ester (857934-56-6)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 24h;	96%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 2-(2-methoxyethoxy)-N,N-dimethylethan-1-amine → 2-(2-methoxyethoxy)-N-[2-(2-methoxyethoxy)ethyl]-N,N-dimethylethan-1-aminium chloride

Conditions	Yield
With sulfuric acid at 50℃; for 168h;	95%

N,N-dimethyl-ethanamine (598-56-1) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → (N-ethyl-2-(2-methoxyethoxy)-N,N-dimethylethanaminium) chloride

Conditions	Yield
With air In methanol at 50℃; for 360h;	93%
In tetrahydrofuran at 60℃; Sealed tube;
In tetrahydrofuran at 60℃; Sealed tube;

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 1-hydroxyanthracene (610-50-4) → C19H20O3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Solvent; Inert atmosphere;	91%

isovanillin (621-59-0) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → C13H18O5

Conditions	Yield
Williamson Ether Synthesis;	91%

5-bromopyridine-3-ol (74115-13-2) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → 3-bromo-5-(2-(2-methoxyethoxy)ethoxy)pyridine (1364125-18-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃;	89%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 2-(2-methoxyethoxy)ethanamine (31576-51-9) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
With sodium carbonate at 110℃; for 24h; Temperature;	85.48%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 9H-carbazole (86-74-8) → 9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole (197297-41-9)

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 80℃; for 1.5h; Stage #2: 1-chloro-2-(2-methoxyethoxy)ethane In N,N-dimethyl-formamide at 80℃;	83%
With NaH In N,N-dimethyl-formamide	83%
Stage #1: 9H-carbazole With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 80℃; for 1.5h; Stage #2: 1-chloro-2-(2-methoxyethoxy)ethane In N,N-dimethyl-formamide; mineral oil at 80℃;	83%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 1,3-benzothiazol-2-ylhydrazine (615-21-4) → C12H17N3O2S

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	83%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	73%

pyrrole (109-97-7) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → 1-(2-(2-methoxyethoxy)ethyl)-1H-pyrrole (132387-61-2)

Conditions	Yield
With resin-supported MPEG-550; potassium tert-butylate In tetrahydrofuran at 45℃;	80%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 1,5-dihydroxynaphthalene (83-56-7) → 1,5-bis(2-(2-methoxyethoxy)ethoxy)naphthalene

Conditions	Yield
With potassium carbonate In acetonitrile for 72h; Heating;	79%
With potassium carbonate In acetonitrile for 72h; Heating;

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + methyl galloate (99-24-1) → methyl 3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzoate (422267-94-5)

Conditions	Yield
With potassium carbonate; potassium iodide In dimethyl sulfoxide at 120℃; Inert atmosphere;	76%

1-methyl-1H-imidazole (616-47-7) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → 1-(2-(2-methoxyethoxy)ethyl)-3-methylimidazolium chloride

Conditions	Yield
at 80℃; for 24h;	75%
at 80℃; for 60h;
for 36h; Reflux;

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 1,5-naphthalenedithiol (5325-88-2) → 1,5-Bis-[2-(2-methoxy-ethoxy)-ethylsulfanyl]-naphthalene

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Heating;	74%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + gallaldehyde (13677-79-7) → (3,4,5-tris(2-(2-methoxyethoxy)ethoxy)phenyl)methanol (422267-98-9)

Conditions	Yield
Williamson Ether Synthesis;	74%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 1,3-diethynylbenzene (1785-61-1) → (1,3-bis(1-(2-(2-methoxyethoxy)ethyl)-1H-1,2,3-triazol-4-yl)benzene)

Conditions	Yield
Stage #1: 1-chloro-2-(2-methoxyethoxy)ethane With sodium azide In water; N,N-dimethyl-formamide at 125℃; for 3.5h; Microwave irradiation; Stage #2: 1,3-diethynylbenzene With copper(ll) sulfate pentahydrate; ascorbic acid In water; N,N-dimethyl-formamide at 20℃;	72%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + tributylphosphine (998-40-3) → tri-n-butyl[2-(2-methoxyethoxy)ethyl]phosphonium chloride

Conditions	Yield
In acetonitrile for 48h; Reflux;	69%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + dimethyl amine (124-40-3) → 2-(2-methoxyethoxy)-N,N-dimethylethan-1-amine

Conditions	Yield
In diethyl ether at 80℃; for 8h; metal container;	68%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + (3R,6S)-hexahydrofuro[3,2-b]furan-3,6-diol (1214839-99-2) → (3R,6S)-3,6-Bis-[2-(2-methoxy-ethoxy)-ethoxy]-hexahydro-furo[3,2-b]furan

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide; sodium chloride In xylene at 100℃; for 0.666667h; Alkylation; microwave irradiation;	68%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + phenylacetylene (536-74-3) → 1-[2-(2-methoxy-ethoxy)-ethyl]-4-phenyl-1H-[1,2,3]triazole

Conditions	Yield
Stage #1: 1-chloro-2-(2-methoxyethoxy)ethane With sodium azide; sodium iodide In water; N,N-dimethyl-formamide at 125℃; for 3h; Microwave irradiation; Stage #2: phenylacetylene With copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate In water; N,N-dimethyl-formamide at 20℃; for 20h;	67%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + (4S)-4-(4-hydroxybenzyl)-1,3-oxazolidin-2-one (187332-12-3) → (S)-4-{4-[2-(2-methoxyethoxy)ethoxy]benzyl}oxazolidin-2-one

Conditions	Yield
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 24h;	65%

4H-cyclopenta[2,1-b;3,4-b']dithiophene (389-58-2) + 1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → 4,4-bis(2-(2-methoxyethoxy)ethyl)-4H-cyclopenta[2,1-b:3,4-b']dithiophene

Conditions	Yield
With potassium iodide; potassium hydroxide In dimethyl sulfoxide at 0 - 20℃;	58%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + diethylene glycol (111-46-6) → tetraethylene glycol monomethyl ether (23783-42-8)

Conditions	Yield
With sodium	57%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 2-methyl-6-phenylbenzo[c][1,7]-naphthyridin-4(3H)-one → 4-[2-(2-methoxyethoxy)ethoxy]-2-methyl-6-phenylbenzo-[c][1,7]naphthyridine + 3-[(2-methoxyethoxy)ethyl]-2-methyl-6-phenylbenzo-[c][1,7]naphthyridin-4(3H)-one

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; Cooling;	A 20% B 54%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 2,3-dihydro-1H-benzo[e][1,4]diazepine (5945-91-5) → 1-<2-(2-Methoxyethoxy)ethyl>-2,3-dihydro-1H-1,4-benzodiazepine (120588-14-9)

Conditions	Yield
With potassium carbonate; tetrabutylammomium bromide In acetonitrile for 5h; Heating;	34%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 1-methyl-2-pyrrolidine-methanol (3554-65-2) → 2-[2-(2-methoxyethoxy)ethoxymethyl]-1-methylpyrrolidine

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2.5h;	34%
With potassium hydroxide In dimethyl sulfoxide Etherification;

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + N-methyl-4-nitrobenzylamine (19499-60-6) → 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-nitrobenzene (334952-05-5)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 100℃; for 6h;	29%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + methyl 2-cyanoacetate (105-34-0) → methyl 2-cyano-4-(2-methoxyethoxy)-2-[2-(2-methoxyethoxy)ethyl]butanoate (871660-77-4)

Conditions	Yield
With sodium hydride In methanol for 6h; Heating;	20%

Upstream product

• 111-44-4 3-oxa-1,5-dichloropentane 
• 50586-80-6 toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 124-41-4 sodium methylate 

Downstream Products

• 57721-93-4 1,2-bis[2-(2-methoxyethoxy)ethoxy]benzene 
• 857934-56-6 3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]benzoic acid methyl ester 
• 1364125-18-7 3-bromo-5-(2-(2-methoxyethoxy)ethoxy)pyridine 
• 70384-51-9 Tris(3,6-dioxaheptyl)amine 
• 64994-51-0 4-[2-(2-methoxyethoxy)ethoxy]benzaldehyde 
• 422267-94-5 methyl 3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzoate 
• 334952-05-5 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-nitrobenzene 
• 180690-29-3 2,7-dibromo-9,9-bis(2-(2-methoxyethoxy)ethyl)-9H-fluorene 
• 720681-07-2 {3,5-bis-[3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzyloxy]-phenyl}-methanol 
• 720681-06-1 3,5-bis-[3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzyloxy]-benzoic acid methyl ester 
• 720681-04-9 [3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-methanol 
• 720681-03-8 3,5-bis-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-benzoic acid methyl ester 

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