52808-36-3

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

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

Downstream Products

• 64715-83-9 (S)-(-)-2-Amino-1-(2-methoxyethoxyethoxy)-3-phenylpropan 
• 30492-38-7 1,3-Di-tert-butyl-2-[2-(2-methoxy-ethoxy)-ethoxy]-5-methyl-benzene 
• 5732-47-8 8-aza-2,5,11,14-tetraoxa-pentadecane 
• 70384-51-9 Tris(3,6-dioxaheptyl)amine 
• 31576-51-9 2-(2-methoxyethoxy)ethanamine 
• 57721-93-4 1,2-bis[2-(2-methoxyethoxy)ethoxy]benzene 
• 23783-42-8 tetraethylene glycol monomethyl ether 
• 857934-56-6 3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]benzoic acid methyl ester 
• 334952-05-5 4-[(N-(2-(2-methoxy-ethoxy)-ethyl)-N-methyl-amino)-methyl]-nitrobenzene 
• 64994-51-0 4-[2-(2-methoxyethoxy)ethoxy]benzaldehyde 
• 1364125-18-7 3-bromo-5-(2-(2-methoxyethoxy)ethoxy)pyridine 
• 422267-94-5 methyl 3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzoate 
• 180690-29-3 2,7-dibromo-9,9-bis(2-(2-methoxyethoxy)ethyl)-9H-fluorene 

Relevant academic research and scientific papers

Ionic liquids as modulators of fragrance release in consumer goods

When organic esters or alcohols were dissolved in each of three novel ionic liquids (which have no effective vapour pressure), the vapour-liquid equilibria (as measured by infrared spectroscopy of the gas phase) revealed significant positive deviation from Raoult's law for a wide range of perfume raw materials. The addition of water amplified the repulsive effect of the ionic liquid matrix, and this was exemplified by a series of ternary phase diagrams.

Novel method for preparing tris (3,6 -dioxo-heptyl) amine

The invention relates to a new method for preparing tris(3,6-dioxaheptyl)amine. The new method is characterized in that ammonia water, diethylene glycol monomethyl ether and thionyl chloride are takenas raw materials, and the tris(3,6-dioxaheptyl)amine is synthesized through three steps. The new method provided by the invention has the following advantages that reaction conditions are mild, the operation is safe, and the danger of using high-risk chemicals such as hydrogen and Raney nickel is avoided; the reaction conversion rate is high, and the product yield is high; only products, sodium chloride and a very small amount of pre-distillation fractions are produced in the process, excess materials can be recycled after treatment, three wastes are very few, and the production process is green and environmentally friendly.

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A series of polyethylene glycol-containing imidazolium-functionalized phosphine ligands (mPEG-im-PPh2) were successfully synthesized and used in the rhodium-catalyzed hydrosilylation of olefins. The results indicate that the RhCl3/mPEG-im-PPh2 catalytic system exhibits both excellent activity and selectivity for the β-adduct. In addition, the catalytic system may be recycled at least six times.

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The invention discloses a preparation method of ethyl methoxyethoxy ethyl sulfone. The preparation method comprises steps as follows: S1, halogenation: diethylene glycol monomethyl ether is halogenated, and a halogenated product is obtained; S2, vulcanization: the halogenated product is vulcanized, and a vulcanized product is obtained; S3, oxidization: the vulcanized product is oxidized, and ethyl methoxyethoxy ethyl sulfone is obtained. According to the preparation method of ethyl methoxyethoxy ethyl sulfone, preferably, triethylamine is taken as a precipitant, so that toxicity is reduced, the reaction is more sufficient, and production and control are facilitated; meanwhile, a technology utilizing metachloroperbenzoic acid as an oxidizing agent is adopted to oxidize the components into sulfone, a system is relatively simple, operation is easy, furthermore, oxidizing capacity is higher, and yield is higher and can reach 80%-90%; besides, aftertreatment operation of metachloroperbenzoic acid is simple, and metachloroperbenzoic acid is easy to clean.

Fluorescent dye

PROBLEM TO BE SOLVED: To provide a fluorescent dye that has improved water solubility and thus provides high fluorescence intensity. SOLUTION: A fluorescent dye of the present invention is an azole derivative having a polyoxyalkylene group represented by general formula E-O-(CH2CH2O)p-, where E is a C1-4 alkyl group and p is an integer from 1 to 40. The dye has improved water solubility and provides high fluorescence intensity. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

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