623-46-1

Usage

Uses

Used in Environmental Applications:
1,2-Dichloro-2-ethoxyethane is used as a target compound for biodegradation studies, specifically by Rhodococcus strain DEE5151, to understand and enhance the process of breaking down harmful halogenated compounds in the environment. This contributes to the development of eco-friendly solutions for waste management and pollution control.

InChI:InChI=1/C4H8Cl2O/c1-2-7-4(6)3-5/h4H,2-3H2,1H3

Synthetic route

2-chloroethanal (107-20-0) + ethanol (64-17-5) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
With hydrogenchloride

diethyl ether (60-29-7) → 1-chloroethyl ethyl ether (7081-78-9) + 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
With chlorine

diethyl ether (60-29-7) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
at 34℃; Chlorieren unter Belichtung;
Chlorieren;
With chlorine

1-chloroethyl ethyl ether (7081-78-9) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
With chlorine

E/Z-2-chlorovinyl ethyl ether (928-56-3) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
With hydrogenchloride

ethyl vinyl ether (109-92-2) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
With tetrachloromethane; chlorine
With chlorine
With chlorine In diethyl ether at -15℃; Darkness; Green chemistry;

ethyl vinyl ether (109-92-2) → 1,2-dichloro-2-ethoxyethane (623-46-1) + 1,1,2-trichloro-2-ethoxy-ethane (687-44-5)

Conditions	Yield
With chlorine

chloroacetaldehyde diethyl acetal (621-62-5) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + paracetaldehyde (123-63-7) + 2-chloro-ethanol (107-07-3) → 1,1-di(2-chloroethoxy)ethane (14689-97-5) + 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
at 0 - 10℃;

chlorine (7782-50-5) + ethyl vinyl ether (109-92-2) → 1,2-dichloro-2-ethoxyethane (623-46-1)

hydrogenchloride (7647-01-0) + acetaldehyde (75-07-0) + 2-chloro-ethanol (107-07-3) → 1,2-dichloro-2-ethoxyethane (623-46-1)

2-chloroethanal (107-20-0) + hydrogenchloride (7647-01-0) + ethanol (64-17-5) → 1,2-dichloro-2-ethoxyethane (623-46-1)

hydrogenchloride (7647-01-0) + chloroacetaldehyde diethyl acetal (621-62-5) → 1,2-dichloro-2-ethoxyethane (623-46-1)

Conditions	Yield
at 100 - 110℃;

1,1-di(2-chloroethoxy)ethane (14689-97-5) + phosphorus pentachloride (10026-13-8, 874483-75-7) → 1,2-dichloro-2-ethoxyethane (623-46-1)

ethanol (64-17-5) + 1,2-dichloro-2-ethoxyethane (623-46-1) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With sodium ethanolate at 20℃; for 1h; Cooling with ice; Green chemistry;	96.7%

1,2-dichloro-2-ethoxyethane (623-46-1) + thiourea (17356-08-0) → 2-thiazolylamine (96-50-4)

Conditions	Yield
Hantzsch thiazole synthesis;	90%
	90%
With water

1,2-dichloro-2-ethoxyethane (623-46-1) + 2-thioureidobenzimidazole (62530-07-8) → N-(Thiazolyl-2')-2-benzimidazolylamine (14374-16-4)

Conditions	Yield
for 2h; Heating;	85%

1,2-dichloro-2-ethoxyethane (623-46-1) + 1-(3,4,5-trimethoxybenzylidene)thiosemicarbazide → 1-(3,4,5-trimethoxybenzilidene)-2-(thiazol-2-yl)hydrazine

Conditions	Yield
In ethanol for 3h; Heating;	75%

2-benzylsulfanyl-6-(2-chloro-phenyl)-pyrido[2,3-d]pyrimidin-7-ylamine + 1,2-dichloro-2-ethoxyethane (623-46-1) → C22H15ClN4S (610786-19-1)

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃;	63%

tert-butyl {3-[3-[(aminocarbonothioyl)amino]-5-(trifluoromethyl)-1H-indazol-1-yl]propyl}carbamate (943247-34-5) + 1,2-dichloro-2-ethoxyethane (623-46-1) → tert-butyl {3-[3-(1,3-thiazol-2-ylamino)-5-(trifluoromethyl)-1H-indazol-1-yl]propyl}carbamate (943246-92-2)

Conditions	Yield
Stage #1: tert-butyl {3-[3-[(aminocarbonothioyl)amino]-5-(trifluoromethyl)-1H-indazol-1-yl]propyl}carbamate; 1,2-dichloro-2-ethoxyethane In ethanol; water at 90℃; for 4h; Stage #2: With di-tert-butyl dicarbonate; sodium hydrogencarbonate In ethanol; water; ethyl acetate at 20℃;	61%

1,2-dichloro-2-ethoxyethane (623-46-1) + dilithio-1,3-dithiepin-2-carbodithiolate → 2-(4-ethoxy-1,3-dithiolan-2-ylidene)-1,3-dithiepin

Conditions	Yield
1.) -70 deg C; 2.) r.t.;	60%

2-amino-3-chloro-5-(2.4-dichloro-phenyl)-isonicotinonitrile (952206-52-9) + 1,2-dichloro-2-ethoxyethane (623-46-1) → 8-chloro-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (952206-53-0)

Conditions	Yield
at 150℃; for 0.283333h; Microwave irradiation;	60%

2-(benzylthio)-6-(4-fluorophenoxy)pyrido[2,3-d]pyrimidin-7-amine + 1,2-dichloro-2-ethoxyethane (623-46-1) → phenoxy-tricyclic-imidazole

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃;	57%

1,2-dichloro-2-ethoxyethane (623-46-1) + 1-(3,5-dimethoxy-4-ethoxybenzoyl)thiosemicarbazide → 1-(3,5-dimethoxy-4-ethoxybenzoyl)-2-(thiazol-2-yl)hydrazine

Conditions	Yield
In ethanol for 3h; Heating;	55%

N-(5-bromo-1H-indazol-3-yl)thiourea (943247-20-9) + 1,2-dichloro-2-ethoxyethane (623-46-1) → 5-bromo-N-1,3-thiazol-2-yl-1H-indazol-3-amine (943246-87-5)

Conditions	Yield
In ethanol; water at 20 - 80℃; for 3h;	55%

1,2-dichloro-2-ethoxyethane (623-46-1) + 1-(3,4,5-trimethoxybenzoyl)thiosemicarbazide → 1-(3,4,5-trimethoxybenzoyl)-2-(thiazol-2-yl)hydrazine

Conditions	Yield
In ethanol for 3h; Heating;	50%

1,2-dichloro-2-ethoxyethane (623-46-1) + (Et4N)2 → 4,5-(ethoxyethylenedithio)-1,3-dithiole-2-thione (110789-38-3)

Conditions	Yield
In acetone for 21h; Heating;	50%

2-[2-(1H-indazol-3-yl)-7,7-dimethyl-6-oxo-6,7-dihydro-3H-imidazo[4,5-f]indol-5-yl]-thioacetamide + 1,2-dichloro-2-ethoxyethane (623-46-1) → 2-(1H-indazol-3-yl)-7,7-dimethyl-5-thiazol-2-ylmethyl-5,7-dihydro-3H-imidazo[4,5-f]indol-6-one

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 3.5h;	48%

1,2-dichloro-2-ethoxyethane (623-46-1) + 4-(2-benzyloxy-5-bromophenyl)-4-thiocarbamoylpiperidine-1-carboxylic acid tert-butyl ester (1295645-06-5) → 4-(2-benzyloxy-5-bromophenyl)-4-thiazol-2-ylpiperidine-1-carboxylic acid tert-butyl ester (1295645-07-6)

Conditions	Yield
Stage #1: 1,2-dichloro-2-ethoxyethane; 4-(2-benzyloxy-5-bromophenyl)-4-thiocarbamoylpiperidine-1-carboxylic acid tert-butyl ester In N,N-dimethyl-formamide at 75℃; for 16h; Sealed; Stage #2: With di-tert-butyl dicarbonate; triethylamine In dichloromethane for 0.5h;	46%

1,2-dichloro-2-ethoxyethane (623-46-1) + 1-(3,5-dimethoxy-4-ethoxybenzylidene)thiosemicarbazide → 1-(3,5-dimethoxy-4-ethoxybenzilidene)-2-(thiazol-2-yl)hydrazine

Conditions	Yield
In ethanol for 3h; Heating;	45%

1,2-dichloro-2-ethoxyethane (623-46-1) + 1-(3,4-methylenedioxybenzylidene)thiosemicarbazide → 1-(3,4-methylenedioxybenzilidene)-2-(thiazol-2-yl)hydrazine

Conditions	Yield
In ethanol for 3h; Heating;	40%

1,2-dichloro-2-ethoxyethane (623-46-1) + 1-(3,4-methylenedioxybenzoyl)thiosemicarbazide → 1-(3,4-methylenedioxybenzoyl)-2-(thiazol-2-yl)hydrazine

Conditions	Yield
In ethanol for 3h; Heating;	35%

1,2-dichloro-2-ethoxyethane (623-46-1) + 2-(benzhydrylthio)ethanethioamide → 2-(benzhydrylthiomethyl)thiazole

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 125℃; for 4h;	34%

1,2-dichloro-2-ethoxyethane (623-46-1) + N-[5-(2-thienyl)-1H-indazol-3-yl]thiourea (1093964-97-6) → N-1,3-thiazol-2-yl-5-(2-thienyl)-1H-indazole-3-amine (1093967-47-5)

Conditions	Yield
Stage #1: 1,2-dichloro-2-ethoxyethane; N-[5-(2-thienyl)-1H-indazol-3-yl]thiourea In ethanol; water at 90℃; Stage #2: With sodium hydrogencarbonate In ethanol; water; ethyl acetate	18%

1,2-dichloro-2-ethoxyethane (623-46-1) + 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carbothioamide (1391944-18-5) → 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4-(thiazol-2-yl)isoxazole (1391944-16-3)

Conditions	Yield
In N,N-dimethyl-formamide at 90 - 130℃; for 4h;	17%
In N,N-dimethyl-formamide at 90 - 130℃; for 4h;	17%

1,2-dichloro-2-ethoxyethane (623-46-1) + 4,4-dimethylimidazolidine-2-thione (6086-42-6) → 3-((5,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl)thio)-6,6-dimethyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole dihydrochloride

Conditions	Yield
With hydrogenchloride In ethanol; water at 40℃; for 21h; Inert atmosphere;	16%

1,2-dichloro-2-ethoxyethane (623-46-1) + 3β-acetoxy-androsta-5,16-dien-17-thiocarboxamide (637776-05-7) → 3β-acetoxy-17-(2'-thiazolyl)-androsta-5,16-diene (637776-26-2)

Conditions	Yield
In N,N-dimethyl-formamide for 0.5h; Heating;	15.75%

1,2-dichloro-2-ethoxyethane (623-46-1) + 3β-acetoxy-androsta-5,16-dien-17-carboxamide (389076-82-8) → 3β-acetoxy-17-(2'-oxazolyl)-androsta-5,16-diene (388083-41-8)

Conditions	Yield
In N,N-dimethyl-formamide for 0.5h; Heating; 1;	15.1%

thiophene (188290-36-0) + 1,2-dichloro-2-ethoxyethane (623-46-1) → 2,2'-(2-chloro-1,1-ethanediyl)dithiophene (31161-25-8)

Conditions	Yield
With phosphorus pentaoxide; chloroform

pyridine (110-86-1) + 1,2-dichloro-2-ethoxyethane (623-46-1) → 1-(1-ethoxy-2-chloro-ethyl)-pyridinium; chloride

Conditions	Yield
With diethyl ether

phenylethynylmagnesium bromide (6738-06-3) + 1,2-dichloro-2-ethoxyethane (623-46-1) → ethyl-(1-chloromethyl-3-phenyl-prop-2-ynyl)-ether

pyridine-2-carbothioamide (5346-38-3) + 1,2-dichloro-2-ethoxyethane (623-46-1) → 2-(pyridine-2-yl)thiazole (2433-17-2)

Ketene (463-51-4) + ethanol (64-17-5) + 1,2-dichloro-2-ethoxyethane (623-46-1) → 3-ethoxy-4-chloro-butyric acid ethyl ester (20460-26-8)

Conditions	Yield
With aluminium trichloride

Upstream product

• 107-20-0 2-chloroethanal 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 7081-78-9 1-chloroethyl ethyl ether 
• 928-56-3 E/Z-2-chlorovinyl ethyl ether 
• 109-92-2 ethyl vinyl ether 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 7647-01-0 hydrogenchloride 
• 123-63-7 paracetaldehyde 
• 107-07-3 2-chloro-ethanol 
• 7782-50-5 chlorine 
• 75-07-0 acetaldehyde 
• 14689-97-5 1,1-di(2-chloroethoxy)ethane 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 2433-17-2 2-(pyridine-2-yl)thiazole 
• 25045-82-3 6-nitroimidazo[1,2-a]pyridine 
• 5905-06-6 [2,2']bifuranyl-3-carboxylic acid 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 14542-13-3 2-methoxythiazole 
• 412311-51-4 1-thiazol-2-yl semicarbazide 
• 87431-37-6 2,5,2',5'-tetramethyl-stilbene 
• 25347-49-3 1,2-bis(p-ethylphenyl)ethylene 
• 30216-55-8 1-phenyl-ethanone thiazol-2-ylhydrazone 
• 112584-15-3 N-(p-tolyl)thiazol-2-amine 
• 861318-51-6 4-chloromethyl-2,6-diphenyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 384858-14-4 N-[(4-methoxyphenyl)methyl]thiazole 2-amine 
• 458-72-0 N-[(4-fluorophenyl)methyl]thiazole 2-amine 
• 13159-90-5 (4-chloro-benzyl)-thiazol-2-yl-amine 

Relevant academic research and scientific papers

Green method for preparing chloroacetaldehyde dialkyl alcohol from vinyl ether

The invention discloses a green method for preparing chloroacetaldehyde dialkyl alcohol from vinyl ether. The method takes alkyl vinyl ether, chlorine and alcohol as raw materials and takes corresponding sodium alcoholate as a nucleophilic reagent and comprises the steps: carrying out electrophilic addition on alkyl ether and chlorine in low-boiling-point solvents such as ethers, hydrocarbons, halogenated hydrocarbons and the like; and after chlorination is finished, adding into an alcoholic solution of sodium alcoholate for nucleophilic substitution to obtain high-yield chloroacetaldehyde dialkyl alcohol, such as chloroacetaldehyde dimethyl acetal, chloroacetaldehyde diethyl acetal and chloroacetaldehyde methylisobutyl alcohol. The method is easy to operate, single in reaction, high in yield, less in side reaction, green and pollution-free; the recovered solvent and alcohol can be repeatedly used; no waste acid or waste water is generated in the whole process, the only byproduct sodium chloride can be used for other industrial purposes, and environment-friendly circulation and zero emission are achieved.