623-46-1

Basic information

• Product Name: 1,2-Dichloro-2-ethoxyethane
• Synonyms: 1,2-DICHLORODIETHYL ETHER;1,2-DICHLORO-1-ETHOXYETHANE;1,2-DICHLOROETHYL ETHER;1,2-DICHLOROETHYL ETHYL ETHER;A,B-DICHLOROETHYL ETHER;Ethyl-1,2-dichloroethyl ether;1,2-dichloro-1-ethoxy-ethan;Ether, 1,2-dichloroethyl ethyl
• CAS NO: 623-46-1
• Molecular Formula: C₄H₈Cl₂O
• Molecular Weight: 143.01
• EINECS: 210-794-2
• Mol File: 623-46-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 140-145 °C(lit.)
• Flash Point: 110 °F
• Appearance: /
• Density: 1.167 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.25mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• BRN: 1733607
• CAS DataBase Reference: 1,2-Dichloro-2-ethoxyethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dichloro-2-ethoxyethane(623-46-1)
• EPA Substance Registry System: 1,2-Dichloro-2-ethoxyethane(623-46-1)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-36/37/38
• Safety Statements: 26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: KI0780000
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 623-46-1(Hazardous Substances Data)

Usage

General Description

1,2-Dichloroethyl ethyl ether is an halogenated ethyl ether and its degradation by Rhodococcus strain DEE5151 has been studied.

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

• 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 
• 457-58-9 2-(4-fluoro-benzyl)-thiazole 

Relevant articles and documents

-

-