621-62-5

Basic information

• Product Name: Chloroacetaldehyde diethyl acetal
• Synonyms: CHLOROACETALDEHYDE DIETHYL ACETAL, STAB.;CHLOROAETALDEHYDE DIETHYLACETAL;Ethane, 2-chloro-1,1-diethoxy-;2-chloroacetal;2-Chloro-1,1-diethoxyethane, Chloroacetal;1-Chloro-2,2-diethoxyethane;Chloroethanal diethyl acetal;Chloroacetaldehyde diethyl acetal,99%
• CAS NO: 621-62-5
• Molecular Formula: C₆H₁₃ClO₂
• Molecular Weight: 152.62
• EINECS: 210-695-4
• Product Categories: Pharmaceutical Intermediates
• Mol File: 621-62-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: -45 °C
• Boiling Point: 157 °C(lit.)
• Flash Point: 85 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.018 g/mL at 25 °C(lit.)
• Vapor Pressure: <0.02 atm ( 20 °C)
• Refractive Index: n20/D 1.416(lit.)
• Storage Temp.: Flammables area
• Solubility: 1.8g/l
• Explosive Limit: 1.40%(V)
• Water Solubility: 1.8 g/L (20 ºC)
• Sensitive: Moisture Sensitive
• BRN: 969254
• CAS DataBase Reference: Chloroacetaldehyde diethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: Chloroacetaldehyde diethyl acetal(621-62-5)
• EPA Substance Registry System: Chloroacetaldehyde diethyl acetal(621-62-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 10-22-36/37/38
• Safety Statements: 28A-26-16-36-23-7/9
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 1
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 621-62-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOWISH LIQUID

Hazard

Moderate fire risk.

InChI:InChI=1/C6H13ClO2/c1-3-8-6(5-7)9-4-2/h6H,3-5H2,1-2H3

Synthetic route

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%

2-chloroethanal (107-20-0) + ethanol (64-17-5) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform Reflux; Large scale;	93%

vinyl acetate (108-05-4) + ethanol (64-17-5) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With chlorine at 1 - 4℃; for 2h; Chlorination; Acetalization;	64%
With chlorine im Dunkeln unter Kuehlung mit CO2-Aceton;
With chlorine im Dunkeln unter Kuehlung mit CO2-Aceton;

Cyclohexanone oxime (100-64-1) → chlorofluorocyclohexane (371-89-1) + 1,1-dichlrocyclohexane (2108-92-1) + chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With hydrogen fluoride; chlorine In ethanol at -10℃; for 4h;	A 59% B 32% C n/a

ethanol (64-17-5) + acetaldehyde (75-07-0) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
Stage #1: acetaldehyde With chlorine Chlorination; Stage #2: ethanol With calcium chloride at 20 - 30℃; for 4h; Acetalization;	48%

diethyl acetal (105-57-7) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
beim Chlorieren;
beim Chlorieren;
With chlorine Versetzen des Reaktionsgemisches mit Natriumaethylat bei 50grad;

1,2-dichloroethyl acetate (10140-87-1) + ethanol (64-17-5) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
at 55℃;

ethanol (64-17-5) + chloroethylene (75-01-4) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With chlorine

ethanol (64-17-5) + 1,1-Dichloroethylene (75-35-4) + sodium ethanolate (141-52-6) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
at 40 - 50℃;

ethanol (64-17-5) + E/Z-2-chlorovinyl ethyl ether (928-56-3) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With sulfuric acid
With hydrogenchloride

ethanol (64-17-5) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With chlorine
With chlorine dann Erhitzen auf 55grad und laesst man mit Marmor in der Kaelte Stehen, faellt dann mit Wasser und fraktioniert das gefaellte Oel;

ethanol (64-17-5) → dichloroacetaldehyde diethyl acetal (619-33-0) + chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With chlorine; calcium carbonate

1,2-dichloro-2-ethoxyethane (623-46-1) + sodium ethanolate (141-52-6) → chloroacetaldehyde diethyl acetal (621-62-5)

ethanol (64-17-5) + ethyl vinyl ether (109-92-2) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With chlorine
With tert-butylhypochlorite
(i) SO2Cl2, Et2O, (ii) /BRN= 1718733/, H2SO4; Multistep reaction;
With tert-butylhypochlorite; potassium carbonate In diethyl ether at -50℃;

paracetaldehyde (123-63-7) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With hydrogenchloride; potassium permanganate at 20 - 25℃; moeglichst im Sonnelicht, dann mit Alkohol und Wasser;

1,2-dichloro-2-ethoxyethane (623-46-1) + allylmagnesium bromide (1730-25-2) → 2-ethoxy-4,5-dibromo-1-chloro-pentane + chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
Behandeln des Reaktiongemischs mit Brom;

ethanol (64-17-5) + paracetaldehyde (123-63-7) → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
(i) Cl2, (ii) /BRN= 1718733/; Multistep reaction;

ethanol (64-17-5) + chlorine (7782-50-5) + ethyl vinyl ether (109-92-2) → chloroacetaldehyde diethyl acetal (621-62-5)

ethanol (64-17-5) + <1.2-dichloro-ethyl>-acetate → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
at 64℃;
at 64℃;

ethanol (64-17-5) + chloroaldehyde alcoholate → chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
With hydrogenchloride

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

diethyl ether (60-29-7) + 1,2-dichloro-2-ethoxyethane (623-46-1) + allylmagnesium bromide (1730-25-2) → chloroacetaldehyde diethyl acetal (621-62-5) + α-chloro-δ.ε-dibromo-β-ethoxy-pentane

Conditions	Yield
nachfolgenden Behandlung mit Brom;

ethanol (64-17-5) + chlorine (7782-50-5) → dichloroacetaldehyde diethyl acetal (619-33-0) + 2,2-dichloroacetaldehyde (79-02-7) + chloral (75-87-6) + chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
at 80 - 90℃; unter der Einwirkung von stillen elektrischen Entladungen; weitere Prod.: Trichloracetaldehyd-diaethylacetal und Hexachloraethan;

1-chloro-2-ethoxy-2-ethanol (74283-45-7) → chloroacetaldehyde diethyl acetal (621-62-5) + monochloroaldehyde hydrate

Conditions	Yield
bei der Destillation;

vinyl acetate (108-05-4) → 1,2-dichloroethyl acetate (10140-87-1) + chloroacetaldehyde diethyl acetal (621-62-5)

Conditions	Yield
	A n/a B 790 grams (56 % pure)

chloroacetaldehyde diethyl acetal (621-62-5) + phenol (108-95-2) → (2,2-diethoxy-ethoxy)-benzene (32438-31-6)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 175℃; for 1h; Microwave irradiation;	100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃;	58%
With potassium hydroxide 1.) H2O, 90 to 100 deg C, 2.) reflux, 6 h; Multistep reaction;

tert-butylamine (75-64-9) + chloroacetaldehyde diethyl acetal (621-62-5) → N-(tert-butylamino)acetaldehyde diethyl acetal (84500-89-0)

Conditions	Yield
at 140℃; for 20h;	99%

4-bromo-6-chloro-3-pyridazineamine (446273-59-2) + chloroacetaldehyde diethyl acetal (621-62-5) → 8-bromo-6-chloro-imidazo[1,2-b]pyridazine (933190-51-3)

Conditions	Yield
With toluene-4-sulfonic acid In isopropyl alcohol at 80℃; for 20h;	98%
Stage #1: 4-bromo-6-chloro-3-pyridazineamine; chloroacetaldehyde diethyl acetal With toluene-4-sulfonic acid In isopropyl alcohol at 80℃; for 20h; Stage #2: With sodium hydrogencarbonate	98%
With toluene-4-sulfonic acid In isopropyl alcohol at 80℃; for 20h;	98%
With toluene-4-sulfonic acid In isopropyl alcohol at 80℃; for 16h;	15%

3,4-difluorobenzenethiol (60811-24-7) + chloroacetaldehyde diethyl acetal (621-62-5) → (2,2-diethoxyethyl)(3,4-difluorophenyl)sulfane (847684-97-3)

Conditions	Yield
With sodium ethanolate for 36h; Heating;	95%
Stage #1: 3,4-difluorobenzenethiol With sodium ethanolate In ethanol Stage #2: chloroacetaldehyde diethyl acetal In ethanol at 20℃;

1-benzyl-5-(2,2-diethoxyethyl)-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one (35877-37-3) + chloroacetaldehyde diethyl acetal (621-62-5) → 5-(2,2-diethoxyethyl)-1-methyl-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one (1392411-81-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 7h; Reflux;	94%

phenethylamine (64-04-0) + chloroacetaldehyde diethyl acetal (621-62-5) → N-(2-phenylethyl)aminoacetaldehyde diethyl acetal (94508-09-5)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide for 18h; Heating;	92%

3,4-dimethyl-pyrrole-2-carboxylic acid benzyl ester (954-92-7) + chloroacetaldehyde diethyl acetal (621-62-5) → dibenzyl 5-(chloromethyl)-2,3,7,8-tetramethyldipyrromethane-1,9-dicarboxylate (156726-87-3)

Conditions	Yield
With Montmorillonite K-10 clay; trifluoroacetic acid In dichloromethane	91%
With Montmorillonite K-10 clay; trifluoroacetic acid In dichloromethane	91%

ethyl amidinoacetate (50551-10-5) + chloroacetaldehyde diethyl acetal (621-62-5) → 2-amino-1H-pyrrole-3-carboxylic acid ethyl ester (108290-86-4)

Conditions	Yield
Stage #1: chloroacetaldehyde diethyl acetal With hydrogenchloride In water; toluene at 10℃; for 0.333333h; Stage #2: ethyl amidinoacetate In water; toluene at 80℃; for 3h;	91%

urethane (51-79-6) + chloroacetaldehyde diethyl acetal (621-62-5) → 1-chloro-2-di(ethoxycarbonylamino)ethane (5336-13-0)

Conditions	Yield
With sulfuric acid at 75 - 80℃; for 5h;	90%
With hydrogenchloride

methyl carbamate (598-55-0) + chloroacetaldehyde diethyl acetal (621-62-5) → 1-chloro-2-di(methoxycarbonylamino)ethane (76934-25-3)

Conditions	Yield
With sulfuric acid at 75 - 80℃; for 5h;	90%

2-Methyl-2-(3-methyl-4-thiocarbamoyloxy-phenyl)-malonic acid diethyl ester (93914-69-3) + chloroacetaldehyde diethyl acetal (621-62-5) → 2-[3-Methyl-4-(thiazol-2-yloxy)-phenyl]-propionic acid ethyl ester

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid at 90 - 95℃; for 1.5h;	89%

1-benzyl-5-(2,2-diethoxyethyl)-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one (289651-72-5) + chloroacetaldehyde diethyl acetal (621-62-5) → 5-(2,2-diethoxyethyl)-1-(4-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (1392411-82-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 7h; Reflux;	89%

2-Methyl-2-(2-methyl-4-thiocarbamoyloxy-phenyl)-malonic acid diethyl ester + chloroacetaldehyde diethyl acetal (621-62-5) → 2-[2-Methyl-4-(thiazol-2-yloxy)-phenyl]-propionic acid ethyl ester (93914-44-4)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid at 90 - 95℃; for 1.5h;	88%

2-(3-Fluoro-4-thiocarbamoyloxy-phenyl)-2-methyl-malonic acid diethyl ester (93914-70-6) + chloroacetaldehyde diethyl acetal (621-62-5) → 2-[3-Fluoro-4-(thiazol-2-yloxy)-phenyl]-propionic acid ethyl ester

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid at 90 - 95℃; for 1.5h;	88%

2-(2-Fluoro-4-thiocarbamoyloxy-phenyl)-2-methyl-malonic acid diethyl ester + chloroacetaldehyde diethyl acetal (621-62-5) → 2-[2-Fluoro-4-(thiazol-2-yloxy)-phenyl]-propionic acid ethyl ester (93914-45-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid at 90 - 95℃; for 1.5h;	87%

ethyl 3-[2-formyl-N-(methoxymethyl)indol-3-yl]acrylate (1162648-73-8) + chloroacetaldehyde diethyl acetal (621-62-5) → ethyl 3-[2-(3-ethoxy-1-hydroxyprop-2-yn-1-yl)-N-(methoxymethyl)indol-3-yl]acrylate (1162648-74-9)

Conditions	Yield
Stage #1: chloroacetaldehyde diethyl acetal With n-butyllithium; diethylamine In tetrahydrofuran; hexane for 1.66667h; Cooling with ice; Stage #2: ethyl 3-[2-formyl-N-(methoxymethyl)indol-3-yl]acrylate In tetrahydrofuran for 1.5h; Cooling with ice;	87%

1-phenyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (21314-17-0) + chloroacetaldehyde diethyl acetal (621-62-5) → 5-(2,2-diethoxyethyl)-1-phenyl-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one (1060548-22-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 7h; Reflux;	87%

2-Methyl-2-(4-thiocarbamoyloxy-phenyl)-malonic acid diethyl ester (88975-84-2) + chloroacetaldehyde diethyl acetal (621-62-5) → ethyl 2-[4-(2-thiazolyloxy)-phenyl]propionate (56355-16-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid at 90 - 95℃; for 1.5h;	85.3%

[4-phenyl-1(2H)-oxo-phthalazin-2-yl]acetic acid hydrazide (126080-81-7) + chloroacetaldehyde diethyl acetal (621-62-5) → {[2-(1-Oxo-4-phenyl-1H-phthalazin-2-yl)-acetyl]-hydrazono}-acetic acid (126080-87-3)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	85%

2-(2-Chloro-4-thiocarbamoyloxy-phenyl)-2-methyl-malonic acid diethyl ester (93914-68-2) + chloroacetaldehyde diethyl acetal (621-62-5) → 2-[2-Chloro-4-(thiazol-2-yloxy)-phenyl]-propionic acid ethyl ester

Conditions	Yield
With toluene-4-sulfonic acid In acetic acid at 90 - 95℃; for 1.5h;	85%

(5,6-diphenyl-1,2,4-triazin-3-yl)oxyacetyl hydrazide (87121-29-7) + chloroacetaldehyde diethyl acetal (621-62-5) → {[2-(5,6-Diphenyl-[1,2,4]triazin-3-yloxy)-acetyl]-hydrazono}-acetic acid

Conditions	Yield
With sodium hydroxide for 2h; Heating;	85%

chloroacetaldehyde diethyl acetal (621-62-5) → ethanol ethyl acetate (117204-61-2)

Conditions	Yield
	85%

N-(phenylsulfonyl)-2-styrylindole-3-carbaldehyde (1269103-70-9) + chloroacetaldehyde diethyl acetal (621-62-5) → 3-(3-ethoxy-1-hydroxyprop-2-yn-1-yl)-N-(phenylsulfonyl)-2-styrylindole (1269103-71-0)

Conditions	Yield
Stage #1: chloroacetaldehyde diethyl acetal With n-butyllithium; diethylamine In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: N-(phenylsulfonyl)-2-styrylindole-3-carbaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	85%

monophenylthiourea (103-85-5) + chloroacetaldehyde diethyl acetal (621-62-5) → 2-phenylaminothiazole (33142-18-6)

Conditions	Yield
With hydrogenchloride In water for 4h; Hantzsch cyclization; Reflux;	84%

1,5-dibromo-pentane (111-24-0) + chloroacetaldehyde diethyl acetal (621-62-5) → 7-bromo-1-ethoxyhept-1-yne (159756-65-7)

Conditions	Yield
With n-butyllithium; diethylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide 0 deg C, 2 h, RT, 12 h;	84%

6-chloropurine (87-42-3) + chloroacetaldehyde diethyl acetal (621-62-5) → 6-chloro-9-(2-chloro-1-ethoxyethyl)-9H-purine

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; acetic anhydride In acetonitrile at 20℃; for 0.25h; regioselective reaction;	82%

1-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (5334-56-5) + chloroacetaldehyde diethyl acetal (621-62-5) → 1-benzyl-5-(2,2-diethoxyethyl)-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one (1392411-80-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 7h; Reflux;	81%

Upstream product

• 107-20-0 2-chloroethanal 
• 64-17-5 ethanol 
• 105-57-7 diethyl acetal 
• 10140-87-1 1,2-dichloroethyl acetate 
• 108-05-4 vinyl acetate 
• 75-01-4 chloroethylene 
• 75-35-4 1,1-Dichloroethylene 
• 141-52-6 sodium ethanolate 
• 623-46-1 1,2-dichloro-2-ethoxyethane 
• 928-56-3 E/Z-2-chlorovinyl ethyl ether 
• 109-92-2 ethyl vinyl ether 
• 123-63-7 paracetaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 100-64-1 cyclohexanone-oxime 

Downstream Products

• 1129-52-8 2,4,6-tris(chloromethyl)-1,3,5-trioxane 
• 107-20-0 2-chloroethanal 
• 95-92-1 oxalic acid diethyl ester 
• 2568-30-1 2-chloromethyl-1,3-dioxolane 
• 141-78-6 ethyl acetate 
• 41964-04-9 1-chloro-4-(2,2-diethoxyethoxy)benzene 
• 30515-06-1 2-(1-methyl-2-phenyl-ethylamino)-acetaldehyde diethylacetal 
• 161364-38-1 2-(2-methoxyphenoxy)acetaldehyde diethyl acetal 
• 92328-94-4 (4-chloro-phenethylamino)-acetaldehyde diethylacetal 
• 101086-49-1 (4-methoxy-phenethylamino)-acetaldehyde diethylacetal 
• 32871-88-8 N-(3,4-dimethoxybenzyl)aminoacetaldehyde diethyl acetal 
• 96-50-4 2-thiazolylamine 
• 120-72-9 indole 
• 22758-34-5 N-phenyl-2-aminoacetaldehyde diethylacetal 

Relevant articles and documents

Green method for preparing chloroacetaldehyde dialkyl alcohol from vinyl ether

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