35573-93-4

Basic information

• Product Name: 3-Chloropropionaldehyde diethylacetal
• Synonyms: 3-chloro-1,1-diethoxy-propan;Propane, 3-chloro-1,1-diethoxy-;Propionaldehyde, 3-chloro-, diethyl acetal;B-CHLOROPROPIONALDEHYDE DIETHYL ACETAL;3-CHLORO-1,1-DIETHOXYPROPANE;3-CHLOROPROPIONALDEHYDE DIETHYL ACETAL;3-CHLOROPROPIONIC ALDEHYDE DIETHYL ACETAL;1-Chloro-3,3-diethoxypropane~3-Chloropropanal diethyl acetal
• CAS NO: 35573-93-4
• Molecular Formula: C₇H₁₅ClO₂
• Molecular Weight: 166.65
• EINECS: 252-623-4
• Mol File: 35573-93-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 84 °C25 mm Hg(lit.)
• Flash Point: 98 °F
• Appearance: clear colourless to yellow liquid
• Density: 0.995 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.42(lit.)
• Storage Temp.: 2-8°C
• BRN: 1698609
• CAS DataBase Reference: 3-Chloropropionaldehyde diethylacetal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloropropionaldehyde diethylacetal(35573-93-4)
• EPA Substance Registry System: 3-Chloropropionaldehyde diethylacetal(35573-93-4)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26-36-16
• RIDADR: UN 1989 3/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 35573-93-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to yellow liquid

Uses

Different sources of media describe the Uses of 35573-93-4 differently. You can refer to the following data:
1. 3-Chloroprionaldehyde Diethyl Acetal is an acetal acompound with safener activity against thiocarbamate herbicides.
2. 3-Chloropropionaldehyde diethylacetal has been used in the synthesis of:N-[4-[[3-(2, 4-diamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propyl]amino]benzoyl]-L-glutamic acid, an acyclic analog of 5,6,7,8-tetrahydrofolic acid1-(D,L)-(3′-amino, 3′-carboxypropyl)uracil, nucleoamino acid7-methoxychromanonegrignard reagent

InChI:InChI=1/C6H14O2.C3H5ClO/c1-4-7-6(3)8-5-2;4-2-1-3-5/h6H,4-5H2,1-3H3;3H,1-2H2

Synthetic route

ethanol (64-17-5) + acrolein (107-02-8) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

Conditions	Yield
With hydrogenchloride; calcium chloride at 0℃; for 24h;	90%
With hydrogenchloride
With hydrogenchloride

3-chloropropanaldehyde (19434-65-2) + ethanol (64-17-5) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

Conditions	Yield
With hydrogenchloride at 25℃; Gleichgewicht und Geschwindigkeit der Bildung;

1,3-dichloro-1-ethoxy-propane (89212-07-7) + ethanol (64-17-5) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

1,3-dichloro-1-ethoxy-propane (89212-07-7) + sodium ethanolate (141-52-6) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

ethanol (64-17-5) + 1,3-dichloro-1-methoxy-propane (4446-86-0) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

acrolein (107-02-8) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride; calcium chloride
With hydrogenchloride

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + acrolein (107-02-8) → 3-chloro-1,1-diethoxy-propane (35573-93-4)

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran (141645-16-1) + 3-chloro-1,1-diethoxy-propane (35573-93-4) → (2-butyl-5-nitro-1-benzofuran-3-yl)[4-(3,3-diethoxypropoxy)phenyl]methanone (1420181-01-6)

Conditions	Yield
With potassium carbonate; sodium iodide for 6h; Reflux;	99%

thiophene-2-carbaldehyde (98-03-3) + 3-chloro-1,1-diethoxy-propane (35573-93-4) → 4,4-diethoxy-1-(thiophen-2-yl)butan-1-ol (1258208-43-3)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: thiophene-2-carbaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	97%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 3,5-dimethylbenzaldehyde (5779-95-3) → 1-(3,5-dimethylphenyl)-4,4-diethoxybutan-1-ol (1258208-42-2)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: 3,5-dimethylbenzaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	97%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 1-phenyl-propan-1-one (93-55-0) → 6,6-diethoxy-3-phenylhexan-3-ol (1258208-68-2)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: 1-phenyl-propan-1-one In tetrahydrofuran at -40 - 0℃; for 2.5h;	97%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 5-(4-hydroxyphenyl)-10,15,20-triphenylporphyrin → 5-[4-(oxy 3-propionaldehyde diethyl acetal)phenyl]-10,15,20-triphenyl-porphyrin

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	97%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 2-methyldiphenylsilyl-1,3-dithiane (135746-47-3) → <2-(3,3-Diethoxypropyl)-1,3-dithian-2-yl>methyldiphenylsilane (162318-00-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane 1.) -25 deg C, 2.5 h, 2.) -25 deg C, 4 h;	96%

3-chloro-1,1-diethoxy-propane (35573-93-4) + phenyl isopropyl ketone (611-70-1) → 6,6-diethoxy-2-methyl-3-phenylhexan-3-ol (1258208-69-3)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: phenyl isopropyl ketone In tetrahydrofuran at -40 - 0℃; for 2.5h;	96%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 3-methyl-1-phenylbutan-1-one (582-62-7) → 1,1-diethoxy-6-methyl-4-phenylheptan-4-ol (1258208-70-6)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: 3-methyl-1-phenylbutan-1-one In tetrahydrofuran at -40 - 0℃; for 2.5h;	95%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 4-methoxy-benzaldehyde (123-11-5) → 4,4-diethoxy-1-(4-methoxyphenyl)butan-1-ol (1258208-39-7)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	95%

sodium cyanide (773837-37-9) + 3-chloro-1,1-diethoxy-propane (35573-93-4) → 4,4-diethoxybutanenitrile (18381-45-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide at 50℃; for 15h;	94%
In dimethyl sulfoxide at 80℃; for 24h;	86%

3-chloro-1,1-diethoxy-propane (35573-93-4) + β-naphthaldehyde (66-99-9) → 4,4-diethoxy-1-(naphthalen-2-yl)butan-1-ol (1258208-41-1)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: β-naphthaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	94%

3-chloro-1,1-diethoxy-propane (35573-93-4) + benzaldehyde (100-52-7) → 4-hydroxy-4-phenylbutanal diethyl acetal (112084-43-2)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: benzaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	92%

3-chloro-1,1-diethoxy-propane (35573-93-4) + lithium acetylide-ethylenediamine complex (1216963-74-4) → 4-pentynyl diethyl acetal (68654-84-2)

Conditions	Yield
In dimethyl sulfoxide at 15℃; for 3h;	91%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine (17242-85-2) → (1'RS)-1-(3'-Chloro-1'-ethoxypropyl)-5-fluorouracil (133625-58-8)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -30℃;	91%

O-methylresorcine (150-19-6) + 3-chloro-1,1-diethoxy-propane (35573-93-4) → 3-m-methoxyphenoxypropionaldehyde diethyl acetal (153750-80-2)

Conditions	Yield
With sodium hydroxide In water 1.) room temperature, 30 min, 2.) reflux, 15 h;	91%
Stage #1: O-methylresorcine With sodium hydroxide In water for 0.5h; Stage #2: 3-chloro-1,1-diethoxy-propane In water for 16h; Reflux;	47%

2,5-Dimethylphenol (95-87-4) + 3-chloro-1,1-diethoxy-propane (35573-93-4) → 3-(2,5-dimethylphenoxy)propanal diethylacetal (1025804-42-5)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide Heating;	90%

3-chloro-1,1-diethoxy-propane (35573-93-4) → 3-azidopropanal diethyl acetal (688317-69-3)

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 50℃; for 16h;	90%
With sodium azide; potassium iodide In dimethyl sulfoxide at 20 - 90℃; Inert atmosphere;	88%
With sodium azide In dimethyl sulfoxide at 50℃; for 16h;

3-chloro-1,1-diethoxy-propane (35573-93-4) + 4-fluorobenzaldehyde (459-57-4) → 4,4-diethoxy-1-(4-fluorophenyl)butan-1-ol (1258208-40-0)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	90%

3-chloro-1,1-diethoxy-propane (35573-93-4) + p-hydroxybenzamide (619-57-8) → 4-(3,3-diethoxypropoxy)benzamide (1409760-30-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 18h;	89%

3-chloro-1,1-diethoxy-propane (35573-93-4) + D,L-1,2,4-butanetriol (3068-00-6) → cis-[2-(2-chloroethyl)-1,3-dioxan-4-yl]methanol

Conditions	Yield
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction;	89%

3-chloro-1,1-diethoxy-propane (35573-93-4) + phenylacetonitrile (140-29-4) → α-(2,2-diethoxypropyl)benzyl cyanide (93722-30-6)

Conditions	Yield
Stage #1: phenylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 3-chloro-1,1-diethoxy-propane In tetrahydrofuran at -78℃; Cooling;	87%
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 2h;	80%

3-chloro-1,1-diethoxy-propane (35573-93-4) + benzyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate (51089-83-9) → Dibenzyl 5-(2-chloroethyl)-3,7-diethyl-2,8-dimethyldihydrodipyrrin-1,9-dicarboxylate (161690-40-0)

Conditions	Yield
With Montmorillonite K-10 clay; trifluoroacetic acid In dichloromethane	87%
With Montmorillonite K-10 clay; trifluoroacetic acid In dichloromethane for 5h; Ambient temperature;	87%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline → 6-(furan-2-yl)-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With iodine; magnesium In 2-methyltetrahydrofuran; ethylene dibromide at 60 - 65℃; for 5h; Stage #2: 6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline In 2-methyltetrahydrofuran; ethylene dibromide at 25 - 30℃; for 5h; Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water; ethylene dibromide at 50 - 55℃; for 4h;	86.2%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 2-o-Tolyl-pentanenitrile (145611-08-1) → 5,5-Diethoxy-2-propyl-2-o-tolyl-pentanenitrile (145611-11-6)

Conditions	Yield
With sodium amide In toluene for 5h; Heating;	85%

3-chloro-1,1-diethoxy-propane (35573-93-4) + N-(2-hydroxymethylphenyl)-4-methylbenzenesulfonamide (90312-02-0) → C21H29NO5S

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	85%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 1-(3,4-dimethoxyphenyl)-2-methylpropan-2-ol (23037-61-8) → 1-(2-chloroethyl)-3,3-dimethyl-6,7-dimethoxyisochroman (79842-27-6)

Conditions	Yield
With tetrafluoroboric acid-diethyl ether complex In nitromethane for 1.3h;	84%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 2-(3,4-dimethoxy-phenyl)-2-methyl-propan-1-ol (70822-01-4) → 1-(2-chloroethyl)-4,4-dimethyl-6,7-dimethoxyisochroman (70822-39-8)

Conditions	Yield
With tetrafluoroboric acid-diethyl ether complex In nitromethane at 22℃; for 3h;	84%

3-chloro-1,1-diethoxy-propane (35573-93-4) + potassium phtalimide (1074-82-4) → N-(3,3-diethoxypropyl)phthalimide (2453-90-9)

Conditions	Yield
In N,N-dimethyl-formamide at 145℃; for 5h;	83%

3-chloro-1,1-diethoxy-propane (35573-93-4) + triethyl phosphite (122-52-1) → diethyl 3,3-diethoxypropylphosphonate (15110-17-5)

Conditions	Yield
	82%

Upstream product

• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 107-02-8 acrolein 
• 4446-86-0 1,3-dichloro-1-methoxy-propane 
• 89212-07-7 1,3-dichloro-1-ethoxy-propane 
• 141-52-6 sodium ethanolate 
• 19434-65-2 3-chloropropanaldehyde 

Downstream Products

• 16630-61-8 1,1-diethoxy-3-methylsulfanyl-propane 
• 116598-45-9 2-(3,3-diethoxy-propyl)-5-(4-methoxy-phenyl)-cyclohexane-1,3-dione 
• 19515-61-8 diethyl 2-(3-oxo-propyl)malonate 
• 18381-45-8 4,4-diethoxybutanenitrile 
• 750514-42-2 5-(2-chloro-ethyl)-imidazolidine-2,4-dione 
• 16777-87-0 3,3-diethoxypropan-1-ol 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 41365-75-7 aminopropane diethyl acetal 
• 854253-50-2 bis-(3,3-diethoxy-propyl)-amine 
• 6956-37-2 (3,3-diethoxypropyl)benzene 
• 3598-70-7 N-[4-(2,4-dinitro-phenylhydrazono)-butyl]-acetamide 
• 53908-65-9 4-acetamido-4,4-bis(ethyloxycarbonyl)butyraldehyde 
• 16851-30-2 β-Dimethylamino-propionaldehyd-diethylacetal 
• 32380-88-4 3-benzylthiopropanal diethyl acetal 

Relevant articles and documents

A Convenient Synthesis of Antihyperlipoproteinemic Agent Gemfibrozil

A new synthesis of antihyperlipoproteinemic agent 2,2-dimethyl-5-(2,5-dimethylphenoxy) pentanoic acid (gemfibrozil, 1) is developed via hydrogenolysis of a novel β-lactone 6, prepared from cycloaddition of 3-(2,5-dimethylphenoxy) propanal with dimethylketene.The mild conditions applied in this process are especially convenient for the preparation of gemfibrozil on an industral scale of production.Key Words Gemfibrozil; 2,2-Dimethyl-5-(2,5-dimethylphenoxy)pentanoic acid; Dimethylketene; cycloaddition; 2,2-Dimethyl-5-(2,5-dimethylphenoxy)-3-hydroxypentanoic acid β-lactone.