4744-08-5

Basic information

• Product Name: PROPIONALDEHYDE DIETHYL ACETAL
• Synonyms: PROPIONALDEHYDE DIETHYL ACETAL;PROPANAL DIETHYL ACETAL;1,1-DIETHOXYPROPANE;1,1-diethoxy-propan;4-Ethyl-3,5-dioxaheptane;Propane, 1,1-diethoxy-;propylene glycol diethyl ether;Propionaldehyde diethyl acetal,97%
• CAS NO: 4744-08-5
• Molecular Formula: C₇H₁₆O₂
• Molecular Weight: 132.2
• EINECS: 225-257-8
• Mol File: 4744-08-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 122.8 °C(lit.)
• Flash Point: 55 °F
• Appearance: /
• Density: 0.815 g/mL at 25 °C(lit.)
• Vapor Pressure: 16.5mmHg at 25°C
• Refractive Index: n20/D 1.389(lit.)
• Storage Temp.: Flammables area
• BRN: 1697731
• CAS DataBase Reference: PROPIONALDEHYDE DIETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: PROPIONALDEHYDE DIETHYL ACETAL(4744-08-5)
• EPA Substance Registry System: PROPIONALDEHYDE DIETHYL ACETAL(4744-08-5)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23
• RIDADR: UN 1989 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 4744-08-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Propionaldehyde diethyl acetal was used as a reducing agent in the aerobic epoxidation of alkenes.

InChI:InChI=1/C7H16O2/c1-4-7(8-5-2)9-6-3/h7H,4-6H2,1-3H3

Synthetic route

Triethyl orthopropionate (115-80-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In n-heptane at 100℃; under 67506.8 Torr; Temperature;	98.6%

triethylaluminum (97-93-8) + orthoformic acid triethyl ester (122-51-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
In dichloromethane at -20 - 20℃;	98%
In hexane at 35 - 40℃;	78%

ethanol (64-17-5) + 1-bromopropylamine → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With copper(l) chloride In cyclohexane at 45 - 65℃; for 12h; Temperature;	91%

propionaldehyde (123-38-6) + orthoformic acid triethyl ester (122-51-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With ammonium nitrate In ethanol at 20 - 36℃;	81.6%
Stage #1: propionaldehyde; orthoformic acid triethyl ester With ammonium nitrate; ethanol at 20 - 36℃; Stage #2: With sodium carbonate In water at 20℃; pH=7.5;	81.6%
With sulfuric acid

3,3-diethoxypropyl lithium → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With water In tetrahydrofuran at -78 - 20℃; for 2h;	80%
With water In tetrahydrofuran at -78 - 20℃; for 2h; Product distribution; also other electrophiles (D2O, (PhCH2)2S2, n-C3H7CHO, PhCHO, n-C7H15CHO, PhCH=NPh);	80%

ethanol (64-17-5) + propionaldehyde (123-38-6) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With calcium chloride at 25 - 35℃; for 10h; Temperature;	78.8%
With hydrogenchloride
With hydrogenchloride at 25℃; Gleichgewicht der Reaktion;

Triethyl orthopropionate (115-80-0) → 1,1-diethoxypropane (4744-08-5) + ethylpropylether (628-32-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In n-heptane at 150℃; under 67506.8 Torr; Temperature;	A 63% B 36.9%

diethoxymethyl acetate (14036-06-7) + diethylaluminium chloride (96-10-6) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
In diethyl ether at 20℃; for 4h;	53%

(E)-1-ethoxyprop-1-ene (4696-26-8) → (Z)-1-ethoxyprop-1-ene (4696-25-7) + 1,1-diethoxypropane (4744-08-5) + propionaldehyde (123-38-6)

Conditions	Yield
(sulphos)Rh(CO)2 In 1,2-dichloro-ethane at 100℃; for 1h;	A 22% B 31% C 14%

ethanol (64-17-5) + ethyl 1-propenyl ether (928-55-2) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With Fuller's Earth

tetraethoxy orthosilicate (78-10-4) + propionaldehyde (123-38-6) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With ethanol; phosphoric acid

ethylmagnesium bromide (925-90-6) + orthoformic acid triethyl ester (122-51-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With diethyl ether Hydrolyse mit verduennter Essigsaeure und sofortige Neutralisation;

(E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) + orthoformic acid triethyl ester (122-51-0) + acetylene (74-86-2) → malondialdehyde bis(diethyl acetal) (122-31-6) + 1,1-diethoxypropane (4744-08-5) + 1,1,4,4-tetraethoxy-2-butyne (3975-08-4)

Conditions	Yield
under 8826.09 - 12503.6 Torr;
at 170℃; under 8826.09 - 12503.6 Torr;

carbon monoxide (201230-82-2) + orthoformic acid triethyl ester (122-51-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With hydrogen; dicobalt octacarbonyl

n-propylmagnesium bromide (927-77-5) + orthoformic acid triethyl ester (122-51-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
In diethyl ether

3-chloro-1,1-diethoxy-propane (35573-93-4) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With water; naphthalen-1-yl-lithium 1.) THF, -78 deg C, 6 h, 2.) 20 deg C, 2 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: lithium naphthalenide / tetrahydrofuran / 6 h / -78 °C 2: 80 percent / H2O / tetrahydrofuran / 2 h / -78 - 20 °C / also other electrophiles (D2O, (PhCH2)2S2, n-C3H7CHO, PhCHO, n-C7H15CHO, PhCH=NPh) View Scheme

sulfuric acid (7664-93-9) + propionaldehyde (123-38-6) + orthoformic acid triethyl ester (122-51-0) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
analoge Reaktion mit Orthoameisensaeure-tripropylester;

2-bromo-3,3-diethoxypropene (17592-40-4) + alcoholic KOH-solution → 1,1-diethoxypropane (4744-08-5)

orthoformic acid triethyl ester (122-51-0) + sunlight → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / formic acid / 24 h 2: 53 percent / diethyl ether / 4 h / 20 °C View Scheme

ethanol (64-17-5) + carbon monoxide (201230-82-2) + allyl alcohol (107-18-6) → 2-ethoxytetrahydrofuran (13436-46-9) + propan-1-ol (71-23-8) + Butane-1,4-diol (110-63-4) + 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With hydrogen; acetylacetonatodicarbonylrhodium(l) at 125℃; under 30003 Torr; for 2.5h; Product distribution; Further Variations:; reagent ratios;

acrylaldehyde diethyl acetal (3054-95-3) → 1,1-diethoxypropane (4744-08-5)

Conditions	Yield
With borane-ammonia complex; cobalt(II)(2,6-bis(morpholinomethyl)pyridine)bromide In methanol at 80℃; for 14h;	99 %Chromat.

ethanol (64-17-5) → diethyl ether (60-29-7) + 1,1-diethoxypropane (4744-08-5) + ethyl vinyl ether (109-92-2)

Conditions	Yield
at 280℃; for 4h; Reagent/catalyst; Autoclave; Inert atmosphere;

4-iodopyridine-2-carboxylic acid methyl ester (380381-28-2) + 1,1-diethoxypropane (4744-08-5) → 4-(3,3-Diethoxy-prop-1-ynyl)-pyridine-2-carboxylic acid methyl ester (663614-43-5)

Conditions	Yield
With triethylamine; palladium diacetate; copper(l) iodide; triphenylphosphine at 20℃; for 3h;	100%

1,1-diethoxypropane (4744-08-5) + 3-(dimethylphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene (251475-02-2) → 4-ethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-hexene

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 3h;	99%
With titanium tetrachloride In dichloromethane TiCl4, CH2Cl2, -78°C, 3 h;	99%

1,1-diethoxypropane (4744-08-5) + (4R)-4-ethyl-1,3-oxazolidin-2-one (98974-04-0) → (R)-3-(1-ethoxypropyl)-4-ethyl-1,3-oxazolidin-2-one (925427-50-5)

Conditions	Yield
With 10-camphorsufonic acid In dichloromethane at 55℃;	97%

5-iodo-1,2,3-trimethoxybenzene (25245-29-8) + 1,1-diethoxypropane (4744-08-5) → 1,1-diethoxy-3-(3,4,5-trimethoxyphenyl)-2-propyne

Conditions	Yield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In triethylamine at 20℃; for 3h;	97%

1,1-diethoxypropane (4744-08-5) + 3-cyclohexyl-3-(dimethylphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene (252062-23-0) → (E)-1-cyclohexyl-4-ethoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-hexene

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 3h;	95%
With titanium tetrachloride In dichloromethane TiCl4, CH2Cl2, -78°C, 3 h;	95%

1,1-diethoxypropane (4744-08-5) + 3-(dimethylphenylsilyl)-5-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pentene (252062-22-9) → (E)-6-ethoxy-1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxacarborolan-2-yl)-3-octene

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 3h;	94%
With titanium tetrachloride In dichloromethane TiCl4, -78°C, CH2Cl2, 3 h;	94%
With aluminium trichloride In dichloromethane AlCl3, CH2Cl2, -78°C, 0.5 h; -20°C for 2.5 h;	82%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane TMSOTf, CH2Cl2, -78°C, 0.5 h; -20°C for 2.5 h;	30%

1,1-diethoxypropane (4744-08-5) + acetophenone (98-86-2) → 3-ethoxy-1-phenyl-pentan-1-one

Conditions	Yield
Stage #1: acetophenone With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 0.5h; Stage #2: 1,1-diethoxypropane In dichloromethane at -78℃; for 0.5h;	90%

1,1-diethoxypropane (4744-08-5) + 7-chloro-4,6-dimethoxy-2,3-dihydrobenzofuran-3-one (3261-06-1) → (Z)-7-chloro-4,6-dimethoxy-2-(1-propylidene)-3(2H)-benzofuranone (129529-56-2)

Conditions	Yield
With titanium tetrachloride In dichloromethane for 24h; Ambient temperature;	89%

1,1-diethoxypropane (4744-08-5) + 1,3-diphenylpropanedione (120-46-7) → 2-(1-Ethoxy-propyl)-1,3-diphenyl-propane-1,3-dione (116863-89-9)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃;	89%

1,1-diethoxypropane (4744-08-5) + (Z)-1-Phenyl-6-trimethylsilanyl-hex-4-en-1-ol (164076-17-9) → (2S,3S,6S)-2-Ethyl-6-phenyl-3-vinyl-tetrahydro-pyran

Conditions	Yield
With toluene-4-sulfonic acid for 24h; Product distribution; Ambient temperature; reactions of derivatives with var. acetals;	84%
With toluene-4-sulfonic acid for 24h; Ambient temperature;	84%

acetamide (60-35-5) + 1,1-diethoxypropane (4744-08-5) → N,N'-(propane-1,1-diyl)diacetamide (7073-48-5)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane for 0.25h; Heating;	83%
With sulfuric acid

1,1-diethoxypropane (4744-08-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,3-diethoxy-2-methyl-propionaldehyde (22634-86-2)

Conditions	Yield
With trichlorophosphate at 70℃; for 2h; Vilsmeier reaction;	83%

1,1-diethoxypropane (4744-08-5) + ethyl vinyl ether (109-92-2) → 1,1,3-triethoxypentane (39595-61-4)

Conditions	Yield
Montmorillonite clay K-10 at 10 - 15℃;	80%
NdNaY at 0 - 25℃; for 0.5h;	61%
With iron(III) chloride
With iron(III) chloride
With boron trifluoride diethyl etherate at 65℃;

1,1-diethoxypropane (4744-08-5) → ethyl 1-propenyl ether (928-55-2)

Conditions	Yield
2-ethyl-N-(2-ethylhexyl)-1-hexanamine; toluene-4-sulfonic acid	77.5%
With quinoline; phosphorus pentoxide distillation at a bath temp. 150 deg C;	75%
With quinoline; phosphorus pentoxide vermutlich entsteht als Gemisch von cis- und trans-Form;
With sodium hydrogen sulfate vermutlich entsteht als Gemisch von cis- und trans-Form;
With silver-asbestos at 280℃; vermutlich entsteht als Gemisch von cis- und trans-Form;

1,1-diethoxypropane (4744-08-5) → (Z)-1-ethoxyprop-1-ene (4696-25-7)

Conditions	Yield
With 2-ethyl-N-(2-ethylhexyl)-1-hexanamine; toluene-4-sulfonic acid at 160℃; Distillation;	77.5%

1,1-diethoxypropane (4744-08-5) + propionaldehyde (123-38-6) + 3-(dimethylphenylsilyl)-5-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pentene (252062-22-9) → (2R*,4S*,4aR*,10bS*)-2,4-diethyl-1,4,4a,5,6,10b-hexahydro-10b-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-naphtho[2,1-c]pyran

Conditions	Yield
Stage #1: propionaldehyde; 3-(dimethylphenylsilyl)-5-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pentene With titanium tetrachloride In dichloromethane at -78℃; for 2h; Stage #2: 1,1-diethoxypropane In dichloromethane at 0℃; for 3h;	75%

1,1-diethoxypropane (4744-08-5) + propionaldehyde (123-38-6) + 3-(dimethylphenylsilyl)-5-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pentene (252062-22-9) → C6H4(CH2)2CHCH(C2H5)OCH(C2H5)CH2CBO2C2(CH3)4 (347868-66-0)

Conditions	Yield
With titanium tetrachloride; sodium hydrogencarbonate In dichloromethane B salt mixed with TiCl4 at -78°C, stirred at -78°C for 2 h, treated with aldehydes at -78°C, stirred at 0°C for 3 h,treated with aq.NaHCO3; extd.(AcOC2H5), chromy.(silica gel);	75%

1,1-diethoxypropane (4744-08-5) + 1,1'-oxybisethene (109-93-3) → 1,1,3,5-tetraethoxyheptane

Conditions	Yield
at 0 - 50℃; for 2.5h; Time;	75%

1,1-diethoxypropane (4744-08-5) + P,P-diphenylphosphinothioic amide (17366-80-2) → C18H20NPS (1138700-42-1)

Conditions	Yield
at 120 - 160℃;	73%

1,1-diethoxypropane (4744-08-5) + di-tert-butyl 1-(6-methoxypyridin-3-yl)hydrazine-1,2-dicarboxylate (1338466-39-9) → 3-methylpyrrolo<3,2-b>pyridinee (138469-76-8)

Conditions	Yield
Stage #1: 1,1-diethoxypropane; di-tert-butyl 1-(6-methoxypyridin-3-yl)hydrazine-1,2-dicarboxylate With sulfuric acid In water for 1h; Reflux; Inert atmosphere; Stage #2: With sodium carbonate In water Saturated solution; Inert atmosphere;	72%

1,1-diethoxypropane (4744-08-5) + trimethylsilyl cyanide (7677-24-9) → diethyl ether-acetonitrile (87271-68-9)

Conditions	Yield
zinc(II) iodide at 25℃; for 3h;	71%

1,1-diethoxypropane (4744-08-5) + Phenoxymagnesium bromide (35770-74-2) → 1,1-bis(2-hydroxyphenyl)propane (34240-91-0)

Conditions	Yield
In benzene for 24h; Heating;	70%

1,1-diethoxypropane (4744-08-5) + benzamide (55-21-0) → N-(n-propyl)benzamide (10546-70-0)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In acetonitrile at 22℃; for 18h;	65%

Upstream product

• 64-17-5 ethanol 
• 928-55-2 ethyl 1-propenyl ether 
• 78-10-4 tetraethoxy orthosilicate 
• 123-38-6 propionaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 74-86-2 acetylene 
• 201230-82-2 carbon monoxide 
• 927-77-5 n-propylmagnesium bromide 
• 35573-93-4 3-chloro-1,1-diethoxy-propane 
• 115-80-0 Triethyl orthopropionate 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 107-18-6 allyl alcohol 
• 4696-26-8 (E)-1-ethoxyprop-1-ene 

Downstream Products

• 39595-61-4 1,1,3-triethoxypentane 
• 10546-70-0 N-(n-propyl)benzamide 
• 2568-96-9 2-ethyl-1,3-dioxolane 
• 64-17-5 ethanol 
• 78706-60-2 2-[1-(2-hydroxy-ethoxy)-propoxy]-ethanol 
• 289-95-2 PYRIMIDINE 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 105-37-3 Ethyl propionate 
• 5278-43-3 3-methyl-2-phenyl-quinoline 
• 19125-76-9 3-dimethylamino-2-methyl-acrylaldehyde 
• 42588-57-8 3-ethoxymethacrolein 
• 1576-87-0 trans-2-pentenal 
• 116863-89-9 2-(1-Ethoxy-propyl)-1,3-diphenyl-propane-1,3-dione 

Relevant articles and documents

Preparation method 1 and 1 - diethoxypropane

The invention discloses a preparation method of 1-1 - diethoxypropane. Ethanol and propionaldehyde are used for contacting with a solid acid catalyst under the condition of vaporization, and water is taken out. 1,1 - Diethoxypropane crude product is discharged from the bottom side of the rectification tower, and the rectification obtains 98%, 1 diethoxypropane with a purity greater than 1 . To the method, the problem of long reaction time at low temperature is solved, the single conversion rate is relatively high, 1 and 1 - diethoxy propane in the obtained crude product is 50 - 80%, 99% diethoxypropane can be obtained through rectification, the highest yield can reach 1 97% 1 - continuous feeding is facilitated, and pipeline continuous reaction is carried out.

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Method for preparing 2,4-heptadienal

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