927-63-9

Basic information

• Product Name: 3-Dimethylaminoacrolein
• Synonyms: (2E)-3-(Dimethylamino)-2-propenal;2-Propenal, 3-(dimethylamino)-;beta-(Dimethylamino)acrolein;n,n-dimethylamino-2-propen-3-al;3-(DIMETHYLAMINO)ACROLEIN;3-DIMETHYLAMINOACRYLALDEHYDE;(E)-3-(DIMETHYLAMINO)ACRYLALDEHYDE;(2E)-3-(DIMETHYLAMINO)PROP-2-ENAL
• CAS NO: 927-63-9
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13
• EINECS: 213-157-7
• Product Categories: C1 to C6;Aldehydes;Carbonyl Compounds
• Mol File: 927-63-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 270-273 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00643mmHg at 25°C
• Refractive Index: n20/D 1.584(lit.)
• Storage Temp.: 2-8°C
• PKA: 6.79±0.70(Predicted)
• BRN: 969389
• CAS DataBase Reference: 3-Dimethylaminoacrolein(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Dimethylaminoacrolein(927-63-9)
• EPA Substance Registry System: 3-Dimethylaminoacrolein(927-63-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• F: 8-19
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 927-63-9(Hazardous Substances Data)

Usage

Description

3-Dimethylaminoacrolein?is an organic compound with the formula Me2NC(H)=CHCHO. It is a pale yellow water-soluble liquid. The compound has a number of useful and unusual properties, e.g. it causes a reversal of the?hypnotic effect?of?morphine?in miceand has astimulating effect in humans.

Uses

3-Dimethylaminoacrolein was used in synthesis of:benzochlorins, benzoisobacteriochlorins and benzobacteriochlorinsstyryl-substituted Z/E-chlorin derivatives with chlorophyll-a skeletonY shaped cyanines having dimethylamino end groups

InChI:InChI=1/C5H9NO/c1-6(2)4-3-5-7/h3-5H,1-2H3/b4-3+

Synthetic route

N-(4-Nitrophenyl)acetamide (104-04-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N1,N1-dimethyl-N2-(4-nitro-phenyl)-formamidine (1205-59-0) + (E)-3-Dimethylamino-2-formyl-N-(4-nitro-phenyl)-acrylamide (78708-10-8) + 4-nitro-aniline (100-01-6) + 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
With trichlorophosphate at 75℃; for 1.5h;	A 45% B 53% C 5% D 0.05 g

cycloactanone (502-49-8) + acetal-aminal of β-dimethylaminoacrolein (5043-86-7) → 2-[(E)-3-Dimethylamino-prop-2-en-(Z)-ylidene]-cyclooctanone (75143-08-7) + 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
With silica gel 1,) 80 deg C to 90 deg C, 1.5 h, 2.) CHCl3, 1 h;	A 49% B n/a

Propargylic aldehyde (624-67-9) + dimethyl amine (124-40-3) → 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
With methanol

diethyl acetal (105-57-7) + phosgene (75-44-5) + 1,2-dichloro-ethane (107-06-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-dimethylaminopropyl-2-ene-1-imino-N,N-dimethylammonium chloride (13984-13-9, 70669-77-1) + 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
beim Behandeln des Reaktionsgemisches mit Eis sowie anschliessend mit wss. Kaliumcarbonat-Loesung;

phosgene (75-44-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
With 1,2-dichloro-ethane und Behandeln des Reaktionsgemisches mit Acetaldehyd-diaethylacetal;

methanol (67-56-1) + β-dimethylaminoacrolein aminal (5043-87-8) → Methanolate((E)-3-dimethylamino-allylidene)-dimethyl-ammonium; + 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
at 28℃; Product distribution; other temperature;

3-dimethyl-amino-1,1,3-trimethoxypropane (51513-20-3) + cyclotetradecanone (3603-99-4) → 2-[(E)-3-Dimethylamino-prop-2-en-(Z)-ylidene]-cyclotetradecanone (75143-09-8) + 3-dimethylaminoacrolein (927-63-9)

Conditions	Yield
at 95 - 100℃; for 4h;	A 0.12 g B n/a

2-methyl-1-ethylbenzindolium tetrafluoroborate + 3-dimethylaminoacrolein (927-63-9) → 1-ethyl-2-(4-dimethylamino-1,3-butadienyl)benzindolium tetrafluoroborate

Conditions	Yield
With acetic anhydride at 120 - 125℃; for 0.5h;	100%

3-dimethylaminoacrolein (927-63-9) + methanesulfonyl-acetonitrile (2274-42-2) → 2-methylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile

Conditions	Yield
With potassium hydrogencarbonate at 60℃; for 0.5h; Reagent/catalyst; Temperature; Microwave irradiation; Green chemistry;	97.2%
With tetra(n-butyl)ammonium hydroxide In water at 90℃; for 2h; Reagent/catalyst; Temperature;	97.1%
With triethylamine at 120℃; Sonication;	96.7%
With N-butyl-N-ethylpiperidinium bromide at 55℃; for 1h; Microwave irradiation;	95.6%
With trimethyldodecylammonium chloride In dichloromethane; water at 95℃;

1,2-bis(2,2'-bipyrrol-5-yl)benzene + 3-dimethylaminoacrolein (927-63-9) → 1,2-bis(5'-acroleinyl-2,2'-bipyrrol-5-yl)benzene

Conditions	Yield
Stage #1: 1,2-bis(2,2'-bipyrrol-5-yl)benzene; 3-dimethylaminoacrolein With trichlorophosphate In dichloromethane at 0℃; for 1h; Vilsmeier-Haack Formylation; Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 1h;	97%

cyano-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (102069-19-2) + n-Octylamine (111-86-4) + 3-dimethylaminoacrolein (927-63-9) → (2,2-dimethyl-1,3-dioxolan-4-yl)methyl (2E,4E)-2-cyano-5-(dimethylamino)penta-2,4-dienoate

Conditions	Yield
Stage #1: cyano-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; n-Octylamine With acetic acid In toluene Reflux; Inert atmosphere; Stage #2: 3-dimethylaminoacrolein In toluene for 36h; Reflux;	97%

4,6-dimethoxy-2,3-diphenyl-1H-indole (91107-10-7) + 3-dimethylaminoacrolein (927-63-9) → trans-3-(4,6-dimethoxy-2,3-diphenylindol-7-yl)propen-1-al

Conditions	Yield
With trichlorophosphate In tetrahydrofuran; dichloromethane at -10 - 20℃; for 1h;	97%

Butylcyanomethylsulfonat (98548-92-6) + 3-dimethylaminoacrolein (927-63-9) → 2-n-butylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile

Conditions	Yield
With tetrabutyl-ammonium chloride In water at 90℃; for 1h;	95.5%
With N,N-butyl-methyl-piperidinium bromide at 46℃; for 4h; Microwave irradiation;	95%
With sodium ethanolate at 60℃; Sonication;	95.7%
With pyridine at 40℃; for 2h; Microwave irradiation; Green chemistry;	94.5%

triphenylphosphine[5,10,15-tris-(4-methylphenyl)corrolato] cobalt(III) (1392321-89-9) + 3-dimethylaminoacrolein (927-63-9) → [3,17-(2-formylvinyl)-5,10,15-tritolylcorrolato] cobalt(III) + triphenylphosphine [3-(2-formylvinyl)-5,10,15-tritolylcorrolato]cobalt(III)

Conditions	Yield
Stage #1: 3-dimethylaminoacrolein With trichlorophosphate In dichloromethane at 0℃; Vilsmeier Reaction; Inert atmosphere; Stage #2: triphenylphosphine[5,10,15-tris-(4-methylphenyl)corrolato] cobalt(III) In dichloromethane for 0.166667h; Inert atmosphere;	A 4% B 95%

benzyl 2-cyanoacetate (14447-18-8) + 3-dimethylaminoacrolein (927-63-9) → benzyl 2-bromonicotinate (1107646-58-1)

Conditions	Yield
Stage #1: benzyl 2-cyanoacetate; 3-dimethylaminoacrolein With acridine at 120℃; Sonication; Stage #2: With hydrogen bromide	94.3%
Stage #1: benzyl 2-cyanoacetate; 3-dimethylaminoacrolein With 1-methyl-1-hexylpyridinium bromide at 120℃; for 3h; Stage #2: With hydrogen bromide	92.3%

ethyl 2-cyanoacetate (105-56-6) + 3-dimethylaminoacrolein (927-63-9) → 5-(N,N-dimethyl)amino-2-cyano-2,4-pentadienoic acid ethyl ester (51513-16-7)

Conditions	Yield
With N-butyl-N-ethylpiperidinium bromide In water at 55℃; for 1h; Sonication;	94.2%
With triethylamine at 120℃; Sonication;	93.1%
With triethylamine at 50℃; Microwave irradiation;	90.9%

3-dimethylaminoacrolein (927-63-9) + methanesulfonyl-acetonitrile (2274-42-2) → 2-chloro-3-(methylsulfonyl)pyridine (70682-09-6)

Conditions	Yield
Stage #1: 3-dimethylaminoacrolein; methanesulfonyl-acetonitrile With N,N-dibutylpiperidinium chloride at 80℃; for 4h; Stage #2: With hydrogenchloride	94.1%

dimethyl sulfate (77-78-1) + 3-dimethylaminoacrolein (927-63-9) → C6H12NO(1+)*CH3O4S(1-) (24316-94-7)

Conditions	Yield
	94%

ethyl 2-cyanoacetate (105-56-6) + 3-dimethylaminoacrolein (927-63-9) → Ethyl 2-bromo-3-pyridinecarboxylate (53087-78-8)

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate; 3-dimethylaminoacrolein With 1-dodecyl-3-methylimidazol-1-ium chloride at 90℃; for 4h; Stage #2: With hydrogen bromide	94%
Stage #1: ethyl 2-cyanoacetate; 3-dimethylaminoacrolein With pyridine at 40℃; Sonication; Stage #2: With hydrogen bromide at 40℃; Sonication;	93.5%

methyl 2-cyanoacetate (105-34-0) + 3-dimethylaminoacrolein (927-63-9) → methyl 2-chloropyridine-3-carboxylate (40134-18-7)

Conditions	Yield
Stage #1: methyl 2-cyanoacetate; 3-dimethylaminoacrolein With N-ethyl-pyridinium tetrafluoroborate at 140℃; for 1h; Microwave irradiation; Stage #2: With hydrogenchloride	93.9%

2-(ethanesulfonyl)acetonitrile (13654-62-1) + 3-dimethylaminoacrolein (927-63-9) → 2-bromo-3-ethanesulfonylpyridine

Conditions	Yield
Stage #1: 2-(ethanesulfonyl)acetonitrile; 3-dimethylaminoacrolein With 1-dodecyl-3-methylimidazol-1-ium chloride at 90℃; for 3h; Stage #2: With hydrogen bromide	93.9%

(p-hydroxy) benzylcyanomethyl sulfone + 3-dimethylaminoacrolein (927-63-9) → 2-bromo-3-(4'-hydroxy)benzylsulfonylpyridine

Conditions	Yield
Stage #1: (p-hydroxy) benzylcyanomethyl sulfone; 3-dimethylaminoacrolein With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide at 110℃; for 1h; Stage #2: With hydrogen bromide	93.7%

3-dimethylaminoacrolein (927-63-9) → malonaldehyde-potassium salt (126025-73-8)

Conditions	Yield
With methanol; potassium hydroxide In tetrahydrofuran for 5h; Inert atmosphere; Reflux;	93%

(m-fluorobenzyl) cyanomethyl sulfone + 3-dimethylaminoacrolein (927-63-9) → 2-fluoro-3-(3'-fluoro)benzylsulfonylpyridine

Conditions	Yield
Stage #1: (m-fluorobenzyl) cyanomethyl sulfone; 3-dimethylaminoacrolein With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide at 100℃; for 1.5h; Microwave irradiation; Stage #2: With hydrogen fluoride	93%

ethyl 2-cyanoacetate (105-56-6) + 3-dimethylaminoacrolein (927-63-9) → 2-iodonicotinic acid ethyl ester (154366-01-5)

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate; 3-dimethylaminoacrolein With 1-hydroxyethyl-3-methyl-1H-imidazolium chloride at 110℃; for 3h; Stage #2: With hydrogen iodide	92.9%

1,1,2,2-tetrafluoro-N,N-dimethylethan-1-amine (1550-50-1) + methylhydrazine (60-34-4) + 3-dimethylaminoacrolein (927-63-9) → 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde (1094484-55-5)

Conditions	Yield
Stage #1: 1,1,2,2-tetrafluoro-N,N-dimethylethan-1-amine; 3-dimethylaminoacrolein With boron trifluoride In acetonitrile for 2.5h; Stage #2: methylhydrazine In acetonitrile at 5 - 20℃; for 2.5h;	92.8%

ethyl 2-cyanoacetate (105-56-6) + 3-dimethylaminoacrolein (927-63-9) → ethyl 2-chloronicotinate (1452-94-4)

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate; 3-dimethylaminoacrolein With N-butyl-N-ethylpiperidinium chloride at 80℃; for 6h; Stage #2: With hydrogenchloride	92.7%
Stage #1: ethyl 2-cyanoacetate; 3-dimethylaminoacrolein With acridine at 100℃; Sonication; Stage #2: With hydrogenchloride at 100℃; Sonication;	92.1%

(1-methylethylsulfonyl)acetonitrile (120069-21-8) + 3-dimethylaminoacrolein (927-63-9) → 2-chloro-3-isopropylsulfonylpyridine (139272-28-9)

Conditions	Yield
Stage #1: (1-methylethylsulfonyl)acetonitrile; 3-dimethylaminoacrolein With tetrabutylphosphine bromide at 140℃; for 0.333333h; Stage #2: With hydrogenchloride	92.5%

(3,4-dichloro) benzylcyanomethyl sulfone + 3-dimethylaminoacrolein (927-63-9) → 2-chloro-3-(3',4'-dichloro)benzylsulfonylpyridine

Conditions	Yield
Stage #1: (3,4-dichloro) benzylcyanomethyl sulfone; 3-dimethylaminoacrolein With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide at 100℃; for 2h; Stage #2: With hydrogenchloride	92.5%

(m-methoxy) benzylcyanomethyl sulfone + 3-dimethylaminoacrolein (927-63-9) → 2-fluoro-3-(3'-methoxy)benzylsulfonylpyridine

Conditions	Yield
Stage #1: (m-methoxy) benzylcyanomethyl sulfone; 3-dimethylaminoacrolein With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide at 100℃; for 1.5h; Stage #2: With hydrogen fluoride	92%

p-bromobenzyl cyanomethyl sulfone + 3-dimethylaminoacrolein (927-63-9) → 2-bromo-3-(4'-bromo)benzylsulfonylpyridine

Conditions	Yield
Stage #1: p-bromobenzyl cyanomethyl sulfone; 3-dimethylaminoacrolein With 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide at 100℃; for 1.5h; Microwave irradiation; Stage #2: With hydrogen bromide	91.8%

cyanoacetic acid octadecyl ester (71888-58-9) + 3-dimethylaminoacrolein (927-63-9) → n-octadecyl 2-chloronicotinate

Conditions	Yield
Stage #1: cyanoacetic acid octadecyl ester; 3-dimethylaminoacrolein With 1-hexyl-3-methylimidazol-1-ium chloride at 200℃; for 0.5h; Microwave irradiation; Stage #2: With hydrogenchloride	91.1%

(C2H5)8C20H4N4CH2CH2(C2H5)8C20H4N4Ni + 3-dimethylaminoacrolein (927-63-9) → (C2H5)8C20H4N4CH2CH2(C2H5)8C20H3N4CHCHCH(O)Ni

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane; water addn. of dimethylaminoacrolein to soln. of Ni complex, stirring (room temp., 1.5 h), addn. of CH2Cl2, washing (water), concn., addn. of MeOH, addn. of aq. soln. of NaOH (20 %), stirring (room temp., 15 min); quenching (water), extn. into CHCl3, concn. of org. phase, flash chromy.(CH2Cl2/ether 9/1);	91%

2-(ethanesulfonyl)acetonitrile (13654-62-1) + 3-dimethylaminoacrolein (927-63-9) → 3-(ethanesulfonyl)-2-fluoropyridine

Conditions	Yield
Stage #1: 2-(ethanesulfonyl)acetonitrile; 3-dimethylaminoacrolein With 1-butyl-3-methylimidazolium trifluoroacetate at 120℃; for 0.5h; Stage #2: With hydrogen fluoride	90.7%

cyanoacetic acid n-propyl ester (14447-15-5) + 3-dimethylaminoacrolein (927-63-9) → propyl 2-chloronicotinate (1011481-58-5)

Conditions	Yield
Stage #1: cyanoacetic acid n-propyl ester; 3-dimethylaminoacrolein With sodium t-butanolate at 80℃; Sonication; Stage #2: With hydrogenchloride at 80℃; Sonication;	90.5%

ethyl 2-cyanoacetate (105-56-6) + 3-dimethylaminoacrolein (927-63-9) → 3-(ethoxycarbonyl)-2-fluoropyridine (113898-56-9)

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate; 3-dimethylaminoacrolein With 1-butyl-3-methylimidazolium trifluoroacetate at 120℃; for 2h; Stage #2: With hydrogen fluoride	90.4%

1-(1-methylethyl)piperazine (4318-42-7) + formaldehyd (50-00-0) + 3-dimethylaminoacrolein (927-63-9) → (2E)-3-(dimethylamino)-2-[(4-isopropylpiperazin-1-yl)methyl]acrylaldehyde

Conditions	Yield
With acetic acid In ethanol; water at 22 - 50℃; for 18.5h; Mannich reaction;	90%

Upstream product

• 624-67-9 Propargylic aldehyde 
• 124-40-3 dimethyl amine 
• 51513-20-3 3-dimethyl-amino-1,1,3-trimethoxypropane 
• 3603-99-4 cyclotetradecanone 
• 542-78-9 Malondialdehyde 
• 506-59-2 N,N-dimethylammonium chloride 
• 1186-70-5 bis(dimethylamino)methoxymethane 
• 75-07-0 acetaldehyde 
• 92444-70-7 N-benzyl-N-acetylaminoethane 
• 68-12-2 N,N-dimethyl-formamide 
• 109-53-5 isobutyl vinyl ether 
• 109-92-2 ethyl vinyl ether 
• 52950-92-2 dimethyl<3-(dimethylamino)-2-propylidene>immonium tetrafluoroborate 
• 104-04-1 N-(4-Nitrophenyl)acetamide 

Downstream Products

• 542-78-9 Malondialdehyde 
• 27110-82-3 2-(furan-2-yl)pyrimidine 
• 26387-66-6 3-dimethylamino-2-bromo-2-propenal 
• 1534-15-2 3-(Dimethylamino)-2-propenal N-phenylimine 
• 34231-55-5 3-phenylisoxazole-4-carbaldehyde 
• 256376-59-7 ethyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate 
• 275-02-5 1-deaza-5-azapurine 
• 35170-93-5 3-chloro-1,8-naphthyridine 
• 254-60-4 1,8-naphthyridine 
• 14759-22-9 3-methyl-[1,8]naphthyridine 
• 1569-17-1 4-methyl[1,8]-naphthyridine 
• 35170-94-6 4-chloro-1,8-naphthyridine 
• 3163-76-6 benzene-1,3,5-trialdehyde 
• 119480-92-1 (E)-3-(dimethyl(phenyl)silyl)acrylaldehyde 

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