3-Dimethylaminoacrolein supplier

Name
3-Dimethylaminoacrolein
EINECS 213-157-7
CAS No. 927-63-9
Article Data25
CAS DataBase
Density 0.907 /cm³
Solubility
Melting Point
Formula C₅H₉NO
Boiling Point 271.5 °C at 760 mmHg
Molecular Weight 99.1326
Flash Point 128.9 °C
Transport Information UN 3267 8/PG 2
Appearance
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 3-(Dimethylamino)-2-propenal;Acrolein,3-(dimethylamino)- (6CI,7CI,8CI);3-(Dimethylamino)acrylaldehyde;3-(Dimethylamino)propenal;4-Dimethylamino-2-propen-1-al;β-(Dimethylamino)acrolein;(2E)-3-(dimethylamino)prop-2-enal;2-Propenal, 3-(dimethylamino)-;3-(Dimethylamino)-2-propenal;
PSA 20.31000
LogP 0.26060

Synthetic route

: 104-04-1
N-(4-Nitrophenyl)acetamide

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 1205-59-0
N1,N1-dimethyl-N2-(4-nitro-phenyl)-formamidine

B: 78708-10-8
(E)-3-Dimethylamino-2-formyl-N-(4-nitro-phenyl)-acrylamide

C: 100-01-6
4-nitro-aniline

D: 927-63-9
3-dimethylaminoacrolein

Conditions

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

...Expand

: 502-49-8
cycloactanone

: 5043-86-7
acetal-aminal of β-dimethylaminoacrolein

A: 75143-08-7
2-[(E)-3-Dimethylamino-prop-2-en-(Z)-ylidene]-cyclooctanone

B: 927-63-9
3-dimethylaminoacrolein

Conditions

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

...Expand

: 624-67-9
Propargylic aldehyde

: 124-40-3
dimethyl amine

: 927-63-9
3-dimethylaminoacrolein

Conditions

Conditions	Yield
With methanol

: 105-57-7
diethyl acetal

: 75-44-5
phosgene

: 107-06-2
1,2-dichloro-ethane

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 13984-13-9, 70669-77-1
3-dimethylaminopropyl-2-ene-1-imino-N,N-dimethylammonium chloride

B: 927-63-9
3-dimethylaminoacrolein

Conditions

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

...Expand

: 75-44-5
phosgene

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 927-63-9
3-dimethylaminoacrolein

Conditions

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

: 67-56-1
methanol

: 5043-87-8
β-dimethylaminoacrolein aminal

A: Methanolate((E)-3-dimethylamino-allylidene)-dimethyl-ammonium;

B: 927-63-9
3-dimethylaminoacrolein

Conditions

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

...Expand

: 51513-20-3
3-dimethyl-amino-1,1,3-trimethoxypropane

: 3603-99-4
cyclotetradecanone

A: 75143-09-8
2-[(E)-3-Dimethylamino-prop-2-en-(Z)-ylidene]-cyclotetradecanone

B: 927-63-9
3-dimethylaminoacrolein

Conditions

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

...Expand

: 2-methyl-1-ethylbenzindolium tetrafluoroborate

: 927-63-9
3-dimethylaminoacrolein

: 1-ethyl-2-(4-dimethylamino-1,3-butadienyl)benzindolium tetrafluoroborate

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: 2274-42-2
methanesulfonyl-acetonitrile

: 2-methylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: 1,2-bis(5'-acroleinyl-2,2'-bipyrrol-5-yl)benzene

Conditions

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%

: 102069-19-2
cyano-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 111-86-4
n-Octylamine

: 927-63-9
3-dimethylaminoacrolein

: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl (2E,4E)-2-cyano-5-(dimethylamino)penta-2,4-dienoate

Conditions

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%

...Expand

: 91107-10-7
4,6-dimethoxy-2,3-diphenyl-1H-indole

: 927-63-9
3-dimethylaminoacrolein

: trans-3-(4,6-dimethoxy-2,3-diphenylindol-7-yl)propen-1-al

Conditions

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

: 98548-92-6
Butylcyanomethylsulfonat

: 927-63-9
3-dimethylaminoacrolein

: 2-n-butylsulfonyl-5-(N,N-dimethyl)amino-2,4-pentadienenitrile

Conditions

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%

: 1392321-89-9
triphenylphosphine[5,10,15-tris-(4-methylphenyl)corrolato] cobalt(III)

: 927-63-9
3-dimethylaminoacrolein

: [3,17-(2-formylvinyl)-5,10,15-tritolylcorrolato] cobalt(III)

: triphenylphosphine [3-(2-formylvinyl)-5,10,15-tritolylcorrolato]cobalt(III)

Conditions

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%

...Expand

: 14447-18-8
benzyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 1107646-58-1
benzyl 2-bromonicotinate

Conditions

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%

: 105-56-6
ethyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 51513-16-7
5-(N,N-dimethyl)amino-2-cyano-2,4-pentadienoic acid ethyl ester

Conditions

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%

: 927-63-9
3-dimethylaminoacrolein

: 2274-42-2
methanesulfonyl-acetonitrile

: 70682-09-6
2-chloro-3-(methylsulfonyl)pyridine

Conditions

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

: 77-78-1
dimethyl sulfate

: 927-63-9
3-dimethylaminoacrolein

: 24316-94-7
C6H12NO(1+)*CH3O4S(1-)

Conditions

Conditions	Yield
	94%

: 105-56-6
ethyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 53087-78-8
Ethyl 2-bromo-3-pyridinecarboxylate

Conditions

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%

: 105-34-0
methyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 40134-18-7
methyl 2-chloropyridine-3-carboxylate

Conditions

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%

: 13654-62-1
2-(ethanesulfonyl)acetonitrile

: 927-63-9
3-dimethylaminoacrolein

: 2-bromo-3-ethanesulfonylpyridine

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: 2-bromo-3-(4'-hydroxy)benzylsulfonylpyridine

Conditions

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%

: 927-63-9
3-dimethylaminoacrolein

: 126025-73-8
malonaldehyde-potassium salt

Conditions

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

: (m-fluorobenzyl) cyanomethyl sulfone

: 927-63-9
3-dimethylaminoacrolein

: 2-fluoro-3-(3'-fluoro)benzylsulfonylpyridine

Conditions

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%

: 105-56-6
ethyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 154366-01-5
2-iodonicotinic acid ethyl ester

Conditions

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%

: 1550-50-1
1,1,2,2-tetrafluoro-N,N-dimethylethan-1-amine

: 60-34-4
methylhydrazine

: 927-63-9
3-dimethylaminoacrolein

: 1094484-55-5
3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

Conditions

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%

...Expand

: 105-56-6
ethyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 1452-94-4
ethyl 2-chloronicotinate

Conditions

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%

: 120069-21-8
(1-methylethylsulfonyl)acetonitrile

: 927-63-9
3-dimethylaminoacrolein

: 139272-28-9
2-chloro-3-isopropylsulfonylpyridine

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: 2-chloro-3-(3',4'-dichloro)benzylsulfonylpyridine

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: 2-fluoro-3-(3'-methoxy)benzylsulfonylpyridine

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: 2-bromo-3-(4'-bromo)benzylsulfonylpyridine

Conditions

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%

: 71888-58-9
cyanoacetic acid octadecyl ester

: 927-63-9
3-dimethylaminoacrolein

: n-octadecyl 2-chloronicotinate

Conditions

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

: 927-63-9
3-dimethylaminoacrolein

: (C2H5)8C20H4N4CH2CH2(C2H5)8C20H3N4CHCHCH(O)Ni

Conditions

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%

: 13654-62-1
2-(ethanesulfonyl)acetonitrile

: 927-63-9
3-dimethylaminoacrolein

: 3-(ethanesulfonyl)-2-fluoropyridine

Conditions

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%

: 14447-15-5
cyanoacetic acid n-propyl ester

: 927-63-9
3-dimethylaminoacrolein

: 1011481-58-5
propyl 2-chloronicotinate

Conditions

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%

: 105-56-6
ethyl 2-cyanoacetate

: 927-63-9
3-dimethylaminoacrolein

: 113898-56-9
3-(ethoxycarbonyl)-2-fluoropyridine

Conditions

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%

: 4318-42-7
1-(1-methylethyl)piperazine

: 50-00-0
formaldehyd

: 927-63-9
3-dimethylaminoacrolein

: (2E)-3-(dimethylamino)-2-[(4-isopropylpiperazin-1-yl)methyl]acrylaldehyde

Conditions

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

...Expand

3-Dimethylaminoacrolein Specification

The 3-Dimethylaminoacrolein, with the CAS registry number 927-63-9 and EINECS registry number 213-157-7, has the IUPAC name of (E)-3-(dimethylamino)prop-2-enal. It belongs to the following product categories: C1 to C6; Aldehydes; Carbonyl Compounds. And the molecular formula of the chemical is C₅H₉NO. What's more, it should be stored at 2-8°C.

The physical properties of 3-Dimethylaminoacrolein are as followings: (1)ACD/LogP: 0.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): 0.4; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.18; (7)ACD/KOC (pH 5.5): 13.21; (8)ACD/KOC (pH 7.4): 38.94; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 20.31 Å²; (13)Index of Refraction: 1.446; (14)Molar Refractivity: 29.17 cm³; (15)Molar Volume: 109.2 cm³; (16)Polarizability: 11.56×10^-24cm³; (17)Surface Tension: 28.6 dyne/cm; (18)Density: 0.907 g/cm³; (19)Flash Point: 128.9 °C; (20)nthalpy of Vaporization: 50.97 kJ/mol; (21)Boiling Point: 271.5 °C at 760 mmHg; (22)Vapour Pressure: 0.00643 mmHg at 25°C.

Uses of 3-Dimethylaminoacrolein: It can react with 2-hydroxymethyl-phenol to produce 4H-chromene-3-carbaldehyde. This reaction will need reagent acetic anhydride, and the menstruum acetic acid. The reaction time is 2 hours with heating, and the yield is about 40%.

You should be cautious while dealing with this chemical. It may cause burns. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection; In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\C=C\N(C)C
(2)InChI: InChI=1/C5H9NO/c1-6(2)4-3-5-7/h3-5H,1-2H3/b4-3+
(3)InChIKey: RRLMPLDPCKRASL-ONEGZZNKBT

Product Name

3-Dimethylaminoacrolein

Synthetic route

3-Dimethylaminoacrolein Specification

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