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3-Dimethylaminoacrolein

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Name

3-Dimethylaminoacrolein

EINECS 213-157-7
CAS No. 927-63-9 Density 0.907 /cm3
PSA 20.31000 LogP 0.26060
Solubility N/A Melting Point N/A
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 N/A
Safety 26-36/37/39-45 Risk Codes 34
Molecular Structure Molecular Structure of 927-63-9 (3-Dimethylaminoacrolein) Hazard Symbols CorrosiveC
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;

Article Data 25

3-Dimethylaminoacrolein 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
ConditionsYield
With trichlorophosphate at 75℃; for 1.5h;A 45%
B 53%
C 5%
D 0.05 g
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
ConditionsYield
With silica gel 1,) 80 deg C to 90 deg C, 1.5 h, 2.) CHCl3, 1 h;A 49%
B n/a
624-67-9

Propargylic aldehyde

124-40-3

dimethyl amine

927-63-9

3-dimethylaminoacrolein

Conditions
ConditionsYield
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
ConditionsYield
beim Behandeln des Reaktionsgemisches mit Eis sowie anschliessend mit wss. Kaliumcarbonat-Loesung;
75-44-5

phosgene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

927-63-9

3-dimethylaminoacrolein

Conditions
ConditionsYield
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
ConditionsYield
at 28℃; Product distribution; other temperature;
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
ConditionsYield
at 95 - 100℃; for 4h;A 0.12 g
B n/a

2-methyl-1-ethylbenzindolium tetrafluoroborate

927-63-9

3-dimethylaminoacrolein

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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

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