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4-(Dimethylamino)cinnamaldehyde

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Name

4-(Dimethylamino)cinnamaldehyde

EINECS 228-267-0
CAS No. 6203-18-5 Density 1.057 g/cm3
PSA 20.31000 LogP 1.96470
Solubility dioxane: 50 mg/mL, clear Melting Point 138-140 °C(lit.)
Formula C11H13NO Boiling Point 328.9 °C at 760 mmHg
Molecular Weight 175.23 Flash Point 131.2 °C
Transport Information UN 1789 8/PG 3 Appearance white to light yellow crystal powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 6203-18-5 (4-(Dimethylamino)cinnamaldehyde) Hazard Symbols IrritantXi
Synonyms

Cinnamaldehyde,p-(dimethylamino)- (6CI,7CI,8CI);3-(4-Dimethylaminophenyl)propenal;3-[4-(Dimethylamino)phenyl]-2-propenal;4-(N,N-Dimethylamino)cinnamaldehyde;4-Dimethylaminocinnamic aldehyde;4-Dimethylaminozimtaldehyde;NSC 62138;p-(Dimethylamino)cinnamaldehyde;p-(Dimethylamino)cinnamic aldehyde;p-(N,N-Dimethylamino)cinnamaldehyde;4-Dimethylaminocinnamaldehyde;

Article Data 43

4-(Dimethylamino)cinnamaldehyde Synthetic route

3054-95-3

acrylaldehyde diethyl acetal

586-77-6

4-bromo-N,N-dimethylaniline

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
Stage #1: acrylaldehyde diethyl acetal; 4-bromo-N,N-dimethylaniline With potassium chloride; tetrabutylammonium acetate; potassium carbonate In N,N-dimethyl acetamide at 120℃; for 2.5h; Heck reaction;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; chemospecific reaction;
77%
20850-05-9

3-(4-dimethylaminophenyl)-prop-2-en-1-ol

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen In acetonitrile at 60℃; for 2h;67%
586-77-6

4-bromo-N,N-dimethylaniline

927-63-9

3-dimethylaminoacrolein

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran 1.) -78 deg C, 1 h; warm to 0 deg C, 2.) -78 deg C to room temperature;26%
75-07-0

acetaldehyde

100-10-7

4-dimethylamino-benzaldehyde

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With sulfuric acid at -3 - 0℃;
100-10-7

4-dimethylamino-benzaldehyde

123-63-7

paracetaldehyde

A

128184-34-9

7-<4-(N,N-dimethylamino)phenyl>hepta-2,4,6-trien-1-al

B

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With sulfuric acid at 1 - 4℃;
73178-24-2

2-<4-(Dimethylamino)styryl>-N-phenyl-1,3-oxazolidine

A

122-98-5

2-Anilinoethanol

B

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
oxonium In 1,4-dioxane; water at 30℃; Mechanism; Rate constant; different pH values, μ = 0.5 M (KCl), other catalysts;
74401-95-9

2-(p-dimethylaminostyryl)-N,N'-dimethyl-1,3-imidazolidine

A

110-70-3

N,N`-dimethylethylenediamine

B

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With water at 30℃; Mechanism; Rate constant; pH dependence of rate constant, intermediate formation of cationic Schiff base;
74401-96-0

2-(p-dimethylaminostyryl)-N-isopropyl-N'-phenyl-1,3-imidazolidine

A

69038-55-7

N-isopropyl-N'-phenylethylenediamine

B

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With water at 30℃; Mechanism; Rate constant; pH dependence of rate constant, D2O solvent isotope effect, intermediate formation of cationic Schiff bases and their interconversion, buffer catalysis;
74401-94-8

2-(p-dimethylaminostyryl)-N,N'-diphenyl-1,3-imidazolidine

A

150-61-8

N,N'-diphenylethylenediamine

B

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
With water at 30℃; Mechanism; Rate constant; pH dependence of rate constant, D2O solvent isotope effect, intermediate formation of cationic Schiff base;
7664-93-9

sulfuric acid

75-07-0

acetaldehyde

100-10-7

4-dimethylamino-benzaldehyde

6203-18-5

p-dimethylaminocinnamaldehyde

Conditions
ConditionsYield
at -3 - 0℃;

4-(Dimethylamino)cinnamaldehyde Specification

The 4-(Dimethylamino)cinnamaldehyde belongs to the classes of (1)Aromatic Aldehydes & Derivatives (substituted); (2)Cinnamic acid; (3)Absolute Configuration Determination (Exciton Chirality CD Method); (4)Analytical Chemistry; (5)Enantiomer Excess & Absolute Configuration Determination; (6)Exciton Chirality CD Method (for Primary Amino Groups); (7)Aldehydes; (8)C10 to C21; (9)Carbonyl Compounds; (10)DResearch Essentials; (11)Core Bioreagents; (12)Stains and Dyes; (13)Stains&Dyes, A to. Its cas register number is 6203-18-5. Its EINECS register number is 228-267-0. Its systematic name is (2E)-3-[4-(dimethylamino)phenyl]prop-2-enal . This chemical is sensitive to Air & Light. It is stable, but incompatible with strong oxidizing agents, strong bases. The appearance is white to light yellow crystal powder. Store it at temperature of -20°C.

Physical properties about this chemical are: (1) ACD/LogP: 2.63 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): 2.58 ; (4) ACD/LogD (pH 7.4): 2.63 ; (5) ACD/BCF (pH 5.5): 52.29 ; (6) ACD/BCF (pH 7.4): 58.58 ; (7) ACD/KOC (pH 5.5): 572.04 ; (8) ACD/KOC (pH 7.4): 640.91 ; (9) #H bond acceptors: 2 ; (10) #H bond donors: 0 ; (11) #Freely Rotating Bonds: 3 ; (12) Index of Refraction: 1.599 ; (13) Molar Refractivity: 56.64 cm3 ; (14) Molar Volume: 165.7 cm3 ; (15) Surface Tension: 41.7 dyne/cm; (16) Density: 1.057 g/cm3 ; (17) Flash Point: 131.2 °C ; (18) Enthalpy of Vaporization: 57.13 kJ/mol ; (19) Boiling Point: 328.9 °C at 760 mmHg ; (20) Vapour Pressure: 0.000184 mmHg at 25°C.

Uses of 4-(Dimethylamino)cinnamaldehyde : it can used to produce other chemicals such as 3-(4-dimethylamino-phenyl)-acrylic acid .


The reaction will need ragent pyridinium chlorochromate . The reaction occurs at temperature of 20 ℃ for 4 hours. The yield is about 80%.

When you are using this chemical, please be cautious about it as the following:
The 4-(Dimethylamino)cinnamaldehyde is irritating to eyes, respiratory system and skin.Wear suitable protective clothing when you are using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\C=C\c1ccc(N(C)C)cc1;
(2)InChI: InChI=1/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+;
(3)InChIKey: RUKJCCIJLIMGEP-ONEGZZNKBZ

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