4-(Dimethylamino)cinnamaldehyde supplier

Name
4-(Dimethylamino)cinnamaldehyde
EINECS 228-267-0
CAS No. 6203-18-5
Article Data43
CAS DataBase
Density 1.057 g/cm³
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
Hazard Symbols Xi
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;
PSA 20.31000
LogP 1.96470

Synthetic route

: 3054-95-3
acrylaldehyde diethyl acetal

: 586-77-6
4-bromo-N,N-dimethylaniline

: 6203-18-5
p-dimethylaminocinnamaldehyde

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sulfuric acid at 1 - 4℃;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at -3 - 0℃;

...Expand

: 7664-93-9
sulfuric acid

: 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

...Expand

: Dimethyl-(4-{(E)-3-[(E)-phenylimino]-propenyl}-phenyl)-amine

A: 62-53-3
aniline

B: 6203-18-5
p-dimethylaminocinnamaldehyde

Conditions

Conditions	Yield
With citrate buffer; sodium dodecyl-sulfate at 20℃; pH=4.0; Equilibrium constant; Kinetics; Further Variations:; Reagents; pH-values;

: 4-(CH3)2NC6H4CHCHCHOFe(CO)3

: 603-35-0
triphenylphosphine

: 14741-34-5, 21255-52-7
(CO)3Fe{P(C6H5)3}2

: 4-(CH3)2NC6H4CHCHCHOFe(CO)2P(C6H5)3

C: 6203-18-5
p-dimethylaminocinnamaldehyde

Conditions

Conditions	Yield
Kinetics; byproducts: CO; at 30-70 °C;
Kinetics; byproducts: CO; at 30.2 °C;

...Expand

: 52509-14-5
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

: 100-10-7
4-dimethylamino-benzaldehyde

: 6203-18-5
p-dimethylaminocinnamaldehyde

Conditions

Conditions	Yield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; 4-dimethylamino-benzaldehyde With sodium methylate In tetrahydrofuran Wittig Olefination; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water

: 586-77-6
4-bromo-N,N-dimethylaniline

: 107-02-8
acrolein

: 6203-18-5
p-dimethylaminocinnamaldehyde

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl-ammonium chloride; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 4h; Heck Reaction; Microwave irradiation; Inert atmosphere;

: 940-93-2
2,4,6-trimethylpyrylium chlorate(VII)

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2,4,6-tris(4-dimethylaminostyryl)pyrylium perchlorate

Conditions

Conditions	Yield
In ethanol for 5h; Heating;	97%

: 5351-17-7
4-aminobenzohydrazide

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 4-Amino-benzoic acid [(E)-3-(4-dimethylamino-phenyl)-prop-2-en-(E)-ylidene]-hydrazide

Conditions

Conditions	Yield
In ethanol for 1h; Heating;	97%

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 20850-05-9
3-(4-dimethylaminophenyl)-prop-2-en-1-ol

Conditions

Conditions	Yield
With formic acid; C14H15ClIrN2O2(1+)*Cl(1-); triethylamine In water at 80℃; for 0.5h; pH=1;	97%
With formic acid; chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride In water at 80℃; for 0.5h; Schlenk technique; chemoselective reaction;	94%
With sodium tetrahydroborate In ethanol at 0℃; for 2h;

: 22956-26-9
2-phenyl-4-methyl-1-benzothiopyrylium perchlorate

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 4-[(1E,3E)-4-(4-Dimethylamino-phenyl)-buta-1,3-dienyl]-2-phenyl-thiochromenylium; perchlorate

Conditions

Conditions	Yield
In ethanol for 3h; Ambient temperature;	96%

: 22956-26-9
2-phenyl-4-methyl-1-benzothiopyrylium perchlorate

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 4-[(1Z,3E)-4-(4-Dimethylamino-phenyl)-buta-1,3-dienyl]-2-phenyl-thiochromenylium; perchlorate

Conditions

Conditions	Yield
	96%

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 85665-76-5
3-[4-(dimethylamino)phenyl]propan-1-ol

Conditions

Conditions	Yield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium formate In water at 80℃; for 0.5h; Schlenk technique; chemoselective reaction;	96%
With potassium hydroxide; isopropyl alcohol; PdMCM-41 for 5h;	69%

: 134-81-6
benzil

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 1025772-66-0
C25H23N3

Conditions

Conditions	Yield
With ammonium acetate In ethanol at 75℃; for 2h;	95%
With ammonium acetate In ethanol for 10h; Reflux; Green chemistry;	79%

: 7328-91-8
2,2-Dimethyl-1,3-diaminopropane

: 6203-18-5
p-dimethylaminocinnamaldehyde

: N,N'-bis((E)-3-(4-(dimethylamino)phenyl)allylidene)-2,2-dimethylpropane-1,3-diamine

Conditions

Conditions	Yield
In ethanol at 20℃; for 4h;	94%

: 7328-91-8
2,2-Dimethyl-1,3-diaminopropane

: 6203-18-5
p-dimethylaminocinnamaldehyde

: N,N’-bis(dimethylaminocinnamaldehyde)-2,2-dimethyl-1,3-propanediamine

Conditions

Conditions	Yield
In ethanol at 20℃; for 4h;	94%

: 1038502-72-5
1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one

: 6203-18-5
p-dimethylaminocinnamaldehyde

: (4S,5R)-4-(4-(dimethylamino)phenyl)-1-tosyl-5-vinyl-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;	93%

: C16H16F3NO3

: 6203-18-5
p-dimethylaminocinnamaldehyde

: C27H29F3N2O4

Conditions

Conditions	Yield
Stage #1: p-dimethylaminocinnamaldehyde With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine In acetonitrile at 20℃; for 0.0833333h; Stage #2: C16H16F3NO3 With triethylamine In acetonitrile at 20℃; for 12h; stereoselective reaction;	93%

: 5351-23-5
4-hydroxybenzoic acid hydrazide

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 4-hydroxybenzoyl-[3-(4-dimethylaminophenyl)allylidene]hydrazide

Conditions

Conditions	Yield
In ethanol for 8h; Reflux; Inert atmosphere;	92%
In ethanol for 5h; Reflux;	65.3%

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2-(4-N,N′-dimethylaminocinnamylmethoxy)pinacolborane

Conditions

Conditions	Yield
With C41H78N6PSi4Y In benzene-d6 at 25℃; for 0.166667h; Glovebox; Sealed tube; Schlenk technique; Inert atmosphere;	92%

: 1445-69-8
2,3-dihydrophthalazine-1,4-dione

: 109-77-3
malononitrile

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 1-(4-(dimethylamino)styryl)-3-amino-5,10-dihydro-5,10-dioxo-1H-pyrazolo[1,2-b]phthalazine-2-carbonitrile

Conditions

Conditions	Yield
With amino-functionalized Si-magnetite nanoparticles-coated silicotungstic acid In methanol at 70℃; for 0.266667h; Catalytic behavior; Green chemistry;	91.95%

...Expand

: 4-hydroxy-2-methyl-1-benzothiopyrylium perchlorate

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2-[(1E,3E)-4-(4-Dimethylamino-phenyl)-buta-1,3-dienyl]-4-phenyl-thiochromenylium; perchlorate

Conditions

Conditions	Yield
	91%

: 55181-01-6
2-Methyl-4-phenyl-1-benzo-1-thiopyrylium perchlorate

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2-[(1E,3E)-4-(4-Dimethylamino-phenyl)-buta-1,3-dienyl]-4-phenyl-thiochromenylium; perchlorate

Conditions

Conditions	Yield
In ethanol for 3h; Ambient temperature;	91%

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 100-10-7
4-dimethylamino-benzaldehyde

Conditions

Conditions	Yield
With pyrrolidine; water In acetonitrile at 20℃; for 12h; Inert atmosphere;	91%
With morpholine; palladium 10% on activated carbon; oxygen; copper(l) chloride In isopropyl alcohol at 100℃; for 24h; regioselective reaction;	87%

: 30889-48-6
3‐phenylnaphthalen‐2‐ol

: 6203-18-5
p-dimethylaminocinnamaldehyde

: C27H23NO2

Conditions

Conditions	Yield
With potassium phosphate; 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; C35H38N3OSi(1+)*BF4(1-) In tetrahydrofuran at 0℃; for 36h; enantioselective reaction;	91%

: 940-93-2
2,4,6-trimethylpyrylium chlorate(VII)

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2,6-dimethyl-4-(4-dimethylaminostyryl)pyrylium perchlorate

Conditions

Conditions	Yield
In ethanol for 5h; Heating;	90%

: 5,8-Dimethoxy-4-methyl-2-phenyl-thiochromenylium; perchlorate

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 4-[(1E,3E)-4-(4-Dimethylamino-phenyl)-buta-1,3-dienyl]-5,8-dimethoxy-2-phenyl-thiochromenylium; perchlorate

Conditions

Conditions	Yield
In ethanol for 3h; Ambient temperature;	90%

: 3829-73-0
2-(triphenylphosphanylideneamino)naphtho-1,2,3-triazole-4,9-dione

: 6203-18-5
p-dimethylaminocinnamaldehyde

: C21H17N5O2

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water Reflux;	90%

: 67-63-0
isopropyl alcohol

: 6203-18-5
p-dimethylaminocinnamaldehyde

: C14H21NO

Conditions

Conditions	Yield
With alumina at 180℃; under 11251.1 Torr; for 0.666667h; Microwave irradiation; Sealed tube;	90%

: 2142-68-9
1-(2-chlorophenyl)ethanone

: 6203-18-5
p-dimethylaminocinnamaldehyde

: (2E,4E)-1-(2-chlorophenyl)-5-(4-(dimethylamino)phenyl)penta-2,4-dien-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	89.6%

: 5,7-dihydroxy-4-methyl-2-phenyl-1-benzopyrilium chloride

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 8-hydroxy-5-phenyl-2-[2-(4-(N,N)-dimethylamino)phenyl]ethenyl-1,6-dioxaphenalene chloride

Conditions

Conditions	Yield
In methanol for 7h; Heating;	89%

: 2786-35-8
2-ethyl-3-methylbenzothiazolium iodide

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2-{2-[4-(dimethylamino)phenyl]-1-methylbuta-1,3-dien-1-yl}-3-methylbenzothiazolium iodide

Conditions

Conditions	Yield
With pyridine In methanol for 15h; Heating;	89%

: 2295-31-0
2,4-thiazolidinedion

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 1433720-66-1
(5S,6R,10S)-2,4-dioxo-6,10-bis(4-(dimethylamino)phenyl)-1-thia-3-azaspiro[4.5]dec-7-ene-7-carboxaldehyde

Conditions

Conditions	Yield
With (S)-2-(diphenyl((triethylsilyl)oxy)methyl)pyrrolidine In dichloromethane at 20℃; for 36h; Michael Addition; enantioselective reaction;	89%

: 95-55-6
2-amino-phenol

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2-{[3-4-(dimethylamino)phenyl-2-propenylidene]amino}phenol

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water at 70℃; for 3h;	89%

: 32933-40-7
N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 2-cyano-5-[4-(dimethylamino)phenyl]-N-(4-sulfamoylphenyl)penta-2,4-dienamide

Conditions

Conditions	Yield
With piperidine In ethanol for 4h; Reflux;	89%
With piperidine In ethanol for 8h; Reflux;	59%

: 645-13-6
4-isopropylacetophenone

: 6203-18-5
p-dimethylaminocinnamaldehyde

: (2E,4E)-5-(4-(dimethylamino)phenyl)-1-(4-isopropylphenyl)penta-2,4-dien-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃;	88.5%

: 3-allyl-2-ethylbenzothiazolium bromide

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 3-allyl-2-{4-[4-(dimethylamino)phenyl]-1-methylbuta-1,3-dien-1-yl}benzothiazolium bromide

Conditions

Conditions	Yield
With pyridine In methanol for 15h; Heating;	88%

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

Product Name

4-(Dimethylamino)cinnamaldehyde

Synthetic route

4-(Dimethylamino)cinnamaldehyde Specification

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