Product Name

  • Name

    4-Dimethylaminobenzaldehyde

  • EINECS 202-819-0
  • CAS No. 100-10-7
  • Article Data274
  • CAS DataBase
  • Density 1.072 g/cm3
  • Solubility 0.3 g/L (20 °C) in water
  • Melting Point 72-75 °C(lit.)
  • Formula C9H11NO
  • Boiling Point 266.5 °C at 760 mmHg
  • Molecular Weight 149.192
  • Flash Point 103.3 °C
  • Transport Information UN 2920 8/PG 2
  • Appearance White to off white crystalline powder
  • Safety 7-16-24/25-26-61-45-39-36/37/39-36
  • Risk Codes 36/37/38-52/53-22-67-41-37/38-10-66-37-34-20-20/21/22
  • Molecular Structure Molecular Structure of 100-10-7 (4-Dimethylaminobenzaldehyde)
  • Hazard Symbols CorrosiveC,HarmfulXn,IrritantXi
  • Synonyms p-Dimethylaminobenzaldehyde;Benzaldehyde,p-(dimethylamino)- (8CI);4-(Dimethylamino)benzaldehyde;4-(Dimethylamino)benzenecarbonal;4-(N,N-Dimethylamino)benzaldehyde;4-Formyl-N,N-dimethylaniline;Erlich reagent;N,N-Dimethyl-4-aminobenzaldehyde;N,N-Dimethyl-4-formylaniline;N,N-Dimethyl-p-aminobenzaldehyde;NSC 5517;p-(Dimethylamino)benzaldehyde;p-(N,N-Dimethylamino)benzaldehyde;p-DAB;p-Formyl-N,N-dimethylaniline;p-Formyldimethylaniline;Benzaldehyde,4-(dimethylamino)-;
  • PSA 20.31000
  • LogP 1.56510

Synthetic route

Sodium; 6-{[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

Sodium; 6-{[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

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

N,N-dimethyl-formamide

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With PdCl(2-HO-C6H4-CH(Ph)-NH-(CH2)3-SeC6H5); potassium carbonate; phenylboronic acid In water Heating;100%
N,N-dimethyl-4-hydroxymethylaniline
1703-46-4

N,N-dimethyl-4-hydroxymethylaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;99.3%
With potassium carbonate In water at 90℃; for 3h;99%
With potassium hydroxide In toluene at 110℃; for 4h; Catalytic behavior;99%
4-(N,N'-dimethylamino)phenyl-1,3-dithiane
24588-75-8

4-(N,N'-dimethylamino)phenyl-1,3-dithiane

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In methanol; water for 0.166667h; Ambient temperature;99%
With silica gel In neat (no solvent) at 20℃; for 0.0583333h;90%
4-(1,3-dioxolan-2-yl)phenyl trifluoromethanesulfonate

4-(1,3-dioxolan-2-yl)phenyl trifluoromethanesulfonate

dimethyl amine
124-40-3

dimethyl amine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
Stage #1: 4-(1,3-dioxolan-2-yl)phenyl trifluoromethanesulfonate With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 80℃; for 0.0833333h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;
Stage #2: dimethyl amine In tetrahydrofuran at 80℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;		99%
4-dimethylaminobenzaldehyde oxime
2929-84-2, 37961-71-0, 77145-76-7

4-dimethylaminobenzaldehyde oxime

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃; for 0.0166667h; neat (no solvent);97%
With water; Dess-Martin periodane In dichloromethane at 5℃; for 0.333333h;92%
With dihydrogen peroxide; tripropylammonium fluorochromate (VI) In acetone at -10℃; for 0.166667h;90%
carbon monoxide
201230-82-2

carbon monoxide

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

4-bromo-N,N-dimethylaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;95%
With Cr(CO)3; hydrogen; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In toluene at 130℃;35%
With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.3 Torr; for 16h;98 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.38 Torr; for 16h;98 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; catacxium A In toluene at 20 - 100℃; under 3750.38 Torr; Autoclave;99 %Chromat.
4-(N,N-dimethylamino)benzaldehyde dimethyl acetal
86459-85-0

4-(N,N-dimethylamino)benzaldehyde dimethyl acetal

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With iron(III) p-toluenesulfonate hexahydrate In water at 20℃; for 0.75h;94%
bismuth(III) iodide In water at 20℃; for 2h;85%
With copper(II) sulfate; sodium iodide In acetone at 20℃; for 3h;82%
4-formylphenyl N,N-dimethylcarbamate
92310-70-8

4-formylphenyl N,N-dimethylcarbamate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0) In toluene at 160℃; for 14h; Inert atmosphere; Sealed tube; Glovebox;93%
p-(1,3-dithiolan-2-yl)-N,N-dimethylaniline
31362-12-6

p-(1,3-dithiolan-2-yl)-N,N-dimethylaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With silica gel In neat (no solvent) at 20℃; for 0.0666667h;92%
With boron trifluoride diethyl etherate; water; mercury(II) oxide In tetrahydrofuran for 1h; Ambient temperature;90%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.333333h;82%
4-dimethylamino-benzaldehyde azine
2143-98-8

4-dimethylamino-benzaldehyde azine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With hexaaquairon(III) perchlorate for 2h;91%
p-dimethylaminocinnamaldehyde
6203-18-5

p-dimethylaminocinnamaldehyde

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
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%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

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

N,N-dimethyl-formamide

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With bis(trichloromethyl) carbonate In tetrachloromethane at 40 - 50℃; for 2h; Vilsmeier-Haack formylation;90%
With trichlorophosphate for 0.0833333h; Vilsmeier-Haack reaction; Microwave irradiation;80%
With silica gel; trichlorophosphate for 0.025h; Formylation; Microwave irradiation (300 W);78%
N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Chloromethylene-dimethyl-ammonium; GENERIC INORGANIC ANION

Chloromethylene-dimethyl-ammonium; GENERIC INORGANIC ANION

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
90%
formylation;90%
4-(azidomethyl)-N,N-dimethylaniline
1369488-99-2

4-(azidomethyl)-N,N-dimethylaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With iron(III) chloride; dihydrogen peroxide In dichloromethane; water for 14h; Reflux; Air;90%
Stage #1: 4-(azidomethyl)-N,N-dimethylaniline With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 4h; Inert atmosphere;
Stage #2: With water In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere;		80%
N-(4-dimethylaminobenzylidene)-p-toluidine
17087-90-0, 149742-33-6

N-(4-dimethylaminobenzylidene)-p-toluidine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With tribromo-isocyanuric acid In acetonitrile for 1h; Reflux;90%
5-(4-N,N-dimethylaminobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
15795-57-0

5-(4-N,N-dimethylaminobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With oxone In water; acetonitrile at 45℃; for 1h;89%
N,N-dimethyl-4-((phenylimino)methyl)aniline
889-37-2, 1613-99-6

N,N-dimethyl-4-((phenylimino)methyl)aniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With hexaaquairon(III) perchlorate for 2h;88%
Ru3(CO)10H(OCC6H4N(CH3)2)
140111-19-9

Ru3(CO)10H(OCC6H4N(CH3)2)

A

dodecacarbonyl-triangulo-triruthenium
15243-33-1

dodecacarbonyl-triangulo-triruthenium

B

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With CO In benzene High Pressure; heating (3 bar CO, 90 min, 80°C); chromy. (hexane);A 88%
B 81%
2-(4-N,N-dimethylaminophenyl)-4,5-dihydrooxazole

2-(4-N,N-dimethylaminophenyl)-4,5-dihydrooxazole

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol at -10 - 10℃;87%
formic acid
64-18-6

formic acid

4-Iodo-N,N-dimethylaniline
698-70-4

4-Iodo-N,N-dimethylaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;87%
4-(N,N-dimethylamino)benzaldehyde thiosemicarbazone
2929-81-9

4-(N,N-dimethylamino)benzaldehyde thiosemicarbazone

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With hexaaquairon(III) perchlorate for 2h;86%
4-(bromomethyl)-N,N-dimethylaniline

4-(bromomethyl)-N,N-dimethylaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.0583333h; Microwave irradiation;86%
Vilsmeier reagent
3724-43-4, 149409-22-3

Vilsmeier reagent

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
Stage #1: Vilsmeier reagent; N,N-dimethyl-aniline In N,N-dimethyl-formamide at 70℃; for 1h;
Stage #2: With water; sodium carbonate In N,N-dimethyl-formamide		84%
und anschliessend mit Wasser;
4-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-3,6,6-trimethyl-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester
117227-36-8

4-{[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-3,6,6-trimethyl-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester

A

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

B

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With sodium methylate In ethanol for 3h; Product distribution; Heating;A 12%
B 84%
4-dimethylamino-benzaldehyde semicarbazone
2929-82-0

4-dimethylamino-benzaldehyde semicarbazone

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With hexaaquairon(III) perchlorate for 2h;84%
With sodium perborate In acetic acid at 40℃; for 1.5h; Oxidation;
2-[4-(dimethylamino)phenyl]acetic acid
17078-28-3

2-[4-(dimethylamino)phenyl]acetic acid

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;84%
1-(dibromomethyl)-4-fluorobenzene
6425-24-7

1-(dibromomethyl)-4-fluorobenzene

dimethyl amine
124-40-3

dimethyl amine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With water at 60℃; for 2h;82%
N-(4-methylbenzyl)methanesulfonamide
42060-28-6

N-(4-methylbenzyl)methanesulfonamide

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

Conditions
ConditionsYield
With MS3 Angstroem; oxygen; sodium acetate; triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 80℃; under 760 Torr; for 14h;82%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

5-(4-dimethylaminobenzylidene)barbituric acid
1753-47-5

5-(4-dimethylaminobenzylidene)barbituric acid

Conditions
ConditionsYield
In methanol Knoevenagel Condensation; Reflux;100%
In methanol at 20℃; Knoevenagel condensation;98%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 0.166667h; Knoevenagel condensation;98%
N,N'-diethyl-2-thiobarbituric acid
5217-47-0

N,N'-diethyl-2-thiobarbituric acid

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

5-(4-(dimethylamino)benzylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
86872-78-8

5-(4-(dimethylamino)benzylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Conditions
ConditionsYield
at 20℃; for 1h; Knoevenagel condensation;100%
In water for 0.5h; Reflux;93%
In ethanol at 20℃; Condensation; Knoevenagel condensation;87%

4-dimethylamino-benzaldehyde

4-dimethylamino-benzaldehyde

2'-hydroxy-4-dimethylaminochalcone
65786-13-2, 6342-97-8

2'-hydroxy-4-dimethylaminochalcone

Conditions
ConditionsYield
Stage #1: o-hydroxyacetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: 4-dimethylamino-benzaldehyde In ethanol; water		100%
With potassium hydroxide In ethanol at 25℃;85%
With potassium hydroxide In ethanol at 25℃;85%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

ethyl (E)-2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enoate
1886-52-8, 74897-86-2, 14394-77-5

ethyl (E)-2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enoate

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.25h; Knoevenagel condensation;100%
With diazabicyclo[5.4.0]undec-7-ene-water complex at 20℃; for 1h; Knoevenagel condensation;100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;99%
4,4'-thiobisaniline
139-65-1

4,4'-thiobisaniline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

4,4'-(((thiobis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(N,N-dimethylaniline)
3430-66-8

4,4'-(((thiobis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(N,N-dimethylaniline)

Conditions
ConditionsYield
With piperidine In ethanol100%
With acetic acid In ethanol for 4h; Reflux;85%
With ethanol; zinc(II) chloride
phenylmagnesium bromide

phenylmagnesium bromide

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

4-(dimethylamino)phenyl(phenyl)methanol
7494-77-1

4-(dimethylamino)phenyl(phenyl)methanol

Conditions
ConditionsYield
In diethyl ether for 1h; Ambient temperature;100%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

acetone
67-64-1

acetone

4-p-dimethylaminophenyl-3-buten-2-one
5432-53-1

4-p-dimethylaminophenyl-3-buten-2-one

Conditions
ConditionsYield
With sodium hydroxide for 72h; Ambient temperature;100%
With water; potassium hydroxide at 20℃; for 0.2h;82%
With sodium hydroxide In water at 0 - 20℃; Aldol condensation;67.73%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

methylamine
74-89-5

methylamine

4-(dimethylamino)-N-methylbenzylimine
877-79-2

4-(dimethylamino)-N-methylbenzylimine

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction;100%
at 20℃; for 12h;100%
With benzene
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

malononitrile
109-77-3

malononitrile

p-(N-dimethylamino benzylidene) malononitrile
2826-28-0

p-(N-dimethylamino benzylidene) malononitrile

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 30℃; for 0.333333h; Knoevenagel condensation;100%
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;100%
With potassium hydrogen phthalate In water at 20℃; for 0.116667h; Knoevenagel Condensation; Green chemistry;99%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

methyl (E)-2-cyano-3-(4-(N,N-dimethylamino)phenyl)-2-propenoate
3785-86-2, 13432-69-4

methyl (E)-2-cyano-3-(4-(N,N-dimethylamino)phenyl)-2-propenoate

Conditions
ConditionsYield
at 170℃; for 1h; Knoevenagel condensation;100%
With silica sodium carbonate nanoparticles In acetonitrile at 70℃; Knoevenagel Condensation; Sonication; Green chemistry;95%
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 20℃; for 0.166667h; Knoevenagel condensation;94%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

4-dimethylaminobenzaldehyde oxime
2929-84-2, 37961-71-0, 77145-76-7

4-dimethylaminobenzaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In acetonitrile for 4h; Reflux;100%
With sodium hydroxide; hydroxylamine hydrochloride at 20℃; for 0.5h; grinding;98%
With 3 A molecular sieve; hydroxylamine hydrochloride; sodium acetate In ethanol for 0.25h;94%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.25h; Condensation; microwave irradiation;100%
With ammonia; iodine In water; N,N-dimethyl-formamide at 20℃; for 0.666667h;99%
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction;98%
(p-cyanobenzyl)triphenylphosphonium bromide
26104-68-7

(p-cyanobenzyl)triphenylphosphonium bromide

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

4-(dimethylamino)-4'-cyanostilbene
2844-17-9

4-(dimethylamino)-4'-cyanostilbene

Conditions
ConditionsYield
With potassium tert-butylate In methanol for 24h; Heating;100%
(i) LiOMe, MeOH, (ii) I2, xylene; Multistep reaction;
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

(E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide
97006-42-3

(E)-2-cyano-3-[4-(dimethylamino)phenyl]-2-propenamide

Conditions
ConditionsYield
With triethylamine at 20℃; for 24h; Knoevenagel condensation;100%
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 20℃; for 0.166667h; Knoevenagel condensation;94%
With Tonsil Actisil FF at 80℃; for 0.333333h; Irradiation;55%
With potassium-exchanged zirconium hydrogen phosphate at 100℃; for 4h; Knoevenagel condensation;49%
With diethylamine
morpholine
110-91-8

morpholine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(4-(dimethylamino)phenyl)(morpholino)methanone
87294-98-2

(4-(dimethylamino)phenyl)(morpholino)methanone

Conditions
ConditionsYield
With bromobenzene; potassium carbonate; triphenylphosphine; palladium diacetate In 1,2-dimethoxyethane for 24h; Heating;100%
morpholine
110-91-8

morpholine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

4-<4-(Dimethylamino)thiobenzoyl>morpholine
5925-53-1

4-<4-(Dimethylamino)thiobenzoyl>morpholine

Conditions
ConditionsYield
With sulfur for 0.0666667h; Willgerodt-Kindler reaction; microwave irradiation;100%
With 4-methyl-morpholine; sulfur In N,N-dimethyl-formamide at 135℃; for 6h; Willgerodt-Kindler reaction;92%
With sulfur In dimethyl sulfoxide at 20℃; for 16h;89%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

1-(3'-coumarinyl)-3-(4''-dimethylaminophenyl)-2-propen-1-one
91527-77-4

1-(3'-coumarinyl)-3-(4''-dimethylaminophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In chloroform for 7h; Heating;97%
With piperidine at 45 - 50℃; for 0.5h;91%
cyclohexylamine
108-91-8

cyclohexylamine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

N-<<4-(dimethylamino)phenyl>methylene>cyclohexylamine
31235-64-0

N-<<4-(dimethylamino)phenyl>methylene>cyclohexylamine

Conditions
ConditionsYield
With sodium sulfate In methanol for 4h; Ambient temperature;100%
propylamine
107-10-8

propylamine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

p-Dimethylamino-N-n-propyl-iminomethylbenzol
59488-01-6

p-Dimethylamino-N-n-propyl-iminomethylbenzol

Conditions
ConditionsYield
at 20℃; for 12h;100%
In methanol at 25℃; Mechanism; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.); kinetic solvent isotope effect;
2-(hydroxyimino)propionic acid
21209-71-2

2-(hydroxyimino)propionic acid

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

1-Carboxy-N-(4-dimethylaminophenylmethylen)ethylamin-N-oxid
93563-01-0

1-Carboxy-N-(4-dimethylaminophenylmethylen)ethylamin-N-oxid

Conditions
ConditionsYield
In ethanol Heating;100%
L-Cysteine
52-90-4

L-Cysteine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(2RS,4R)-2-(4-dimethyloamino-phenyl)-thiazolidine-4-carboxylic acid
222404-26-4

(2RS,4R)-2-(4-dimethyloamino-phenyl)-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
In ethanol at 20℃; for 5h;100%
In methanol; water84%
In ethanol; water at 20℃;
(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(S,E)-N,N-dimethyl-4-((1-phenylethylimino)methyl)aniline

(S,E)-N,N-dimethyl-4-((1-phenylethylimino)methyl)aniline

Conditions
ConditionsYield
With 4 A molecular sieve In dichloromethane at 20℃; for 70h;100%
2-tert-butyl-4-methylbenzopyrylium perchlorate

2-tert-butyl-4-methylbenzopyrylium perchlorate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

2-tert-butyl-4-<2-(4-dimethylaminophenyl)ethenyl>benzopyrylium perchlorate

2-tert-butyl-4-<2-(4-dimethylaminophenyl)ethenyl>benzopyrylium perchlorate

Conditions
ConditionsYield
In acetic anhydride at 120℃; for 0.5h;100%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

acetone
67-64-1

acetone

4-(4-N,N-dimethylaminophenyl)-3-buten-2-one
30625-58-2

4-(4-N,N-dimethylaminophenyl)-3-buten-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 25℃; for 3h;100%
With sodium hydroxide In water at 5 - 10℃; for 0.583333h;98%
With sodium hydroxide for 2.5h; Ambient temperature;96%
isopropylamine
75-31-0

isopropylamine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

<4-Dimethylamino-benzyliden>-isopropylamin
27976-83-6

<4-Dimethylamino-benzyliden>-isopropylamin

Conditions
ConditionsYield
at 20℃; for 12h;100%
at 20℃; for 48h;79%
3-acetyl-2,4-dihydroxyquinoline
26138-64-7

3-acetyl-2,4-dihydroxyquinoline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(E)-1-(2,4-Dihydroxy-quinolin-3-yl)-3-(4-dimethylamino-phenyl)-propenone

(E)-1-(2,4-Dihydroxy-quinolin-3-yl)-3-(4-dimethylamino-phenyl)-propenone

Conditions
ConditionsYield
100%
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

2-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium; dihydrogen phosphate

2-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium; dihydrogen phosphate

Conditions
ConditionsYield
With phosphoric acid In water; isopropyl alcohol for 6h; Heating;100%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(2S)-1-(diphenylphosphino)-3-methylbutan-2-amine
146476-37-1

(2S)-1-(diphenylphosphino)-3-methylbutan-2-amine

(S)-[1-[(diphenylphosphino)methyl]-2-methylpropyl]-N-(4-(dimethylamino)benzylidene)amine

(S)-[1-[(diphenylphosphino)methyl]-2-methylpropyl]-N-(4-(dimethylamino)benzylidene)amine

Conditions
ConditionsYield
In toluene Ambient temperature;100%
In toluene at 20℃; Substitution;
N-(4-nitrophenyl)ethylenediamine
6332-77-0

N-(4-nitrophenyl)ethylenediamine

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

N-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine
250386-77-7

N-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine

Conditions
ConditionsYield
In methanol at 25℃; for 1h; Condensation;100%

4-Dimethylaminobenzaldehyde Consensus Reports

Reported in EPA TSCA Inventory.

4-Dimethylaminobenzaldehyde Specification

The 4-Dimethylaminobenzaldehyde is also known as Benzaldehyde,4-(dimethylamino)-. The IUPAC name is 4-(Dimethylamino)benzaldehyde. It belongs to product categories of Intermediates of Dyes and Pigments; Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde; Exciton Chirality CD Method (for Primary Amino Groups); Absolute Configuration Determination (Exciton Chirality CD Method); Analytical Chemistry; Enantiomer Excess & Absolute Configuration Determination. This chemical is a white to off white crystalline powder and soluble in alcohol, ether, acetone, chloroform and acetic acid, slightly soluble in water. What's more, it should be sealed in ventilated and cool place away from fire, heat, oxidants, alkali without air.

Physical properties about 4-Dimethylaminobenzaldehyde are: (1)ACD/LogP: 1.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.81; (4)ACD/LogD (pH 7.4): 1.81; (5)ACD/BCF (pH 5.5): 13.98; (6)ACD/BCF (pH 7.4): 13.98; (7)ACD/KOC (pH 5.5): 229.91; (8)ACD/KOC (pH 7.4): 229.95; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.595; (12)Molar Refractivity: 47.31 cm3; (13)Molar Volume: 139 cm3; (14)Surface Tension: 42.1 dyne/cm; (15)Density: 1.072 g/cm3; (16)Flash Point: 103.3 °C; (17)Enthalpy of Vaporization: 50.45 kJ/mol; (18)Boiling Point: 266.5 °C at 760 mmHg; (19)Vapour Pressure: 0.00861 mmHg at 25 °C.

Preparation of 4-Dimethylaminobenzaldehyde: 4-Dimethylaminobenzaldehyde is prepared by reaction of 4-bromo-N,N-dimethyl-aniline with carbon monoxide. This reaction needs reagents Cr(CO)3, PPh3, Et3N, H2, catalyst Pd(PPh3)2Cl2 and solvent toluene at the temperature of 130 °C. The yield is about 35%.

4-Dimethylaminobenzaldehyde is prepared by reaction of 4-bromo-N,N-dimethyl-aniline with carbon monoxide.

Uses of 4-Dimethylaminobenzaldehyde: 4-Dimethylaminobenzaldehyde is used as a dye intermediate. Besides, it can be used as a reagent for determining urinary choline, indole, alkaloids and also can be used as chromatography reagent. Furthermore, it is used to produce 4-dimethylamino-benzoic acid 4-dimethylamino-benzyl ester. The reaction occurs with reagents Na, biphenyl and solvents benzene, hexane with other condition of heating for 12 hours. The yield is about 86%.

4-Dimethylaminobenzaldehyde is used to produce 4-dimethylamino-benzoic acid 4-dimethylamino-benzyl ester.

When you are using 4-Dimethylaminobenzaldehyde, please be cautious about it. As a chemical, it is harmful by inhalation, in contact with skin and if swallowed. There is risk of serious damage to eyes. 4-Dimethylaminobenzaldehyde is also harmful to aquatic organisms that may cause long-term adverse effects in the aquatic environment and repeated exposure may cause skin dryness or cracking. As it is flammable, it causes burns and its vapours may cause drowsiness and dizziness. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes and release to the environment. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately. After using it, keep container tightly closed away from sources of ignition.

You can still convert the following datas into molecular structure:
1) Canonical SMILES: CN(C)C1=CC=C(C=C1)C=O
2) InChI: InChI=1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3
3) InChIKey: BGNGWHSBYQYVRX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 National Technical Information Service. Vol. OTS0533441,
mouse LD50 oral 800mg/kg (800mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 National Technical Information Service. Vol. OTS0533441,
rat LD50 intraperitoneal 620mg/kg (620mg/kg)   Hine Laboratories Reports. Vol. AF33(657)-11756, Pg. 1964,
rat LDLo oral 500mg/kg (500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947.

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