4-Dimethylaminobenzaldehyde

4-Dimethylaminobenzaldehyde Chemical Properties
Melting point 72-75 °C(lit.)
Boiling point 176-177 °C (17 mmHg)
density 1.10 g/mL at 20 °C
vapor pressure <0.1 hPa (20 °C)
refractive index n20/D 1.417
Fp 164 °C
storage temp. 2-8°C
solubility alcohol: passes test (APHA ≤60)
pkapK1:1.647(+1) (25°C)
form Liquid
color White to pale yellow
OdorCharacteristic odor
Water Solubility 0.3 g/L (20 ºC)
Sensitive Air Sensitive
Merck 14,3230
BRN 606802
Stability:Stable, but light sensitive. Incompatible with bases, strong oxidizing agents.
InChIKeyBGNGWHSBYQYVRX-UHFFFAOYSA-N
LogP1.810
CAS DataBase Reference100-10-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzaldehyde, 4-(dimethylamino)-(100-10-7)
EPA Substance Registry SystemBenzaldehyde, 4-(dimethylamino)- (100-10-7)
Safety Information
Hazard Codes C,Xn,Xi,F
Risk Statements 36/37/38-52/53-22-67-41-37/38-10-66-37-34-20-20/21/22-36-11
Safety Statements 7-16-24/25-26-61-45-39-36/37/39-36
RIDADR UN 2920 8/PG 2
WGK Germany 1
RTECS CU5775000
8
Autoignition Temperature445 °C
TSCA Yes
HS Code 29223900
ToxicityLD50 orally in Rabbit: > 6400 mg/kg
MSDS Information
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4-Dimethylaminobenzaldehyde English
SigmaAldrich English
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4-Dimethylaminobenzaldehyde Usage And Synthesis
Chemical Properties4-Dimethylaminobenzaldehyde is white to off white crystalline powder
UsesIn the presence of oxygen, some bacteria, like E.coli, are able to split tryptophan into indole and alpha-aminopropionic acid. This reagent is for detecting the indole and identify the indole-positive and indole-negative microorganisms.
UsesForms colored condensation products (Schiff bases) with pyrroles1 and primary amines.2
UsesIn the presence of oxygen, some bacteria, like E. coli, are able to split tryptophan into indole and α-aminopropionic acid. This reagent is for detecting the indole and identifying the indole-positive and indole-negative microorganisms.
Uses4-(Dimethylamino)benzaldehyde is used in Ehrlich's reagent for spectrophotometric determination of hydrazine as it reacts to form azo dyes. 4-(Dimethylamino)benzaldehyde is used for determination of u rine bilirubin and porphobilinogen.
UsesUsed as derivitizing agent.
Uses4-Dimethylaminobenzaldehyde is used to prepare colorful Schiff base adducts with amines, pyrroles and indoles. It is often used in the Ehrlich reaction, test for the presence of indoles in a sample containing alkaloids and determination of hydrazine.
Definition4-Dimethylaminobenzaldehyde is a mamber of the class of benzaldehydes carrying a dimethylamino substituent at position 4. Used as an indicator for detection of indoles and hydrazine.
Synthesis Reference(s)Journal of Heterocyclic Chemistry, 26, p. 1563, 1989
Organic Syntheses, Coll. Vol. 4, p. 331, 1963
Tetrahedron Letters, 30, p. 287, 1989 DOI: 10.1016/S0040-4039(00)95181-5
General DescriptionKovac′s reagent for indoles is a solution of 4-(dimethylamino)benzaldehyde and hydrochloric acid in n-butanol.
Biochem/physiol ActionsKovac′s reagent detects the indole and aids in identifying the indole-positive and indole-negative microorganisms. E. coli can split tryptophan into indole and α-aminopropionic acid in the presence of the enzyme tryptophanase. p-Aminobenzaldehyde present in the reagent reacts with indole to form a cherry-red complex, that is soluble in alcohol, ether, and chloroform. It is recommended to use glucose free media and peptone with a high tryptophan content for the test.
Purification MethodsCrystallise DMAB from water, hexane, or from EtOH (2mL/g), after charcoal treatment, by adding excess of water. Alternatively dissolve it in aqueous acetic acid, filter, and precipitate it with ammonia. Finally recrystallise it from EtOH. It is used for the detection of pyrroles [Iyer et al. J Org Chem 59 6038 1994]. [Beilstein 14 IV 51.]
Dacthal Benzenamine, N,N-dimethyl-, sulfate (1:1) N,N-Dimethylformamide ETHANE 4-Dimethylaminobenzaldehyde EhrlichReagent 2-Dimethylaminoethanol 4-(Trifluoromethyl)benzaldehyde Dimethyl fumarate BLOCKING REAGENT GE Benzaldehyde p-Anisaldehyde Dimethyl sulfoxide Dimethyl disulfide Dimethyl ether Dimethyl carbonate LITHIUM PERIODATE Dimethyl sulfate

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