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Sigma-Aldrich

4-(Dimethylamino)benzaldehyde

puriss. p.a., reag. Ph. Eur., ≥99% (perchloric acid titration)

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Synonym(s):
Ehrlich’s reagent
Linear Formula:
(CH3)2NC6H4CHO
CAS Number:
100-10-7
Molecular Weight:
149.19
Beilstein:
606802
EC Number:
202-819-0
MDL number:
MFCD00003381
PubChem Substance ID:
57648761

Agency

USP/NF
reag. Ph. Eur.

Quality Level

200

grade

puriss. p.a.

Assay

≥99% (perchloric acid titration)

ign. residue

≤0.1% (as SO4)

loss

≤0.5% loss on drying

mp

72-75 °C (lit.)
73-75 °C

solubility

ethanol: 0.1 g/10 mL

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤50 mg/kg
K: ≤50 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤50 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

CN(C)c1ccc(C=O)cc1

InChI

1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3

InChI key

BGNGWHSBYQYVRX-UHFFFAOYSA-N

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General description

4-(Dimethylamino)benzaldehyde is also commonly referred as Ehrlich′s reagent. Its crystal structure has been investigated by X-ray analysis. Its crystals belong to the monoclinic crystal system and exhibits space group P21/n. 4-(Dimethylamino)benzaldehyde exhibits dual fluorescence. Its dipole moment in various excited states has been evaluated using their electronic spectra and Bilot-Kawski theory.

Application

4-(Dimethylamino)benzaldehyde in micelle (sodium dodecyl sulphate) containing medium may be used for the quantification of hydroxyproline in meat samples by spectrophotometric methods.
Forms colored condensation products (Schiff bases) with pyrroles and primary amines.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1B

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

327.2 °F - closed cup

Flash Point(C)

164 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Kawski A, et al.
Chemical Physics Letters, 448(4), 208-212 (2007)
4-(Dimethylamino) benzaldehyde.
Gao B and Zhu J-L.
Acta Crystallographica Section E, Structure Reports Online, 64(7), 1182-1182 (2008)
Determination of pyrrole derivatives and hydroxyproline with 4-(dimethylamino) benzaldehyde in a micellar medium.
Esteve-Romero JS, et al.
Analytical Letters, 27(8), 1557-1567 (1994)
Jun-Min Guo et al.
Journal of agricultural and food chemistry, 58(11), 6556-6561 (2010-05-15)
A simple colorimetric method for the differentiation of indoleacetic acid (IAA) and indolebutyric acid (IBA) in plant samples is described. The color change is based upon the reaction between the auxins and p-(dimethylamino)benzaldehyde (PDAB, Ehrlich reagent) following the electrophilic substitution
F J Hidalgo et al.
Analytical biochemistry, 262(2), 129-136 (1998-09-29)
The Ehrlich reaction was optimized to determine pyrrolized proteins produced as a consequence of lipid peroxidation and oxidative stress. The procedure consisted of the treatment of the modified protein with p-(dimethylamino)benzaldehyde at a controlled acidity and temperature, and the determination
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