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33130

Sigma-Aldrich

4-(Dimethylamino)benzaldehyde

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

Synonym(s):

Ehrlich’s reagent

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About This Item

Linear Formula:
(CH3)2NC6H4CHO
CAS Number:
Molecular Weight:
149.19
Beilstein/REAXYS Number:
606802
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21

agency

USP/NF
reag. Ph. Eur.

Quality Level

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

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

327.2 °F - closed cup

flash_point_c

164 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)


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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
Spectrophotometric determination of certain cephalosporins through oxidation with cerium(IV) and 1-chlorobenzotriazole.
M M Ayad et al.
Journal of pharmaceutical and biomedical analysis, 20(3), 557-564 (2000-03-04)

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