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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:
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

Signal Word

Warning

Hazard Statements

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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4-(Dimethylamino) benzaldehyde.
Gao B and Zhu J-L.
Acta Crystallographica Section E, Structure Reports Online, 64(7), 1182-1182 (2008)
Kawski A, et al.
Chemical Physics Letters, 448(4), 208-212 (2007)
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
M Stefek et al.
Biochimica et biophysica acta, 1502(3), 398-404 (2000-11-09)
In the present work, pepsin digests of tail tendons from streptozotocin-diabetic rats were found to contain material that reacted rapidly at room temperature with p-dimethylaminobenzaldehyde (Ehrlich's reagent) to give an adduct with an absorbance spectrum characteristic of the Ehrlich chromogen

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