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Sigma-Aldrich

4-(Dimethylamino)benzaldehyde

98%

Synonym(s):

Ehrlich’s reagent

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About This Item

Linear Formula:
(CH3)2NC6H4CHO
CAS Number:
100-10-7
Molecular Weight:
149.19
Beilstein:
606802
EC Number:
202-819-0
MDL number:
MFCD00003381
UNSPSC Code:
12352100
PubChem Substance ID:
24846936
NACRES:
NA.22
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Quality Level

100

Assay

98%

form

solid

mp

72-75 °C (lit.)

solubility

H2O: slightly soluble

functional group

aldehyde
amine

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)benzaldehydeis an organic carbonyl compound containing amino and aldehyde groups. The compound is used in Ehrlich and Kovac′s reagents to test indole.4-(Dimethylamino)benzaldehyde is used to prepare aldehydes from Grignard reagents. In addition, it is used as a color test reagent for pyrroles, primary amines, and hydrazines.[1]

Application

4-(Dimethylamino)benzaldehyde was used in the chitinase assay[2].

4-(Dimethylamino)benzaldehyde is used:
  • In the synthesis of azo-azomethine dyes by condensation reaction.[3]
  • As a reagent in the synthesis of molecular adduct 4DMAB4NP (4-(dimethylamino)benzaldehyde 4-nitrophenol) by reacting with 4-nitrophenol.[4]
  • In the preparation of Schiff base.[5]
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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2152
BCCL1057
BCCJ4266
BCCF0489
BCCC1324

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Synthesis, structural, spectral, third order nonlinear optical and quantum chemical investigations on hydrogen bonded novel organic molecular adduct 4-(dimethylamino) benzaldehyde 4-nitrophenol for opto-electronic applications
Karthick S, et al.
Journal of Molecular Structure, 1178, 352-365 (2019)
Facile synthesis of Co3O4 and ZnO nanoparticles by thermal decomposition of novel Co (II) and Zn (II) Schiff base complexes for studying their biological properties and photocatalytic degradation of crystal violet dye
Katouah HA
Journal of Molecular Structure, 1241, 130676-130676 (2021)
Synthesis, spectroscopic and TD-DFT quantum mechanical study of azo-azomethine dyes. A laser induced trans-cis-trans photoisomerization cycle
Georgiev A, et al.
Spectrochimica Acta Part A: Molecular Spectroscopy, 192, 263-274 (2018)
4-(Dimethylamino) benzaldehyde
Brickner SJ
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
M Legrand et al.
Proceedings of the National Academy of Sciences of the United States of America, 84(19), 6750-6754 (1987-10-01)
Four endochitinases (poly[1,4-(N-acetyl-beta-D-glucosaminide)] glycanohydrolase, EC 3.2.1.14) have been purified from leaves of Nicotiana tabacum cv. Samsun NN reacting hypersensitively to tobacco mosaic virus. Two of them are acidic proteins of molecular weights 27,500 and 28,500 and have been identified as
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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