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4-Dimethylaminobenzaldehyde

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4-Dimethylaminobenzaldehyde Basic information

Product Name:
4-Dimethylaminobenzaldehyde
Synonyms:
  • P-dimethylaminobenzaldehyde test solution(ChP)
  • 4-(Dimethylamino)benzaldehyde test solution(ChP)
  • 4-Dimethylaminobenzaldehyde 、p-Dimethylaminobenzaldehyde
  • HYDRAZINE METER SOLUTION
  • DIMETHYLAMINOBENZALDEHYDE
  • ERLICH'S REAGENT
  • EHRLICH'S REAGENT
  • EHRLICH'S REAGENT SICC
CAS:
100-10-7
MF:
C9H11NO
MW:
149.19
EINECS:
202-819-0
Product Categories:
  • aldehyde
  • Analytical Reagents
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  • Analytical/Chromatography
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  • Intermediates of Dyes and Pigments
  • Aromatic Aldehydes & Derivatives (substituted)
  • Benzaldehyde
  • Exciton Chirality CD Method (for Primary Amino Groups)
  • Absolute Configuration Determination (Exciton Chirality CD Method)
  • Analytical Chemistry
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  • Stains &amp
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  • Isoquinolines ,Quinolines ,Quinaldines
  • 100-10-7
Mol File:
100-10-7.mol
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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
Flash point:
164 °C
storage temp. 
2-8°C
solubility 
alcohol: passes test (APHA ≤60)
pka
pK1:1.647(+1) (25°C)
form 
Liquid
color 
White to pale yellow
Odor
Characteristic 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.
InChIKey
BGNGWHSBYQYVRX-UHFFFAOYSA-N
CAS DataBase Reference
100-10-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzaldehyde, 4-(dimethylamino)-(100-10-7)
EPA Substance Registry System
Benzaldehyde, 4-(dimethylamino)- (100-10-7)
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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 Temperature
445 °C
TSCA 
Yes
HS Code 
29223900
Toxicity
LD50 orally in Rabbit: > 6400 mg/kg

MSDS

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4-Dimethylaminobenzaldehyde Usage And Synthesis

Chemical Properties

4-Dimethylaminobenzaldehyde is white to off white crystalline powder

Uses

In 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.

Uses

Forms colored condensation products (Schiff bases) with pyrroles1 and primary amines.2

Uses

In 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.

Uses

4-(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.

Uses

Used as derivitizing agent.

Uses

4-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.

Definition

4-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 Description

Kovac′s reagent for indoles is a solution of 4-(dimethylamino)benzaldehyde and hydrochloric acid in n-butanol.

Biochem/physiol Actions

Kovac′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 Methods

Crystallise 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.]

4-DimethylaminobenzaldehydeSupplier

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