Para-Dimethylaminobenzaldehyde

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para-Dimethylaminobenzaldehyde
Para-Dimethylaminobenzaldehyde.png
Names
Preferred IUPAC name
4-(Dimethylamino)benzaldehyde
Other names
p-Dimethylaminobenzaldehyde; 4-Formyl-N,N-dimethylaniline; N,N-Dimethyl-4-formylaniline; DMAB; PDAB
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.563 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3 Yes check.svgY
    Key: BGNGWHSBYQYVRX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3
  • O=Cc1ccc(N(C)C)cc1
Properties
C9H11NO
Molar mass 149.193 g·mol−1
Appearanceyellow-white powder
Density 1.1 g/mL
Melting point 74 °C (165 °F; 347 K)
Boiling point 176 to 177 °C (349 to 351 °F; 449 to 450 K)
0.3 g/L
Hazards
Safety data sheet External MSDS
Hazard X.svg Xn
Flash point 164 °C (327 °F; 437 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

para-Dimethylaminobenzaldehyde is an organic compound containing amine and aldehyde moieties which is used in Ehrlich's reagent and Kovac's reagent to test for indoles. The carbonyl group typically reacts with the electron rich 2-position of the indole but may also react at the C-3 or N-1 positions. [1] It may also be used for determination of hydrazine.

Contents

Ehrlich's reagent

para-Dimethylaminobenzaldehyde is the main ingredient in Ehrlich's reagent. It acts as a strong electrophile which reacts with the electron-rich α-carbon (2-position) of indole rings to form a blue-colored adduct. [2] It can be used to detect the presence of indole alkaloids. Not all indole alkaloids give a colored adduct as result of steric hindrance which does not allow the reaction to proceed.[ citation needed ]

Ehrlich's reagent is also used as a stain in thin layer chromatography and as a reagent to detect urobilinogen in fresh, cool urine. If a urine sample is left to oxidize in air to form urobilin the reagent will not detect the urobilinogen. By adding few drops of reagent to 3 mL of urine in a test tube one can see a change of color, to dark pink or red. The degree of color change is proportional to the amount of urobilinogen in the urine sample.

Hydrazine determination

p-Dimethylaminobenzaldehyde reacts with hydrazine to form p-Dimethylaminobenzalazine azo-dye which has a distinct yellow color. It is therefore used for spectrophotometric determination of hydrazine in aqueous solutions at 457 nm. [3]

Isaac Asimov essay

Isaac Asimov, in a 1963 humorous essay entitled "You, too, can speak Gaelic", [4] reprinted in the anthology Adding a Dimension among others, traces the etymology of each component of the chemical name "para-di-methyl-amino-benz-alde-hyde" (e.g. the syllable "-benz-" ultimately derives from the Arabic lubān jāwī (لبان جاوي, "frankincense from Java"). Asimov points out that the name can be pronounced to the tune of the familiar jig "The Irish Washerwoman", and relates an anecdote in which a receptionist of Irish descent, hearing him singing the syllables thus, mistook them for the original Gaelic words to the jig. This essay inspired Jack Carroll's 1963 filk song "The Chemist's Drinking Song," (NESFA Hymnal Vol. 2 2nd ed. p. 65) set to the tune of that jig, which begins "Paradimethylaminobenzaldehyde, / Sodium citrate, ammonium cyanide, / ..." [5]

See also

Related Research Articles

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Thin-layer chromatography

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The Madelung synthesis is a chemical reaction that produces indoles by the intramolecular cyclization of N-phenylamides using strong base at high temperature. The Madelung synthesis was reported in 1912 by Walter Madelung, when he observed that 2-phenylindole was synthesized using N-benzoyl-o-toluidine and two equivalents of sodium ethoxide in a heated, airless, reaction. Common reaction conditions include use of sodium or potassium alkoxide as base in hexane or tetrahydrofuran solvents, at temperatures ranging between 200–400 °C. A hydrolysis step is also required in the synthesis. The Madelung synthesis is important because it is one of few known reactions that produce indoles from a base-catalyzed thermal cyclization of N-acyl-o-toluidines. The overall reaction for the Madelung synthesis follows.

Urobilinogen Chemical compound

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 Additional information needed

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References

  1. Ehmann, A. (1977). "The van URK-Salkowski reagent — a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives" (PDF). Journal of Chromatography A. 132 (2): 267–276. doi:10.1016/S0021-9673(00)89300-0. PMID   188858.
  2. Kovar, Karl-Arthur; Laudszun, Martina (February 1989). "Chemistry and Reaction Mechanisms of Rapid Tests for Drugs of Abuse and Precursors Chemicals" (PDF). UNODC: 14–15.
  3. G. W. Watt, J. D. Chrisp (1952). "A spectrophotometric method for determination of hydrazine". Anal. Chem. 24 (12): 2006–2008. doi:10.1021/ac60072a044.
  4. Asimov, Isaac (March 1963). "You, too, can speak Gaelic". The Magazine of Fantasy and Science Fiction . 24 (3): 72–81.
  5. Carroll, John A. (1963). "The Chemist's Drinking Song". Dagonell's Bardic Notebook. David P. Salley. Retrieved 14 May 2013.