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.[2] It may also be used for determination of hydrazine.
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.[3] 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 determinationedit
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.[4]
Isaac Asimov essayedit
Isaac Asimov, in a 1963 humorous essay entitled "You, too, can speak Gaelic",[5] 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, / ..."[6]
^"4-(Dimethylamino)benzaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 24 December 2021.
^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.
^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.
^G. W. Watt, J. D. Chrisp (1952). "A spectrophotometric method for determination of hydrazine". Anal. Chem.24 (12): 2006–2008. doi:10.1021/ac60072a044.
^Carroll, John A. (1963). "The Chemist's Drinking Song". Dagonell's Bardic Notebook. David P. Salley. Retrieved 14 May 2013.
January 01, 1970
para, dimethylaminobenzaldehyde, organic, compound, containing, amine, aldehyde, moieties, which, used, ehrlich, reagent, kovac, reagent, test, indoles, carbonyl, group, typically, reacts, with, electron, rich, position, indole, also, react, positions, also, u. 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 2 It may also be used for determination of hydrazine para Dimethylaminobenzaldehyde Names Preferred IUPAC name 4 Dimethylamino benzaldehyde Other names p Dimethylaminobenzaldehyde 4 Formyl N N dimethylaniline N N Dimethyl 4 formylaniline DMAB PDAB Identifiers CAS Number 100 10 7 Y 3D model JSmol Interactive image ChEBI CHEBI 91114 Y ChemSpider 7199 Y ECHA InfoCard 100 002 563 EC Number 202 819 0 PubChem CID 7479 UNII V7E88PR1YB Y CompTox Dashboard EPA DTXSID5021835 InChI InChI 1S C9H11NO c1 10 2 9 5 3 8 7 11 4 6 9 h3 7H 1 2H3 YKey BGNGWHSBYQYVRX UHFFFAOYSA N YInChI 1S C9H11NO c1 10 2 9 5 3 8 7 11 4 6 9 h3 7H 1 2H3 SMILES O Cc1ccc N C C cc1 Properties Chemical formula C 9H 11N O Molar mass 149 193 g mol 1 Appearance yellow 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 Solubility in water 0 3 g L Hazards GHS labelling 1 Pictograms Signal word Warning Hazard statements H302 H317 H319 H411 Precautionary statements P261 P264 P270 P272 P273 P280 P301 P312 P302 P352 P305 P351 P338 P321 P330 P333 P313 P337 P313 P363 P391 P501 Flash point 164 C 327 F 437 K Safety data sheet SDS External MSDS Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Ehrlich s reagent 2 Hydrazine determination 3 Isaac Asimov essay 4 See also 5 ReferencesEhrlich s reagent editpara Dimethylaminobenzaldehyde is the main ingredient in Ehrlich s reagent It acts as a strong electrophile which reacts with the electron rich a carbon 2 position of indole rings to form a blue colored adduct 3 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 editp 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 4 Isaac Asimov essay editIsaac Asimov in a 1963 humorous essay entitled You too can speak Gaelic 5 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 luban jawi 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 6 See also editPaul EhrlichReferences edit 4 Dimethylamino benzaldehyde pubchem ncbi nlm nih gov Retrieved 24 December 2021 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 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 G W Watt J D Chrisp 1952 A spectrophotometric method for determination of hydrazine Anal Chem 24 12 2006 2008 doi 10 1021 ac60072a044 Asimov Isaac March 1963 You too can speak Gaelic The Magazine of Fantasy and Science Fiction 24 3 72 81 Carroll John A 1963 The Chemist s Drinking Song Dagonell s Bardic Notebook David P Salley Retrieved 14 May 2013 Retrieved from https en wikipedia org w index php title Para Dimethylaminobenzaldehyde amp oldid 1061845050, wikipedia, wiki, book, books, library,
