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{{DISPLAYTITLE:''para''-Dimethylaminobenzaldehyde}} {{DISPLAYTITLE:''para''-Dimethylaminobenzaldehyde}}
{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 455341161
| Watchedfields = changed
⚫ | Name=''para''-Dimethylaminobenzaldehyde
⚫ | verifiedrevid = 455342021
⚫ | ImageFile = para-Dimethylaminobenzaldehyde.png
⚫ | Name =''para''-Dimethylaminobenzaldehyde
⚫ | ImageSize = 75px
⚫ | ImageFile = Para-Dimethylaminobenzaldehyde.svg
| IUPACName = 4-dimethylaminobenzaldehyde
⚫ | ImageSize = 200px
⚫ | OtherNames = 4-Formyl-N,N-dimethylaniline </br> N,N-Dimethyl-4-formylaniline
| PIN= 4-(Dimethylamino)benzaldehyde
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = ''p''-Dimethylaminobenzaldehyde; 4-Formyl-''N'',''N''-dimethylaniline; ''N'',''N''-Dimethyl-4-formylaniline; DMAB; PDAB
⚫ | CASNo = 100-10-7
⚫ |Section1={{Chembox Identifiers
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 100-10-7
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 7199
| EC_number = 202-819-0
⚫ | PubChem = 7479
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 91114
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V7E88PR1YB
⚫ | InChI = 1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3 | StdInChI = 1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BGNGWHSBYQYVRX-UHFFFAOYSA-N | StdInChIKey = BGNGWHSBYQYVRX-UHFFFAOYSA-N
⚫ | SMILES = O=Cc1ccc(N(C)C)cc1
⚫ | PubChem = 7479
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 7199
⚫ | SMILES = O=Cc1ccc(N(C)C)cc1
⚫ | InChI = InChI=1S/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=9 | H=11 | N=1 | O=1 | C=9 | H=11 | N=1 | O=1
| Appearance = | Appearance = yellow-white powder
| Density = yellow-white powder | Density = 1.1 g/mL
| MeltingPtC = 74 | MeltingPtC = 74
| BoilingPt = 176-177 °C | BoilingPtC = 176 to 177
| BoilingPt_notes =
| Solubility = | Solubility = 0.3 g/L
⚫ }}
⚫ | Section3 = {{Chembox Hazards
| EUClass = {{Hazchem Xn}}
⚫ | ExternalMSDS =
| FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=4-(Dimethylamino)benzaldehyde |url=https://pubchem.ncbi.nlm.nih.gov/compound/7479#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=24 December 2021 |language=en}}</ref>
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|317|319|411}}
| PPhrases = {{P-phrases|261|264|270|272|273|280|301+312|302+352|305+351+338|321|330|333+313|337+313|363|391|501}}
⚫ | ExternalSDS =
| FlashPtC = 164
| AutoignitionPtC =
⚫ }}
}} }}


'''''para''-Dimethylaminobenzaldehyde''' is an organic compound containing ] and ] ] which is used in Ehrlich's reagent for determination of hydrazine. '''''para''-Dimethylaminobenzaldehyde''' is an organic compound containing ] and ] ] which is used in ] and ] to test for ]. 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.<ref>{{Cite journal | last1 = Ehmann | first1 = A. | title = The van URK-Salkowski reagent — a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives | doi = 10.1016/S0021-9673(00)89300-0 | journal = Journal of Chromatography A | volume = 132 | issue = 2 | pages = 267–276| year = 1977 | pmid = 188858| url = https://erowid.org/psychoactives/testing/testing_field_article2.pdf}}</ref> It may also be used for determination of ].


==Ehrlich's reagent==
==Urobilinogen determination==
⚫ ''para''-Dimethylaminobenzaldehyde is the main ingredient in ]. It acts as a strong electrophile which reacts with the electron-rich ] (2-position) of indole rings to form a blue-colored adduct.<ref>{{Cite journal|last1=Kovar|first1=Karl-Arthur|last2=Laudszun|first2=Martina|date=February 1989|title=Chemistry and Reaction Mechanisms of Rapid Tests for Drugs of Abuse and Precursors Chemicals|url=https://www.unodc.org/pdf/scientific/SCITEC6.pdf|journal=UNODC|pages=14–15}}</ref> It can be used to detect the presence of ]s. Not all indole alkaloids give a colored adduct as result of ] which does not allow the reaction to proceed.{{citation needed|date=April 2014}}
⚫ It is used in Ehrlich's reagent, which may be used as a ], or as a reagent to detect ] in fresh, cool ].If urine sample is left to ] in ] to form ] the ] will not detect the urobilinogen. By adding few drops of reagent to 3 ml of urine in a ] one can see a change of color from above, to dark pink or red. The degree of color change is proportional to the amount of urobilinogen in the urine sample.


⚫ Ehrlich's reagent is also used as a stain in ] and as a reagent to detect ] in fresh, cool ]. If a urine sample is left to ] in air to form ] the ] will not detect the urobilinogen. By adding few drops of reagent to 3 mL of urine in a ] 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.
⚫ Ehrlich's reagent is a strong electrophile which reacts with the electron-rich ] of indole rings to form a blue-coloured adduct. It can be used to detect the presence of ]. Not all indole alkaloids give a coloured adduct as result of steric hindrance which does not allow the reaction to proceed.


==Hydrazine determination== ==Hydrazine determination==
p-Dimethylaminobenzaldehyde reacts with ] to form an ], which has a distinct yellow color. It is therefore used for ] determination of hydrazine in aqueous solutions at 457&nbsp;nm.<ref>{{Cite journal| author = G. W. Watt, J. D. Chrisp | year = 1952 | title = A spectrophotometric method for determination of hydrazine | journal = ] | volume = 24 | pages = 2006–2008 | doi = 10.1021/ac60072a044}}</ref> ''p''-Dimethylaminobenzaldehyde reacts with ] to form ''p''-Dimethylaminobenzalazine ] which has a distinct yellow color. It is therefore used for ] determination of hydrazine in aqueous solutions at 457&nbsp;nm.<ref>{{Cite journal| author = G. W. Watt, J. D. Chrisp | year = 1952 | title = A spectrophotometric method for determination of hydrazine | journal = ] | volume = 24 | pages = 2006–2008 | doi = 10.1021/ac60072a044| issue = 12}}</ref>


==Isaac Asimov essay== ==Isaac Asimov essay==


], in a 1963 humorous essay entitled "You, too, can speak Gaelic,"<ref>{{Cite journal| author = Asimov, Isaac | year = 1963 | month = March | title = You, too, can speak Gaelic | journal = ] | volume = 24 | number=3 | pages = 72–81 }}</ref>, reprinted in the anthology ] among others, traces the ] of each component of the chemical name "paradimethylaminobenzaldehyde" (e.g. the syllable "-benz-" ultimately derives from the Arabic lubān jāwī (لبان خاوي, "frankincense from Java"). Asimov points out that the name can be pronounced to the tune of the familiar ] "]," and relates an anecdote in which a receptionist of Irish descent, hearing him singing the syllables thus, mistook them for the original ] words to the jig. This essay likely inspired the ] song "The Chemist's Drinking Song," set to the tune of that jig, which begins "Paradimethylaminobenzaldehyde, / Sodium citrate, ammonium cyanide, / ..."<ref>http://www-cs.canisius.edu/~salley/SCA/Bardbook/chemist.html</ref> ], in a 1963 humorous essay entitled "You, too, can speak Gaelic",<ref>{{Cite journal| last= Asimov |first= Isaac |date=March 1963 | title = You, too, can speak Gaelic | journal = ] | volume = 24 | pages = 72–81 | issue=3 }}</ref> reprinted in the anthology '']'' among others, traces the ] 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, "] from ]"). Asimov points out that the name can be pronounced to the tune of the familiar ] "]", and relates an anecdote in which a receptionist of Irish descent, hearing him singing the syllables thus, mistook them for the original ] words to the jig. This essay inspired Jack Carroll's 1963 ] song "The Chemist's Drinking Song," (] Hymnal Vol.&nbsp;2 2nd&nbsp;ed. p.&nbsp;65) set to the tune of that jig, which begins "Paradimethylaminobenzaldehyde, / ], ], / ..."<ref>{{cite web |url= http://www-cs.canisius.edu/~salley/SCA/Bardbook/chemist.html
| title = The Chemist's Drinking Song |first=John A. |last= Carroll
| year = 1963 |work= Dagonell's Bardic Notebook |publisher= David P. Salley
| access-date = 14 May 2013 }}</ref>


== See also == == See also ==
* ] * ]


==Reference== ==References==
{{reflist}}
<references/>


{{DEFAULTSORT:Dimethylaminobenzaldehyde, Para-}} {{DEFAULTSORT:Dimethylaminobenzaldehyde, Para-}}
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