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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 401999093 |
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|Watchedfields = changed |
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| ImageFile = Benzyldimethylamine.svg |
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|verifiedrevid = 414428222 |
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| ImageSize = |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| IUPACName = N,N-dimethyl-1-phenylmethanamine |
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|ImageFileL1 = Benzyldimethylamine.svg |
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| OtherNames = N,N-Dimethylbenzenemethanamine, N-Benzyldimethylamine, Dimethylbenzylamine, Benzyl-N,N-dimethylamine, N-(Phenylmethyl)dimethylamine, BDMA, Sumine 2015, Benzenemethanamine, Dabco B-16, Araldite accelerator 062, N,N-Dimethyl(phenyl)methanamine |
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|ImageSizeL1 = 135 |
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| Section1 = {{Chembox Identifiers |
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|ImageFileR1 = Dimethylbenzylamine 3D ball.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ImageSizeR1 = 115 |
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|PIN = ''N'',''N''-Dimethyl-1-phenylmethanamine |
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|OtherNames = ''N'',''N''-Dimethylbenzenemethanamine, ''N'',''N''-Dimethylbenzylamine, ''N''-Benzyldimethylamine, Dimethylbenzylamine, Benzyl-''N'',''N''-dimethylamine, ''N''-(Phenylmethyl)dimethylamine, BDMA, Sumine 2015, Benzenemethanamine, Dabco B-16, Araldite accelerator 062, ''N'',''N''-Dimethyl(phenyl)methanamine, DMBA<ref>{{cite web|website = The Good Scents Company|title = N,N-dimethyl benzyl amine|access-date = 1 November 2020|url =http://www.thegoodscentscompany.com/data/rw1263471.html }}</ref> |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 103-83-3 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7398 |
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| ChemSpiderID = 7398 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = XXBDWLFCJWSEKW-UHFFFAOYAQ |
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| ChEMBL = 45591 |
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| ChEMBL = 45591 |
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| EINECS = 203-149-1 |
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| PubChem = 7681 |
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| RTECS = DP4500000 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = TYP7AXQ1YJ |
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| UNNumber = 2619 |
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| SMILES = N(C)(Cc1ccccc1)C |
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| InChI = 1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 |
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| InChIKey = XXBDWLFCJWSEKW-UHFFFAOYAQ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 |
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| StdInChI = 1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XXBDWLFCJWSEKW-UHFFFAOYSA-N |
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| StdInChIKey = XXBDWLFCJWSEKW-UHFFFAOYSA-N |
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}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section2={{Chembox Properties |
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| CASNo = 103-83-3 |
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| EINECS = 203-149-1 |
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|C=9 | H=13 | N=1 |
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|Appearance = colourless liquid |
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| PubChem = 7681 |
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|Density = 0.91 g/cm<sup>3</sup> at 20 °C |
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| SMILES = N(C)(Cc1ccccc1)C |
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|MeltingPtC = -75 |
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| InChI = 1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 |
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|BoilingPtC = 180 to 183 |
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}} |
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|Solubility = 1.2 g/100mL |
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| Section2 = {{Chembox Properties |
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}} |
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|C=9|H=13|N=1 |
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|Section3={{Chembox Hazards |
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| Appearance = colourless to yellow liquid |
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|NFPA-H = 3 |
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| Density = 0.91 g/cm<sup>3</sup> at 20 °C |
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|NFPA-F = 3 |
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| MeltingPt = -75 °C |
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|NFPA-R = 0 |
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| BoilingPt = 180 - 183 °C |
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| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} |
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| Solubility = 1.2 g/L (27 °C) |
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| GHSSignalWord = Danger |
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}} |
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| HPhrases = {{H-phrases|226|302|312|314|332|412}} |
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| Section3 = {{Chembox Hazards |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|330|363|370+378|403+235|405|501}} |
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| MainHazards = |
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| NFPA-H = 3 |
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|FlashPtC = 55 |
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|AutoignitionPtC = 410 |
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| NFPA-F = 2 |
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}} |
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| NFPA-R = 0 |
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| NFPA-O = |
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| RPhrases = {{R10}}, {{R20}}, {{R21}}, {{R22}}, {{R34}}, {{R52}}, {{R53}} |
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| SPhrases = {{S26}}, {{S36}}, {{S45}}, {{S61}} |
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| FlashPt = 55 °C |
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| Autoignition = 410 °C |
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'''Dimethylbenzylamine''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>. The molecule contains the ] group, C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>, attached to a dimethyl] ]. It is used as a catalyst for the formation of ] foams and epoxy resins. |
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'''Dimethylbenzylamine''' is the ] with the ] C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>. The molecule consists of a ] group, C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>, attached to a dimethyl] ]. It is a colorless liquid. It is used as a catalyst for the formation of ] foams and epoxy resins. |
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==Synthesis== |
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Like some other benzyl compounds, the molecule undergoes ] with ]. Because of this reaction, many derivatives are known with the formula 2-X-C<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub> (X = SR, PR<sub>2</sub>, etc). |
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''N'',''N''-Dimethylbenzylamine can be synthesized by the ] of ]<ref>{{cite journal|last1 = Icke|first1 = R. N.|last2 = Wisegarver|first2 = B. B.|last3 = Alles|first3 = G. A.|year = 1945|title = β-Phenylethyldimethylamine|volume = 25|journal=Organic Syntheses|page = 89| doi=10.15227/orgsyn.025.0089}}</ref><ref>{{cite journal| doi = 10.1021/ja01338a041|year = 1933|last1 = Clarke|first1 = H. T.|author-link1 = Hans Thacher Clarke|last2 = Gillespie|first2 = H. B.|last3 = Weisshaus|first3 = S. Z.|journal = ]|volume = 55|issue = 11|page = 4571|title = The Action of Formaldehyde on Amines and Amino Acids}}</ref> |
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==Reactions== |
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The amine is basic and undergoes quaternization with ] to give the ammonium salt <sup>+</sup>I<sup>-</sup>.<ref>{{cite journal | author = Brasen, W. R.; Hauser, C. R. | date = 1963 | title = 2-Methylbenzyldimethylamine | journal = Organic Syntheses | volume = Coll. 4 | issue = | pages = 585| pmid = | doi = | url = http://www.orgsyn.org/orgsyn/pdfs/CV4P0585.pdf | accessdate = }}</ref> Such salts are useful ]s. |
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It undergoes ] with ]: |
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:[C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub> + BuLi → 2-LiC<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub> |
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==See also== |
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:LiC<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub> + E<sup>+</sup> → 2-EC<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub> |
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*] |
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Via these reactions, many derivatives are known with the formula 2-X-C<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub> (E = SR, PR<sub>2</sub>, etc.). |
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The amine is basic and undergoes ] with ] (e.g. ]) to give quaternary ammonium salts:<ref>{{cite journal|title=o-Methylethylbenzyl Alcohol|author=W. R. Brasen |author2=C. R. Hauser |journal=Org. Synth.|year=1954|volume=34|page=58|doi=10.15227/orgsyn.034.0058}}</ref> |
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:<sup>+</sup>X<sup>−</sup> |
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Such salts are useful ]s. |
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==Uses== |
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As the molecule has tertiary amine functionality, two of the key uses are as an epoxy-amine cure enhancement catalyst and also as a polyurethane catalyst.<ref>{{Cite journal |last1=Firouzmanesh |first1=Mr |last2=Azar |first2=A Aref |date=June 2003 |title=Study of the effect of BDMA catalyst in the epoxy novolac curing process by isothermal DSC |url=https://onlinelibrary.wiley.com/doi/10.1002/pi.1135 |journal=Polymer International |language=en |volume=52 |issue=6 |pages=932–937 |doi=10.1002/pi.1135 |issn=0959-8103}}</ref><ref>{{Cite journal |last1=Firouzmanesh |first1=M. R. |last2=Azar |first2=A. Aref |date=March 2005 |title=Study of the Effect of BDMA Catalyst in Epoxy Novolac Curing Process by Isothermal DSC |url=http://journals.sagepub.com/doi/10.1177/0731684405033953 |journal=Journal of Reinforced Plastics and Composites |language=en |volume=24 |issue=4 |pages=345–353 |doi=10.1177/0731684405033953 |bibcode=2005JRPC...24..345F |s2cid=93979685 |issn=0731-6844}}</ref><ref>{{Cite journal |last1=Zhang |first1=Qian |last2=Hu |first2=Xiang-Ming |last3=Wu |first3=Ming-Yue |last4=Zhao |first4=Yan-Yun |last5=Yu |first5=Chuang |date=2018-07-15 |title=Effects of different catalysts on the structure and properties of polyurethane/water glass grouting materials |journal=Journal of Applied Polymer Science |language=en |volume=135 |issue=27 |page=46460 |doi=10.1002/app.46460|doi-access=free }}</ref><ref>{{Cite journal |title=Benzyldimethylamine (BDMA): Catalyst of Choice with Epoxy Embedding Media |date=2003 |doi=10.1017/s1551929500053104 |last1=Mascorro |first1=José A. |journal=Microscopy Today |volume=11 |issue=4 |page=47 |doi-access=free }}</ref> |
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==References== |
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==References== |
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==External links== |
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==External links== |
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* {{Webarchive|url=https://web.archive.org/web/20071011092357/http://ptcl.chem.ox.ac.uk/MSDS/DI/N,N-dimethylbenzylamine.html |date=2007-10-11 }} |
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