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Wikipedia

Dimethylbenzylamine

April 09, 2024

Dimethylbenzylamine is the organic compound with the formula C6H5CH2N(CH3)2. The molecule consists of a benzyl group, C6H5CH2, attached to a dimethylamino functional group. It is a colorless liquid. It is used as a catalyst for the formation of polyurethane foams and epoxy resins.

Dimethylbenzylamine
Names
Preferred IUPAC name
N,N-Dimethyl-1-phenylmethanamine
Other names
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[1]
Identifiers
  • 103-83-3 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL45591 Y
ChemSpider
  • 7398 Y
ECHA InfoCard 100.002.863
EC Number
  • 203-149-1
  • 7681
RTECS number
  • DP4500000
UNII
  • TYP7AXQ1YJ N
UN number 2619
  • DTXSID8021854
  • InChI=1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 Y
    Key: XXBDWLFCJWSEKW-UHFFFAOYSA-N Y
  • InChI=1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3
    Key: XXBDWLFCJWSEKW-UHFFFAOYAQ
  • N(C)(Cc1ccccc1)C
Properties
C9H13N
Molar mass 135.210 g·mol−1
Appearance colourless liquid
Density 0.91 g/cm3 at 20 °C
Melting point −75 °C (−103 °F; 198 K)
Boiling point 180 to 183 °C (356 to 361 °F; 453 to 456 K)
1.2 g/100mL
Hazards
GHS labelling:
Danger
H226, H302, H312, H314, H332, H412
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 55 °C (131 °F; 328 K)
410 °C (770 °F; 683 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Synthesis edit

N,N-Dimethylbenzylamine can be synthesized by the Eschweiler–Clarke reaction of benzylamine[2][3]

Reactions edit

It undergoes directed ortho metalation with butyl lithium:

[C6H5CH2N(CH3)2 + BuLi → 2-LiC6H4CH2N(CH3)2
LiC6H4CH2N(CH3)2 + E+ → 2-EC6H4CH2N(CH3)2

Via these reactions, many derivatives are known with the formula 2-X-C6H4CH2N(CH3)2 (E = SR, PR2, etc.).

The amine is basic and undergoes quaternization with alkyl halides (e.g. hexyl bromide) to give quaternary ammonium salts:[4]

[C6H5CH2N(CH3)2 + RX → [C6H5CH2N(CH3)2R]+X−

Such salts are useful phase transfer catalysts.

Uses edit

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.[5][6][7][8]

References edit

  1. ^ "N,N-dimethyl benzyl amine". The Good Scents Company. Retrieved 1 November 2020.
  2. ^ Icke, R. N.; Wisegarver, B. B.; Alles, G. A. (1945). "β-Phenylethyldimethylamine". Organic Syntheses. 25: 89. doi:10.15227/orgsyn.025.0089.
  3. ^ Clarke, H. T.; Gillespie, H. B.; Weisshaus, S. Z. (1933). "The Action of Formaldehyde on Amines and Amino Acids". J. Am. Chem. Soc. 55 (11): 4571. doi:10.1021/ja01338a041.
  4. ^ W. R. Brasen; C. R. Hauser (1954). "o-Methylethylbenzyl Alcohol". Org. Synth. 34: 58. doi:10.15227/orgsyn.034.0058.
  5. ^ Firouzmanesh, Mr; Azar, A Aref (June 2003). "Study of the effect of BDMA catalyst in the epoxy novolac curing process by isothermal DSC". Polymer International. 52 (6): 932–937. doi:10.1002/pi.1135. ISSN 0959-8103.
  6. ^ Firouzmanesh, M. R.; Azar, A. Aref (March 2005). "Study of the Effect of BDMA Catalyst in Epoxy Novolac Curing Process by Isothermal DSC". Journal of Reinforced Plastics and Composites. 24 (4): 345–353. Bibcode:2005JRPC...24..345F. doi:10.1177/0731684405033953. ISSN 0731-6844. S2CID 93979685.
  7. ^ Zhang, Qian; Hu, Xiang-Ming; Wu, Ming-Yue; Zhao, Yan-Yun; Yu, Chuang (2018-07-15). "Effects of different catalysts on the structure and properties of polyurethane/water glass grouting materials". Journal of Applied Polymer Science. 135 (27): 46460. doi:10.1002/app.46460.
  8. ^ Mascorro, José A. (2003). "Benzyldimethylamine (BDMA): Catalyst of Choice with Epoxy Embedding Media". Microscopy Today. 11 (4): 47. doi:10.1017/s1551929500053104.

External links edit

April 09, 2024
dimethylbenzylamine, organic, compound, with, formula, c6h5ch2n, molecule, consists, benzyl, group, c6h5ch2, attached, dimethylamino, functional, group, colorless, liquid, used, catalyst, formation, polyurethane, foams, epoxy, resins, namespreferred, iupac, na. Dimethylbenzylamine is the organic compound with the formula C6H5CH2N CH3 2 The molecule consists of a benzyl group C6H5CH2 attached to a dimethylamino functional group It is a colorless liquid It is used as a catalyst for the formation of polyurethane foams and epoxy resins Dimethylbenzylamine NamesPreferred IUPAC name N N Dimethyl 1 phenylmethanamineOther names 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 1 IdentifiersCAS Number 103 83 3 Y3D model JSmol Interactive imageChEMBL ChEMBL45591 YChemSpider 7398 YECHA InfoCard 100 002 863EC Number 203 149 1PubChem CID 7681RTECS number DP4500000UNII TYP7AXQ1YJ NUN number 2619CompTox Dashboard EPA DTXSID8021854InChI InChI 1S C9H13N c1 10 2 8 9 6 4 3 5 7 9 h3 7H 8H2 1 2H3 YKey XXBDWLFCJWSEKW UHFFFAOYSA N YInChI 1 C9H13N c1 10 2 8 9 6 4 3 5 7 9 h3 7H 8H2 1 2H3Key XXBDWLFCJWSEKW UHFFFAOYAQSMILES N C Cc1ccccc1 CPropertiesChemical formula C 9H 13NMolar mass 135 210 g mol 1Appearance colourless liquidDensity 0 91 g cm3 at 20 CMelting point 75 C 103 F 198 K Boiling point 180 to 183 C 356 to 361 F 453 to 456 K Solubility in water 1 2 g 100mLHazardsGHS labelling PictogramsSignal word DangerHazard statements H226 H302 H312 H314 H332 H412Precautionary statements P210 P233 P240 P241 P242 P243 P260 P261 P264 P270 P271 P273 P280 P301 P312 P301 P330 P331 P302 P352 P303 P361 P353 P304 P312 P304 P340 P305 P351 P338 P310 P312 P321 P322 P330 P363 P370 P378 P403 P235 P405 P501NFPA 704 fire diamond 330Flash point 55 C 131 F 328 K Autoignitiontemperature 410 C 770 F 683 K 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 Synthesis 2 Reactions 3 Uses 4 References 5 External linksSynthesis editN N Dimethylbenzylamine can be synthesized by the Eschweiler Clarke reaction of benzylamine 2 3 Reactions editIt undergoes directed ortho metalation with butyl lithium C6H5CH2N CH3 2 BuLi 2 LiC6H4CH2N CH3 2 LiC6H4CH2N CH3 2 E 2 EC6H4CH2N CH3 2Via these reactions many derivatives are known with the formula 2 X C6H4CH2N CH3 2 E SR PR2 etc The amine is basic and undergoes quaternization with alkyl halides e g hexyl bromide to give quaternary ammonium salts 4 C6H5CH2N CH3 2 RX C6H5CH2N CH3 2R X Such salts are useful phase transfer catalysts Uses editAs 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 5 6 7 8 References edit N N dimethyl benzyl amine The Good Scents Company Retrieved 1 November 2020 Icke R N Wisegarver B B Alles G A 1945 b Phenylethyldimethylamine Organic Syntheses 25 89 doi 10 15227 orgsyn 025 0089 Clarke H T Gillespie H B Weisshaus S Z 1933 The Action of Formaldehyde on Amines and Amino Acids J Am Chem Soc 55 11 4571 doi 10 1021 ja01338a041 W R Brasen C R Hauser 1954 o Methylethylbenzyl Alcohol Org Synth 34 58 doi 10 15227 orgsyn 034 0058 Firouzmanesh Mr Azar A Aref June 2003 Study of the effect of BDMA catalyst in the epoxy novolac curing process by isothermal DSC Polymer International 52 6 932 937 doi 10 1002 pi 1135 ISSN 0959 8103 Firouzmanesh M R Azar A Aref March 2005 Study of the Effect of BDMA Catalyst in Epoxy Novolac Curing Process by Isothermal DSC Journal of Reinforced Plastics and Composites 24 4 345 353 Bibcode 2005JRPC 24 345F doi 10 1177 0731684405033953 ISSN 0731 6844 S2CID 93979685 Zhang Qian Hu Xiang Ming Wu Ming Yue Zhao Yan Yun Yu Chuang 2018 07 15 Effects of different catalysts on the structure and properties of polyurethane water glass grouting materials Journal of Applied Polymer Science 135 27 46460 doi 10 1002 app 46460 Mascorro Jose A 2003 Benzyldimethylamine BDMA Catalyst of Choice with Epoxy Embedding Media Microscopy Today 11 4 47 doi 10 1017 s1551929500053104 External links editSafety MSDS data Archived 2007 10 11 at the Wayback Machine Retrieved from https en wikipedia org w index php title Dimethylbenzylamine amp oldid 1202033414, wikipedia, wiki, book, books, library,

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