Dimethylbenzylamine

Last updated
Dimethylbenzylamine
Benzyldimethylamine.svg
Dimethylbenzylamine 3D ball.png
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.863 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-149-1
PubChem CID
RTECS number
  • DP4500000
UNII
UN number 2619
  • InChI=1S/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 Yes check.svgY
    Key: XXBDWLFCJWSEKW-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolourless 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:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
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)
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Synthesis

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

Reactions

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

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]

Related Research Articles

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In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Polyurethane</span> Polymer composed of a chain of organic units joined by carbamate (urethane) links

Polyurethane refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from a wide range of starting materials. This chemical variety produces polyurethanes with different chemical structures leading to many different applications. These include rigid and flexible foams, and coatings, adhesives, electrical potting compounds, and fibers such as spandex and polyurethane laminate (PUL). Foams are the largest application accounting for 67% of all polyurethane produced in 2016.

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Thermosetting polymer</span> Polymer obtained by irreversibly hardening (curing) a resin

In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening ("curing") a soft solid or viscous liquid prepolymer (resin). Curing is induced by heat or suitable radiation and may be promoted by high pressure or mixing with a catalyst. Heat is not necessarily applied externally, and is often generated by the reaction of the resin with a curing agent. Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

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<span class="mw-page-title-main">Benzoyl chloride</span> Organochlorine compound (C7H5ClO)

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<span class="mw-page-title-main">Aminoethylpiperazine</span> Chemical compound

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<span class="mw-page-title-main">1-Phenylethylamine</span> Chemical compound

1-Phenylethylamine is the organic compound with the formula C6H5CH(NH2)CH3. This primary amine is a colorless liquid is often used in chiral resolutions. Like benzylamine, it is relatively basic and forms stable ammonium salts and imines.

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References

  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 .