2-Methyltetrahydroquinoline

Last updated
2-Methyltetrahydroquinoline
2-Methyltetrahydroquinoline.png
Names
Preferred IUPAC name
2-Methyl-1,2,3,4-tetrahydroquinoline
Other names
Tetrahydroquinaldine, 1,2,3,4-Tetrahydroquinaldine
Identifiers
3D model (JSmol)
ChEMBL
EC Number
  • 217-226-2
PubChem CID
UNII
  • InChI=1S/C10H13N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-5,8,11H,6-7H2,1H3/t8-/m1/s1
    Key: JZICUKPOZUKZLL-MRVPVSSYSA-N
  • (R):InChI=1S/C10H13N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-5,8,11H,6-7H2,1H3/t8-/m0/s1
    Key: JZICUKPOZUKZLL-QMMMGPOBSA-N
  • CC1CCC2=CC=CC=C2N1
  • C[C@@H]1CCC2=CC=CC=C2N1
  • (R):C[C@H]1CCC2=CC=CC=C2N1
Properties
C10H13N
Molar mass 147.221 g·mol−1
Appearancecolorless oil
Boiling point 125 °C (257 °F; 398 K) (17 Torr)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Methyltetrahydroquinoline is one of the methyl-substituted derivatives of tetrahydroquinoline. A colorless oil, it is a chiral compound owing to the presence of the methyl substituent. It is produced by the hydrogenation of quinaldine. [1] It is of interest in medicinal chemistry. [2]

Related Research Articles

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A methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula CH3. In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond, it can be found on its own in any of three forms: methanide anion, methylium cation or methyl radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

Organometallic chemistry Study of organic compounds containing metal(s)

Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.

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3
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Hydrogen auto-transfer

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1,2-Dimethyldiborane Chemical compound

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Tetramethyldiborane Chemical compound

Dimethylborane, (CH3)2BH is the simplest dialkylborane, consisting of a methyl group substituted for a hydrogen in borane. As for other boranes it normally exists in the form of a dimer called tetramethyldiborane or tetramethylbisborane or TMDB ((CH3)2BH)2. Other combinations of methylation occur on diborane, including monomethyldiborane, trimethyldiborane, 1,2-dimethylborane, 1,1-dimethylborane and trimethylborane. At room temperature the substance is at equilibrium between these forms. The methylboranes were first prepared by H. I. Schlesinger and A. O. Walker in the 1930s.

Methyldiborane Chemical compound

Methyldiborane, CH3B2H5, or monomethyldiborane is the simplest of alkyldiboranes, consisting of a methyl group substituted for a hydrogen in diborane. As with other boranes it exists in the form of a dimer with a twin hydrogen bridge that uses three-center two-electron bonding between the two boron atoms, and can be imagined as methyl borane (CH3BH2) bound to borane (BH3). Other combinations of methylation occur on diborane, including 1,1-dimethylborane, 1,2-dimethyldiborane, trimethyldiborane, tetramethyldiborane, and trimethylborane (which is not a dimer). At room temperature the substance is at equilibrium between these molecules.

Transition metal alkyl complexes Coordination complex

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Tetrahydroquinoline Chemical compound

Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil.

References

  1. Chakraborty, Sumit; Brennessel, William W.; Jones, William D. (2014). "A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles". Journal of the American Chemical Society. 136 (24): 8564–8567. doi:10.1021/ja504523b. PMID   24877556.
  2. Sridharan, Vellaisamy; Suryavanshi, Padmakar A.; Menéndez, J. Carlos (2011). "Advances in the Chemistry of Tetrahydroquinolines". Chemical Reviews. 111 (11): 7157–7259. doi:10.1021/cr100307m. PMID   21830756.