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Chemical Compound Review: 

Bromopropyne     3-bromoprop-1-yne

Synonyms: PubChem20264, AGN-PC-0CQAJK, NSC-8801, P51001_ALDRICH, ANW-15466, ...
 
 
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High impact information on Propynyl bromide

  • The propargyl sulfonium salts obtained by alkylation of thioethers 7, 8, 10, and 11 with propargyl bromide have been further converted to two- and three-cage oligomers containing both ortho-carborane and dodecaborane moieties [1].
  • [reaction: see text] A variety of alpha-aroylacetones 4a-g have been prepared in excellent yields following a new protocol wherein alpha-aminonitriles 1a-g as the aryl acyl anion equivalents readily react with propargyl bromide as the alpha-bromoacetone equivalent [2].
  • The hydroboration of propargyl bromide. Simple one-Pot three-component routes to (Z)-1-bromoalk-1-en-4-ols and to anti-homoallylic alcohols [3].
 

Associations of Propynyl bromide with other chemical compounds

  • Successive alkylation of dimethyl homoterephthalate with propargyl bromide and 2,4-diamino-6-(bromomethyl)pteridine followed by ester saponification at room temperature afforded 2,4-diamino-4-deoxy-10-carboxy-10-propargyl-10-deazapteroic acid [4].
  • Alkylation with propargyl bromide gave (R)-(-)- or (S)-(+)-4-fluoronordeprenyl which was reductively methylated (Borch conditions) to produce (R)-(-)- or (S)-(+)-4-fluorodeprenyl [5].
  • [reaction: see text] Chiral phase-transfer catalyst 5 containing an electron-deficient trifluorobenzyl moiety promoted the alkylation of glycine derivative 6 with propargyl bromide 7a in good yield and excellent ee [6].

References

  1. S-alkylation and S-amination of methyl thioethers--derivatives of closo-[B(12)H(12)](2-). synthesis of a boronated phosphonate, gem-bisphosphonates, and dodecaborane-ortho-carborane oligomers. Kultyshev, R.G., Liu, J., Liu, S., Tjarks, W., Soloway, A.H., Shore, S.G. J. Am. Chem. Soc. (2002) [Pubmed]
  2. Propargyl bromide as an excellent alpha-bromoacetone equivalent: convenient and new route to alpha-aroylacetones. Mahalingam, S.M., Aidhen, I.S. J. Org. Chem. (2006) [Pubmed]
  3. The hydroboration of propargyl bromide. Simple one-Pot three-component routes to (Z)-1-bromoalk-1-en-4-ols and to anti-homoallylic alcohols. Lombardo, M., Morganti, S., Trombini, C. J. Org. Chem. (2000) [Pubmed]
  4. Synthesis and antitumor activity of 10-propargyl-10-deazaaminopterin. DeGraw, J.I., Colwell, W.T., Piper, J.R., Sirotnak, F.M. J. Med. Chem. (1993) [Pubmed]
  5. Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl and positron emission tomography studies in baboon brain. Plenevaux, A., Dewey, S.L., Fowler, J.S., Guillaume, M., Wolf, A.P. J. Med. Chem. (1990) [Pubmed]
  6. Catalytic asymmetric synthesis of the central tryptophan residue of celogentin C. Castle, S.L., Srikanth, G.S. Org. Lett. (2003) [Pubmed]
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