HALOACETYLENE DERIVATIVES C ?CX

1. Whiting, M. C., Chem. Eng. News, 1972, 50(23), 86

2. Brandsma, 1971, 99

3. Kloster-Jensen, E. et al., Chem. Eng. News, 1978, 56(19), 38

The tendency towards explosive decomposition noted for dihalo-2,4-hexadiyne derivatives appears to be associated more with the co-existence of halo- and acetylene functions in the same molecule, than with its being a polyacetylene. Haloacetylenes should be used with exceptional precautions [1]. Explosions may occur during distillation of bromoacetylenes when bath temperatures are too high, or if air is admitted to a hot vacuum-distillation residue [2]. Precautions necessary in isolating and handling such compounds on the small (1 g) scale are detailed [3]. Individually indexed compounds are:

• 1-Bromo-1,2-cyclotridecadien-4,8,10-triyne, 3593

• Bromoacetylene, 0647

• Bromochloroacetylene, 0575

• 3-Bromopropyne, 1087

• * Calcium hypochlorite, : Acetylene, 3918

• 3-Chloro-1-iodopropyne, 1070

• 4-Chloro-2-butynol, 1451

• 1-Chloro-3-phenylpent-1-en-4-yn-3-ol, 3387

• Chloroacetylene, 0648

• Chlorocyanoacetylene, 1033

• Chloroiodoacetylene, 0595

• 3-Chloropropyne, 1089

• Copper(I) chloroacetylide, 1350

• * 3-Cyanopropyne, 1412

• 1,4-Dibromo-1,3-butadiyne, 1347

• Dibromoacetylene, 0579

• 1,4-Dichloro-1,3-butadiyne, 1349

• 1,6-Dichloro-2,4-hexadiyne, 2150

• 1,4-Dichloro-2-butyne, 1424

• Dichloroacetylene, 0599

• Dicyanoacetylene, 1795

• Difluoroacetylene, 0619

• 1,4-Diiodo-1,3-butadiyne, 1793

• 1,6-Diiodo-2,4-hexadiyne, 2166

• Diiodoacetylene, 0981

• Fluoroacetylene, 0658

• 1-Iodo-1,3-butadiyne, 1377

• 3-Iodo-1-phenylpropyne, 3114

• 1-Iodo-3-penten-1-yne, 1839

• Iodoacetylene, 0666

• 3-Iodopropyne, 1102

• * Lithium 3-(1,1,2,2-tetrafluoroethoxy)propynide, 1814

• Lithium bromoacetylide, 0577

• Lithium chloroacetylide, 0596

• Lithium trifluoropropynide, 1043

• Mercury bis(chloroacetylide), 1352

• * Silver chloroacetylide, 0563

• Silver trifluoropropynide, 1026

• Sodium bromoacetylide, 0578

• Sodium chloroacetylide, 0598

• Tetrakis(chloroethynyl)silane, 2874

• Thallium(I) iodacetylide, 0980

• 3,3,3-Trifluoropropyne, 1063

HALOALKANES RX

1. Bretherick, L., Chem. & Ind., 1986, 729; Chem. Eng. News, 1986, 64(51), 2

2. Suzuki, A. et al., Bull. Chem. Soc. Jap.,...