| Product | Structure | Molecular Weight | Boiling point (°C/mm) | Melting point (°C) | Density | Refractive Index | Additional Comments | References |
|---|---|---|---|---|---|---|---|---|
| SIB1760.0 Bis(phenylethynyl)dimethylsilane [2170-08-3] |  | 260.41 | 180/4 | 78-81 | -- | -- | Reductive cyclization yields siloles, oligosiloles.1 Useful in silicon-mediated Sonogashira cross-coupling reactions.2 | 1. Tamao, K. J. Am. Chern. Soc. 1994, 176, 11715. 2. Larson, G. L “Silicon-Based Cross-Coupling Reagenis” Gelest, Inc. 2011. |
| SIB1816.3 4,2-Bis(triethoxysilyl)acetylene, tech-95 4,4,7,7-Tetraethoxy-3,8-dioxa-4,4-disiladec-5-yne [17947-91-0] |  | 350.56 | 38-40/0.05 | -- | 1.101 | -- | Forms mesoporous structures. | -- |
| SIB1850.0 Bis(trimethylsilyl)acetylene [14630-40- 1] |  | 170.4 | 133-135 | 22 | 0.770 | 1.413 | Flashpoint: 2 °C Versatile reagent for introducing unsaturation Key reviews.1,2,3 Used to prepare 1,2-bis(aryl)acetylenes.3 Reacts with internal acetylenes to form 1,2,4,5-tetrasubstituted benzenes.4 Useful in silicon-mediated Sonogashira cross-coupling reactions.5 Used to prepare 4-alkynylthiazoles.6 | 1. Weber, W. In Silicon Reagents for Organic Synthesis; Springer-Verlag: 1983, p129. 2. Vollhardt, P. Acc. Chem. Res. 1977, 70, 1. 3. Nishihara, Y. et al. J. Org. Chem. 2000, 65, 1780. 4.Li, S. etal. Org. Lett 2009, 17, 3318. 5. Larson, G. L “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. 6. Arunkukmar, K. et al. Tefrahedron Lett. 2012, 53, 3885. F&F: Val. 4, p 42; Vol. 5, p 44; Vol. 8, p 146; Vol.9, p 142; Vol. 10, p 126; Vol. 10, p 126; Vol. 13, p 97, p 309; Vol. 14, p 116. |
| SIB1852.0 Bis(trimethylsilyl)acetylenedicarboxylate [76734-92-4] |  | 258.42 | 78-80/0.05 | -- | 0.988 | 1.4390 | Flashpoint: 67 °C Synthetic intermediate with readily cleavable silyl groups.1 | 1. Verboom, W. et al. Synthesis 1981, 807. |
| SIB1854.0 Bis(trimethylsilyl)butadiyne [4526-07-2] |  | 194.42 | -- | 107-109 | -- | -- | Stable crystalline form of butadiyne; synthon for heterocycles.1 Used to prepare multidentate 1,2,3-triazole chelate ligands.2 Undergoes 6+2 cycloaddition with cycloheptatriene.3 See also SIT8597.0 | 1. Jacobs, P. M. et al. Heferocyc!. Chem. 1977, 14, 1115. 2. Fuller, T. J. et al. Organometallics 2008, 27, 5430. 3. Hilt, G. et al. Synthesis 2009, 3305. |
| SIB1858.0 4,3-Bis[(trimethylsilyl)ethynyl]benzene [38170-80-8] |  | 270.52 | -- | 57-59 | -- | -- | store <5 °C | -- |
| SIB1858.2 1,4-Bis[(trimethylsilyl)ethynyl]benzene [17938-13-5] |  | 270.52 | -- | 119-121 | -- | -- | -- | -- |
| SIB1899.0 (4-Bromophenylethynyl)trimethylsilane [16116-78-2] |  | 253.22 | 60-80/0.2 | 61-63 | 1.192 | -- | See also SIC2326.4 | -- |
| SIB1907.0 3-Bromo-1-(trimethylsilyl)-1-propyne, 95% [38002-45-8] |  | 191.15 | 44-45/2 | -- | 1.351 | 1.4950 | Flashpoint: 62 °C Reagent for preparation of terminal conjugated enynes.1 Used to prepare homopropargylic and alleny! alcohols.2 See also S116452.2 | 1. Gibson, A etal. Synthesis 1991, 5, 414. 2. Liu, M.-J.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 13042. |
| SIB1931.0 3-Buten-1-ynyltrimethylsilane [2696-32-4] |  | 124.26 | 52-53/80 | -- | 0.7714 | 1.4512 | Cycloannulation reagent | |
| SIB1939.5 4-(t- Butyldimethylsiloxy)butyne [78592-82-2] |  | 184.35 | 70-74/10 | -- | 0.893 | 1.4300 | Flashpoint: 58 °C Protected butynol Potential for the synthesis of silyl-protected butynol derivatives.1 | 1. Larson, G. L. “Sificon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIC2325.6 (5-Chloro-1-pentynyl)trimethylsilane 1-Chloro-5-trimethylsilyl-4-pentyne [77113-48-5] |  | 174.75 | 75-76/20 | -- | 0.997 | 1.4560 | Flashpoint: 65 °C Forms functionalized triazoles by "click" chemistry See also SIE4901.87, SIH5848.0 | -- |
| SIC2326.4 (4-Chlorophenylethynyl)trimethylsilane [78704-49-1] |  | 208.76 | 75-79/2.5 | 47-51 | -- | -- | Flashpoint: 105 °C See also SIB1899.0 | -- |
| SID3425.0 1,3-Diethynyltetramethyldisiloxane [4180-02-3] |  | 182.37 | 122-128 | -- | 0.842 | 1.4104 | Flashpoint: 20 °C End-capper for acetylene functional silicones Useful in silicon- mediated Sonogashira cross-coupling reactions.1 | 1. Larson, G. L. "Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SID3610.0 1-Dimethylamino-3-(trimethylsilyl)-2-propyne n,n-Dimethyl-3-(trimethylsilyl)-2-propyn-1-amine [56849-88-8] |  | 155.31 | -- | -- | 0.774 | -- | -- | -- |
| SIE4901.8 Ethyl 3-(trimethylsilyl)propynoate [16205-84-5] |  | 170.29 | 95-99/30 | -- | 0.897 | 1.4410 | Flashpoint: 71 °C | -- |
| SIE4901.83 Ethynyl-t-butyldimethylsilane t-Butyldimethylsilylacetylene [86318-61-9] |  | 140.30 | 116-117 | -- | 0.75125 | 1.451 | Flashpoint: 6 °C | -- |
| SIE4901.85 Ethynylcyclohexyldiethylsilane |  | 194.39 | 74-77/3 | -- | 0.86925 | 1.470525 | -- | -- |
| SIE4901.87 Ethynylcyclopentyldiethylsilane |  | 180.36 | 82-83/8 | -- | 0.85825 | 1.416625 | -- | -- |
| SIE4901.9 Ethynyldiphenylmethylsilane [17156-65-9] |  | 222.37 | 86/0.5 | -- | 1.010 | 1.575 | Flashpoint: 113 °C See also SIE4901.83 | -- |
| SIE4902.0 Ethynyltriethylsilane Triethylsilylacetylene [1777-03-3] |  | 140.3 | 136 | -- | 0.783 | 1.4430 | Flashpoint: 17 °C Reacts with enol silyl ethers to form α,α-bis-trans-ß-triethylsilylethenyl ketones.1 Useful in Sonogashira cross-coupling reactions with more stable silyl group than the trimethylsilyl group2 See also SIE4903.0 | 1. Amemiya, R. et al. Tefrahedron Left. 2006, 47, 1797. 2. Larson, G. L “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIE4903.0 Ethynyltriisopropylsilane Triisopropylsilylacetylene [89343-06-6] |  | 182.83 | 50-52/0.6 | -- | 0.813 | 1.4527 | See also SIE4902.0 | -- |
| SNE4900 Ethynyltri-n-butyltin, 95% Tributylstannylacetylene [994-89-8] |  | 315.07 | 71/0.2 | -- | 1.092 | 1.4760 | Flashpoint: 73 °C Undergoes reactions at triple bond.1 Pd catalyzed reactions with alkenyl and aryl iodides yields acetylenes.2,3 | 1. Stamm, W. J. Org. Chem. 1963, 28, 3264. 2. Stille, J. et al. J. Am. Chem. Soc. 1987, 109, 2138. 3. Stille, J. etal. J. Org. Chem. 1989, 54, 5856. |
| SIE4904.0 Ethynyltrimethylsilane, 98% Trimethylsilylacetylene [1066-54-2] |  | 98.22 | 52 | -- | 0.709 | 1.3880 | Vapor pressure, 20 °C: 214 mm Flashpoint: -26 °C Autoignition temperature: 310 °C Doped polymer films are conductive Review of synthetic utility.1 Ethynylates aromatic compounds.2 Precursor to trimethylsilylethynyl copper reagent.3 Lithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomers.4 Employed in ortho ethenylation of phenols.5 Undergoes Diels-Alder reactions with butadienes.6 Converts imines to propargyl amines.7 Forms propargylic amines from aldehydes and amines in aqueous system.8 Regioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employed.9 Reacts with aryl aldehydes to form diethynylmethane derivatives.10 Useful in the preparation of unsymmetrical diarylacetylenes.11 | 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 569-580. 2. Austin, W. etal. J. Org. Chem. 1981, 46, 2280. 3. Sakata, H. et al. Tetrahedron Lett. 1987, 28, 5719. 4. Kouveetakis, J. et al. Cham. Mater. 1994, 6, 636. 5. Kobayashi, K.; Yamaguchi, M. Org. Lett. 2001, 3, 241. 6. Paik, S.-J. et al. Org. Leff. 1999, 7, 2045. 7. Fischer, C.; Carreira, E. M. Org. Leté. 2001, 3, 4319. 8. Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584. 9. Matsuyama, N. et al. J. Org. Chem. 2009, 74, 3576. 10. Girard, D. et al. Tetrahedron Lett. 2007, 48, 6022. 11. Mio, M. etal. Org. Lett, 2002, 4, 3199. 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L Ed., John Wiley and Sons, Lid., : See also SIT8606.5 |
| SIH5848.0 1-Heptynyltrimethylsilane [15719-56-9] |  | 168.35 | 176 | -- | -- | 1.4344 | Flashpoint: 42 °C Useful in silicon-mediated Sonogashira cross-coupling reactions.1 | 1. Larson, G. L “Silicon-Based Cross-Coupling Reagents" Gelest, Inc. 2011. |
| SII6452.2 1-Iodo-2-(trimethylsilyl)acetylene [18163-47-8] |  | 224.11 | 130 | -- | 1.460 | 1.511 | Light sensitive Intermediate for benzofused nitrogen heterocycles.1 See also SIB1907.0 | 1. Mak, X. etal. J. Org. Chem. 2011, 76, 1852. |
| SIL6470.0 Lithium (trimethylsilyl)acetylide, 0.5 M in tetrahydrofuran (12-13 wt%) [54655-07-1] |  | 104.15 | -- | -- | 0.829 | -- | Flashpoint: -14 °C Forms conductive anisotropic films on reaction with halotriazines.1 Intermediate for synthesis of alkylgalliumacetylides.2 See also SIT8594.1 | 1. Kouvetakis, J. Chem. Mater. 1994, 6, 636. 2. Lee, K. et al. J. Organomet. Chem. 1993, 449, 53. |
| SIP6732.0 Phenylethynyldimethylsilane [87290-97-9] |  | 160.29 | 33-34/0.3 | -- | 0.906 | 1.5407 | Flashpoint: 76 °C | -- |
| SNP6734 Phenylethynyltri-n-butyltin, 85% [3757-88-85] |  | 391.17 | -- | -- | 1.116 | 1.5320 | Flashpoint: 113 °C | -- |
| SIP6736.0 Phenylethynyltrimethylsilane [2170-06-1] |  | 174.32 | 67/5 | -- | 0.896 | 1.5284 | Flashpoint: 82 °C Reacts with tetraphenylcyclopentadienone to form pentaphenylphenyltrimethylsilane.1 Cross couples with aryl halides and triflates as well as homocouples to 1,2-diynes.2 Undergoes alkynyl cross metathesis reactions.3 Provides the ethynyl silver acetylide.4 Reacts with propargyl chlorides to form 1,2-diene-4-ynes.5 Ethynylsilanes react with propargyl halides to form 1,4-diynes.6 See also SIB1760.0 Bis(phenylethynyl)dimethylsilane | 1. Jianhua, C. et al. In Sificon Chemistry; Corey, J., et al. Ed.; Wiley: 1988: p. 105. 2. Nashihara, Y. et al. J. Org. Chem. 2000, 65, 1780. 3. Furstner, A; Mathes, C. Org. Lett. 2001, 3, 221. 4. Vitérisi, A. et al. Tetrahedron Lett. 2006, 47, 2779. 5. Montel, F. et al. Org. Lett. 2006, 8, 1905. 6. Kuninobu, Y.; Ishii, E.; Takai, K. Angew. Chem., int. Ed. Engl. 2007, 46, 3296. |
| SIP6902.4 Propargyloxy-t-butyldimethylsilane [76782-82-6] |  | 170.32 | 40/8 | -- | 0.84 | 1.429 | -- | -- |
| SIP6903.0 Propargyloxytrimethylsilane O-Trimethylsilylpropargyl alcohol [5582-62-7] |  | 128.25 | 110-111 | -- | 0.833 | 1.4090 | Flashpoint 27 °C TOXICITY: oral rat, LD50: 650 mg/kg Reagent for the preparation of 1,4-dienes1, 4-en-1-ynes.2 Sonogashira cross-coupling would yield silyl-pratected propargyl alcohol derivatives.3 See also SIP6902.4 | 1. Knochel, P. et al. J. Organomet. Chem. 1888, 309, 1. 2. Mesnard, D. et al. J. Organomet. Chem. 1991, 420, 163. 3. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIP6902.6 O-(Propargyl)-n-(triethoxysilylpropyl) carbamate, 90% [870987-68-1] |  | 303.43 | 110-120/0.2 | -- | 0.990 | 1.44625 | Flashpoint 95 °C Inhibited with MEHQ Surface derivatization reagent enabling “click” chemistry of nanoparticles.1 | 1. Achatz, D. et al. Sensors and Actuators B 2010, 150, 211. |
| SIT8386.0 1-(Triisopropylsilyl)-1-propyne [82192-57-2] |  | 196.41 | 70/1 | -- | 0.826 | 1.4624 | Flashpoint: 71 °C See also SIE4902.0 , SIT8606.5 | -- |
| SIT8571.25 3-(Trimethylsiloxy)-1-butyne (3-Butynyloxy)trimethylsilane [17869-76-0] |  | 142.27 | -- | 111 | 0.819 | 1.4043 | Flashpoint 6 °C | -- |
| SIT8583.0 1-Trimethylsilylbut-1-yne-3-ol 4-Trimethylsilyl-3-butyn-1-ol [6999-19-5] |  | 142.27 | 82/35 | -- | 0.85 | 1.4449 | Flashpoint: 50 °C Phosphate ester adds to α,ß-unsaturated malonates.1 Useful in silicon-mediated Sonogashira cross-coupling reactions to give substituted propargyl alcohols.2 | 1. Song, Y. et al. Org. Lett, 2001, 3, 3543. 2. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIT8583.2 4-Trimethylsilylbut-3-yn-2-one [5930-98-3] |  | 140.26 | 156 | -- | 0.854 | 1.4415 | Flashpoint: 28 °C | -- |
| SIT8588.6 4-(Trimethylsilyl)diphenylacetylene [4-(Phenylethynyl)phenyl]trimethylsilane [136459-72-8] |  | 250.42 | -- | 37-41 | -- | -- | -- | -- |
| SIT8588.63 4-[(Trimethylsilyl)ethynyl]benzaldehyde [77123-57-0] |  | 202.33 | -- | 66-70 | -- | -- | Employed as reagent for “click” immobilization of metallo-porphyrins.1 | 1. McDonald, A. et al. J. Organomet. Chem.. 2009, 694, 2153. |
| SIT8588.7 2-[(Trimethylsilyl)ethynyl]toluene [3989-15-9] |  | 188.34 | 50-58/0.5 | -- | 0.88 | 1.5320 | Flashpoint: 90 °C See also SIP6736.0 | -- |
| SIT8588.8 Trimethylsilylethynyltri-n-butyltin 1-Tributylstannyl-2-trimethylsilylacetylene [81353-38-0] |  | 387.26 | 128/22 | -- | 1.055 | 1.475 | Converts vinyl mesylates to enynes.1 | 1. Barret, D. et al. J. Antibiotics 1997, 50, 100. |
| SIT8589.7 4-Trimethylsilyl-1-hexyne [3844-94-8] |  | 154.33 | 155 | -- | 0.770 | 1.431 | Flashpoint: 37 °C Undergoes Pd-catalyzed hydroesterification to form B-ethoxyvinylsilanes.1 | 1. Takeuchi, R. J. Chem. Soc., Perkin. Trans. 1 1993, 1031. |
| SIT8597.0 1-Trimethylsilyl-1,4-pentadiyne [71789-10-1] |  | 136.27 | 42/25 | -- | 0.789 | -- | Flashpoint: 8 °C See also SIB1854.0 | -- |
| SIT8604.0 3-Trimethylsilylpropargyl alcohol 3-Trimethylsilyl-2-propyn-1-ol [5272-36-6] |  | 128.25 | 170-172 | -- | 0.875 | 1.4518 | Flashpoint: 65 °C TOXICITY: oral rat, LD50: 150 mg/kg Hydromagnesiation of triple bond yields intermediates for terpene synthesis Useful in silicon-mediated Sonogashira cross-coupling reactions to give substituted propargyl alcohols.1 | 1. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIT8605.0 3-Trimethylsilylpropargylmethacrylate, 95% 3-Methacryloxyprop-2-ynyltrimethylsilane [214268-06- 1] |  | 196.32 | -- | -- | -- | -- | CAUTION: SENSITZER Forms polymers that undergo "click" chemistry.1,2 | 1. Quemener, D. et al. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 155. 2. Ladmiril, V. et al. J. Am. Chem. Soc., 2006, 128, 4823. |
| SIT8606.3 3-Trimethylsilylpropynal [2975-46-4] |  | 126.23 | 52/30 | -- | 0.862 | 1.443 | Flashpoint: 29 °C Used in the preparation of 1,3,5-triynes.1 Potential for the synthesis of 3-substituted alkynals.2 | 1. Mukai, C. etal. J. Org. Chem. 2001, 66, 5875. 2. Larson, G. L. “Silicon-Based Cross-Coupling Reagents" Gelest, Inc. 2011 |
| SIT8606.5 1-Trimethylsilylpropyne [6224-91-5] |  | 112.25 | 99-100 | -69 | 0.758 | 1.4091 | Forms polymers with very high oxygen permeability.1 Polymerization catalyzed with TaCl5/(C6H5)3Bi.2 Converts aldehydes to 1,3-dienes in presence of Cp2Zr(H)Cl.3 Synthetic reagent.4 Used in the preparation of alkynylxenon fluoride.5 Useful in silicon- mediated Sonogashira cross-coupling reactions.6 See also SIB1931.0 , SIT8386.0 | 1. Masuda, T. et al. J. Am. Chem. Soc. 1983, 105, 7473, 2. Masuda, T. et al. J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 1353. 3. Maeta, H. etal. Tetrahedron Lett. 1992, 33, 5969. 4. F&F: Vol. 2, p 239; Vol. 6, p 638. 5. Schmidt, H. et al. Inorg. Chem. 2004, 43, 1837. 6. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIT8606.6 3-Trimethylsilylpropynoic acid [5683-31-8] |  | 142.23 | 105-109 | 47-49 | -- | -- | Flashpoint: 96 °C Potential for the preparation of propiolic acid derivatives.1 See also SIT8623.0 | 1. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
| SIT8606.7 (3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide [42134-49-6] |  | 453.44 | -- | 166-167 | -- | -- | Wittig Reagent Employed in synthesis of terminal enynes.1,2 | 1. Corey, E. J.; Ruden, R. A. Tetrahedron Lett. 1973, 14, 1495. 2. Corey, E. J. etal. Tetrahedron Lett. 1973, 14, 3963. |
| SIT8623.0 Trimethylsilyl (trimethylsilyl)propynoate [97927-35-0] |  | 214.42 | 64-65/1.5 | -- | -- | 1.4400 | Flashpoint: 43 °C Potential for the synthesis of 3-substituted propiolic acid derivatives.1 | 1. Larson, G. L. “Silicon-Based Cross-Coupling Reagents” Gelest, Inc. 2011. |
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