[ CAS No. 4526-07-2 ] {[proInfo.proName]}

Name: 4526-07-2|1,4-Bis(trimethylsilyl)buta-1,3-diyne|95%
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Quality Control of [ 4526-07-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4526-07-2 ]

Product Details of [ 4526-07-2 ]

CAS No. :	4526-07-2	MDL No. :	MFCD00009839
Formula :	C₁₀H₁₈Si₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LBNVCJHJRYJVPK-UHFFFAOYSA-N
M.W :	194.42	Pubchem ID :	138279
Synonyms :

Calculated chemistry of [ 4526-07-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.24
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.55
Log Po/w (XLOGP3) :	4.69
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	3.66
Log Po/w (SILICOS-IT) :	0.11
Consensus Log Po/w :	2.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.0
Solubility :	0.0194 mg/ml ; 0.0001 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.42
Solubility :	0.00743 mg/ml ; 0.0000382 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.58
Solubility :	0.51 mg/ml ; 0.00262 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.46

Safety of [ 4526-07-2 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P210-P240-P241-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	1325
Hazard Statements:	H228-H315-H319	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 4526-07-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 4526-07-2 ]
Downstream synthetic route of [ 4526-07-2 ]

[ 4526-07-2 ] Synthesis Path-Upstream 1~3

1
[ 1122-91-4 ]
[ 536-74-3 ]
[ 4526-07-2 ]
[ 57341-98-7 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8551 - 8553

2
[ 109-04-6 ]
[ 1066-54-2 ]
[ 4526-07-2 ]
[ 86521-05-3 ]

Reference： [1] Chemistry - An Asian Journal, 2011, vol. 6, # 10, p. 2816 - 2824

3
[ 1122-91-4 ]
[ 1066-54-2 ]
[ 4526-07-2 ]
[ 77123-57-0 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8551 - 8553

[ 4526-07-2 ] Synthesis Path-Downstream 1~55

1
[ 18163-47-8 ]
[ 4526-07-2 ]

Reference： [1]Tetrahedron Letters,1972,vol. 13,p. 5209 - 5212

2
[ 61210-52-4 ]
[ 4526-07-2 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 9547 - 9550
[2]Chemische Berichte,1963,vol. 96,p. 930 - 943
[3]Gazzetta Chimica Italiana,1990,vol. 120,p. 783 - 791
[4]Heteroatom Chemistry,2011,vol. 22,p. 397 - 404

3
[ 1066-54-2 ]
[ 4526-07-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With oxygen; potassium carbonate; In dimethyl sulfoxide; at 50℃; for 8h;	General procedure: In a 25ml two necked round bottom flask containing phenyl acetylene (1mmol), base (1mmol), catalyst (100mg) and DMSO (3ml), O2 gas was purged with the help of a balloon. The flask was heated at 50C for 8h and the progress of the reaction was monitored by TLC. After the completion of the reaction, the catalyst was separated while the solution was still hot and the reaction quenched by pouring the filtrate in chilled water. The reaction mixture was extracted with ethyl acetate and a light yellow crude product was isolated after removing the solvent in a rotary evaporator. The crude after purification was identified by NMR (Scheme 2).
86%	With copper(l) iodide; ethyl 2,2-dibromoacetoacetate; triethylamine; In dichloromethane; at 20℃; for 30h;	General procedure: Ethyl alpha,alpha-dibromoacetoacetate 2a (46.1 mg, 0.16 mmol,30 mol %), alkynes 1a-v(0.55 mmol, 1.0 equiv), CuI (30.5 mg,0.16 mmol, 30 mol %), and triethylamine (0.15 mL, 1.1 mmol,2.0 equiv) were added under ambient temperature to 2 mL of CH2Cl2in air. After stirred at room temperature for the appropriate time (monitored by TLC), the reaction was quenched by addition of H2O (3 mL) and then extracted with ethyl acetate (33 mL). The combined organic layer was washed with brine, dried over Na2SO4,and concentrated. The crude product was purified by column chromatography on silica gel with mixture of petroleum ether and ethyl acetate as eluent to afford the corresponding products 3a-v
67%	With piperidine; In dichloromethane; at 20℃; for 8h;	General procedure: To a stirred solution of alkynes (1 mmol) in dichloromethaneat room temperature and open air, the catalyst (20 mg,0.05 mol%) was added. Then the diluted solution of piperidine(30 mol%) in dichloromethane was added drop wise.The reaction was continued at room temperature and monitoredby TLC. Once the reaction was complete, the reactionmixture was filtered and diluted by addition of 25 mlof dichloromethane to the reaction mixture. The reactionmixture was washed with 0.1 N HCl (2 × 25 ml) followed bywashing with water (2 × 25 ml) and brine (25 ml). The crudeproduct was isolated and purified by column chromatographyusing hexane/ethyl acetate as eluent. The products werecharacterised by 1H and 13C NMR spectroscopy.

59.3%

With dmap; copper(l) iodide; oxygen; In acetonitrile; at 20 - 32℃;

A 250 mL, three-necked, round bottom flask was equipped with a dry ice condenser, thermometer, and a 2.5 cm Teflon-coated, egg-shaped magnetic stirrer bar. The top of the dry ice condenser was connected by rubber tube to a glass T-piece which was connected to an oxygen cylinder and a bubbler. The three-necked flask was charged with acetonitrile (100 mL), copper(I) iodide (1.44 g, 7.6 mmol, 0.05 equiv.), and DMAP (1.86 g, 15.3 mmol, 0.1 equiv.) giving a green-brown solution (Fig. S1, Supplementary Material). After flushing the system with oxygen for 5 min while stirring, the three-necked flask was closed with a rubber septum. An external water bath at ambient temperature was applied to cool the three-necked flask, the dry ice condenser was charged with an acetone-dry ice cooling mixture, and the oxygen flow regulated to a constant flow of approximately one bubble per second (Fig. S2, Supplementary Material). During the reaction a high stirring speed was applied to ensure a good gas intake into the solution through creation of a vortex. Trimethylsilylacetylene (15 g, 152.7 mmol, 1 equiv.) was added to the green-brown catalyst solution via a funnel through the free side neck. The internal temperature slowly rose to a maximum of 32C and the colour changed to a blue-green within 5 min (Fig. S3, Supplementary Material). After 10 min, the internal temperature stabilised at 27C. After 15 min the mixture presented as a dark green solution with light-coloured precipitate. After 2 h the colour of the mixture changed back to the green-brown colour of the initial catalyst solution with a light-coloured precipitate and the temperature equilibrated at ambient temperature. For these first two hours the dry ice condenser was refilled with dry ice every 15 min. The reaction mixture was stirred for another 6 h during which the mixture darkened to black and the temperature dropped to ambient temperature indicating the completion of the reaction. The black thick slurry was poured into a 1 L single-necked, round bottom flask. The three-necked flask with a thick oily black residue remaining on the walls of the flask was washed with CH2Cl2 (2 * 50 mL) and hexanes (2 * 50 mL) to help transfer the remaining black solids to the 1 L, single-necked, round bottom flask, leaving only a partial copper mirror in the three necked flask. The solvent of the black mixture was removed by rotary evaporation. During the removal of the solvent high temperatures and very low pressures were avoided as the product sublimes under such conditions. The oily black residue thus obtained was suspended in hexanes (4 * 25 mL) by sonication for 1 min and filtered through a silica plug (silica, approx. 10 cm * 4.5 cm) and eluted with hexanes (900 mL). After removing the solvent on a rotary evaporator, the product was obtained as a white crystalline solid. The product was dried under vacuum at ambient temperature (5 mbar for 40 min, 1 mbar for 1 min). Yield: 8.7-8.8 g (58.5-59.3 %). Mp 104-106C (lit. 106-108C,[42] 107-108C[43]). deltaH (300 MHz, CDCl3 (7.26 ppm)) 0.18 (s, 18H). deltaC (75 MHz, CDCl3 (77.16 ppm)) 0.26, 86.08, 88.09. numax (ATR)/cm-1 2066 (m), 1263(m), 1250 (s). The purity of the sample was determined to be 99.5 % by quantitative NMR in CDCl3 with 1,3,5-trimethoxybenzene as internal standard and estimated to be 100 % by standard GC-MS analysis.

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[4]European Journal of Organic Chemistry,2011,p. 2524 - 2530
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[6]ACS Catalysis,2016,vol. 6,p. 5069 - 5080
[7]Journal of Molecular Catalysis A: Chemical,2016,vol. 423,p. 77 - 84
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[9]Tetrahedron,2014,vol. 70,p. 256 - 261
[10]European Journal of Organic Chemistry,2012,p. 4178 - 4184
[11]Green Chemistry,2019,vol. 21,p. 2899 - 2904
[12]Organic Letters,2019,vol. 21,p. 4106 - 4110
[13]Synthesis,2006,p. 1155 - 1161
[14]Chemical Communications,2003,p. 632 - 633
[15]ACS Catalysis,2018,vol. 8,p. 7495 - 7506
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[19]Australian Journal of Chemistry,2018,vol. 71,p. 307 - 310
[20]Synthesis,2009,p. 395 - 398
[21]Journal of Organic Chemistry,1993,vol. 58,p. 6614 - 6619
[22]Tetrahedron,2004,vol. 60,p. 9453 - 9461
[23]Journal of Organic Chemistry,1979,vol. 44,p. 178 - 179
[24]Journal of Organometallic Chemistry,1972,vol. 37,p. 45 - 56
[25]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1960,vol. 251,p. 730 - 732
[26]Journal of Organometallic Chemistry,1986,vol. 316,p. 85 - 94
[27]Liebigs Annales,1996,p. 1301 - 1311
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[31]Russian Chemical Bulletin,2008,vol. 57,p. 2090 - 2092
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[33]Chemical Communications,2020,vol. 56,p. 2582 - 2585

4
[ 20662-89-9 ]
[ 4526-07-2 ]
[ 86842-14-0 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 2473 - 2476

5
[ 75-77-4 ]
[ 87-68-3 ]
[ 4526-07-2 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 4221 - 4224
Angew. Chem.,2013,vol. 125,p. 4315 - 4318,4
[2]Chemistry - A European Journal,2009,vol. 15,p. 9105 - 9116
[3]Journal of Organic Chemistry,2017,vol. 82,p. 1743 - 1760
[4]Physical Chemistry Chemical Physics,2016,vol. 18,p. 21976 - 21993
[5]Organic Letters,2008,vol. 10,p. 4525 - 4528
[6]Liebigs Annalen der Chemie,1984,p. 586 - 599

6
[ 108-36-1 ]
[ 1066-54-2 ]
[ 4526-07-2 ]
[ 38170-80-8 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 2489 - 2496

7
[ 1066-54-2 ]
[ 4526-07-2 ]
[ 38170-80-8 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 2489 - 2496

8
[ 4526-07-2 ]
[ 4526-06-1 ]

Yield	Reaction Conditions	Operation in experiment
61%	With methyllithium lithium bromide; In diethyl ether; at 25℃; for 3h;Inert atmosphere;	Synthesis of trimethylsilylbutadiyne (compound 2 of Figure 9) . This compound is prepared with a slight modification of a previously reported procedure. Bis (trimethylsilyl ) butadiyne (25 g, 129 mmol) , MeLi-LiBr (200 ml, 1.5 M in Et20, 300 mmol), and dry Et20 (800 ml) are combined in a 2000 mL round bottom flask equipped with a magnetic stir bar and a rubber stopper under N2 atmosphere. The solution is stirred for 3 h at 25 C and then cooled to 0 C in an ice bath. MeOH is added to the cooled solution to neutralize the excess Li adduct . The mixture is extracted with saturated NH4C1 (3 chi 200 ml) and the Et20 layer is collected, washed with brine (3 chi 200 ml) , dried over MgS04, and filtered. Et20 is then gently removed at 25 C on a rotary evaporator. Remaining Et20 is removed in a vacuum distillation setup at 60 millitorr and 0 C in an ice bath as a first fraction. Then, the mixture is taken out of the ice bath and compound 2 is collected at 25 C as a clear oil from the same distillation setup. Yield = 9.6 g (61%) . XH NMR (500 MHz, CDC13) is shown in Fig. 10, where delta 0.21 (s, 9H, -Si (C) 3) , 2.12 (s, 1H, -C?CH) . 13C NMR (126 MHz, CDC13) is shown in Fig. 11, where delta 0.35, 66.85, 68.46, 84.91, and 87.55.
	With methyllithium lithium bromide; In diethyl ether; at 20℃;	Step 1 : Preparation of (R)- methanesulfonic acid 3-(3-methyl-benzo[<5/]isoxazol-6-yl)-2-oxo- oxazolidin-5-yhnethyl ester3-(3-Me%l-benzo[<lisoxazol-6-yl)-5(R)-(4-trimethylsilanylethynyl-[l,2,3]triazol-l- ylmethyl)-oxazolidin-2-one is prepared based on the procedure of Reck, F.; et al. J. Med. Chem. 2005, 48, 499-506: Methyllithium lithium bromide complex (1.5 M in ether, 5.1 mL, <n="24"/>7.7 mmol) is added to a solution of l,4-bis(trimethylsilyl)butadiyne (1.00 g, 5.14 mmol) in ether (20 mL). After stirring overnight at RT, water is added and the layers are separated. The org layer is washed with sat NH4Cl, brine, dried over Na2SO4 and cone in vacuo (130 torr) to give buta-l,3-diynyl(trimethyl)silane. A mixture of buta-l,3-diynyl(trimethyl)silane (0.112 g, 0.915 mmol), 5(jR)-azidomethyl-3-(3-methyl-benzo[fif]isoxazol-6-yl)-oxazolidin-2- one (0.100 g, 0.366 mmol), acetonitrile (2.5 mL), 2,6-lutidine (50 mL, 0.403 mmol), and copper(I) iodide (0.020 g, 0.105 mmol) is stirred at RT overnight. Water is added and the mixture is stirred for several minutes. The resultant solid is collected by filtration and washed with water and ether. Purification by silica gel chromatography afforded 0.080 g (55%) of the title compound. 1H NMR (400 MHz, CDCl3): delta 7.86 (s, IH), 7.55 (m, 2H), 7.44 (dd, /= 8.8, 2.0 Hz, IH), 5.07 (m, IH), 4.76 (m, 2H), 4.24 (t, J= 9.2 Hz, IH), 3.97 (dd, J= 9.2, 6.6 Hz, IH), 2.53 (s, 3H), 0.22 (s, 9H). MS-APCI (taun/z+): 396 (M+l).
	With methyllithium lithium bromide; In diethyl ether; at 20℃; for 3.75h;	Compound 8 (1.00 g, 5.14 mmol, 1.0 eq.) was dissolved in 10 mL of Et2O. MeLi?LiBr (3.8 mL, 1.5 M in Et2O, 5.7 mmol, 1.1 eq.) was added at r.t. and a milky precipitate formed. The vessel was sealed and stirred for 3h 45min, after which the green suspension was quenched with 3 mL of NH4Cl (aq., sat.) and stirred for 15 minutes. The vessel contents were transferred to a separatory funnel; approx. 20 mL of NH4Cl (aq., sat.) was added and the resulting liquid was extracted twice with small portions of Et2O. The ether extracts were used immediately without further purification

	With methyl lithium lithium bromide complex; In diethyl ether; at 20℃; for 3.5h;Inert atmosphere; Cooling with ice;	To an ice bath-cooled solution of 1,4-bis(trimethylsilyl)buta-1,3-diyne (12.5 g, 64.3 mmol) in diethyl ether (400 mL) under an inert atmosphere was cannulated methyllithium-lithium bromide complex (1.5 M in ether, 100 mL, 150 mmol). The solution was stirred for 3.5 hours at ambient temperature. The solution was cooled in an ice water bath and quenched by the dropwise addition of methanol (6.06 mL, 150 mmol). The mixture was washed sequentially with saturated aqueous NH4Cl solution and brine, dried over magnesium sulfate, filtered, and partially concentrated to give product 2.1a (26 g of approximately 23% by weight solution in ether.) 1H NMR (400 MHz, CDCl3): 2.10 (s, 1H), 0.20 (s, 9H).
	With methyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; at -78 - 20℃; for 3.5h;Inert atmosphere;	The preparation of HC?CC?CSiMe3 was carried out by amodification of reported literature procedures [28]. Both diethyletherand THF were investigated as reaction solvents but reactionsin diethylether appeared to progress only slowly andincompletely. Full conversion of Me3SiC?CC?CSiMe3 to HC?CC?CSiMe3 was not achieved even in THF with a 1.5 M excessof MeLi/LiBr as evidenced by IR spectra of isolated products whichexhibited a n(C?C) band at 2066 cm1 (CH2Cl2) (lit 2065 cm-1 [29])) due to unreacted Me3SiC?CC?CSiMe3 in addition to product bands at 2189 and 2034 cm-1 (lit. 2190, 2035 cm1 [30]). Me3SiC?CC?CSiMe3 (2.00 g, 10.3 mmol) was dissolved in distilled, degassed THF (25 cm3) and stirred under N2 forming abeige solution. The solution was cooled to 78 C before MeLi/LiBr (10 cm3 of a 1.5 M solution in diethyl ether, 15.0 mmol) was added dropwise over 10 min. The reaction mixture was stirred at 78 C for 1 h and then allowed to warm to room temperature and stirring continued for a further 2.5 h. Saturated aqueous NH4Cl solution(30 cm3) was added portion-wise with cooling and the mixture was then stirred for 1 h. The reaction mixture was extracted with pentane (40 cm3) and the organic layer was washed with brine,dried with MgSO4, filtered and evaporated to give the product as a yellow-brown oil; IR: n(C?C) (cm-1), (CH2Cl2), 2189, 2066, 2034. The isolated product was used directly without further purificationin subsequent reactions with an assumed yield of HC?CC?CSiMe3 of ca. 50% consistent with previous reports [28b].
	With methyllithium lithium bromide; In diethyl ether; at 20℃; for 12h;	To a solution of l,4-bis(trimethylsiliyl)-buta-l,3-diyne (1.0 g, 5.14 mmol) in 15 mL of dry ethyl ether, MeLi LiBr (1.5 M in ether, 6.68 mmol, 4.45 mL) was added and the reaction mixture was stirred at room temperature for 12 h. The reaction was quenched with saturated NH4C1 (aq) at 0 C and the product was extracted with ethyl ether. The combined organic layer was dried over anhydrous a2S04. After filtration, the solution was carefully evaporated in vacuum to give the crude S6 as slightly dark oil, which was diluted in 5 mL of i-BuOH and stored below 0 C.
	With methyllithium lithium bromide; In diethyl ether; at 20℃; for 12h;	To a solution of 1,4-bis(trimethylsiliyl)-buta-1,3-diyne (1.0 g, 5.14 mmol) in 15 mL of dry ethyl ether, MeLi LiBr (1.5 M in ether, 6.68 mmol, 4.45 mL) was added and the reaction mixture was stirred at room temperature for 12 h. The reaction was quenched with saturated NH4C1 (aq) at 0 C and the product was extracted with ethyl ether, The combined organIc layer was drjed over anhydrous Na2SO4. After filtration, the solution was carefully evaporated in vacuum to give the crude S6 as slightly dark oil, which was diluted in 5 rnL of t-BuOH and stored below 0 C.
	With methyllithium lithium bromide; In diethyl ether; at 20℃; for 15h;Inert atmosphere;	To a stirred solution of l,4-bis(trimethylsilyl)buta-l,3-diyne (131) (0.37 g, 1.9 mmol) in 10 mL of diethyl ether, 1.5 mL (2.25 mmol) of 1.5 M methyllithium lithium bromide complex solution in diethyl ether was added under argon. The mixture was stirred at room temperature for 15 h, then cooled in an ice bath, and quenched with 10 mL of saturated NH4CI solution. The organic layer was washed with brine, dried over Na2SC>4 and the solvent was stripped off on rotovap in a weak vacuum. To a solution of (trimethylsilyl)buta-l,3-diyne (132) in 14 mL of THF, iodide 3(1) (0.65 g, 1.26 mmol), 4 mL of TEA, Pd(PPli3)4 (73 mg, 0.063 mmol), and Cul (25 mg, 0.13 mmol) were added, and the mixture was stirred under argon at 45 C for 15 h. The mixture was filtered through celite, rotovapped, and subjected to column chromatography on S1O2 (chloroform : acetone 19: 1) to afford 0.432 g (67 %) of (S)-2-{5-[6-(4-trimethylsilanyl-buta-l,3-diynyl)-biphenyl-3-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (3(31)), LC-MS (ESI) 510 (M+H)+.

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9
[ 4526-07-2 ]
[ 78-80-8 ]
[ 136053-37-7 ]

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10
[ 4526-07-2 ]
[ 571-58-4 ]
4-trimethylsilyl-2-(1,4-dimethyl-2-naphthyl)-1-buten-3-yne [ No CAS ]
(Z)-1,4-bis(trimethylsilyl)-2-(1,4-dimethylnaphthyl)-1-buten-3-yne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 33% 2: 22%	With gallium(III) trichloride In tetrahydrofuran; dichloromethane at -98℃; for 1h;

Reference： [1]Yonehara, Fumi; Kido, Yoshiyuki; Yamaguchi, Masahiko [Chemical Communications, 2000, # 13, p. 1189 - 1190]

11
[ 4526-07-2 ]
[ 38053-91-7 ]
1-trimethylsilanyl-2-trimethylsilanylethynyl-4-trimethylsilanyloxy-cyclohexa-1,4-diene [ No CAS ]

Reference： [1]Synlett,2002,p. 1081 - 1084

12
[ 4526-07-2 ]
[ 6324-50-1 ]
1-(2,4,6-trichlorophenyl)-4-(trimethylsilyl)butadiyne [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 1603 - 1609

13
[ 1119-64-8 ]
[ 18146-00-4 ]
[ 4526-07-2 ]
(Z)-5-trimethylsilyl-4-trimethylsilylethynylundeca-1,4-dien-6-yne [ No CAS ]