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[ CAS No. 1066-54-2 ]

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2D
Chemical Structure| 1066-54-2
Chemical Structure| 1066-54-2
Structure of 1066-54-2 *Storage: {[proInfo.prStorage]}

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Product Details of [ 1066-54-2 ]

CAS No. :1066-54-2MDL No. :MFCD00008569
Formula : C5H10Si Boiling Point : 52-53°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :98.22Pubchem ID :66111
Synonyms :

Computed Properties of [ 1066-54-2 ]

TPSA : 0 H-Bond Acceptor Count : 0
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.60 Rotatable Bond Count : 1

Safety of [ 1066-54-2 ]

Signal Word:DangerClass:3
Precautionary Statements:P210-P261-P305+P351+P338UN#:1993
Hazard Statements:H225-H315-H319-H335Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1066-54-2 ]

  • Upstream synthesis route of [ 1066-54-2 ]
  • Downstream synthetic route of [ 1066-54-2 ]

[ 1066-54-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 90-96-0 ]
  • [ 1066-54-2 ]
  • [ 101597-25-5 ]
YieldReaction ConditionsOperation in experiment
57.6%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 4 h; Inert atmosphere
Stage #2: With sodium hydroxide In methanol at 0℃;
General procedure: To a solution of (trimethylsilyl)acetylene (4.5 g, 45 mmol) in anhydrous THF (150 mL) under nitrogen atmosphere was added slowly n-BuLi (1.6 M in hexane, 28.5 mL, 45 mmol) at -10°C and the solution stirred 1h at - 10°C. A solution of benzophenone (7.44 g, 40.8 mmol) in dry THF (75 mL) was then added at -10°C. After 3h stirring at -10°C, the temperature was raised to 0°C and a solution of NaOH (2.16 g, 54 mmol) in MeOH (40,8 mL) was added. After the solution was warmed to room temperature, the solution was neutralized to pH 7 with acetic acid and the resulting solution poured into water (546 mL). The organic layer was extracted with EA (3x105 mL). The combined organic layers were dried over MgSO4. The crude product was recristallized from EA/PE to give 7,5 g of 1c as a light yellow solid (88,4percent).
Reference: [1] European Journal of Organic Chemistry, 2003, # 7, p. 1220 - 1230
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 17, p. 4341 - 4345[3] Angew.Chem.Int.Ed., 2014, vol. 53, p. 4341 - 4345,5
[4] Tetrahedron, 2011, vol. 67, # 2, p. 401 - 407
[5] European Journal of Organic Chemistry, 2011, # 11, p. 2111 - 2119
  • 2
  • [ 51934-41-9 ]
  • [ 1066-54-2 ]
  • [ 10602-03-6 ]
Reference: [1] Chemistry Letters, 2013, vol. 42, # 10, p. 1308 - 1310
[2] Patent: CN104151174, 2016, B, . Location in patent: Paragraph 0011; 0020; 0021
  • 3
  • [ 51934-41-9 ]
  • [ 7681-65-4 ]
  • [ 1066-54-2 ]
  • [ 10602-03-6 ]
Reference: [1] Patent: US2002/120006, 2002, A1,
[2] Patent: US6624154, 2003, B1,
  • 4
  • [ 16932-44-8 ]
  • [ 1066-54-2 ]
  • [ 126829-31-0 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With copper(l) iodide; diisopropylamine In toluene at 20 - 60℃; for 49 h; Inert atmosphere
Stage #2: With methanol; sodium hydroxide In tetrahydrofuran at 20℃; for 1 h; Inert atmosphere
Example 15; 1 ) Me3SiCCH,9I (93percent)[0125] 2,6-Dimethoxyphenylacetylene (91). To a stirred, degassed solution of 2-iodo-l ,3- dimethoxybenzene (13.2 g, 50 mmol), trans-dichlorobis(triphenylphosphine)palladium(II) (702 mg, 1 mmol), triphenylphospine (524 mg, 2 mmol), and copper(I) iodide (288 mg, 1.5 mmol) in 3 : 1 (v/v) toluene : diisopropylamine (200 mL) under argon is addedtrimethylsilylacetylene (8.0 mL, 57 mmol). The resulting mixture is stirred under argon at room temperature for lh, followed by 48 hour at 60°C, during which period a heavy precipitate attributed to iPr2NHHI is formed. Contents are passed on a Si02 plug with ethyl acetate as eluent. Volatiles are evaporated under reduced pressure, and the contents are passed on a short Si02 column with 95 :5 to 90: 10 pentane : ethyl acetate (v/v) as the eluent to afford the crude TMS-protected alkyne as an off-white solid that is directly carried to the next step without further purification. The solid is dissolved in THF (90 mL) and the solution is degassed by bubbling argon gas through for ca. 30 min. To the stirred mixture is added by a solution of sodium hydroxide (6 g) in methanol (30 mL). The reaction mixture is stirred at room temperature for lh, before pouring of the contents in saturated aqueous NaCl. After extration with diethyl ether and evaporation of the volatiles, the crude alkyne is purified by passage through a short Si02 column using 1 : 1 dichloromethane : pentane (v/v) as the eluent to afford alkyne 91 as a beige solid (7.55 g, 93percent over 2 steps). 1H-NMR (CDC13, 300 MHz): δ = 7.25 (t, J = 8.4 Hz, 1H), 6.54 (d, J = 8.4 Hz, 2H), 3.89 (s, 6H), 3.57 (s, 1H). 13C-NMR (CDC13, 75 MHz): δ =161.9, 130.2, 103.2, 99.9, 85.3, 76.3, 55.9. Characterization data for 91 are consistent with literature values (See Wayland, B. B.; Sherry, A. E.; Poszmic, G.; Bunn, A. G. J. Am. Chem. Soc. 1992, 1 14, 1673-1681).
Reference: [1] Patent: WO2011/139704, 2011, A2, . Location in patent: Page/Page column 41
  • 5
  • [ 59247-47-1 ]
  • [ 1066-54-2 ]
  • [ 111291-97-5 ]
Reference: [1] Patent: US4818819, 1989, A,
  • 6
  • [ 1066-54-2 ]
  • [ 111291-97-5 ]
Reference: [1] Patent: US4818819, 1989, A,
  • 7
  • [ 626-01-7 ]
  • [ 1066-54-2 ]
  • [ 110598-30-6 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4165 - 4169
[2] Chemistry Letters, 2010, vol. 39, # 7, p. 788 - 789
[3] Macromolecules, 2012, vol. 45, # 20, p. 8155 - 8165
[4] Journal of the American Chemical Society, 2014, vol. 136, # 40, p. 13999 - 14002
[5] Chemistry - A European Journal, 2001, vol. 7, # 21, p. 4706 - 4714
[6] Tetrahedron, 1997, vol. 53, # 22, p. 7595 - 7604
[7] Tetrahedron Letters, 2002, vol. 43, # 39, p. 7091 - 7094
[8] Canadian Journal of Chemistry, 2008, vol. 86, # 5, p. 410 - 415
[9] Macromolecules, 2012, vol. 45, # 20, p. 8155 - 8165,11
[10] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8281 - 8291
  • 8
  • [ 615-43-0 ]
  • [ 1066-54-2 ]
  • [ 110598-30-6 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 44, p. 9977 - 9982
  • 9
  • [ 591-19-5 ]
  • [ 1066-54-2 ]
  • [ 110598-30-6 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4165 - 4169
  • 10
  • [ 223463-13-6 ]
  • [ 1066-54-2 ]
  • [ 111770-86-6 ]
Reference: [1] Catalysis Communications, 2014, vol. 47, p. 40 - 44
  • 11
  • [ 13472-79-2 ]
  • [ 1066-54-2 ]
  • [ 1064706-78-0 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 36, p. 8522 - 8529
  • 12
  • [ 84249-14-9 ]
  • [ 1066-54-2 ]
  • [ 1094679-27-2 ]
YieldReaction ConditionsOperation in experiment
33% With bis(benzonitrile)palladium(II) dichloride; caesium carbonate; triethylamine; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane In N,N-dimethyl-formamide at 50℃; for 2 h; Compound 2 (400 mg, 2.31 mmol), trimethylsilylacetylene (0.38 ml, 2.77 mmol), cesium carbonate (39.1 mg, 0.12 mmol), 4,5- bis (diphenylphosphino) -9,9-dimethylxanthene (69.4 mg , 0.12 mmol) and was dissolved bis (benzonitrile) palladium (II) dichloride (46.0 mg, a 0.12 mmol) in DMF (5 ml). Further added triethylamine (2 ml) to this was stirred for 2 hours at 50 in an oil bath. After completion of the reaction, THF and (3 ml) and tetrabutylammonium fluoride (2.77 ml) was added and the solvent was concentrated under reduced pressure, and allowed to react for 30 minutes at room temperature. The solvent was evaporated, adsorbed resulting residue was applied to a silica gel column,Methanol - was eluted with a mixed solvent of chloroform (1:50) to give Compound 5a (90.1 mg, 33percent).
Reference: [1] Patent: JP2015/221769, 2015, A, . Location in patent: Paragraph 0031; 0033
Historical Records

Related Functional Groups of
[ 1066-54-2 ]

Organosilicon

Chemical Structure| 14630-40-1

[ 14630-40-1 ]

Bis(trimethylsilyl)acetylene

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