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Chemical Structure| 251-41-2 Chemical Structure| 251-41-2
Chemical Structure| 251-41-2

1,4-Dithiapentalene

CAS No.: 251-41-2

Synonyms: 1,4-Thiophthene

4.5 *For Research Use Only !

Cat. No.: A104028 Purity: 98%

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Product Details of [ 251-41-2 ]

CAS No. :251-41-2
Formula : C6H4S2
M.W : 140.23
SMILES Code : C1=CSC2=C1SC=C2
Synonyms :
1,4-Thiophthene
MDL No. :MFCD00179479
InChI Key :VJYJJHQEVLEOFL-UHFFFAOYSA-N
Pubchem ID :136063

Safety of [ 251-41-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis [ 251-41-2 ]

* 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 [ 251-41-2 ]
  • Downstream synthetic route of [ 251-41-2 ]

[ 251-41-2 ] Synthesis Path-Upstream   1~2

  • 1
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YieldReaction ConditionsOperation in experiment
61.25%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.16667 h; Inert atmosphere; Cooling with ice
Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water
To a solution of thieno[3,2-b]thiophene (1 .5 g, 10.70 mmol) in THF (25.5 mL) at -78 °C under N 2 is added dropwise a solution of BuLi in hexanes (8.988 mL of 2.5 M, 22.47 mmol), stirred for 20 min, cooling bath is replaced with ice bath and stirred for 50 min. The resultant thick suspension is quenched with 2- isopropoxy-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (4.181 g, 4.584 mL, 22.47 mmol). The reaction mixture is kept for overnight and then quenched with saturated aq. NH4Cl solution. After extraction with CH2Cl2 (2 x 100 mL), the combined extracts are washed with brine and dried (Na2S04). Organic solution is diluted with -20 mL of ethyl acetate, concentrated slowly on rotary evaporator until CH2Cl2 is removed. The resultant white fine crystals are collected by filtration. The solid is washed with heptanes and dried under high vacuum to afford 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1 ,3,2-dioxaborolane (2.57 g, 6.554 mmol, 61.25percent) as half-white solid. 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 2H), 1.343 (s, 12H).
References: [1] Patent: WO2011/119853, 2011, A1, . Location in patent: Page/Page column 126-127.
[2] Patent: WO2011/119858, 2011, A1, . Location in patent: Page/Page column 86.
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References: [1] Dalton Transactions, 2015, vol. 44, # 29, p. 13007 - 13016.
 

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