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Home > Encyclopedia > Benzo[1,2-b:4,5-b']dithiophene-4,8-dione

Benzo[1,2-b:4,5-b']dithiophene-4,8-dione

Benzo[1,2-b:4,5-b']dithiophene-4,8-dione structure

Benzo[1,2-b:4,5-b']dithiophene-4,8-dione 

structure
  • CAS No:

    32281-36-0

  • Formula:

    C10H4O2S2

  • Chemical Name:

    Benzo[1,2-b:4,5-b']dithiophene-4,8-dione

  • Synonyms:

    Benzo[1,2-b:4,5-b']dithiophene-4,8-dione;4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophen-4,8-dione;8-Dihydrobenzo[1,2-b:4,5-b']dithiophen-4,8-dione;NSC 149690;benzo[1,2-b:4,5-b']bisthiophene-4,8-dione;4,8‐Dihydrobenzo[1,2‐b:4,5‐b']dithiophen‐4,8‐dion;4,8-Dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione;Thieno[2,3-f]benzothiophene-4,8-dione

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Benzo[1,2-b:4,5-b']dithiophene-4,8-dione Basic Attributes

220.268

219.965271

G1C271HP09

149690

DTXSID00186030

2934999090

Characteristics

90.6

2.9

1.595

260-262℃

408°C at 760 mmHg

200.6±25.9 °C

1.736

Safety Information

NONH for all modes of transport

3

24/25

Benzo[1,2-b:4,5-b']dithiophene-4,8-dione Use and Manufacturing

Methods of Manufacturing

100ml three bottles, 6.82 g (37.25 mmol, 1.0 eq) of thiophene-3- (N, N-diethyl) formamide was added, Nitrogen was substituted 3 times, Then add freshly distilled tetrahydrofuran 30ml;Ice salt bath cooling to an internal temperature to 0 degrees, 15.0 ml (37.25 mmol, 1.0 eq) of 2.5 M n-butyllithium was dropped, Dropping time 20 minutes. After the addition was completed, the mixture was stirred at room temperature for 30 minutes, Pour 40g crushed ice, stir overnight, suction filtration the next day, Washed with water, methanol, petroleum ether, Vacuum drying yellowThe powder is benzo [1, 2-B: 4, 5-B] dithiol-4, 8-dione;3.50g, yield 86.1percent;In a well-dried flask, N, N-Diethylthiophene-3-carboxamide, 1(18.3 g, 100 mmol) was dissolved in dry THF (200 mL) under inertatmosphere. The solution was cooled down to 0 C by an ice-waterbath followed by the drop wise addition of n-BuLi (2.5 M in hexanes, 40 mL, 100 mmol). The resultant mixture was heated to roomtemperature and stirred for 30 min. After the completion of reaction, reaction mixture was poured into ice water (300 mL) andstirred for 2 h. The mixture was filtered and the yellow precipitateobtained was subjected to serial washings with water (100 mL), methanol (30 mL) and hexane (30 mL) to obtain the title compoundas yellow powder (yield 78percent).1H NMR (500 MHz, CDCl3, d ppm): 7.65 (d, J 5.0 Hz, 2H), 7.69(d, J 5.0 Hz, 2H).2 (2.00 g, 10.9 mmol) was dissolved in 30 mL THF under argon atmosphere. The solution was cooled to 0 °C, and n-butyllithium (5.2 mL, 2.5 mol/L) was added dropwise within 30 min. Then, the reactant was stirred at room temperature for 30 min. The reactant was poured into 100 mL ice water and stirred for another 2 h. The mixture was filtrated, and the precipitate was washed by 10 mL water, 5 mL of methanol. 3 was obtained as yellow powder in 71percent yield. Mp >200 °C 250mL round bottom flask and then placed in a N, N- diethyl-3-thiophene carboxamide amide (compound g-2) 7g, it makes the vacuum. Then, n-BuLi (2.0M in hexane) at 0°C and then slowly inject 28.6 mL, then stirred at room temperature for 30 minutes. After 2 hours, when complete the reaction through a distilled water, there is no solid raksaek is generated if the filter through which the distilled water, methanol, hexane 4, 8-dihydro-benzo [1, 2-b: 4, 5-b0] The ET 4, 8-thiophene is obtained the ion (compound g-3). (Yield: 48percent)

Uses

suzuki reaction

Computed Properties

Molecular Weight:220.3
XLogP3:2.9
Hydrogen Bond Acceptor Count:4
Exact Mass:219.96527171
Monoisotopic Mass:219.96527171
Topological Polar Surface Area:90.6
Heavy Atom Count:14
Complexity:273
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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