1015423-45-6|4,6-Dibromothieno[3,4-c]furan-1,3-dione| Ambeed

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Quality Control of [ 1015423-45-6 ] Purity: 95% (stabilized with Cu+HQ+MgO) SDS Specification

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Product Details of [ 1015423-45-6 ]

CAS No. :	1015423-45-6
Formula :	C₆Br₂O₃S
M.W :	311.94
SMILES Code :	O=C(C1=C(Br)SC(Br)=C12)OC2=O
MDL No. :	MFCD27923031
InChI Key :	OQMJQMGTDSIYNQ-UHFFFAOYSA-N
Pubchem ID :	71721475

Safety of [ 1015423-45-6 ]

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

Application In Synthesis of [ 1015423-45-6 ]

* 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.

Downstream synthetic route of [ 1015423-45-6 ]

[ 1015423-45-6 ] Synthesis Path-Downstream 1~34

1
[ 111-26-2 ]
[ 1015423-45-6 ]
[ 566939-56-8 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4656 - 4659.

2
[ 111-68-2 ]
[ 1015423-45-6 ]
[ 1427705-63-2 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4656 - 4659.

3
[ 111-86-4 ]
[ 1015423-45-6 ]
[ 566939-58-0 ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4656 - 4659.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 9608 - 9618.

4
[ 4282-29-5 ]
[ 1015423-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; sodium bromide; In dimethyl sulfoxide; at 20 - 120℃; for 16.1h;	10mmol 3,4-dicarboxythiophene (1.72g), 40mmol NaBr (4.12g), 40mmol DMSO (3.12g) were added to 300mmol acetic anhydride (28.3mL), and stirred at room temperature for 10min. The temperature was increased to 120C to continue the reaction for 16 hours, and then the temperature was reduced to room temperature. The precipitated crystals were collected by filtration and washed twice with n-hexane (10 mL×2), The final product 4,6-dibromo-thienofuran-1,3-dione 2.43g, with a yield of 78%, The purity is 93%.

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 4656 - 4659.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 9608 - 9618.
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 12996 - 13000.
Angew. Chem.,2016,vol. 128,p. 13190 - 13194.
[4]Journal of Materials Chemistry C,2018,vol. 6,p. 500 - 511.
[5]Patent: CN112159416,2021,A .Location in patent: Paragraph 0018; 0024-0033.

5
[ 190723-12-7 ]
[ 1015423-45-6 ]

References: [1]Journal of Materials Chemistry C,2018,vol. 6,p. 500 - 511.
[2]Journal of the American Chemical Society,2013,vol. 135,p. 4656 - 4659.
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 12996 - 13000.
Angew. Chem.,2016,vol. 128,p. 13190 - 13194.

6
[ 108-24-7 ]
[ 190723-12-7 ]
[ 1015423-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 140℃; for 12h;Inert atmosphere;	Acetic anhydride (7.6 mL) was added to 1 (0.50 g, 1.52 mmol) under a nitrogen atmosphere. The mixture was heated to 140 C for 12 h and then cooled to room temperature. The volatile compounds were removed in vacuo and the crude product was used in the next step without purification. After the brown solid was dissolved in toluene (1 mL), 4-trifluoromethylaniline (294 mg, 1.83 mmol) was added to the solution and the mixture was heated under reflux for 24 h. After removing the volatile components, thionyl chloride was added to the residue and the reaction mixture was stirred at 90 C for 12 h. The volatile components were removed in vacuo and the residue was extracted with chloroform. The organic phase was dried with anhydrous sodium sulfate and the solvent was removed under a reduced pressure. The crude product was purified by column chromatography with silica gel using chloroform as the eluent. The product was recrystallized from ethanol to afford TPD1 as an off-white solid with a yield of 81%. 1H NMR (500 MHz, CDCl3, rt): δ 7.76 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 2H). 13C NMR (125 MHz, CDCl3, rt): δ 158.73, 134.55, 133.86, 130.14, 126.42, 126.26, 126.23, 114.90. Anal. Calcd for C13H4Br2F3NO2S: C, 34.31; H, 0.89; N, 3.08. Found: C, 34.11; H, 0.95; N, 3.06.