[ CAS No. 25121-87-3 ]

Name: 25121-87-3|2,5-Dibromothieno[3,2-b]thiophene|97%
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3d Animation Molecule Structure of 25121-87-3

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Quality Control of [ 25121-87-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 25121-87-3 ]

SDS Specification

Alternatived Products of [ 25121-87-3 ]

Product Details of [ 25121-87-3 ]

CAS No. :	25121-87-3	MDL No. :	MFCD03931293
Formula :	C₆H₂Br₂S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	APDAUBNBDJUQGW-UHFFFAOYSA-N
M.W :	298.02 g/mol	Pubchem ID :	3597455
Synonyms :

Calculated chemistry of [ 25121-87-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	8
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	55.1
TPSA :	56.48 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.48
Log Po/w (XLOGP3) :	4.76
Log Po/w (WLOGP) :	4.49
Log Po/w (MLOGP) :	3.81
Log Po/w (SILICOS-IT) :	5.72
Consensus Log Po/w :	4.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.28
Solubility :	0.00157 mg/ml ; 0.00000527 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.68
Solubility :	0.000627 mg/ml ; 0.00000211 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.31
Solubility :	0.0147 mg/ml ; 0.0000494 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.93

Safety of [ 25121-87-3 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 25121-87-3 ]

* 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 [ 25121-87-3 ]
Downstream synthetic route of [ 25121-87-3 ]

[ 25121-87-3 ] Synthesis Path-Upstream 1~6

1
[ 251-41-2 ]
[ 25121-87-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;	Thienothiophene(2.01 g of Tokyo Chemical Industry Co., Ltd.) and 30 mL of dimethylformamide (DMF) were placed in a reaction vessel.After stirring at room temperature to confirm dissolution,6.10 g (2.4 eq) of N-bromosuccinimide (NBS) was put in a powder state.After confirming the disappearance of the raw materials, n-hexane and ion-exchanged water were added to the reaction solution.Perform liquid separation.After washing the organic layer with ion-exchanged water and saturated saline once,Drying was carried out using Na2SO4.Distilling off the solvent under reduced pressure and dryingThiophenethiophene dibromide4.21g (99percent yield).
95%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 12 h;	Added to the reactor 30 mlDMF, thieno [3, 2 - b] thiophene (2.31 g, 16.5 mmol), followed by cooling to 0 °C, adding NBS (8.81 g, 49.5 mmol), light reaction 12 h, NaHSO reaction after the conclusion₃Washing, removing the upper layer solvent, congeals the organic phase concentration, over silica gel column purification to obtain compound C - 21 - 1 (4.67 g, 95percent).
88%	With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 20℃; for 3 h;	N-bromosuccinimide (1.24 g, 6.94 mmol) was added to a solution of thieno [3,2-b]thiophene (1.0 g, 6.94 mmol) in DMF (30 ml) at room temperature and this mixture was stirred for 3h. After this water ( 100 ml) was added and the precipitate formed was filtrated off, washed with water and dried to give 2 as a white solid (1.87 g, 88 percent). ¹H NMR (300 MHz, CDCl3): 8 (ppm) 7.14 (s, 2H, Ar-H); ¹³C NMR (75 MHz, CDC13): 8 (ppm) 138.3 (quat.), 121.8 (CH), 113.7 (quat.)

85%	at 20℃; Inert atmosphere	A solution of 1.55 g (8.7 mmol) of N-bromosuccinimide (NBS) in 1 ml of DMF was slowly added in a stirred solution of 0.61 g (4.35 mmol) of thieno[3,2-b]thiophene in 9 ml of DMF. The reaction mixture was stirred overnight. The product was extracted with dichloromethane and the organic phase was washed 3 times with water, dried with MgSO₄ and the organic solvent was removed with roto-evaporation. The resulting crude residue was purified by column chromatography on silica gel with hexane/dichloromethane 9/1 to give a white solid (1 g, 85percent yield). (m.p. 116.4-118.6 °C) δ_H (200 MHz, CDCl₃) 7.19 (1H, s, 1-H), δ_C (50 MHz, CDCl₃) 128.6, 122.2, 114.4.
68%	With N-Bromosuccinimide In tetrahydrofuran at 10℃; for 80 h; Inert atmosphere	In a 150 mL 3-neckedflask, a solution of thienothiophene(TT) (11.2 g, 80 mmol) in dry THF (100 mL) was cooled to 10 °C under a nitrogenatmosphere. NBS (35.6 g, 200 mmol) was addedslowly in portions and allowed to stir for 8 h at approximately 10 °C. Thereaction mixture was then poured into dichloromethane (DCM).The organic layer was washed with water and dried over anhydrous MgSO₄. After removing thesolvent, the crude product was recrystallized from petroleum ether (PE, boiling range: 60-90 C) to give a colorless solid(16.2 g, 68percent yield). ¹H NMR (300 MHz, CDCl₃):δ (ppm) 7.14 (s, 2H). ¹³C NMR (75 MHz, CDCl₃):δ (ppm) 138.31, 121.75, 113.64. GC-MS (EI, m/z) calcd for (C₆H₂Br₂S₂):297.79, found: 297.77.

Reference： [1] Patent: TWI630193, 2018, B, . Location in patent: Paragraph 0104; 0105
[2] Chemistry - A European Journal, 2011, vol. 17, # 3, p. 866 - 872
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 10, p. 2920 - 2924[4] Angew. Chem., 2013, vol. 125, # 10, p. 2992 - 2996,5
[5] Tetrahedron Letters, 2009, vol. 50, # 51, p. 7148 - 7151
[6] Patent: CN107056798, 2017, A, . Location in patent: Paragraph 0061; 0062; 0063; 0064
[7] Journal of Nanoscience and Nanotechnology, 2010, vol. 10, # 10, p. 6800 - 6804
[8] Journal of Organic Chemistry, 2015, vol. 80, # 20, p. 10127 - 10133
[9] Macromolecules, 2013, vol. 46, # 3, p. 727 - 735
[10] Patent: WO2005/121150, 2005, A1, . Location in patent: Page/Page column 33
[11] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 4, p. 943 - 953
[12] Dyes and Pigments, 2015, vol. 116, p. 146 - 154
[13] Polymer, 2012, vol. 53, # 12, p. 2334 - 2346
[14] Journal of the Institute of Petroleum, 1948, vol. 34, p. 226,229
[15] Dalton Transactions, 2005, # 5, p. 874 - 883
[16] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[17] Journal of the American Chemical Society, 2013, vol. 135, # 6, p. 2040 - 2043
[18] Patent: US8779204, 2014, B2, . Location in patent: Page/Page column 13; 14
[19] Patent: KR101540066, 2015, B1, . Location in patent: Paragraph 0021; 0022; 0023

2
[ 930-96-1 ]
[ 25121-87-3 ]

Reference： [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,

3
[ 201004-08-2 ]
[ 25121-87-3 ]

Reference： [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,

4
[ 1723-27-9 ]
[ 25121-87-3 ]

Reference： [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,

5
[ 25121-87-3 ]
[ 392662-65-6 ]

Reference： [1] Macromolecules, 2013, vol. 46, # 3, p. 727 - 735
[2] Organic Letters, 2007, vol. 9, # 6, p. 1005 - 1008
[3] Macromolecules, 2016, vol. 49, # 7, p. 2541 - 2548

6
[ 25121-87-3 ]
[ 61676-62-8 ]
[ 924894-85-9 ]

Reference： [1] Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9224 - 9231

[ 25121-87-3 ] Synthesis Path-Downstream 1~59

1
[ 25121-87-3 ]
[ 614-45-9 ]
[ 135361-02-3 ]

Reference： [1]Chemistry Letters,1991,p. 1117 - 1120

2
[ 25121-87-3 ]
[ 59020-06-3 ]
[ 143724-45-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 1855 - 1859

3
[ 25121-87-3 ]
[ 3189-43-3 ]
[ 115022-47-4 ]

Reference： [1]Chemistry Letters,1987,p. 2339 - 2342

4
[ 25121-87-3 ]
[ 13154-24-0 ]
[ 863191-91-7 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 10502 - 10503

5
[ 25121-87-3 ]
[ 392662-65-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With lithium diisopropyl amide; In tetrahydrofuran; at -78℃; for 18h;Inert atmosphere;	Take a 500 ml three-neck round bottom bottle and place the stirrer with the upper addition funnel.After drying, it is filled with nitrogen;First, 92 mL of lithium diisopropylamide (0.184 mol, 2.3 eq) was added at a concentration of 2M, followed by dissolving 23.841 g of compound P01 (0.08 mol, 1 eq) in 150 mL of anhydrous tetrahydrofuran in an addition funnel.And the resulting solution was added dropwise to a three-necked round bottom bottle at -78 C.After the reaction gradually returns to temperature, the reaction is continued for 18 hours;The reaction was stopped with 120 mL of saturated aqueous sodium bicarbonate solution.It was then extracted with 200 mL of ethyl acetate and repeated 3 times.The obtained extract is sequentially added with magnesium sulfate to dry, filtered and spin-dried;The crude product was purified by recrystallization from ethanol to give 22.172 g of 3,6-dibromothieno[3,2-b]thiophene (yield: 93%).

Reference： [1]Macromolecules,2013,vol. 46,p. 727 - 735
[2]Organic Letters,2007,vol. 9,p. 1005 - 1008
[3]Patent: CN109836436,2019,A .Location in patent: Paragraph 0076; 0080-0083
[4]Macromolecules,2016,vol. 49,p. 2541 - 2548

6
[ 25121-87-3 ]
3,3';6',3''-ter(thieno[3,2-b]thiophene) [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1005 - 1008

7
[ 25121-87-3 ]
[ 863191-92-8 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 10502 - 10503

8
[ 25121-87-3 ]
[ 863191-93-9 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 10502 - 10503

9
[ 25121-87-3 ]
[ 863191-94-0 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 10502 - 10503

10
[ 25121-87-3 ]
[ 124796-79-8 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 10502 - 10503

11
[ 25121-87-3 ]
[ 139896-69-8 ]