174508-31-7|5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine| Ambeed

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Quality Control of [ 174508-31-7 ] Purity: 95% (stabilized with Cu+HQ+MgO) SDS Specification

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Product Details of [ 174508-31-7 ]

CAS No. :	174508-31-7
Formula :	C₆H₄Br₂O₂S
M.W :	299.97
SMILES Code :	BrC1=C2OCCOC2=C(Br)S1
MDL No. :	MFCD01651770
InChI Key :	FHMRWRBNAIDRAP-UHFFFAOYSA-N
Pubchem ID :	3834570

Safety of [ 174508-31-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 174508-31-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	5
Fraction Csp3	0.33
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	50.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.7 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.39
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.04
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.99
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	4.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.16
Solubility	0.0208 mg/ml ; 0.0000693 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.03
Solubility	0.0281 mg/ml ; 0.0000936 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.39
Solubility	0.122 mg/ml ; 0.000406 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.74 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.04

Application In Synthesis of [ 174508-31-7 ]

* 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 [ 174508-31-7 ]

[ 174508-31-7 ] Synthesis Path-Downstream 1~35

1
[ 126213-50-1 ]
[ 174508-31-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 2h;	step 1),3,4-ethylenedioxythiophene (1.42 g, 10 mmol) was dissolved in 30 mL of DMF.And use an ice bath to drop to 0 C,N-bromosuccinimide (3.78 g, 21 mmol) was dissolved in 30 mL DMF.Slowly drip into the above solution with a constant pressure dropping funnel.After the addition is completed,The reaction was stirred at room temperature for 2 h.After the reaction is over,100 mL of ice water was slowly added to the reaction solution.Produces a large amount of light yellow solids,The product is filtered under reduced pressure,The filter residue was washed three times with 15 mL of deionized water.2.85 g of product, Compound 4, was obtained.Yield 95%;
83%	With N-Bromosuccinimide; acetic acid; In tetrahydrofuran; at 20℃; for 2h;	A THF (20 mL) solution of 3,4-ethoxylene dioxy thiophene(1.42 g,10.60 mmol), N-bromosuccinimide (3.74 g,12.80 mmol) andacetic acid (20 mL) were charged sequentially into a round-bottomflask. The mixturewas stirred for 2 h at room temperature. After thereaction, pouring the reaction mixture into distilled water andstirring with a glass rod, precipitate was filtered to afford A4 as awhite solid (2.50 g, 8.30 mmol, yield 83%). 1H NMR (400 MHz,CDCl3,ppm): delta = 4.27 (s, 4H).
74%	With N-Bromosuccinimide; In tetrahydrofuran; at 10℃; for 80h;Inert atmosphere;	General procedure: 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, 68% yield).

72%	With N-Bromosuccinimide; for 1h;	A mixture of bromosuccinimide (NBS) (2.75 g, 15.45 mmol) and N,N-dimethylformamide (DMF) (15 ml) was added dropwise to the mixture of EDOT (1.0 g, 7.03 mmol) and DMF (15 ml) and the reaction temperature was kept between 18-23 C. After completion of the addition, the mixture was stirred for 1 h, and then poured into an equal of ice water. After vigorous shaking for 5 min, the mixture was extracted with CH2Cl2, and washed with saturated NaHCO3 solution once and with water for three times. The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to leave a crude residue. Purification by recrystallization with n-hexane afforded 1.5 g 2,5-dibromo-3,4-ethylenedioxythiophene as a white solid in 72% yield. 1H NMR (400 MHz, CDCl3): delta 4.27 (s, 4H); 13C NMR: delta 139.7, 85.5, 64.9.
33%	With N-Bromosuccinimide; acetic acid; In tetrahydrofuran; at 20℃; for 3h;	5-Br was synthesized based onliterature.5 3,4-Ethylenedioxythiophene (1.0 g, 7.04 mmol) and a mixture of THF/CH3COOH(24 mL, 1:1 v/v) were added to a dry 100 mL 2-neck round-bottom flask. NBS (3.13 g, 17.6 mmol)was added and the solution was stirred at room temperature for 3 h. Then, distilled water (50 mL)was poured to the reaction mixture. A silver crystalline solid was precipitated, filtered, dried andused without further purification (0.7 g, 33%). 1H NMR (300 MHz, DMSO-d6), delta: 4.30 (s, 4H).13C NMR (75 MHz, DMSO-d6), delta: 140.1, 84.2, 64.7.
	With N-Bromosuccinimide; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	Compound 1 (0.3 g, 2.11 mmol) and N-bromosuccinimide (NBS)?(0.75 g, 4.22 mmol) were dissolved in 20 mL fleshly distilled THE and stirred at r.t. for 2 hr under N2. The reaction solution was transferred by syringe to a N2 protected 50 mL flask containing K2C03 (2 M, 5 ml), Pd(0)(PPh3)4 (0.129,0.1 mmol) and compound 4(1.47 g, 4.22 mmol). The reaction mixture was then stirred at reflux in the dark for 6 hr. The reaction mixture was cooled down to r.t. and poured into water, extracted with dichioromethane (DCM) and washed with water. The DCM layer was dried over MgSO4, concentrated and the residue mixture was purified by column chromatography on silica gel elutirig with DCM to obtain the product as a yellow solid (1.3 g, 82%). 1H NMR (CD2CI2) 6: 7.55 (br, 4H), 7.07 (d, J = 8.4 Hz, 8H), 6.90 (d, J = 7.6 Hz, 4H), 6.86 (d, J = 8.8 Hz, 12H), 4.34 (s, 4H), 3.81 (s, 12H). 13C NMR (CD2CI2) 6: 156.5, 147.7, 141.1, 138.3, 127.0, 125.8, 120.9, 115.1, 65.1, 55.9. HRMS (MALDI-TOF): calcd for C46H40N206S, 748.2607; found, 748.2656. Anal. calcd. for C46H40N206S: C, 73.78; H, 5.38; N, 3.74; S, 4.28 %. Found: C, 74.01; H, 5.29; N, 3.70; S, 4.21 %.

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6746 - 6753.
[2]Patent: CN108997427,2018,A .Location in patent: Paragraph 0064; 0065; 0066; 0072.
[3]Journal of Organic Chemistry,2003,vol. 68,p. 5357 - 5360.
[4]Organic Letters,2018,vol. 20,p. 4728 - 4731.
[5]Journal of the American Chemical Society,2000,vol. 122,p. 10121 - 10125.
[6]Macromolecules,2004,vol. 37,p. 4087 - 4098.
[7]Dyes and Pigments,2017,vol. 136,p. 97 - 103.
[8]Journal of the American Chemical Society,2003,vol. 125,p. 15151 - 15162.
[9]Advanced Materials,2011,vol. 23,p. 1641 - 1646.
[10]RSC Advances,2014,vol. 4,p. 38797 - 38803.
[11]Dyes and Pigments,2015,vol. 116,p. 146 - 154.
[12]Journal of Materials Chemistry,2001,vol. 11,p. 1378 - 1382.
[13]Journal of Materials Chemistry,2009,vol. 19,p. 4914 - 4921.
[14]Chemistry - A European Journal,2002,vol. 8,p. 2384 - 2396.
[15]Electrochimica Acta,2014,vol. 146,p. 666 - 678.
[16]RSC Advances,2019,vol. 9,p. 34691 - 34698.
[17]Journal of Materials Chemistry C,2015,vol. 3,p. 3211 - 3218.
[18]Synlett,2018,vol. 29,p. 2660 - 2668.
[19]Journal of Materials Chemistry,2005,vol. 15,p. 4783 - 4792.
[20]Macromolecules,2011,vol. 44,p. 5200 - 5208.
[21]RSC Advances,2014,vol. 4,p. 2501 - 2508.
[22]Angewandte Chemie - International Edition,2014,vol. 53,p. 4085 - 4088.
Angew. Chem.,2014,vol. 53,p. 4085 - 4088,4.
[23]Patent: WO2015/84256,2015,A1 .Location in patent: Paragraph 0125; 0133; 0135.

2
[ 174508-31-7 ]
oligo(3,4-ethylenedioxythiophene); monomer(s): 2,5-dibromo-3,4-ethylenedioxythiophene [ No CAS ]

References: [1]Journal of Materials Chemistry,2001,vol. 11,p. 1378 - 1382.

3
[ 14575-12-3 ]
[ 174508-31-7 ]
[ 291308-75-3 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 6746 - 6753.

4
[ 174508-31-7 ]
[ 98-80-6 ]
5,7-diphenyl-2,3-dihydrothieno[3,4-b][1,4]-dioxine [ No CAS ]

References: [1]Macromolecules,2011,vol. 44,p. 5200 - 5208.
[2]Chemistry - A European Journal,2002,vol. 8,p. 2384 - 2396.

5
[ 174508-31-7 ]
poly(3,4-ethylenedioxythiophene); monomer(s): 2,5-dibromo-3,4-ethylenedioxythiophene [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 658 - 661.

6
[ 174508-31-7 ]
[ 511286-87-6 ]

References: [1]Journal of Materials Chemistry,2003,vol. 13,p. 27 - 33.

7
[ 174508-31-7 ]
tributyl (7-hexyl-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane [ No CAS ]
5,5''-bis(n-hexyl)-2,2':5',2''-ter[(3,4-ethylenedioxy)thiophene] [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5357 - 5360.

8
[ 174508-31-7 ]
poly(3,4-ethylenedioxythiophene) bromine-doped, C_6.0H_4.10S_1.0Br_1.2; monomer(s): 2,5-dibromo-3,4-ethylenedioxythiophene [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 15151 - 15162.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 15151 - 15162.

9
[ 174508-31-7 ]
[ 479719-88-5 ]
[ 863684-16-6 ]

References: [1]Organic Letters,2005,vol. 7,p. 3409 - 3412.

10
[ 158962-92-6 ]
[ 174508-31-7 ]
2,2',3,3'-tetrahydro-5,5'-bithieno[3,4-b][1,4]dithiine [ No CAS ]
2,5-bis(3,4-ethylenedithiathiophene)-3,4-ethylenedioxythiophene [ No CAS ]

References: [1]Journal of Materials Chemistry,2005,vol. 15,p. 4783 - 4792.

11
[ 862681-08-1 ]
[ 174508-31-7 ]
5,5''''-dihexyl-3',4',3'',4'',3''',4'''-tris(ethylenedioxy)-2,2':5',2'':5'',2''':5''',2''''-quinquithiophene [ No CAS ]

References: [1]Chemistry - A European Journal,2005,vol. 11,p. 3742 - 3752.

12
[ 1003-09-4 ]
[ 174508-31-7 ]
[ 309753-52-4 ]