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Structure of 492-97-7

Chemical Structure| 492-97-7

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Product Details of [ 492-97-7 ]

CAS No. :492-97-7
Formula : C8H6S2
M.W : 166.26
SMILES Code : C2=C(C1=CC=CS1)SC=C2
MDL No. :MFCD00005414
InChI Key :OHZAHWOAMVVGEL-UHFFFAOYSA-N
Pubchem ID :68120

Safety of [ 492-97-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 492-97-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 47.63
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

56.48 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.34
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.75
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.48
Log Po/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.

2.37
Log Po/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

4.98
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.38

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.91
Solubility 0.0206 mg/ml ; 0.000124 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.63
Solubility 0.00391 mg/ml ; 0.0000235 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

-3.44
Solubility 0.0598 mg/ml ; 0.00036 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

No
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

Yes
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.

-4.65 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

1.0
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<2.0
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)

2.39

Application In Synthesis of [ 492-97-7 ]

* 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 [ 492-97-7 ]

[ 492-97-7 ] Synthesis Path-Downstream   1~14

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YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide; acetic acid; In chloroform; at 70℃; for 4h; A mixture of 2,2'-bithiophene (5.40 g, 32.4 mmol) and NBS (11.57 g, 64.8 mmol, 2 equiv) in a solvent mixture CHCl3/acetic acid 100% (1:1 (v/v), 300 mL) was stirred at 70 C for 4 h. The reaction media was diluted with CH2Cl2 (50 mL) and a saturated aqueous solution of Na2CO3 (100 mL). The organic phase was isolated and the aqueous phase extracted with CH2Cl2 (3 x 50 mL). The organic phases were assembled, dried with MgSO4, filtered and evaporated to give a pale yellow solid that was then washed with acetone giving the pure product 1a (10.42 g, 98%). Recrystallization from THF afforded a highly pure product. 1H NMR (DMSO-d6, 600 MHz) δ (ppm): 7.23-7.22 (d, J = 3.9 Hz, 2H), 7.15-7.14 (d, J = 3.9 Hz, 2H). 13C NMR (DMSO-d6, 100 MHz) δ (ppm): 136.86, 131.60, 125.22, 110.84. MS(ESI+): m/z = 324.05. UV-visible (DMSO) λmax = 325 nm. IR(ATR): 3069 cm-1 (Ar-H)str; 1683 cm-1 (C=C conjugated)str; 1416 cm-1 (R1-C=C-R2 cis)str; 1293 cm-1 (C=C)bending. Elemental analysis: calculated: C 29.65; H 1.24; S 19.79; found: C 30.03; H 1.40; S 18.13.
93% With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 8h; The compound 2, 2 '- bithiophene (1.66g, 10mmol) was dissolved in N,N-dimethylformamide (20 mL),N-Bromosuccinimide (0.31 g, 1.7 mmol) was dissolved in N, N-dimethylformamide (40 mL), and the latter was slowly added dropwise to the former. After the completion of the addition, the reaction was continued for 8 hours. After the completion of the reaction, a large amount of water was added. The petroleum ether was extracted, dried and filtered. The solvent was removed by rotary evaporation, and the crude product was recrystallized from ethanol as a white solid 19 (3.00 g, 93%).
93% With N-Bromosuccinimide; In chloroform; acetic acid; for 6h;Reflux; Inert atmosphere; Under a dry argon atmosphere, 2,2′-bithiophene (2T) (3.00 g, 0.0180 mol) and N-bromosuccinimide (6.75 g, 0.0379 mol) were dissolved in chloroform/acetic acid (49 mL, 4:3, v/v). The resulting reaction mixture was refluxed for 6 h. Then, the reaction mixture was poured into the stirred mixture of chloroform and water. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The crude product in the residue was purified by recrystallization from the mixed solvent of chloroform and methanol to afford Br2T as colorless crystals with the yield of 93% (5.46 g, 0.0168 mol). 1H NMR (CDCl3, 400 MHz, ppm): δ 6.96 (d, J=3.6 Hz, 2H, thienyl protons), 6.85 (d, J=4.1 Hz, 2H, thienyl protons). 13C NMR (CDCl3, 100 MHz, ppm): δ 137.8 (thienyl carbon), 130.7 (thienyl carbon), 124.2 (thienyl carbon), 111.6 (thienyl carbon). M.p.: 147 C.
93% With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 2h;Reflux; 2,2′-bithiophene (11.7 g, 70.1 mmol) is dissolved in 500 mL of N,N-dimethylmethanamide, and N-bromo succinimide (31 g, 175.2 mmol) is added in a dropwise fashion to bromide it. Then, the resultant is refluxed for 2 hours, water (1 L) is added thereto, and the produced precipitate is filtered and recovered. The recovered powder is dissolved in chloroform (700 mL), washed with water, and then dried with magnesium sulfate followed by evaporating the resultant. The resultant is washed with n-hexane and dried to obtain Compound 1 (A yield of 93%). (0221) 1H-NMR (300 MHz, CDCl3): δ 6.96 (d, J=3.6 Hz, 1H), 6.85 (d, J=3.6 Hz, 1H)
90% With N-Bromosuccinimide; In N,N-dimethyl-formamide;Cooling with ice; To a solution of 2, 2'-bithiophene (12 mmol, 2 g) in anhydrousDMF (30 ml), NBS (24 mmol, 4.28 g) was added dropwisely (coolingwith ice-water during addition of NBS solution) and stirred for 3 h.The reaction mixture was then poured into 100 mL of ice water andthe beige solid was separated by vacuum filtration [1]. The crudewas purified with column chromatography (silica gel100e200 mesh), using hexane as eluent to yield yellow solid asproduct (3.6 g, yield 90%).
85% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; N-Bromosuccinimide (NBS) (11.65 g, 65.450 mmol) was added in small portions to a solution of 2,2'-bithiophene 1 (5 g, 29.76 mmol) in DMF at 0 C. After being stirred over night at room temperature, the reaction mixture was poured into water (200 mL) and extracted with CH2Cl2. The organic layer was thoroughly washed with water, aqueous sodium bicarbonate, brine and again with water, and then dried over Na2SO4. After removal of solvent, it was purified by column chromatography on silica gel using petroleum ether as eluant to afford 5,5'-dibromo-2,2'-bithiophene (2) (8.20 g, 85%) as a white crystal solid. GC/MS: 324(M+). 1H NMR (400 MHz, CDCl3): δ(ppm) 6.97-6.96 (d, J = 4.0 Hz, 2H), 6.86-6.85 (d, J = 4.0 Hz, 2H).
85.69% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 3h; 2,2-Bithiophene (5.00 g, 30.1 mmol) was dissolved in N,N-dimethylformamide (50 mL). With stirring, N-bromosuccinimide (12.3 g, 69.2 mmol) was added at 0C and the reaction mixture was stirred at rt for 3 h. The mixture was poured into methanol (150 mL) and filtered to obtain a white solid product. Yield: 8.35 g (85.69%). 1H NMR (400 MHz, CDCl3): δ (ppm) 6.96 (d, J = 3.9 Hz, 2H), 6.85 (d, J = 3.9 Hz, 2H).
57% With water; sodium bisulfate hydrate; sodium bromide; In acetonitrile; for 96h;Irradiation; In a 25mL reaction tube, add dithiophene (23.6mg, 0.2mmol), sodium bromide (61.6mg, 0.6mmol), sodium bisulfate hydrate (55.2mg, 0.4mmol), water (72mg, 4mmol) and Acetonitrile (2mL), stirred under the irradiation of three 2-watt LED lamps for 96 hours, after the reaction was completed, extracted, dried, filtered, concentrated, and separated by column chromatography to obtain a white solid 2v (37mg, 57%);
51% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 12h; In dimethyl formamide, dissolved was 2- (thiophen-2- yl) thiophene (30 g, 0.18 mol) . Then, with the light shielded, N-bromosuccinimide (70.7 g, 0.4 mol) was diluted with dimethyl formamide, and the dilution was slowly added dropwise to the solution at 0 C After 12 hours, the reaction was quenched, extracted with methylene chloride, and dried over magnesium sulfate. The solvent was removed, and the residue was purified via chromatography to obtain the desired compound, 2-bromo-5- (5-bromothiophen-2 -yl) thiophene (Compound 16) (29.8 g, yield: 51%) .

References: [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2566 - 2568.
[2]Journal of the Chinese Chemical Society,2018,vol. 65,p. 828 - 834.
[3]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3018 - 3025.
[4]Tetrahedron Letters,2010,vol. 51,p. 205 - 208.
[5]Tetrahedron Letters,2015,vol. 56,p. 368 - 373.
[6]Helvetica Chimica Acta,1996,vol. 79,p. 755 - 766.
[7]Synlett,2009,p. 490 - 494.
[8]Patent: CN103288848,2016,B .Location in patent: Paragraph 0237-0239.
[9]Polymer,2019,vol. 167,p. 93 - 101.
[10]Patent: US2019/36037,2019,A1 .Location in patent: Paragraph 0219; 0220; 0221.
[11]Chemical Communications,2010,vol. 46,p. 6273 - 6275.
[12]Journal of Chemical Research, Miniprint,1996,p. 1285 - 1294.
[13]Macromolecules,2013,vol. 46,p. 5985 - 5997.
[14]European Journal of Medicinal Chemistry,2017,vol. 130,p. 185 - 194.
[15]Journal of Organic Chemistry,2019,vol. 84,p. 10701 - 10709.
[16]Synthesis,1993,p. 1099 - 1103.
[17]Journal of Organic Chemistry,2008,vol. 73,p. 830 - 839.
[18]Organic electronics,2013,vol. 14,p. 875 - 881.
[19]Doklady Chemistry,2015,vol. 460,p. 50 - 56.
    Dokl. Akad. Nauk,2015,vol. 460,p. 666 - 672,7.
[20]Bulletin of the Korean Chemical Society,2019,vol. 40,p. 20 - 23.
[21]Dyes and Pigments,2013,vol. 96,p. 756 - 762.
[22]Journal of the Chemical Society. Perkin Transactions 2 (2001),1997,p. 1597 - 1604.
[23]Phosphorus, Sulfur and Silicon and the Related Elements,1989,vol. 46,p. 153 - 168.
[24]Canadian Journal of Chemistry,2013,vol. 91,p. 679 - 683.
[25]Tetrahedron,1995,vol. 51,p. 3895 - 3904.
[26]Patent: CN111138307,2020,A .Location in patent: Paragraph 0118-0120.
[27]Green Chemistry,2020,vol. 22,p. 5989 - 5994.
[28]Patent: WO2008/120839,2008,A1 .Location in patent: Page/Page column 46.
[29]European Journal of Organic Chemistry,2013,p. 2788 - 2791.
[30]Journal of the American Chemical Society,1994,vol. 116,p. 8152 - 8161.
[31]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 173 - 178.
[32]Macromolecules,2005,vol. 38,p. 7636 - 7644.
[33]Journal of the American Chemical Society,2011,vol. 133,p. 10364 - 10367.
[34]Photochemical and Photobiological Sciences,2013,vol. 12,p. 363 - 368.
[35]Polymer,2015,vol. 65,p. 193 - 201.
  • 6
  • [ 79-37-8 ]
  • [ 5713-61-1 ]
  • [ 704-38-1 ]
  • [ 7333-07-5 ]
  • [ 492-97-7 ]
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  • [ 5713-61-1 ]
  • [ 704-38-1 ]
  • [ 7333-07-5 ]
  • [ 492-97-7 ]
  • 8
  • [ 67665-47-8 ]
  • [ 492-97-7 ]
  • 2,2'-bis(2,2'-bithiophen-5-yl)-9,9'-spirobifluorene [ No CAS ]
  • 9
  • [ 492-97-7 ]
  • [ 171408-84-7 ]
  • 2,7-bis(2,2'-bithiophen-5-yl)-9,9'-spirobifluorene [ No CAS ]
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  • [ 13195-50-1 ]
  • [ 492-97-7 ]
  • [ 122845-17-4 ]
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  • [ 188290-36-0 ]
  • [ 3141-24-0 ]
  • [ 1006384-44-6 ]
  • [ 492-97-7 ]
  • 12
  • [ 188290-36-0 ]
  • [ 3141-24-0 ]
  • [ 1006384-44-6 ]
  • [ 492-97-7 ]
  • [ 105125-00-6 ]
  • 13
  • [ 3141-24-0 ]
  • [ 5713-61-1 ]
  • [ 3140-92-9 ]
  • [ 1006384-44-6 ]
  • [ 492-97-7 ]
  • [ 105125-00-6 ]
  • 14
  • [ 31161-46-3 ]
  • [ 5713-61-1 ]
  • 5,5'-Dibenzoyl-[2,2']bithienyl [ No CAS ]
  • [ 492-97-7 ]
  • [ 58400-12-7 ]
 

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