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[ CAS No. 14282-76-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 14282-76-9
Chemical Structure| 14282-76-9
Chemical Structure| 14282-76-9
Structure of 14282-76-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 14282-76-9 ]

CAS No. :14282-76-9 MDL No. :MFCD00059741
Formula : C5H5BrS Boiling Point : -
Linear Structure Formula :- InChI Key :YYJBWYBULYUKMR-UHFFFAOYSA-N
M.W : 177.06 Pubchem ID :84314
Synonyms :

Calculated chemistry of [ 14282-76-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.98
TPSA : 28.24 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 3.71
Consensus Log Po/w : 2.8

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.35
Solubility : 0.0791 mg/ml ; 0.000447 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.1 mg/ml ; 0.000566 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.221 mg/ml ; 0.00125 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.3

Safety of [ 14282-76-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P264-P270-P280-P305+P351+P338-P310-P330-P370+P378-P403+P235-P501 UN#:1760
Hazard Statements:H227-H302-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 14282-76-9 ]

* 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 [ 14282-76-9 ]
  • Downstream synthetic route of [ 14282-76-9 ]

[ 14282-76-9 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
92.7% at 20℃; NBS (8.90 g, 50.0 mmol) was added portion wise to a stirred solution of 3-mehylthiophene (4.90 g, 50.0 mmol) in acetic acid (20 mL) at rt. After complete addition, the reaction was stirred at rt until it was complete. The reaction mixture was poured into ice- water, and then extracted with a 3:1 mixture solvent of hexane and ether. The organic layer was washed with IN aq. NaOH and brine. After dried over anhydrous sodium sulphate, the organic phase was concentrated on vacuum to afford 2-bromo-3-methylthiphene (8.20 g, 92.7 percent), which was used directly in the next step without further purification.
84.9% With N-Bromosuccinimide In N,N-dimethyl-formamide for 24 h; Darkness Compound 4 (5.00g, 51.01mmol) was dissolved in 30mL of anhydrous DMF. The mixture of N-bromosuccinimide (NBS) (9.08g, 51.01mmol) and anhydrous DMF (40mL) was added dropwise to the solution and stirred for 24h in the dark. The mixture was then poured into water and extracted with petroleum ether. The organic phase was dried over anhydrous MgSO4, and then the solvent was removed by rotary evaporation. The crude product was purified on silica gel chromatography using petroleum ether as eluent to afford a transparent liquid (7.67g, 84.9percent). 1H NMR (400MHz, CDCl3, δ/ppm): 7.17–7.16 (d, 1H, J=5.28Hz), 6.78–6.77 (d, 1H, J=5.33Hz), 2.20 (s, 3H).
83% With N-Bromosuccinimide; acetic acid In chloroformCooling with ice In a 1 L two-necked flask, 24.5 g of 3-methylthiophene (98 g mol-1,24.5 g, 250 mmol) was added and 400 mL of chloroform / glacial acetic acid (V: V = 1: / L,Favoring the inhibition of the bis-brominated product), 44.5 g of NBS (178 g mol-1, 44.5 g, 250 mmol) were added in portions in an ice-water bath.After the addition of NBS to continue stirring for 2-3 hours, TLC monitoring.After treatment: deionized water to quench the reaction, liquid separation, the organic phase was NaOH solution, washed with water, dried, concentrated vacuum pump with fractional distillation.
Reference: [1] Chemistry Letters, 2014, vol. 43, # 5, p. 640 - 642
[2] Synthetic Communications, 1999, vol. 29, # 9, p. 1607 - 1610
[3] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 12, p. 1480 - 1486
[4] Patent: WO2012/116452, 2012, A1, . Location in patent: Page/Page column 66
[5] Macromolecules, 2013, vol. 46, # 21, p. 8488 - 8499
[6] Dyes and Pigments, 2016, vol. 124, p. 222 - 231
[7] Macromolecules, 2011, vol. 44, # 15, p. 6017 - 6025
[8] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 11035 - 11042
[9] Patent: CN106588868, 2017, A, . Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029
[10] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921
[11] Russian Chemical Bulletin, 2009, vol. 58, # 7, p. 1509 - 1515
[12] Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 12214 - 12215
[13] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1836 - 1841
[14] Journal of the Chemical Society. Perkin Transactions 2, 1997, # 8, p. 1597 - 1604
[15] Zeitschrift fuer Physikalische Chemie (Muenchen, Germany), 1981, vol. 127, p. 13 - 22
[16] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 12, p. 1183 - 1187
[17] Bulletin International de Academie des Sciences de Cracovie, 1905, p. 550[18] Chem. Zentralbl., 1905, vol. 76, # II, p. 1796
[19] Justus Liebigs Annalen der Chemie, 1935, vol. 515, p. 273,277
[20] Journal of the American Chemical Society, 1949, vol. 71, p. 1201,1203
[21] Journal of the American Chemical Society, 1951, vol. 73, p. 2779[22] Journal of the American Chemical Society, 1952, vol. 74, p. 1066
[23] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 29 - 35
[24] Journal of Organic Chemistry, 1997, vol. 62, # 4, p. 878 - 884
[25] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 617 - 620
[26] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10930 - 10933
[27] New Journal of Chemistry, 2001, vol. 25, # 2, p. 318 - 321
[28] Patent: US4782079, 1988, A,
[29] Organic Letters, 2008, vol. 10, # 19, p. 4323 - 4326
[30] Dyes and Pigments, 2010, vol. 87, # 3, p. 181 - 187
[31] New Journal of Chemistry, 2011, vol. 35, # 3, p. 558 - 567
[32] Journal of Materials Chemistry, 2012, vol. 22, # 21, p. 10448 - 10451
[33] Soft Matter, 2012, vol. 8, # 42, p. 10921 - 10931,11
[34] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 7, p. 1636 - 1644
[35] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 331, p. 48 - 55
[36] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13583 - 13593
[37] Patent: US2727906, 1951, ,
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  • [ 616-44-4 ]
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Reference: [1] Patent: EP308170, 1989, A1,
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Reference: [1] New Journal of Chemistry, 2001, vol. 25, # 2, p. 318 - 321
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  • [ 13191-36-1 ]
Reference: [1] Canadian Journal of Chemistry, 2013, vol. 91, # 8, p. 679 - 683
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 4018
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 1201,1203
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  • [ 1860-99-7 ]
Reference: [1] Patent: CN106588868, 2017, A,
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  • [ 67869-13-0 ]
Reference: [1] Journal of the American Chemical Society, 1996, vol. 118, # 4, p. 722 - 725
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  • [ 24287-95-4 ]
Reference: [1] Patent: CN106588868, 2017, A,
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  • [ 144-55-8 ]
  • [ 616-38-6 ]
  • [ 81452-54-2 ]
YieldReaction ConditionsOperation in experiment
84% With hydrogenchloride; magnesium In tetrahydrofuran EXAMPLE 6
Methyl 3-methyl-thiophenecarboxylate via Gringnard reaction of 2-bromo-3-methylthiophene
2-Bromo-3-methylthiophene (10.0 g, 0.0565 mol) was slowly added dropwise over a 60 minute period to a slurry of magnesium turnings (1.72 g, 0.0706) in THF.
During the course of the addition, the exotherm was controlled to <40° C. by external cooling with a water bath.
After the addition was completed, the resulting mixture was stirred at ambient temperature for 60 minutes.
Dimethylcarbonate (7.63 g, 0.0847 mol) was then added dropwise over a 5-minute period, and the reaction mixture was stirred at ambient temperature for 4 hours.
The reaction mixture was quenched by the addition of 6 M HCl (50 mL), and extracted with ethylacetate (100 mL).
The organic phase was washed with water (25 mL), followed by saturated aqueous NaHCO3.
Concentration of the organic phase then gave 7.38 g (84percent) of methyl 3-methyl-2-thiophenecarboxylate as a light yellow oil.
Reference: [1] Patent: US6265424, 2001, B1,
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