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[ CAS No. 26137-08-6 ] {[proInfo.proName]}

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Chemical Structure| 26137-08-6
Chemical Structure| 26137-08-6
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Product Details of [ 26137-08-6 ]

CAS No. :26137-08-6 MDL No. :MFCD00173839
Formula : C6H5BrO2S Boiling Point : -
Linear Structure Formula :- InChI Key :PEGSJNCGPSIJOX-UHFFFAOYSA-N
M.W : 221.07 Pubchem ID :2740074
Synonyms :

Calculated chemistry of [ 26137-08-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.3
TPSA : 54.54 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) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 2.48
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 3.04
Consensus Log Po/w : 2.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.216 mg/ml ; 0.000975 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.119 mg/ml ; 0.000537 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.6
Solubility : 0.553 mg/ml ; 0.0025 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.32

Safety of [ 26137-08-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26137-08-6 ]

* 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.

  • Upstream synthesis route of [ 26137-08-6 ]
  • Downstream synthetic route of [ 26137-08-6 ]

[ 26137-08-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 26137-08-6 ]
  • [ 80-48-8 ]
  • [ 81452-54-2 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 73, p. 10180 - 10183
  • 2
  • [ 26137-08-6 ]
  • [ 7311-64-0 ]
Reference: [1] Heterocycles, 1985, vol. 23, # 6, p. 1431 - 1435
[2] Tetrahedron, 2013, vol. 69, # 15, p. 3167 - 3181
[3] Patent: WO2016/92556, 2016, A1, . Location in patent: Page/Page column 28; 29
  • 3
  • [ 26137-08-6 ]
  • [ 22288-78-4 ]
  • [ 7311-64-0 ]
Reference: [1] Patent: US5840917, 1998, A,
  • 4
  • [ 22288-78-4 ]
  • [ 26137-08-6 ]
YieldReaction ConditionsOperation in experiment
91.6%
Stage #1: at 20℃; for 0.25 h;
Stage #2: With sodium nitrite In water at 0 - 5℃; for 1 h;
Stage #3: With hydrogen bromide; copper(I) bromide In water at 60 - 65℃; for 2 h;
3-amino-2-thiophenecarboxylic acid methyl ester (100 g, 0.6369 mol) was suspended in hydrobromic acid (220 ml), and the mixture was stirred at room temperature for 15 mm. The mixture was cooled to 0-5°C, and sodium nitrite (46.0 g, 0.666 mol) in water (100 ml) was added dropwise below 5°C. The mixture was stirred for lhr, and then was addedto a copper (I) bromide (96.0 g, 0.6692 mol) in hydrobromic acid (260 ml) at room temperature. The resulting mixture was stirred at 60-65°C for 2 hrs. The reaction mixture was diluted with 1200 ml of water while maintaining at 25-30°C by cooling and extracted with two 600 ml portions of ethyl acetate. The ethyl acetate extracts were combined, washed two times with 600 ml portions of water, and dried over anhydrous sodiumsulfate. The ethyl acetate was removed by distillation under vacuum at 60°C to give 129.0g (91.6 percent) as a yellow solid, melting point 47°C to 48°C, with 96percent purity by HPLC.‘HNMR (400 MHz, CDC13) 6- Value (ppm): 3.90(s, 0-CR3, 3H), 7.09 (d, 1H), 7.46 (d,1H).13 CNMR (400 MHz, CDC13) 6- Value (ppm): 52.10(1C), 116.96(1C), 127.12(1C),130.61 (1C), 133.63 (1C), 161.0 (1C). Mass: 222.8 [M+1].
86%
Stage #1: With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 0 - 20℃; for 2 h; Inert atmosphere
Stage #2: With hydrogenchloride In water; acetonitrileInert atmosphere
General procedure: Anhydrous copper bromide (12mmol), tert-butyl nitrite (15mmol), and anhydrous acetonitrile (40mL) were added at 0 oC to a three necked round bottom flask that was equipped with a reflux condenser, addition funnel or solid inlet tube, and a gas outlet tube. The coresponding amine (10mmol) in 5mL of acetonitrile or as a solid was slowly added over a period of 5 min to the reaction solution. During this addition, the reaction solution turned completely black from the initial green color and nitrogen was evolved. After gas evolution had been ceased the reaction mixture was stiered at r.t. for 2 hours. Then the mixture was poured into 100 mL of 10percent aqueous hydrochlroic acid and extracted with 100 mL of ether; organic layer was washed once with 100 mL of 10percent aqueous hydrochloric acid. The resulting ether solution was dried over anhydrous Na2SO4 and the ether was removed under reduce prussure. The product was then purified by silca gel column chromatography.  
75% With tert.-butylnitrite; copper(I) bromide In acetonitrile Copper bromide (6.7 g, 30.0 mmol) and t-butyl nitrite (3.57 ml, 30 mmol) were dissolved in acetonitrile (40 ml) A solution of methyl 3-amino-2-carboxylate (3.14 g, 20.0 mmol) After overnight reaction at room temperature, Then heated to 60 ° C for 1 hour, After completion of the reaction, cooled to room temperature, quenched by the addition of 2N HC1, add water, extracted with ethyl acetate, combined with several layers, dried and evaporated to dryness, the product was purified by a rapid preparative column 3.32g, yield 75percent.
Reference: [1] Patent: WO2016/92556, 2016, A1, . Location in patent: Page/Page column 27; 28
[2] Tetrahedron Letters, 2012, vol. 53, # 52, p. 7135 - 7139
[3] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[4] Patent: CN105164112, 2017, B, . Location in patent: Paragraph 0473-0476
[5] Heterocycles, 1985, vol. 23, # 6, p. 1431 - 1435
[6] Tetrahedron, 2013, vol. 69, # 15, p. 3167 - 3181
  • 5
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  • [ 7311-64-0 ]
  • [ 26137-08-6 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; sulfuric acid In 1,4-dioxane for 24 h; Reflux A mixture of S-bromo-thiophene-l-carboxylic acid (2.2g, lO.βmmol), 4N HCl (in dioxane, ImI), H2SO4 (98percent, 0.2ml) and methanol (30ml) was heated under reflux for 24h, cooled to room temperature, diluted with ethyl acetate, washed withwater, aq. NaHCO3, half- sat.-aq. NaCl twice, dried (MgSO4) and concentrated to dryness to give compound 23G (100percent) directly used in next step.
87% for 12 h; Reflux By refluxing 3-bromothiophene-2-carboxylic acid and trimethylsilyl chloride (TMSCI) in a methanol solvent for 12 hours, 3-bromothiophene-2-carboxylic acid methylester was prepared. Yield: 87percent White solid 1H-NMR (400 MHz, CDCl3) δ 7.46(d, J=5.2 Hz, 1H), 7.10(d, J=5.2 Hz, 1H), 3.90(s, 3H)
Reference: [1] Patent: WO2009/79352, 2009, A1, . Location in patent: Page/Page column 63
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3213 - 3219
[3] Synlett, 2004, # 6, p. 1113 - 1116
[4] Patent: US2015/148550, 2015, A1, . Location in patent: Paragraph 0068; 0069; 0070; 0071; 0072
[5] Patent: US2011/230495, 2011, A1, . Location in patent: Page/Page column 33-34
[6] Advanced Synthesis and Catalysis, 2016, vol. 358, # 20, p. 3283 - 3292
[7] Patent: US9783634, 2017, B2, . Location in patent: Page/Page column 6; 9; 10
  • 6
  • [ 7311-64-0 ]
  • [ 26137-08-6 ]
Reference: [1] Archiv der Pharmazie, 1998, vol. 331, # 12, p. 405 - 411
  • 7
  • [ 67-56-1 ]
  • [ 25796-68-3 ]
  • [ 26137-08-6 ]
Reference: [1] Archiv der Pharmazie, 1998, vol. 331, # 12, p. 405 - 411
  • 8
  • [ 26137-08-6 ]
  • [ 70260-17-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 14, p. 2319 - 2332
[2] Patent: US6528510, 2003, B1,
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