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[ CAS No. 5751-82-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 5751-82-6
Chemical Structure| 5751-82-6
Chemical Structure| 5751-82-6
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Product Details of [ 5751-82-6 ]

CAS No. :5751-82-6 MDL No. :MFCD00051732
Formula : C7H7ClO2S Boiling Point : -
Linear Structure Formula :- InChI Key :BMOKMXXTOZFEIZ-UHFFFAOYSA-N
M.W : 190.65 Pubchem ID :521808
Synonyms :

Calculated chemistry of [ 5751-82-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.29
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.42
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) : -5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 3.12
Log Po/w (WLOGP) : 2.58
Log Po/w (MLOGP) : 1.85
Log Po/w (SILICOS-IT) : 3.32
Consensus Log Po/w : 2.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.143 mg/ml ; 0.000748 mol/l
Class : Soluble
Log S (Ali) : -3.93
Solubility : 0.0222 mg/ml ; 0.000116 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.327 mg/ml ; 0.00171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.47

Safety of [ 5751-82-6 ]

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

Application In Synthesis of [ 5751-82-6 ]

* 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 [ 5751-82-6 ]
  • Downstream synthetic route of [ 5751-82-6 ]

[ 5751-82-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 24065-33-6 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 16 h; H2S04 (15 ml) was added at RT to a stirred solution of 5-chloro-thiophene-2-carboxylic acid (15 g, 0.0925mol) in ethanol (300 ml). Then the reaction mixture was stirred at aooc for 16 h. The reaction mixture was concentrated under reduced pressure and concentrated mass was diluted with ethyl acetate (300 ml).The organic mixture was washed with water (3 x 100 ml), NaHC03 solution (3 x 100 ml) and brine (100 ml). Organic layer was dried over Na2S04 and concentrated under reduced pressure to give ethyl 5- chlorothiophene-2-carboxylate (14 g, 80 percent) as colorless liquid.
Reference: [1] Patent: WO2015/18534, 2015, A1, . Location in patent: Page/Page column 39
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 5131
[3] Journal of the American Chemical Society, 1954, vol. 76, p. 5131
[4] Chemistry - A European Journal, 2016, vol. 22, # 1, p. 211 - 221
  • 2
  • [ 2873-18-9 ]
  • [ 1609-47-8 ]
  • [ 5751-82-6 ]
Reference: [1] Synthesis, 2004, # 4, p. 568 - 572
  • 3
  • [ 24065-33-6 ]
  • [ 75-03-6 ]
  • [ 5751-82-6 ]
Reference: [1] Patent: US5840917, 1998, A,
  • 4
  • [ 1003-09-4 ]
  • [ 56-23-5 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
  • [ 5751-83-7 ]
Reference: [1] Petroleum Chemistry, 2008, vol. 48, # 6, p. 471 - 478
  • 5
  • [ 96-43-5 ]
  • [ 56-23-5 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
Reference: [1] Petroleum Chemistry, 2008, vol. 48, # 6, p. 471 - 478
  • 6
  • [ 6310-09-4 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 3, p. 369 - 372
  • 7
  • [ 3437-95-4 ]
  • [ 56-23-5 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
Reference: [1] Petroleum Chemistry, 2008, vol. 48, # 6, p. 471 - 478
  • 8
  • [ 42518-98-9 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 547
  • 9
  • [ 1003-09-4 ]
  • [ 56-23-5 ]
  • [ 64-17-5 ]
  • [ 5751-82-6 ]
  • [ 5751-83-7 ]
Reference: [1] Petroleum Chemistry, 2008, vol. 48, # 6, p. 471 - 478
  • 10
  • [ 5751-82-6 ]
  • [ 89640-03-9 ]
YieldReaction ConditionsOperation in experiment
67% at 0 - 20℃; Ethyl 5-chlorothiophene-2- carboxylate (2.7 g, 14.1 mmol) was added in portions to concentrated sulfuric acid (5 mL) and the stirred solution was cooled to below 0 0C with a methanol/ice bath. Fuming nitric acid (1.78 g, 1.2 mL, 28.3 mmol) was added slowly, keeping the temperature below 0 0C throughout the addition. On completion of addition the stirred mixture was removed from the cold bath and warmed to ambient temperature for 2 hours. The reaction was quenched by addition to ice/water (100 mL) resulting in formation of a sticky solid. The product was extracted into dichloromethane (2 x 100 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent was removed to afford an orange oil. The crude material was purified by silica gel chromatography using a 95:5 mixture of hexane and ethyl acetate as eluent to afford the title product as a solid (2.23 g, 67percent yield). 1H NMR (CDCl3) δ: 8.14 (IH, s), 4.37 (2H, q, J=7.11 Hz), 1.37 (3H, t, J=7.11 Hz).
62% With nitric acid In water at 5 - 10℃; for 0.5 h; To fuming nitric acid (50 mL) cooled in an ice bath to 5° was added neat ethyl 5- chloro-2-thiophene-2-carboxylate (10 g, 0.0524 mol) dropwise at such a rate that the reaction temperature remained below 10°. The reaction was stirred for 30 minutes at 5-10°, then added ice (200 g) and extracted with ethyl acetate (2x100 mL). The combined organic extracts were washed with water (2x100 mL) and brine (50 mL), then dried over magnesium sulfate and filtered. The filtrate was concentrated by rotary evaporation and the residue purified by silica gel flash chromatography eluting with 10:90 ethyl acetate/hexanes to afford the title compound as a crystalline light yellow solid (7.6 g, 0.0322 mol, 62percent). 1H NMR (300 MHz, DMSO-D6) δ ppml.31 (t, J=7.17 Hz, 3 H) 4.35 (q, J=7.23 Hz, 2 H) 8.17 (s, 1 H).
Reference: [1] Patent: WO2010/114881, 2010, A1, . Location in patent: Page/Page column 43-44
[2] Patent: WO2008/133753, 2008, A2, . Location in patent: Page/Page column 126
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