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[ CAS No. 28712-49-4 ] {[proInfo.proName]}

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Chemical Structure| 28712-49-4
Chemical Structure| 28712-49-4
Structure of 28712-49-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 28712-49-4 ]

CAS No. :28712-49-4 MDL No. :MFCD18382465
Formula : C4H2ClIS Boiling Point : -
Linear Structure Formula :- InChI Key :IJEUNSXYUQTZPT-UHFFFAOYSA-N
M.W : 244.48 Pubchem ID :12203264
Synonyms :

Calculated chemistry of [ 28712-49-4 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.05
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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 3.25
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 4.27
Consensus Log Po/w : 3.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.93
Solubility : 0.0286 mg/ml ; 0.000117 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0744 mg/ml ; 0.000304 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.141 mg/ml ; 0.000577 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.96

Safety of [ 28712-49-4 ]

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 [ 28712-49-4 ]

* 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 [ 28712-49-4 ]
  • Downstream synthetic route of [ 28712-49-4 ]

[ 28712-49-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 3437-95-4 ]
  • [ 28712-49-4 ]
YieldReaction ConditionsOperation in experiment
58% With N-chloro-succinimide In hexane at 20℃; for 24 h; Example 1
1-(5-Chlorothiophen-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-tetrazol-1-yl)propan-2-ol (1)
To a stirred solution of 2-iodothiophene (2.5 grams (g), 11.9 millimoles (mmol)) in n-hexane (25 milliliters (mL)) was added N-chlorosuccinimide (NCS; 1.58 g, 11.9 mmol) followed by a catalytic (cat) amount of perchloric acid (HClO4) at room temperature (RT), and stirring was continued for 24 hours (h) at RT.
The reaction mixture was filtered, and the filtrate was washed with water (H2O) and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated in vacuo to afford D (1.7 g, 6.9 mmol, 58percent) as a liquid. 1H NMR (200 MHz, CDCl3): δ 7.18 (d, J=4.2 Hz, 1H), 6.69 (d, J=4.2 Hz, 1H).
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[2] Patent: US2012/329802, 2012, A1, . Location in patent: Page/Page column 18-19
  • 2
  • [ 96-43-5 ]
  • [ 28712-49-4 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc; sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at 0 - 20℃; for 2 h;
Stage #2: With iodine In tetrahydrofuran; hexane; cyclohexane at 20℃;
General procedure: After the substrate (2.0 mmol) has been added to the in situ prepared mixture (see Supplementary data) at 0 °C, the mixture was stirred for 2 h at rt before introduction of a solution of I2 (1.5 g, 6.0 mmol) in THF (5 mL). The mixture was stirred overnight before addition of an aqueous saturated solution of Na2S2O3 (20 mL) and extraction with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure before being purified by means of column chromatography on silica gel.
Reference: [1] Tetrahedron, 2012, vol. 68, # 42, p. 8761 - 8766
[2] Tetrahedron Letters, 1995, vol. 36, # 27, p. 4883 - 4884
[3] Tetrahedron, 2005, vol. 61, # 20, p. 4779 - 4784
[4] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1982, vol. 21, # 4, p. 417 - 418
[5] Journal of Organic Chemistry, 1952, vol. 17, p. 698,701
  • 3
  • [ 188290-36-0 ]
  • [ 96-43-5 ]
  • [ 3437-95-4 ]
  • [ 28712-49-4 ]
  • [ 625-88-7 ]
Reference: [1] Synthesis, 1995, # 3, p. 248 - 250
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