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[ CAS No. 4805-22-5 ] {[proInfo.proName]}

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Chemical Structure| 4805-22-5
Chemical Structure| 4805-22-5
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Product Details of [ 4805-22-5 ]

CAS No. :4805-22-5 MDL No. :MFCD00219110
Formula : C8H4Br2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :SXNCMLQAQIGJDO-UHFFFAOYSA-N
M.W : 324.06 Pubchem ID :638908
Synonyms :

Calculated chemistry of [ 4805-22-5 ]

Physicochemical Properties

Num. heavy atoms : 12
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 : 63.03
TPSA : 56.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 5.03
Log Po/w (WLOGP) : 5.0
Log Po/w (MLOGP) : 3.82
Log Po/w (SILICOS-IT) : 6.22
Consensus Log Po/w : 4.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.57
Solubility : 0.000875 mg/ml ; 0.0000027 mol/l
Class : Moderately soluble
Log S (Ali) : -5.96
Solubility : 0.000358 mg/ml ; 0.0000011 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.13
Solubility : 0.00238 mg/ml ; 0.00000735 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.68

Safety of [ 4805-22-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4805-22-5 ]

* 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 [ 4805-22-5 ]
  • Downstream synthetic route of [ 4805-22-5 ]

[ 4805-22-5 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide; acetic acid In chloroform at 70℃; for 4 h; 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 100percent (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, 98percent). 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 8 h; 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, 93percent).
90% With N-Bromosuccinimide In N,N-dimethyl-formamideCooling 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 90percent).
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, 85percent) 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).
51% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 12 h; 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: 51percent) .

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