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[ CAS No. 98546-51-1 ] {[proInfo.proName]}

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Chemical Structure| 98546-51-1
Chemical Structure| 98546-51-1
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Product Details of [ 98546-51-1 ]

CAS No. :98546-51-1 MDL No. :MFCD00093410
Formula : C7H9BO2S Boiling Point : -
Linear Structure Formula :- InChI Key :IVUHTLFKBDDICS-UHFFFAOYSA-N
M.W : 168.02 Pubchem ID :2733959
Synonyms :

Calculated chemistry of [ 98546-51-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.99
TPSA : 65.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 0.09
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : -0.2
Consensus Log Po/w : 0.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.0
Solubility : 1.69 mg/ml ; 0.0101 mol/l
Class : Very soluble
Log S (Ali) : -2.32
Solubility : 0.799 mg/ml ; 0.00476 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.78
Solubility : 2.79 mg/ml ; 0.0166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 98546-51-1 ]

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

Application In Synthesis of [ 98546-51-1 ]

* 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 [ 98546-51-1 ]
  • Downstream synthetic route of [ 98546-51-1 ]

[ 98546-51-1 ] Synthesis Path-Upstream   1~18

  • 1
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8201 - 8205[2] Angew. Chem., 2017, vol. 129, # 28, p. 8313 - 8317,5
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  • [ 14763-60-1 ]
  • [ 223440-93-5 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 8, p. 1284 - 1286
  • 3
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  • [ 35371-03-0 ]
YieldReaction ConditionsOperation in experiment
95% With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20 h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
90% With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1 h; General procedure: A mixture of the arylboronic acid (0.55mmol), KF (96mg, 1.65mmol) and I2 (127mg, 0.50mmol) in 1,4-dioxane (5mL) was stirred at 80°C for 1h. Then it was filtered through silica gel, eluting with Et2O (10mL) and the solvent was removed by rotary evaporation. When necessary, the product was purified by chromatography on silica gel (petroleum ether/Et2O 98:2).
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
[2] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1122 - 1123
[3] RSC Advances, 2015, vol. 5, # 103, p. 84910 - 84919
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YieldReaction ConditionsOperation in experiment
10%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 0.333333 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 3 h;
Example 62; Preparation of 5-(4-fluoro-phenyl)-1-methyl-7-(4-methylsulfanyl-phenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidine (E 62); Step 1: Preparation of 4-methylsulfanyl phenyl boronic acid To a cold (-78° C.) and stirring solution of 4-bromothioanisole (10) (3 grams, 14.8 mmol) in THF (15 mL) was added n-BuLi (10 mL) slowly under nitrogen atmosphere. The mixture was the allowed to reach the room temperature and stirring continued for 20 minutes. The mixture was then cooled to -78° C. A solution of triisopropyl borate (10 mL, 17.7 mmol) in THF (10 mL) was added to it slowly. The mixture was stirred for 1 hour at -78° C. and then 2 hours at room temperature. The mixture was acidified with cold 5percent HCl, diluted with water (25 mL) and extracted with ethyl acetate. The organic layers were collected, combined, washed with brine solution (20 mL) followed by water (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue thus obtained was purified by column chromatography using EtOAc-Hexane to afford the required aryl boronoc acid (11) (170 mg,). Yield: 10percent; 1H NMR (200 MHz, CDCl3): δ 8.10 (d, J=7.9 Hz, 2H), 7.33 (d, J=7.9 Hz, 2H), 2.55 (s, 3H, SCH3), 1.56 (bs, D2O exchangeable, OH), 1.25 (s, exchangeable, OH). IR: vmax (KBr, cm-1): 3406, 1594.
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 6, p. 2104 - 2117
[2] Tetrahedron Letters, 2010, vol. 51, # 52, p. 6839 - 6842
[3] Patent: US2006/128729, 2006, A1, . Location in patent: Page/Page column 94
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 305 - 311
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YieldReaction ConditionsOperation in experiment
83% With sodium hydroxide In tetrahydrofuran Step 2
Preparation of 4-methylthiophenylboronic acid
Under nitrogen, 113 mL (181 mmol) of n-BuLi (1.6M in hexanes) was added to a stirred solution of 30 g (150 mmol) of 4-bromothioanisole (Lancaster) in 1,500 mL of anhydrous tetrahydrofuran (THF) at --78° C. After 30 minutes, 51 mL (450 mol) of trimethylborate was added.
The reaction was warmed to ambient temperature and stirred overnight.
The resulting solution was treated with 300 mL of 10percent NaOH and stirred vigorously for 1 hour.
The THF was removed in vacuo, the pH adjusted to 4-5 and the solid collected by filtration.
The solid was washed repeatedly with water and hexane.
Drying in vacuo gave 21 g (83percent) of 4-methylthiophenylboronic acid as a colorless solid: NMR (DMSO-d6) δ 2.47 (s, 3H), 7.20 (d, J=8 Hz, 2H), 7.71 (d, J=8 Hz, 2H), 7.96 s,
75% With n-butyllithium In tetrahydrofuran; hexane; water Step 3
4-(Methylthio)benzeneboronic acid
n-BuLi in hexane (2.5M, 625 mmol, 250 ml) is added slowly to a mechanically stirred solution of 4-bromothioanisole (100 g, 492 mmol) in THF (1) below -55° C. (internal temp.).
After aging at -72° C. for 1 h trimethylborate (73 ml, 1.3 eq.) is added at such a rate to keep the internal temperature below -55° C.
After 0.25 h at -78° C. the solution was allowed to warm to 0° C. for 10 min. 2N HCL (500 ml) is added and the solvent is evaporated.
Water (500 ml) is added and the product is extracted with EtOAc (1.5).
The organic layer is dried over Na2SO4, concentrated and the solid is stirred in hexane (500 ml) for 2 h.
Filtartion gave 61.9 g (75percent) of the desired product. 1H NMR (acetone-d6, 400 MHz) δ7.80 (d, 2H), 7.22 (d, 2H), 7.15 (s, 2H), 2.50 (s, 3H).
83% With sodium hydroxide; n-butyllithium In tetrahydrofuran; hexane Step 1:
Preparation of 4-Methylthiophenylboronic Acid
Under nitrogen, a stirred solution of 30 g (150 mmol) of 4-bromothioanisole (Aldrich) in 1500 mL of anhydrous THF at -78° C. was treated with 180 mmol of n-butyllithium in hexane.
After 30 minutes, 51 mL (450 mmol) of trimethylborate was added neat and the reaction was allowed to warm to ambient temperature overnight.
A solution of 300 mL of 10percent NaOH was added and the mixture stirred vigorously for 1 h.
The solvent was removed in vacuo, the pH adjusted to 4-5, and the product collected by filtration.
Repeated washings with hexane and water provided 21 g (83percent) of 4-methylthiophenylboronic acid (21 in Synthetic Scheme VII when R5 =SCH3 and R3, R4, R6, and R7 =H) as a colorless solid: NMR (DMSO-d6) d 2.47 (s, 3H), 7.20 (d, J=8 Hz, 2H), 7.71 (d, J=8 Hz, 2H), 7.96 (br s, 2H).
83% With sodium hydroxide; n-butyllithium In tetrahydrofuran; hexane Step 1:
Preparation of 4-methylthiophenylboronic acid.
Under nitrogen, a stirred solution of 30 g (150 mmol of 4-bromothioanisole (Aldrich) in 1500 mL of anhydrous THF at -78° C. was treated with 180 mmol of n-butyllithium in hexane.
After 30 minutes, 51 mL (450 mmol) of trimethylborate was added neat and the reaction was allowed to warm to ambient temperature overnight.
A solution of 300 mL of 10percent NaOH was added and the mixture stirred vigorously for 1 hour.
The solvent was removed in vacuo, the pH adjusted to 4-5, and the product collected by filtration.
Repeated washings with hexane and water provided 21 g (83percent) of 4-methylthiophenylboronic acid (21 in Synthetic Scheme VII when R5 =SCH3 and R3, R4, R6, and R7 =H) as a colorless solid: NMR (DHSO-d6) δ 2.47 (s, 3H), 7.20 (d, J=8 Hz, 2H), 7.71 (d, J=8 Hz, 2H), 7.96 (br s, 2H).

Reference: [1] Patent: US5739166, 1998, A,
[2] Patent: US6222048, 2001, B1,
[3] Patent: US5344991, 1994, A,
[4] Patent: US5663180, 1997, A,
  • 6
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Reference: [1] Journal of Organometallic Chemistry, 2017, vol. 846, p. 305 - 311
  • 7
  • [ 166386-48-7 ]
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Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 24, p. 3427 - 3430[2] Khim. Prir. Soedin., 2017, vol. 53, # 2, p. 318 - 319,2
  • 8
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Reference: [1] Patent: US5593994, 1997, A,
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  • [ 5419-55-6 ]
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Reference: [1] Patent: US4948801, 1990, A,
  • 10
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  • [ 77-92-9 ]
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Reference: [1] Patent: US6307047, 2001, B1,
  • 11
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Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 28, p. 8944 - 8949
  • 12
  • [ 237429-33-3 ]
  • [ 74-88-4 ]
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Reference: [1] Journal of Organometallic Chemistry, 1999, vol. 581, # 1-2, p. 82 - 86
[2] Journal of Organometallic Chemistry, 1999, vol. 581, # 1-2, p. 82 - 86
  • 13
  • [ 13675-18-8 ]
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of Organometallic Chemistry, 1999, vol. 581, # 1-2, p. 82 - 86
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Reference: [1] Journal of Organometallic Chemistry, 1999, vol. 581, # 1-2, p. 82 - 86
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Reference: [1] Journal of Organometallic Chemistry, 1999, vol. 581, # 1-2, p. 82 - 86
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  • [ 190788-58-0 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5240 - 5246
[2] Chemical Communications, 2015, vol. 51, # 21, p. 4406 - 4409
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  • [ 162011-90-7 ]
Reference: [1] Organic letters, 2002, vol. 4, # 25, p. 4559 - 4561
[2] Organic letters, 2002, vol. 4, # 25, p. 4559 - 4561
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