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[ CAS No. 244205-40-1 ] {[proInfo.proName]}

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Chemical Structure| 244205-40-1
Chemical Structure| 244205-40-1
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Product Details of [ 244205-40-1 ]

CAS No. :244205-40-1 MDL No. :MFCD01114672
Formula : C6H6BBrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PLVCYMZAEQRYHJ-UHFFFAOYSA-N
M.W : 200.83 Pubchem ID :2773294
Synonyms :

Calculated chemistry of [ 244205-40-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.97
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 0.13
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : -0.05
Consensus Log Po/w : 0.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.762 mg/ml ; 0.0038 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 2.11 mg/ml ; 0.0105 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.15
Solubility : 1.44 mg/ml ; 0.00716 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 244205-40-1 ]

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 [ 244205-40-1 ]

* 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 [ 244205-40-1 ]
  • Downstream synthetic route of [ 244205-40-1 ]

[ 244205-40-1 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 244205-40-1 ]
  • [ 1628-29-1 ]
Reference: [1] Chemistry Letters, 2018, vol. 47, # 7, p. 825 - 828
  • 2
  • [ 244205-40-1 ]
  • [ 16567-18-3 ]
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782
  • 3
  • [ 244205-40-1 ]
  • [ 3652-89-9 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 35, p. 13872 - 13875
[2] Patent: EP2415773, 2012, A2,
[3] Organic Electronics: physics, materials, applications, 2013, vol. 14, # 1, p. 67 - 73
[4] Patent: EP2746273, 2014, A1,
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1519 - 1522[6] Angew. Chem., 2016, vol. 128, # 4, p. 1542 - 1545,4
[7] Patent: KR2015/130206, 2015, A,
[8] Patent: KR2016/13678, 2016, A,
[9] Patent: KR2015/64737, 2015, A,
[10] European Journal of Organic Chemistry, 2016, vol. 2016, # 34, p. 5611 - 5615
[11] Patent: US9711732, 2017, B2,
[12] Patent: KR2017/90390, 2017, A,
[13] Patent: KR101763838, 2017, B1,
[14] Patent: WO2017/196081, 2017, A1,
[15] Dyes and Pigments, 2018, vol. 156, p. 369 - 378
  • 4
  • [ 244205-40-1 ]
  • [ 615-36-1 ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25 h; Microwave irradiation General procedure: Reactions facilitated by microwave irradiation were performed on a 1.0 mmol scale. Arylboronic acid 3 (1.0 equiv) and MeCN (5.0 mL) were added to a 10 mL microwave vial equipped with stir bar, followed by HSA (1.5 equiv) and aq 1 M NaOH (5 equiv). The mixture was capped and set to stir for 5 min, then placed in a microwave reactor, and heated to 100 °C for 15 min, and then cooled to r.t. The vial was removed from the microwave and a small aliquot was taken for reaction monitoring via HPLC analysis. The reaction mixture was diluted with H2O (30 mL) and extracted with EtOAc (2 × 30 mL). The combined organic extracts were dried (Na2SO4) and concentrated invacuo. The residue was purified by flash chromatography (EtOAc/hexanes) to afford the desired amine product 2.
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 6, p. 1114 - 1116
[2] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
[3] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2545 - 2553
[4] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18253 - 18256
[5] Synthesis (Germany), 2017, vol. 49, # 11, p. 2555 - 2561
[6] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782
  • 5
  • [ 244205-40-1 ]
  • [ 71-43-2 ]
  • [ 2052-07-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 578 - 580
[2] Tetrahedron, 2008, vol. 64, # 27, p. 6196 - 6201
[3] Tetrahedron, 2010, vol. 66, # 6, p. 1308 - 1312
[4] ChemCatChem, 2018, vol. 10, # 20, p. 4768 - 4776
[5] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4532 - 4544
  • 6
  • [ 1538-62-1 ]
  • [ 244205-40-1 ]
  • [ 2052-07-5 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 4, p. 721 - 724
  • 7
  • [ 108-86-1 ]
  • [ 244205-40-1 ]
  • [ 2052-07-5 ]
Reference: [1] Letters in Organic Chemistry, 2012, vol. 9, # 6, p. 396 - 400
  • 8
  • [ 107-02-8 ]
  • [ 244205-40-1 ]
  • [ 138555-58-5 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 22, p. 5765 - 5769
  • 9
  • [ 98-88-4 ]
  • [ 244205-40-1 ]
  • [ 13047-06-8 ]
YieldReaction ConditionsOperation in experiment
90% With 2C60H80NaO12(2+)*Cl6Pd2(2-); potassium carbonate; triphenylphosphine In toluene at 70℃; for 12 h; General procedure: A 5 mL flask charged with benzoyl chloride (1.0 mmol), arylboronic acid (0.5 mmol),K2CO3 (1.0 mmol), complex 1 (0.5 molpercent, 3.1 mg), PPh3 (0.01 mmol, 1.3 mg) and toluene (2.0mL) was put into a preheated 70 oC oil bath for an appropriate period of time under air. After thereaction was finished, the reaction mixture was cooled to room temperature, filtered through ashort silica column and washed with ethyl acetate. Then the combined filtrates were concentratedin vacuo and the residue was purified by flash chromatography (eluent: ethylacetate/petroleumether). All the products were known compounds and characterized by comparing mp, 1H NMRand 13C NMR spectra with literature.
85% With [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; potassium carbonate In toluene at 60℃; for 12 h; Inert atmosphere General procedure: A reaction vessel was charged with a mixture of phenylboronic acid (0.5 mmol), K2CO3 (1.0 mmol), catalyst 2 (0.5 mol percent) in toluene (2.0 mL), and stirred for about 20 min under nitrogen atmosphere. Then benzoic anhydride or benzoyl chloride was then added. The mixture was heated to 60 °C and incubated in an oil bath at 60 °C for 12 h under nitrogen atmosphere. After the completion of the reaction, the mixture was quenched by 5 mL water and then extracted with ethyl acetate (3.x.10 mL). The combined organic layer was dried over MgSO4. After removal of the solvent in vacuo, the product was obtained by purifying on preparative TLC, eluting with ethyl acetate/petroleum ether and the yield was calculated based on the phenylboronic acid (the purified products were identified by NMR spectra and comparison of the melting points with the literature data). In the recycle experiment, the residue was subjected to a second run of the acylation reaction by charging with the same substrates (benzoic anhydride or benzoyl chloride, phenylboronic acid, dioxane, and K2CO3) without further addition of cyclopalladated catalyst 2.
Reference: [1] Arkivoc, 2013, vol. 2013, # 4, p. 251 - 271
[2] Tetrahedron, 2012, vol. 68, # 10, p. 2283 - 2288
  • 10
  • [ 591-50-4 ]
  • [ 201230-82-2 ]
  • [ 244205-40-1 ]
  • [ 13047-06-8 ]
Reference: [1] ChemSusChem, 2018, vol. 11, # 19, p. 3382 - 3387
  • 11
  • [ 623-33-6 ]
  • [ 244205-40-1 ]
  • [ 2178-24-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 12
  • [ 4973-66-4 ]
  • [ 244205-40-1 ]
  • [ 19614-16-5 ]
YieldReaction ConditionsOperation in experiment
71.1% With sodium hydrogencarbonate; copper(II) sulfate In methanol at 20℃; for 48 h; Inert atmosphere Under an argon atmosphere,In a 100 mL two-necked eggplant-shaped flask, copper (II) sulfate anhydride (95.8 mg, 0.600 mmol)Sodium bicarbonate (1.01 g, 12.0 mmol) was added.In contrast, methanol (40 mL)To a solution of p-tolylmethylthiosulfonate (9) (1.21 g, 6.00 mmol)And a solution of 2-bromophenylboronic acid (8a) (1.81 g, 9.00 mmol) were added, and the mixture was stirred at room temperature for 2 days.Water was added to the reaction mixture to stop the reaction, followed by extraction with ethyl acetate (50 mL × 3).The combined organic layer was washed with saturated brine and dried over sodium sulfate.After filtration, concentration under reduced pressure gave a crude product.This was purified by silica gel column chromatography (30 g, n-hexane only) to obtain (2-bromophenyl) methylsulfide (10a) (867 mg, 4.27 mmol, yield 71.1percent).
71.1% With sodium hydrogencarbonate; copper(II) sulfate In methanol at 20℃; for 48 h; Inert atmosphere To a mixture of NaHCO3 (1.01 g, 12.0 mmol, 2.0 equiv) and CuSO4 (95.8 mg, 0.600 mmol, 10 mol percent) wasadded a solution of S-methyl 4-toluenethiosulfonate (2) (1.21 g, 6.00 mmol) and 2-bromophenylboronic acid (1a)(1.81 g, 9.00 mmol, 1.5 equiv) dissolved in MeOH (40 mL) at room temperature. After stirring for 48 h at thesame temperature, to the mixture was added an aqueous saturated ammonium chloride solution (10 mL). Themixture was extracted with EtOAc (50 mL 3), and the combined organic extract was washed with brine (20 mL),dried (Na2SO4), and after filtration, the filtrate was concentrated under reduced pressure. The residue was purifiedby flash column chromatography (silica-gel 30 g, n-hexane) to give 2-bromophenyl methyl sulfide (867 mg, 4.27mmol, 71.1percent) as a colorless oil.
Reference: [1] Patent: JP2018/30788, 2018, A, . Location in patent: Paragraph 0053
[2] Chemistry Letters, 2018, vol. 47, # 7, p. 825 - 828
  • 13
  • [ 244205-40-1 ]
  • [ 2905-25-1 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641
  • 14
  • [ 244205-40-1 ]
  • [ 4688-76-0 ]
Reference: [1] Chemistry Letters, 2013, vol. 42, # 5, p. 541 - 543
  • 15
  • [ 244205-40-1 ]
  • [ 71-43-2 ]
  • [ 4688-76-0 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4532 - 4544
  • 16
  • [ 244205-40-1 ]
  • [ 221352-10-9 ]
Reference: [1] Patent: WO2011/19618, 2011, A1,
[2] Patent: WO2011/19616, 2011, A1,
  • 17
  • [ 121-43-7 ]
  • [ 583-53-9 ]
  • [ 244205-40-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 7, p. 1201 - 1207
  • 18
  • [ 583-55-1 ]
  • [ 244205-40-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5261 - 5274
  • 19
  • [ 583-53-9 ]
  • [ 244205-40-1 ]
Reference: [1] Journal of the Chinese Chemical Society, 2007, vol. 54, # 3, p. 811 - 816
  • 20
  • [ 855180-11-9 ]
  • [ 244205-40-1 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
78.4%
Stage #1: With hydrogen bromide; dihydrogen peroxide In water; acetonitrile at -20℃;
Stage #2: With palladium diacetate; caesium carbonate; (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere; Reflux
77.5 g (0.3 mol) of 1-amino-N-phenylcarbazole was dissolved in 300 mL of acetonitrile in a 2 L three-necked flask.Add 52.6 g (0.26 mol) mass percent 40percent hydrobromic acid aqueous solution,Control the reaction temperature to slowly add 27.6 mL (0.27 mol) of 30percent hydrogen peroxide at -20 °C.After the addition is complete, the natural temperature is raised overnight.The reaction solution is washed with an aqueous solution of sodium hydrogen sulfite,Divide the organic layer,Add hydrochloric acid to get1-amino-2-bromo-N-phenyloxazole hydrochloride,97.1 g after drying;Under argon protection,Will be 97.1 g (0.25 mol)1-amino-2-bromo-N-phenyloxazole hydrochloride,50.2 g (0.25 mol) o-bromobenzeneboronic acid,36.9 g of Caesium carbonate,250 mL of N-methylpyrrolidone solvent was added to a 2 L three-necked flask.Replacement air system,Then control 0.05g of palladium acetate and 0.23g at 20 °C(R,R)-1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane,Refluxreaction,Liquid chromatograph detection,After the end, add 300 mL of ice water to stop the reaction.Extracted with 300 mL of dichloromethane,Wash the organic layer with sodium hydroxide solution,Dry over anhydrous sodium sulfate overnight.Concentrated to a crude product,300 mL of xylene-210 mL methanol mixed solvent was recrystallized twice to obtain a product.11,12-Dihydro-11-phenylindolo[2,3-a]carbazole 78.2 g,The content is 99.5percent, and the total yield is 78.4percent
Reference: [1] Patent: CN108148065, 2018, A, . Location in patent: Paragraph 0011; 0013; 0014
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