Home Cart 0 Sign in  
X

[ CAS No. 588-96-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 588-96-5
Chemical Structure| 588-96-5
Chemical Structure| 588-96-5
Structure of 588-96-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 588-96-5 ]

Related Doc. of [ 588-96-5 ]

Alternatived Products of [ 588-96-5 ]

Product Details of [ 588-96-5 ]

CAS No. :588-96-5 MDL No. :MFCD00000098
Formula : C8H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :WVUYYXUATWMVIT-UHFFFAOYSA-N
M.W : 201.06 Pubchem ID :68523
Synonyms :

Calculated chemistry of [ 588-96-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.44
TPSA : 9.23 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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 2.85
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 2.83
Consensus Log Po/w : 2.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.182 mg/ml ; 0.000906 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.708 mg/ml ; 0.00352 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.0328 mg/ml ; 0.000163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 588-96-5 ]

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 [ 588-96-5 ]

* 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 [ 588-96-5 ]
  • Downstream synthetic route of [ 588-96-5 ]

[ 588-96-5 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 106-41-2 ]
  • [ 75-03-6 ]
  • [ 588-96-5 ]
YieldReaction ConditionsOperation in experiment
98.27%
Stage #1: With potassium carbonate In acetone at 20℃; for 0.5 h;
Stage #2: for 10 h; Reflux
Step 1: Synthesis of l-bromo-4-ethoxybenzene: Potassium carbonate (118 g) was added to a solution of 4-bromophenol (50 g) in acetone (250 ml) and allowed to stir at room temperature for about 30 minutes then ethyl iodide (67.6 g) was added drop wise. The reaction mixture was refluxed for about 10 hours and completion of reaction was confirmed by TLC. The reaction mixture was filtered and acetone was removed over rotary evaporator. The residue was dissolved in ethyl acetate and washed with water and brine solution, dried over anhydrous Na2S04 and concentrated then filtered and product was purified via silica gel column chromatography with EtOAc and n-Hexane (1: 7) to afford the title compound as liquid (57 g). Yield: 98.27 ; 1H NMR (CDC13, 300 MHz): δ 7.35 (d, / = 8.7 Hz, 2H), 6.76 (d, J = 8.7 Hz, 2H), 3.99 (q, J = 6.9 Hz, 2H), 1.40 (t, J = 6.9 Hz, 3H).
86.2% With potassium carbonate In N,N-dimethyl-formamide General procedure for Compound 1: To a solution of 4-bromo phenol (5.0, 0.0289 moles, 1 eq) in DMF (50 mL), potassium carbonate (9.970 g, 0.0722 moles, 2.5 eq) was added followed by the addition of ethyl iodide (4.70 ml, 0.0578 moles, 2 eq) and stirred for overnight. The progress of the reaction was monitored by TLC. After completion of starting material, the reaction mixture was quenched with water (25 mL) and extracted with ethylacetate (2.x.50 mL). The combined organic layers were washed with brine (40 ml) solution. Ethylacetate layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (9:1, ethyl acetate/hexane) to obtain compound 1 (5.0 g, 86.2percent). MS (201.06) 202.1 (M+1).
Reference: [1] Patent: WO2012/25857, 2012, A1, . Location in patent: Page/Page column 57-58
[2] Patent: US2010/331307, 2010, A1, . Location in patent: Page/Page column 18
[3] Journal of the Korean Chemical Society, 2012, vol. 56, # 6, p. 706 - 711
[4] Journal of the American Chemical Society, 1931, vol. 53, p. 1408,1409
[5] Molecular Crystals and Liquid Crystals, 2004, vol. 411, p. 93/[1135]-102/[1144]
  • 2
  • [ 103-73-1 ]
  • [ 588-96-5 ]
YieldReaction ConditionsOperation in experiment
87 %Chromat. With carbon dioxide; oxygen; lithium bromide; copper(ll) bromide In water at 100℃; for 10 h; Autoclave; Green chemistry General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 molpercent), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 μm and RTX-wax 30 m × 25 μm) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200–300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC–MS or GCD, which are consistent with those reported in the literature.
Reference: [1] Synthetic Communications, 1998, vol. 28, # 4, p. 669 - 676
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 603 - 604
[3] Synthesis, 2011, # 2, p. 207 - 209
[4] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 591 - 593
[5] Chemistry - A European Journal, 2015, vol. 21, # 34, p. 11976 - 11979
[6] Synthetic Communications, 1998, vol. 28, # 8, p. 1463 - 1470
[7] Journal of Chemical Research - Part S, 1998, # 10, p. 662 - 663
[8] Organic Preparations and Procedures International, 1998, vol. 30, # 2, p. 218 - 222
[9] Synthesis, 1986, # 10, p. 868 - 870
[10] Bulletin of the Chemical Society of Japan, 1988, vol. 61, p. 2226 - 2228
[11] Advanced Synthesis and Catalysis, 2011, vol. 353, # 17, p. 3187 - 3195
[12] Ukrainskii Khimicheskii Zhurnal (Russian Edition), 1957, vol. 23, p. 341[13] Chem.Abstr., 1958, p. 4599
[14] Justus Liebigs Annalen der Chemie, 1944, vol. 556, p. 1,7
[15] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1903, vol. 136, p. 378[16] Bulletin de la Societe Chimique de France, 1904, vol. <3> 31, p. 30
[17] Chemische Berichte, 1894, vol. 27, p. 258
[18] Chemische Berichte, 1906, vol. 39, p. 4105[19] Chemische Berichte, 1907, vol. 40, p. 749
[20] Catalysis Today, 2012, vol. 194, # 1, p. 38 - 43
  • 3
  • [ 103-73-1 ]
  • [ 38751-57-4 ]
  • [ 588-96-5 ]
  • [ 583-19-7 ]
Reference: [1] Patent: WO2010/15559, 2010, A1, . Location in patent: Page/Page column 10
  • 4
  • [ 74-96-4 ]
  • [ 106-41-2 ]
  • [ 588-96-5 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 26, p. 5917 - 5922
[2] Organic Letters, 2010, vol. 12, # 19, p. 4364 - 4367
[3] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 158, p. 209 - 240
[4] Journal of Materials Chemistry, 2001, vol. 11, # 4, p. 1063 - 1071
  • 5
  • [ 106-41-2 ]
  • [ 1569262-64-1 ]
  • [ 588-96-5 ]
YieldReaction ConditionsOperation in experiment
54% With tetrafluoroboric acid dimethyl ether complex In dichloromethane for 0.833333 h; Sulfonimidate 1 (299 mg, 1.04 mmol) and 4-bromophenol (129 mg, 0.746 mmol) were added to a magnetically stirred round-bottom flask fitted with a septum. Anhydrous CH2Cl2 (ca. 2 mL) was added, followed by HBF4·OMe2 catalyst (7.7 μL, 10 molpercent of the amount of phenol) [TLC (hexane–EtOAc, 4:1 + 1percent Et3N) monitoring]. After 50 min, when the reaction was complete (loss of TLC spot for 1), the catalyst was quenched with several dry molecular sieve pellets. Molecular sieves were filtered and rinsed with CH2Cl2, and the filtrate was concentrated by rotary evaporation. The concentrate was dissolved in anhydrous CH2Cl2 (1 mL) and loaded onto a flash chromatography column (silica gel, 5 g, hexane); yield: 81 mg (54percent).
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 24, p. 3361 - 3368
  • 6
  • [ 64-17-5 ]
  • [ 589-87-7 ]
  • [ 588-96-5 ]
  • [ 699-08-1 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 284 - 286
  • 7
  • [ 103-73-1 ]
  • [ 588-96-5 ]
  • [ 583-19-7 ]
Reference: [1] Russian Journal of Organic Chemistry, 2005, vol. 41, # 11, p. 1631 - 1636
[2] Russian Journal of Applied Chemistry, 2006, vol. 79, # 6, p. 949 - 956
[3] Russian Journal of Applied Chemistry, 2006, vol. 79, # 6, p. 949 - 956
  • 8
  • [ 64-67-5 ]
  • [ 106-41-2 ]
  • [ 588-96-5 ]
Reference: [1] Tetrahedron, 1993, vol. 49, # 16, p. 3405 - 3410
  • 9
  • [ 64-17-5 ]
  • [ 673-40-5 ]
  • [ 108-86-1 ]
  • [ 589-87-7 ]
  • [ 588-96-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 24, p. 8304 - 8308
  • 10
  • [ 19521-84-7 ]
  • [ 108-86-1 ]
  • [ 588-96-5 ]
Reference: [1] American Chemical Journal, 1891, vol. 13, p. 489
[2] Journal of the Chemical Society, 1909, vol. 95, p. 868
  • 11
  • [ 156-43-4 ]
  • [ 588-96-5 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 160
  • 12
  • [ 106-41-2 ]
  • [ 60-29-7 ]
  • [ 2678-54-8 ]
  • [ 588-96-5 ]
Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 254,259
  • 13
  • [ 7789-69-7 ]
  • [ 103-73-1 ]
  • [ 588-96-5 ]
Reference: [1] Chemische Berichte, 1906, vol. 39, p. 4105[2] Chemische Berichte, 1907, vol. 40, p. 749
  • 14
  • [ 7726-95-6 ]
  • [ 64-19-7 ]
  • [ 103-73-1 ]
  • [ 588-96-5 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1903, vol. 136, p. 378[2] Bulletin de la Societe Chimique de France, 1904, vol. <3> 31, p. 30
  • 15
  • [ 64-17-5 ]
  • [ 589-87-7 ]
  • [ 588-96-5 ]
  • [ 699-08-1 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 284 - 286
  • 16
  • [ 588-96-5 ]
  • [ 22237-13-4 ]
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 5, p. 1434 - 1435
  • 17
  • [ 121-43-7 ]
  • [ 588-96-5 ]
  • [ 22237-13-4 ]
Reference: [1] Patent: US2002/142108, 2002, A1,
  • 18
  • [ 588-96-5 ]
  • [ 22237-13-4 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2003, vol. 391, p. 41 - 56
[2] Chemische Berichte, 1894, vol. 27, p. 261
[3] Molecules, 2009, vol. 14, # 3, p. 1013 - 1031
[4] Journal of Chemical Research, 2009, # 12, p. 732 - 736
  • 19
  • [ 588-96-5 ]
  • [ 79887-14-2 ]
Reference: [1] Molecular Crystals and Liquid Crystals, 2004, vol. 411, p. 93/[1135]-102/[1144]
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 588-96-5 ]

Ethers

Chemical Structure| 39255-23-7

[ 39255-23-7 ]

1-Bromo-4-(2-methoxyethoxy)benzene

Similarity: 0.97

Chemical Structure| 2050-47-7

[ 2050-47-7 ]

4,4'-Oxybis(bromobenzene)

Similarity: 0.97

Chemical Structure| 101-55-3

[ 101-55-3 ]

1-Bromo-4-phenoxybenzene

Similarity: 0.97

Chemical Structure| 6876-00-2

[ 6876-00-2 ]

1-Bromo-3-phenoxybenzene

Similarity: 0.95

Chemical Structure| 2398-37-0

[ 2398-37-0 ]

1-Bromo-3-methoxybenzene

Similarity: 0.92