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Product Details of [ 589-10-6 ]

CAS No. :589-10-6 MDL No. :MFCD00000234
Formula : C8H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :JJFOBACUIRKUPN-UHFFFAOYSA-N
M.W : 201.06 Pubchem ID :68526
Synonyms :
Chemical Name :(2-Bromoethoxy)benzene

Calculated chemistry of [ 589-10-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.61
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) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.31
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 2.7
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.215 mg/ml ; 0.00107 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.725 mg/ml ; 0.00361 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.8
Solubility : 0.0316 mg/ml ; 0.000157 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 589-10-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 589-10-6 ]

* 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 [ 589-10-6 ]
  • Downstream synthetic route of [ 589-10-6 ]

[ 589-10-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 106-93-4 ]
  • [ 108-95-2 ]
  • [ 589-10-6 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In acetonitrile at 80℃; for 6 h; General procedure: The compounds were synthesized according to Scheme 1. A suspension of phenol (10mmol), 1,2-dibromoethane(50mmol), and anhydrous K2CO3 (30mmol) in dry acetonitrile(50mL) was stirred at 80°C for 6 h.The reaction mixturewas filtered, and the K2CO3 was recovered, reactivated (in vacuum at 120°C, 5 h), and the solvent was concentratedunder reduced pressure.The residue was purified by columnchromatography over silica gel using petroleum ether aseluent to give the product as a solid (Scheme 1, Table 4). 1-(2-Bromoethoxy)-benzene [22, 23] (Entry 1). mp: 33-34°C.1H NMR (400MHz, CDCl3), δ: 7.29–7.26 (m, 2H), 6.95–6.92(m, 3H), 4.26–4.23 (t, J = 3.6Hz, 2H), 3.61–3.58 (t, J = 3.6Hz,2H).13C NMR (100MHz, CDCl3) δ: 158, 129.5, 121.4, 114.8,67.8, 29.1. MS m/z (I): 202 (50, M+2), 200 (48, M+), 109 (97),107 (100), 94 (60), 77 (29), 65 (38), 51 (22), 39 (52).
85% With sodium hydroxide In water 1-(2-Bromoethyl)piperidine hydrobromide
In a mixed solution consisting of 50 g of 1,2-dibromoethane, 18.5 g of phenol and 100 ml of water was added dropwise 30 ml of water containing therein 7.9 g of sodium hydroxide at a temperature of 130° C. over 30 minutes with stirring.
The reaction solution was further stirred for 6 hours.
After completion of the reaction, the organic layer was separated from the reaction solution, washed twice with a saturated aqueous potassium carbonate solution, washed twice with water and dried with anhydrous sodium sulfate.
The organic layer was separated by filtration and condensed under reduced pressure to give 34.3 g of 2-phenoxyethyl bromide having a boiling point of 105° C. to 107° C. at 6 mmHg in a yield of 85percent.
85% With sodium hydroxide In water REFERENTIAL EXAMPLE 1
1-(2-Bromoethyl)piperidine hydrobromide
In a mixed solution consisting of 50 g of 1,2-dibromoethane, 18.5 g of phenol and 100 ml of water was added dropwise 30 ml of water containing therein 7.9 g of sodium hydroxide at a temperature of 130° C. over 30 minutes with stirring, and the reaction solution was further stirred for 6 hours.
After completion the reaction, the organic layer was separated from the reaction solution, washed twice with a saturated aqueous potassium carbonate solution, washed twice with water and dried over anhydrous sodium sulfate.
The organic layer was separated by filtration and condensed under reduced pressure to give 34.3 g of 2-phenoxyethyl bromide having a boiling point of 105° C. to 107° C. at 6 mmHg in a yield of 85percent.
67% With sodium hydroxide In water for 5 h; Reflux Example 11
Synthesis of N-ethyl-N-(2-phenoxy)ethylcyclohexylamine
A 22.5percent aqueous sodium hydroxide solution (135 mL) was added to a mixture of phenol (30.0 g (0.32 mol)) and 1,2-dibromoethane (237 g (1.28 mol)), and the mixture was stirred 5 hours under heating at reflux.
The temperature was returned to room temperature, and the mixture was then extracted three times with dichloromethane (100 mL).
The whose organic layer was dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure.
The residue was purified by a silica gel chromatography (petroleum ether : ethyl acetate = 10 : 1) to obtain (2-bromoethoxy)benzene (compound-01) (43.0 g, 0.215 mol, yield 67percent).
64% With potassium carbonate; potassium iodide In acetone at 60℃; General procedure: A solution of 1,2-dibromoethane (0.02 mol) in 40 ml ofacetone was added dropwise into the mixture of respective phenol (0.08 mol) andK2CO3 (0.04 mol) in 30 ml of acetone. Subsequently, acatalytic amount of KI (0.3 mmol) was added and the resulting mixture wasstirred at 60°C for 24–72 hours. After the completion of the reaction theinorganic residues were filtrated off and organic mixture was concentrated undervacuum. The obtained crude product was purified on silica gel with AcOEt/hexaneas eluting system. 2.1. (2-Bromoethoxy)benzene 16{1}Yellow oil(6 g, 64percent yield), following chromatographic purification over silica gel with AcOEt/hexane (0.5/9.5 v/v); UPLC/MSpurity 97percent, tR = 7.98. C8H9BrO, MW 201.06, MonoisotopicMass 199.98, [M+H]+ 200.2. 1H NMR (300 MHz, CDCl3)δ 3.43 (t, J = 6.5Hz, 2H), 4.28 (t, J = 6.5 Hz, 2H), 6.81 (dd, J = 5.2,1.0 Hz, 1H), 6.95 (td, J = 7.6, 1.1 Hz, 1H), 7.02 (m, 1H),7.14 (td, J = 8.0, 1.8 Hz, 1H), 7.21–7.25 (m, 1H).
64% With potassium iodide; sodium hydroxide In methanol for 8 h; Reflux This compound was made according to the previous work [1]. Phenol (2.35 g, 25 mmol), NaOH (1 g,25 mmol), 1,2-dibromoethane (10.8 mL, 125 mmol) and a catalyzed amount of KI were added into 50 mL methanol. The solution was refluxed for 8 h. Then the solvent was evaporated and the crude product was purified on column chromatography by using petroleum ether as eluent. The yield was 64percent.
63% With potassium carbonate In acetonitrile at 100℃; General procedure: 1,2-dibromoethane (573mL, 6.62mmol) was added to a mixture of 2-hydroxybenzthiazole (500mg, 3.31mmol) and potassium carbonate (1.37g, 9.93mmol) in acetonitrile, which were then refluxed (oil bath temp 100°C) till the consumption of benzthiazole (TLC, 7h). The reaction mixture was allowed to cool at room temperature and diluted with water. Further extraction was done using EtOAc (3×5mL). The organic layer was combined and washed with 4N NaOH solution and then with brine. Organic layer was then dried (anh Na2SO4), filtered and concentrated under vacuum. The resulting mixture was purified using column chromatography (ethyl acetate: hexane, 3:97). This resulted in white solid intermediate, 2-(benzthiazol-2-yloxy)ethyl bromide (11b) in 70percent (597mg) yield.
58% With potassium carbonate; potassium iodide In acetone at 60℃; General procedure: A solution of 1,2-dibromoethane (0.02 mol) in 40 ml of acetone was added dropwise into the mixture of respective phenol 1–11 (0.08 mol) and K2CO3 (0.04 mol) in 30 ml of acetone. Subsequently a catalytic amount of KI (0.3 mmol) was added and the resulting mixture was stirred at 60°C for 24–72 hours. After the completion of the reaction the inorganic residues were filtrated off and organic mixture was concentrated under vacuum. The obtained crude product was purified on silica gel with AcOEt/hexane as eluting system.#10;#10;
54% With tetrabutylammomium bromide; sodium hydroxide In waterReflux Phenol 1.0g (10.6mmol) was dissolved in 20mL of water was added NaOH 0.64g (15,8mmol), was added with stirring 1,2-dibromoethane 1.83mL (21,3mmol), was added a catalytic amount of TBAB, was heated to reflux. After the reaction was cooled to room temperature, ethyl acetate (20mL × 3). The combined organic phases, the organic phase was washed with 1N HCl × 2, water × 2, 1N NaOH × 2, × 2 was washed with saturated sodium chloride, dried over anhydrous Na2SO4 dry. Filtration, column chromatography (petroleum ether: ethyl acetate = 50) to give a white solid 1.2g, Yield: 54percent.
52% With sodium hydroxide In water for 12 h; Reflux Equipped with a stirrer, reflux condenser, drying tube, thermometer 100ml three-necked flask was added phenol (1g,8.2mmol), water (14mL) and 1,2-dibromoethane (1.4mL, 16.4mmol), with vigorous stirring, was heated to reflux. Was added dropwise aqueous NaOH (3mL, 3M), the reaction 12h. After the reaction was cooled to room temperature and extracted with ethyl acetate (20mL × 3), washed with saturated brine, dried over anhydrous MgSO4. Column chromatography on silica gel, eluent petroleum ether: ethyl acetate = 20:1 (v / v), to give a pale yellow oil 1.1g (5.47mmol), Yield: 52percent
44% With potassium carbonate In acetone at 80℃; for 24 h; To a solution of phenol (1.88g, 20mmol) and 1,2-dibromoethane (22.56g, 120mmol) in 75 acetone (50mL) was added potassium carbonate (5.52g, 40mmol) under stirring. The mixture was refluxed at 80°C for 24h. After being cooled to room temperature, any insoluable solids were filtered off and the solvent was evaporated from the filtrate to give a residue which was purified by column chromatography (ethyl acetate/petroleum ether=1:50, v/v) to afford the desired product as pale-yellow oil (2b) (1.11g, 44percent). 1H NMR (400MHz, CDCl3, ppm): δ=7.29 (t, J=8.0Hz, 2H), 6.98 (t, J=7.4Hz, 1H), 6.91 (d, J=8.8Hz, 2H), 4.28 (t, J=6.2Hz, 2H), 3.63 (t, J=6.4Hz, 2H).

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[4] Patent: US4533731, 1985, A,
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[11] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 348 - 360,13
[12] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 348 - 360
[13] Patent: CN103739581, 2016, B, . Location in patent: Paragraph 0244; 0245
[14] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 3, p. 328 - 332
[15] Patent: CN105622657, 2016, A, . Location in patent: Paragraph 0036; 0037; 0038
[16] Journal of Materials Chemistry C, 2016, vol. 4, # 14, p. 2843 - 2853
[17] Journal of Organometallic Chemistry, 2017, vol. 853, p. 136 - 142
[18] Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 135 - 137
[19] Dyes and Pigments, 2017, vol. 147, p. 560 - 572
[20] Journal of Medicinal Chemistry, 2007, vol. 50, # 23, p. 5752 - 5764
[21] Chemische Berichte, 1910, vol. 43, p. 2179
[22] Journal of Medicinal Chemistry, 1982, vol. 25, # 1, p. 57 - 63
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  • 2
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YieldReaction ConditionsOperation in experiment
67.6% With lithium bromide In acetone at 20℃; for 24 h; 1L2 (6.49g, 30.0mmol) in acetone (20mL) was added dropwise to LiBr (13.0g, 150mmol) in 100mL acetone at room temperature. After stirring for 24h, a reaction was stopped by the addition of water (50mL) and the organic portion was separated. The aqueous layer was extracted three times with diethyl ether (3×50mL) and the combined organic portions were dried over MgSO4. Filtration followed by evaporation gave the desired product 1L3 (4.08g, yield=67.6percent) as a yellow oil.
Reference: [1] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698,7
[2] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698
[3] Polyhedron, 2014, vol. 67, p. 205 - 212
  • 3
  • [ 122-99-6 ]
  • [ 589-10-6 ]
Reference: [1] Letters in Organic Chemistry, 2012, vol. 9, # 8, p. 598 - 603,6
[2] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 9, p. 1471 - 1480
[3] Journal of Organic Chemistry, 1968, vol. 33, # 6, p. 2271 - 2284
[4] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698,7
[5] Synlett, 2012, vol. 23, # 18, p. 2692 - 2698
[6] Polyhedron, 2014, vol. 67, p. 205 - 212
  • 4
  • [ 124004-35-9 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 8, p. 1519 - 1528
  • 5
  • [ 108-95-2 ]
  • [ 589-10-6 ]
Reference: [1] Polyhedron, 2014, vol. 67, p. 205 - 212
  • 6
  • [ 2033-76-3 ]
  • [ 589-10-6 ]
  • [ 108-95-2 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 30, p. 2911 - 2914
  • 7
  • [ 18800-30-1 ]
  • [ 589-10-6 ]
  • [ 108-95-2 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 30, p. 2911 - 2914
  • 8
  • [ 139-02-6 ]
  • [ 106-93-4 ]
  • [ 104-66-5 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Chemische Berichte, 1907, vol. 40, p. 2781
[3] Journal of the Chemical Society, 1896, vol. 69, p. 175
[4] Chemische Berichte, 1897, vol. 30, p. 810
[5] Journal fuer Praktische Chemie (Leipzig), 1881, vol. <2> 24, p. 242
[6] Chemische Berichte, 1889, vol. 22, p. 3255
  • 9
  • [ 64-17-5 ]
  • [ 106-93-4 ]
  • [ 108-95-2 ]
  • [ 104-66-5 ]
  • [ 589-10-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Chemische Berichte, 1907, vol. 40, p. 2781
[3] Chemische Berichte, 1897, vol. 30, p. 810
[4] Journal fuer Praktische Chemie (Leipzig), 1881, vol. <2> 24, p. 242
  • 10
  • [ 56-23-5 ]
  • [ 64-17-5 ]
  • [ 106-93-4 ]
  • [ 108-95-2 ]
  • [ 104-66-5 ]
  • [ 589-10-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Chemische Berichte, 1907, vol. 40, p. 2781
[3] Chemische Berichte, 1897, vol. 30, p. 810
[4] Journal fuer Praktische Chemie (Leipzig), 1881, vol. <2> 24, p. 242
  • 11
  • [ 37616-36-7 ]
  • [ 589-10-6 ]
  • [ 100252-25-3 ]
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[3] Roczniki Chemii, 1954, vol. 28, p. 461,464[4] Chem.Abstr., 1956, p. 221
  • 12
  • [ 112-18-5 ]
  • [ 589-10-6 ]
  • [ 538-71-6 ]
Reference: [1] Patent: GB607222, 1948, ,
[2] Patent: GB607222, 1948, ,
[3] Patent: GB607222, 1948, ,
  • 13
  • [ 124-22-1 ]
  • [ 589-10-6 ]
  • [ 538-71-6 ]
Reference: [1] Patent: GB607222, 1948, ,
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