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[ CAS No. 5414-19-7 ] {[proInfo.proName]}

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Product Details of [ 5414-19-7 ]

CAS No. :5414-19-7 MDL No. :MFCD00039196
Formula : C4H8Br2O Boiling Point : -
Linear Structure Formula :- InChI Key :FOZVXADQAHVUSV-UHFFFAOYSA-N
M.W : 231.91 Pubchem ID :21521
Synonyms :
Chemical Name :1-Bromo-2-(2-bromoethoxy)ethane

Calculated chemistry of [ 5414-19-7 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.17
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 1.79
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.02
Solubility : 2.21 mg/ml ; 0.00951 mol/l
Class : Soluble
Log S (Ali) : -1.41
Solubility : 9.12 mg/ml ; 0.0393 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.95
Solubility : 0.26 mg/ml ; 0.00112 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.17

Safety of [ 5414-19-7 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P280-P305+P351+P338 UN#:3334
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5414-19-7 ]

* 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 [ 5414-19-7 ]
  • Downstream synthetic route of [ 5414-19-7 ]

[ 5414-19-7 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 5414-19-7 ]
  • [ 106-40-1 ]
  • [ 30483-75-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247
  • 2
  • [ 111-46-6 ]
  • [ 5414-19-7 ]
YieldReaction ConditionsOperation in experiment
41.4 g With phosphorus tribromide In tetrachloromethane at 20℃; for 16 h; Cooling with ice 21.2 g (0.2 mol) of diethylene glycol in a dry 1 L flask, 500 mL of carbon tetrachloride was added, dissolved by stirring, and cooled in an ice-water bath. 60 g (0.22 mol) of phosphorus tribromide was slowly added dropwise. The addition was complete, stirring was continued for 1 hour, the ice-water bath was removed, and the mixture was stirred at room temperature for 15 hours. Concentrate to remove the solvent. Another 500 mL of ethyl acetate was added for dissolution and then washed four times with a 5percent aqueous solution of sodium carbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 41.4 g of an oil (compound 11).
Reference: [1] Journal of Materials Chemistry B, 2014, vol. 2, # 29, p. 4640 - 4652
[2] Journal of Materials Chemistry B, 2015, vol. 3, # 8, p. 1495 - 1506
[3] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3412 - 3422
[4] Journal of the American Chemical Society, 1937, vol. 59, p. 213
[5] Justus Liebigs Annalen der Chemie, 1937, vol. 528, p. 150
[6] Justus Liebigs Annalen der Chemie, 1958, vol. 613, p. 185,194
[7] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1983, p. 2525 - 2528
[8] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 4, p. 707 - 715
[9] Journal of the American Chemical Society, 1981, vol. 103, # 14, p. 4142 - 4145
[10] Journal of Physical Chemistry B, 1998, vol. 102, # 32, p. 6152 - 6160
[11] Asian Journal of Chemistry, 2011, vol. 23, # 2, p. 729 - 732
[12] Asian Journal of Chemistry, 2012, vol. 24, # 11, p. 5011 - 5014
[13] Journal of Chemical and Engineering Data, 2015, vol. 60, # 4, p. 1091 - 1097
[14] Patent: CN107652343, 2018, A, . Location in patent: Paragraph 0096; 0103; 0104
  • 3
  • [ 34604-52-9 ]
  • [ 5414-19-7 ]
YieldReaction ConditionsOperation in experiment
50% With lithium bromide In acetone for 20 h; Heating / reflux A solution of a commercially available PEG (6.66 mmol) and triethylamine (2.32 ml, 16.65 mmol) in dry diethyl ether (10 ml) was cooled at 0° C., under a dry nitrogen atmosphere and treated dropwise with methanesulfonyl chloride (1.03 ml, 13.32 mmol). Stirring was continued for 1 h at 0° C. and at room temperature (22° C.) for 2 h. Afterwards, the diethyl ether was evaporated and dry acetone (12 ml) was added to the residue in order to precipitate most of the triethylamine hydrochloride salt, which was filtered from the solution. The filtrate, containing the dimesylate-PEG derivative was immediately treated with lithium bromide (2.31 g, 26.64 mmol) and heated to reflux for 20 h. Then the product was filtered on a small quantity of silica (3 cm) covered with celite (0.5 cm) with hexanes as the eluent. The filtrate was dried, filtered and evaporated to an oil. The α,ω-dibromo-PEG derivatives were obtained in 50 to 83percent yield. [0159] NB: Some of these α,ω-dibromo-PEG derivatives are also commercially available. [0160] 1,5-dibromo-3-oxapentane (n=1) [0161] 50percent yield [0162] IR (NaCl, νmax, cm-1): 1279 and 1117 (C-O). [0163] 1H-NMR (CDCl3, δ ppm): 3.83 (4H, t, J=6.3 Hz, 2.x.CH2O), 3.47 (4H, t, J=6,3 Hz, 2.x.CH2Br). [0164] 13C-NMR (CDCl3, δ ppm): 71.0 (CH2O), 30.0 (CH2Br).
Reference: [1] Patent: US2004/6051, 2004, A1, . Location in patent: Page/Page column 6-7
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 557 - 560
[3] Steroids, 2006, vol. 71, # 10, p. 911 - 921
  • 4
  • [ 107-61-9 ]
  • [ 5414-19-7 ]
YieldReaction ConditionsOperation in experiment
82.1% at 20℃; for 12 h; 68.1 g of 1,4-thioxane-1,1-dioxo (0.5 mol), 340Gram mass of 48percent hydrobromic acid (2 moles)Was added to a 500 mL four-necked flask and mechanically stirred at 30 ° C. The gas chromatographic was followed by a 12 hour reaction.Layer, the lower layer of organic layer and then 50 ml of saturated sodium bicarbonate washing, water chestnut distillation collection 90-105 ° C boiling range, pale yellow liquid 96.7 grams,The gas content was 98.5percent and the yield was 82.1percent.
Reference: [1] Patent: CN104557476, 2016, B, . Location in patent: Paragraph 0032-0033
  • 5
  • [ 111-44-4 ]
  • [ 5414-19-7 ]
YieldReaction ConditionsOperation in experiment
65% With potassium bromide In ethylene dibromide; N,N-dimethyl-formamide for 24 h; Reflux A suspension of bis-(2-chloroethyl) ether (6) (5.0 g, 0.035 mol) and KBr (8.3 g,0.07 mol) in 2:1 mixture of DMF–1,2-dibromoethane(150 ml) was refluxed for 24 h. Saturated NaCl solution(50 ml) was then added to the reaction mixture, followedby extraction with Et2O. The solution was dried overanhydrous Na2SO4 and evaporated under vacuum, theresidue was purified by vacuum distillation at 4–5 Torr.Yield 5.25 g (65percent), dark-brown oil. NMR spectra matchedthe literature.
Reference: [1] Chemistry of Heterocyclic Compounds, 2017, vol. 53, # 3, p. 364 - 370[2] Khim. Geterotsikl. Soedin., 2017, vol. 53, # 3, p. 364 - 370,7
  • 6
  • [ 799296-23-4 ]
  • [ 540-51-2 ]
  • [ 5414-19-7 ]
  • [ 1202570-30-6 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 1, p. 253 - 256
  • 7
  • [ 111-44-4 ]
  • [ 5414-19-7 ]
  • [ 51070-66-7 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 14, p. 1313 - 1320
  • 8
  • [ 75-21-8 ]
  • [ 74-85-1 ]
  • [ 5414-19-7 ]
Reference: [1] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1951, p. 708,709[2] Chem.Abstr., 1952, p. 7514
[3] Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 1136 - 1138[4] Zhurnal Organicheskoi Khimii, 1971, vol. 7, p. 1109 - 1110
  • 9
  • [ 123-91-1 ]
  • [ 5414-19-7 ]
Reference: [1] Canadian Journal of Chemistry, 1951, vol. 29, p. 785,787
  • 10
  • [ 3741-38-6 ]
  • [ 5414-19-7 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 314 - 315
  • 11
  • [ 107-21-1 ]
  • [ 5414-19-7 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 1500 - 1503[2] Zhurnal Organicheskoi Khimii, 1968, vol. 4, p. 1561 - 1565
  • 12
  • [ 75-21-8 ]
  • [ 74-85-1 ]
  • [ 5414-19-7 ]
  • [ 31255-10-4 ]
Reference: [1] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1951, p. 708,709[2] Chem.Abstr., 1952, p. 7514
  • 13
  • [ 123-91-1 ]
  • [ 5414-19-7 ]
  • [ 31255-10-4 ]
  • [ 31255-26-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 1855 - 1860
  • 14
  • [ 123-91-1 ]
  • [ 10035-10-6 ]
  • [ 5414-19-7 ]
Reference: [1] Canadian Journal of Chemistry, 1951, vol. 29, p. 785,787
  • 15
  • [ 5414-19-7 ]
  • [ 56-05-3 ]
  • [ 10397-13-4 ]
YieldReaction ConditionsOperation in experiment
28% With potassium carbonate In DMF (N,N-dimethyl-formamide) for 3 h; Heating / reflux 2-bromoethylether (3.65g), potassium carbonate (8.29g), and N,N-dimethylformamide (75mL) were added to 2-amino-4,6-dichloropyrimidine (2.46g), and the mixture was refluxed for 3 hours while heated. Subsequently, the reaction mixture was diluted with ethyl acetate, was washed with water, and was dried over anhydrous sodium sulfate. The solvent was removed and the resulting residue was purified on a silica gel column chromatography (hexane: ethyl acetate = 5: 1) to obtain 4,6-dichloro-2-(morpholine-4-yl)pyrimidine (985mg, 28percent). MS(EI)m/z:233(M+) HRMS(EI): Calcd for C8H9Cl2N3O: 233.0123; found:233.0152
Reference: [1] Patent: EP1473295, 2004, A1, . Location in patent: Page 20
  • 16
  • [ 5414-19-7 ]
  • [ 615-36-1 ]
  • [ 87698-82-6 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 2, p. 269 - 276
  • 17
  • [ 5414-19-7 ]
  • [ 591-19-5 ]
  • [ 197846-82-5 ]
YieldReaction ConditionsOperation in experiment
16.4% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 16 h; To a solution of 3-bromoaniline (1.00 g, 5.81 mmol) in anhydrous DMF (20 mL) was added l-bromo-2-(2-bromoethoxy)ethane (1.62 g, 6.18 mmol) and DIPEA (2.25 g, 17.4 mmol). The solution was heated to 100 °C for 16 h, cooled and concentrated. The residue was purified by preparative HPLC purification. (230 mg, yield 16.4percent) MS (ESI+) e/z: 242.0 [M+l]+
Reference: [1] Patent: WO2014/100716, 2014, A1, . Location in patent: Paragraph 00234
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247
  • 18
  • [ 5414-19-7 ]
  • [ 73918-56-6 ]
  • [ 736991-39-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4242 - 4247
  • 19
  • [ 5414-19-7 ]
  • [ 59-48-3 ]
  • [ 304876-29-7 ]
YieldReaction ConditionsOperation in experiment
17%
Stage #1: at -78℃; for 1 h;
Stage #2: at -50 - 25℃; for 18 h;
Oxindole la (CAS number: 59-48-3, 40 g, 264.659 mmol) was added to a solution of LiHMDS (800 ml, 800 mmol) at -78°C. The mixture was stirred 1 hour at -78°C.Bis(2-bromomethyl)ether (CAS number: 5414-19-7, 61.378 g, 264.659 mmol) was then added, maintaining the internal temperature <-5 0°C. The reaction was warmed to ambient temperature. After 18 hours the reaction was quenched with H20 and the mixture was partitioned between EtOAc and H20. The aqueous solution was extracted with EtOAc and the combined organic layers were washed with brine, dried overNa2SO4, filtered, and concentrated in vacuum. The residue was purified by silica gel chromatography, eluting with a gradient of petroleum ether: ethyl acetate = 3:1 to give 10.187 g (17percent) of 2’,3’,5’,6’-tetrahydrospiro[indoline-3 ,4’-pyran]-2-one lb.
Reference: [1] Patent: WO2014/60411, 2014, A1, . Location in patent: Page/Page column 36
  • 20
  • [ 5414-19-7 ]
  • [ 177906-48-8 ]
  • [ 558442-96-9 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In N,N-dimethyl-formamide at 70℃; for 6 h; To a solution of 21.43g (0.1mol) of tert-butyl N-(trans-4-aminocyclohexyl) carbamate in 250mL of N,N-dimethylformamide were added 16.76mL (0.12mol) of bis (2-bromoethyl) ether and 34.85mL (0.25mol) of triethylamine, and the mixture was stirred for 6 hours at 70°C. Then solvent was removed under reduced pressure and the residue was treated with ethyl acetate. The organic layer was washed with sodium carbonate aqueous solution and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform alone to chloroform/methanol = 30/1) to give 19.92g (70percent) of the title compound.
Reference: [1] Patent: EP1775298, 2007, A1, . Location in patent: Page/Page column 33-34
  • 21
  • [ 5414-19-7 ]
  • [ 210907-84-9 ]
  • [ 852227-95-3 ]
Reference: [1] Patent: WO2012/167423, 2012, A1, . Location in patent: Page/Page column 37
[2] Patent: US2014/121200, 2014, A1, . Location in patent: Paragraph 0173; 0174
  • 22
  • [ 5414-19-7 ]
  • [ 99365-40-9 ]
  • [ 1190861-43-8 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -40℃; for 0.75 h;
Stage #2: at 20℃; for 16 h;
n-BuLi (2M in hexane, 22.6 mL, 45.27 mmol) was added drop wise at -40°C to a solution of 6-bromo-indolin-2-one (3 g, 14.14 mmol) and diisopropylamine (6.3 mL, 45.27 mmol) in THF (60 mL). The mixture was stirred for 45 min at -40°C, 1-bromo-2-(2-bromoethoxy)ethane was added drop wise at this temperature and stirring was continued at RT for 16 h. The reaction mixture was quenched with 4N hydrogen chloride solution (40 mL) and the aqueous phase was separated and extracted with EtOAc (3x 60 mL). The combined organic layers were washed with brine (50 mL), dried over Na2S04 and concentrated. The raw product was triturated with hexane (20 mL) and filtered. The filter was washed with hexane/EtOAc = 4:1 (100 mL) affording the target compound as light brown solid. Yield: 1.2 g (31 percent). HPLC (method 1 ): Rt = 2.94 min, m/z [M+H]+ = 282.1 (MW calc. 282.13).
Reference: [1] Patent: WO2017/108204, 2017, A1, . Location in patent: Page/Page column 133
  • 23
  • [ 5414-19-7 ]
  • [ 1229236-82-1 ]
  • [ 1229236-83-2 ]
YieldReaction ConditionsOperation in experiment
31% With potassium carbonate In water at 120℃; for 0.333333 h; Microwave irradiation; Sealed tube PREPARATION 7
(4-Chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone
Combine (8-(aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone (1.15 g, 3.3 mmol), water (12 mL), potassium carbonate (495 mg, 1.1 equiv.), and 2-bromoethyl ether (0.47 mL, 1.1 equiv) in a 20 mL microwave reaction vessel.
Seal with a crimp cap then heat in a microwave reactor at 120° C. for 20 min.
Cool to RT and partition between EA and water.
Wash EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate.
Filter and concentrate in vacuo.
Purify on silica gel (4:1 hexane:EA-->2:1 hexane:EA-->1:1 hexane:EA) to give the title compound (0.43 g, 31percent) as a light yellow foam. LCMS (4 min)=423.0, 425.0, M+1.
Reference: [1] Patent: US2010/152181, 2010, A1, . Location in patent: Page/Page column 4
  • 24
  • [ 5414-19-7 ]
  • [ 56239-26-0 ]
  • [ 1228947-14-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 10071 - 10091
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