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[ CAS No. 31827-94-8 ] {[proInfo.proName]}

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Chemical Structure| 31827-94-8
Chemical Structure| 31827-94-8
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Product Details of [ 31827-94-8 ]

CAS No. :31827-94-8 MDL No. :MFCD01360521
Formula : C8H6BrIO Boiling Point : -
Linear Structure Formula :- InChI Key :FSIBMLJFLPWMTD-UHFFFAOYSA-N
M.W : 324.94 Pubchem ID :256572
Synonyms :

Calculated chemistry of [ 31827-94-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.22
TPSA : 17.07 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) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 2.84
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 3.66
Consensus Log Po/w : 2.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.92
Solubility : 0.0395 mg/ml ; 0.000121 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.452 mg/ml ; 0.00139 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.53
Solubility : 0.00961 mg/ml ; 0.0000296 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.11

Safety of [ 31827-94-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 31827-94-8 ]

* 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 [ 31827-94-8 ]
  • Downstream synthetic route of [ 31827-94-8 ]

[ 31827-94-8 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
100% With bromine In 1,4-dioxane at 20℃; for 1 h; To a stirring solution ofp-iodoacetophenone 1 (30.0 g, 122 mmol) in dioxane (200 mL) over an ice-bath was added bromine (6.56 mL, 128 mmol) dropwise. The reaction mixture was stirred at room temperature and monitored by LC/MS. After completion (about 1 hour), the solvent was evaporated by rotovap, and the residue was dried under vacuum to give solid 2 (40g, 100percent). [00466] (Based on J. Med. Chent. 2001,44, 2990-3000) To a solution of Cbz-D-Ala- OH 3 (5.0 g, 22.4 mmol) in NMP (100 mL) was added cesium carbonate (3.72 g, 11.4 mmol). After stirring at RT for 1 h, 2 (7.60 g, 22.4 mmol) was added. The reaction mixture was stirred at room temperature and monitored by LC/MS to form 4. The reaction solution was diluted with xylene (100 mL) and ammonium acetate (9.25g, 120 mmol) and then stirred at 120°C for 4 hours. Up to 50eq of additional ammonium acetate may be needed depending on the reaction progress. The key is to see solid in the flask at all times. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (200 mL). The EtOAc solution was washed with saturated sodium bicarbonate solution (200 mL) twice, and dried by sodium sulfate, then filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and stirred for 1 h to give a precipitate, and the solid 5 (4.0g) was filtered off and dried under vacuum. The mother solution was concentrated by rotovap, the residue was purified on Bio-tage to give 5 (Hexane: EtOAc = 1:1 to EtOAc 100percent). The two products were combined and dried under vacuum to give 5 (5.8 g, 58percent).
100% With bromine In 1,4-dioxane at 0 - 20℃; for 1 - 1.66667 h; Example 7Experimental Section:7.1 7.22-Bromo-l-(4-iodophenyl)ethanone:[00192] A solution of l-(4-iodophenyl)ethanone (55.9 mmol) in dioxane (160 mL) was cooled to 10 0C. Bromine (1.1 equiv, 61.6 mmol) was added dropwise to the reaction mixture. After 10 min, the cooling bath was removed and the reaction mixture was stirred at room temperature. After 1.5 h, the reaction mixture was concentrated in vacuo, poured into water (100 mL), and extracted with (3 x 100 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to a tan solid (18.2 g) which was used directly in the next step. ; Example 1212Experimental Section:12.1 12.2Ref: J. Med. Chem. 2001, 44, 2990-3000[00211] To a stirring solution of p-iodoacetophenone 12.1 (30.0 g, 122 mmol) in dioxane(200 mL) over an ice-bath was added bromine (6.56 mL, 128 mmol) dropwise. The reaction mixture was stirred at room temperature and monitored by LC/MS. After completion (about 1 hour), the solvent was evaporated by rotovap, and the residue was dried under vacuum to give solid 12.2 (40 g, 100percent).
94% With bromine In chloroform at 20℃; for 4 h; The appropriate carbonyl compound (50 mmol) was dissolved in 50 mL of ethanol and magnetically stirred with an equimolar quantity of thiosemicarbazide for 24 h at room temperature with catalytic amounts of acetic acid. The desired thiosemicarbazone precipitated from reaction mixture, was filtered, crystallized from suitable solvent, and dried. Equimolar quantities of 4-iodo-acetophenone and bromine, both dissolved in chloroform, were stirred for 4 h at room temperature until the presence of HBr disappeared. The solution was evaporated under vacuum and the obtained pale yellow solid was washed with petroleum ether to give α-bromo-4-iodo-acetophenone in good yield (94percent). Equimolar amounts of the prepared thiosemicarbazone (50 mmol) and α-bromo-4-iodo-acetophenone (50 mmol), both suspended in 50 mL of ethanol, were reacted at room temperature under magnetic stirring for 10 h. The precipitate was filtered and purified by chromatography to give compounds 1-25 in high yield.
91% With bromine In acetic acid at 20℃; for 10 h; Example 83A
2-Bromo-1-(4-iodo-phenyl)-ethanone
A solution of bromine (79.3 g, 508 mmo) in glacial acetic acid (50 mL) was added at room temperature to a solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL).
The mixture was stirred for 10 h, then concentrated under reduced pressure and the residue was diluted with ethyl acetate (100 mL), and washed with brine (3*50 mL).
The organic layer was concentrated, and the residue was crystallized from ethyl ether to provide the title compound as a yellow solid (150 g, 462 mmol, 91percent yield).
1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 ppm (d, J=8.5 Hz, 2H); MS (DCl/NH3) m/z 246 (M-Br)+264 (M-Br+NH4)+.
91% With bromine In acetic acid at 20℃; for 10 h; Example 32A
2-Bromo-1-(4-iodo-phenyl)-ethanone
To the solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL) was added the bromine (Aldrich, 79.3 g, 508 mmol, in 50 mL of acetic acid) and stirred at room temperature for 10 hours.
It was concentrated under reduced pressure.
The residue was then diluted with ethyl acetate (100 mL) and washed with brine (3*50 mL).
The organic solution was concentrated.
The title compound was obtained as yellow solid by recrystallization from diethyl ether (150 g, 91percent).
1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 (d, J=8.5 Hz, 2H) ppm; MS (DCl/NH3) m/z 246 (M-Br)+, 264 (M-Br+NH4)+.
80% With bromine In dichloromethane at 20℃; To a clear dark solution of l-(4-iodophenyl)ethanone (1.046 kg, 4.251 mol, 1 equiv.) in DCM (8 L) was charged (dropwise) bromine (228 ml, 4.45 mol, 1.047 equiv.) over the period of 30 to 45 min at the ambient temperature. The reaction was slightly exothermic (temperature incresed to about 20-25 °C) and released a lot of hydrogen bromide gas as the by-product. The reaction was considered as complete after 3 to 4 hrs as indicated by HPLC (typically ~7percent starting material, -10percent di-bromo by- product, and ~83percent> desired mono-bromo product, all in areapercent> by HPLC). It was then quenched and neutralized by aqueous NaHC03solution wash (4 L), followed by brine wash (3 L). Upon drying over Na2S04, it is rotavapped and solvent swapped to THF and the desired product was crystallized from THF (final volume about 2 L) at from 50°C to 20°C to afford the 1st crop: 340 g (98percent HPLC purity); by concentrating the mother liqor to about half-volume to afford the 2nd crop: 426 g (98percento HPLC purity); by further concentating and addition of hexanes (i.e.,THF/hexanes, 1 : 1) to afford the 3rd crop: 339 g (97+percent HPLC purity). The combined crystal title compound was 1.105 kg (80percent yield). 1H NMR (500 MHz, CDC13): 7.88 (d, 2 H), 7.70 (d, 2 H), 4.42 (s, 2 H).
63% With sodium hydroxide; copper(ll) bromide In chloroform; ethyl acetate at 25 - 70℃; for 22 h; A 1 L round bottom flask, equipped with a mechanical stirrer, addition funnel, thermocouple and a reflux condenser attached to an alligator trap filled with aq. NaOH (2M), was charged with CuBr2 (92.4 g, 0.414 mol) and ethyl acetate (320 mL). 4-Iodoacetophenone (53.4 g, 0.217 mol) was dissolved into chloroform (320 mL) and placed into the addition funnel. The chloroform solution was added to the ethyl acetate solution and the reaction mixture stirred at 70° C. for 6 hours then cooled to 25° C. for 16 hours. The CuBr salt was removed by filtering through Celite. The filtrate was washed with aq. saturated sodium bicarbonate (2.x.200 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and the solvents were removed under reduced pressure to give crude product contaminated with unreacted starting material. The product was purified by recrystallization from dichloromethane/hexane to give pure material as a tan solid (44.5 g, 63percent yield): mp 109-111° C.
60.5% With bromine In dichloromethane at 20℃; Example QC-13a To a solution of 4-iodophenyl ethanone (14.76 g, 60.0 mmol) in 150 mL of dichloromethane was added bromine (9.5 g, 59.5 mmol) dropwise. The resulting solution was stirred at room temperature overnight. The solvent was removed under vacuum. The crude product was recrystallized with dichloromethane/hexanes to give Example QC-13a (11.8 g, 60.5percent) as a grey solid. 1H NMR (500 MHz, CDCl3) δ ppm 4.38 (s, 2H) 7.68 (d, J=8.55 Hz, 2H) 7.86 (d, J=8.85 Hz, 2H); LC/MS: Anal. Calcd. for C8H771BrIO [M+H]+ 325.86; found 325.11.
46% With N-Bromosuccinimide In ethyl acetate at 40℃; In a 100 mL round bottom flask, 10 mmol of 4-iodoacetophenone and 11 mmol of N-bromosuccinimide (NBS) were added.35mL of ethyl acetate dissolved,Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted. After TLC tracks the reaction,The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, and the filtrate was spin-dried.Column chromatography (eluent: petroleum ether/ethyl acetate) gave a yellow solid with a yield of 46percent.
46% With N-Bromosuccinimide In ethyl acetate at 40℃; Add 100mL round bottom flask10 mmol 4-iodoacetophenone and 11 mmol N-bromosuccinimide (NBS),35mL of ethyl acetate dissolved,Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted.After TLC tracks the reaction,The reaction solution was filtered to remove Amberlyst 15 ion exchange resin,The filtrate was spin-dry,Column chromatography (eluent: petroleum ether/ethyl acetate) gave a yellow solid,Yield 46percent.

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