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Product Details of [ 13329-40-3 ]

CAS No. :13329-40-3 MDL No. :MFCD00045320
Formula : C8H7IO Boiling Point : -
Linear Structure Formula :- InChI Key :JZJWCDQGIPQBAO-UHFFFAOYSA-N
M.W : 246.05 Pubchem ID :72869
Synonyms :

Calculated chemistry of [ 13329-40-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.35
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) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 3.12
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) : -3.25
Solubility : 0.139 mg/ml ; 0.000563 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 1.0 mg/ml ; 0.00408 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0504 mg/ml ; 0.000205 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.6

Safety of [ 13329-40-3 ]

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 [ 13329-40-3 ]

* 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 [ 13329-40-3 ]
  • Downstream synthetic route of [ 13329-40-3 ]

[ 13329-40-3 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 13329-40-3 ]
  • [ 31827-94-8 ]
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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  • [ 556110-57-7 ]
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  • [ 64-19-7 ]
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  • [ 6921-45-5 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3604 - 3607
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  • [ 201230-82-2 ]
  • [ 6921-45-5 ]
YieldReaction ConditionsOperation in experiment
15.7 mg With (η3-allyl)(N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloropalladium(II); sodium carbonate; lithium chloride In N,N-dimethyl-formamide at 80℃; for 16 h; Inert atmosphere; Sealed tube General procedure: Method A: A sealed tube equiped with a magnetic stirring bar was charged with the arylhalide (1) or (5) (1.0 equiv), sodium carbonate (2.0 equiv), anhydrous lithium chloride (2.0equiv) and (SIPr)Pd(allyl)Cl (0.05 equiv). Tricyclopropylbismuth (2a) (1.0 equiv), preparedas described above, was dissolved in anhydrous DMF (0.1 M) under argon and was addedinto the sealed tube. Carbon monoxide was bubbled in the reaction mixture for 45 seconds,then the tube was sealed and heated at 40 °C for 16 hours. The reaction mixture was cooledto room temperature, transferred in a separatory funnel containing 20 mL of an aq. sat.NaHCO3 solution and was extracted with EtOAc (3 x 20 mL). The combined organic layerswere washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated underreduced pressure. The residue was purified by flash column chromatography using theindicated solvent system to afford the desired aryl cyclopropyl ketone (3) or (6).Method B: Same as method A except that 1.5 equivalents of tricyclopropylbismuth 2ainstead of 1.0 equivalent and 0.1 equivalents of (SIPr)Pd(allyl)Cl instead of 0.05 equivalentswere used and that the reaction was heated at 80 C instead of 40 C.
Reference: [1] Synlett, 2017, vol. 28, # 20, p. 2833 - 2838
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4475 - 4477
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  • [ 25309-64-2 ]
YieldReaction ConditionsOperation in experiment
96% With triethylsilane; indium(III) bromide In chloroform at 60℃; for 1 h; Inert atmosphere General procedure: To a freshly distilled CHCl3 solution (0.6 mL) in a screw-capped vial under N2 atmosphere, InBr3 (10.6 mg, 0.0300 mmol), aromatic ketone 4 (0.6 mmol) and Et3SiH (383 μL, 2.40 mmol) was successively added. The resulting mixture was stirred at 60 °C (bath temperature) or room temperature, and monitored by TLC or GC analysis until consumption of the starting ketone. The reaction was quenched with H2O. The aqueous layer was extracted with CH2Cl2 (5 mL .x. 3), the organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by a silica gel column chromatography (hexane/AcOEt = 19/1) to give the corresponding alkylbenzene 5. 1-Cyano-4-[1-(triethylsiloxy)ethyl]benzene (5k): 85percent yield; colorless oil; 1H NMR (500 MHz, CDCl3) δ 0.54-0.62 (m, 6H), 0.90-0.93 (m, 9H), 1.41 (d, 3H, J = 6 Hz), 4.90 (q, 1H, J = 6 Hz), 7.45 (d, 2H, J = 8 Hz), 7.61 (d, 2H, J = 8 Hz); 13C NMR (125 MHz, CDCl3) δ 4.7, 6.7, 27.0, 69.9, 110.5, 119.0, 125.8, 132.0, 152.3; MS (ESI): m/z 284 (M++Na); HRMS (ESI): Calcd for C15H23NNaOSi: 284.1447, Found: 284.1407.
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  • [ 90086-41-2 ]
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  • [ 62-53-3 ]
  • [ 23600-83-1 ]
YieldReaction ConditionsOperation in experiment
76% With potassium hydroxide In dimethyl sulfoxide at 120℃; Inert atmosphere General procedure: A mixture of amine (2.0 mmol), aryl halides (1.0 mmol), catalyst (1.0 molpercent Pd), and DMSO (6 ml) was stirred for 16 h under nitrogen atmosphere at 120 ◦C. The progress of reaction was monitored by gas chromatography. After completion, the reaction mixture was cooled and filtered to remove the catalyst which could be used for further reaction. The filtrate obtained was purified by flash column chromatography on silica gel to afford the desired product, which was confirmed by GC–MS. All the prepared compounds are known and compared with authentic samples.
83 %Chromat. With C35H34N3OP2PdS(1+)*NO3(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 7 h; General procedure: In a typical run, an oven-dried 10 ml round bottom flask was charged with a known mole percent of catalyst, NaOtBu (1.3 mmol), amine (1.2 mmol) and aryl halide (1 mmol) with the appropriate solvent(s) (4 ml). The flask was placed in a preheated oil bath at required temp. After the specified time the flask was removed from the oil bath, water (20 ml) was added, and extraction with ether (4×10 ml) was done. The combined organic layers were washed with water (3×10 ml), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in acetonitrile and analyzed by GC–MS.
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YieldReaction ConditionsOperation in experiment
89% With sulfated tungstate In neat (no solvent) at 130℃; for 10 h; General procedure: In round bottom flask equipped with condenser a mixture of aryl alkyl ketones (3mmol) and sulfated tungstate (20 wt. percent) were stirred at 130 C, the progress of the reaction was monitored by TLC. After disapperance of the aryl alkyl ketones and the reaction was continued for additional time of 2 h. The reaction mixture was cooled, diluted with 30 mL of ethyl acetate and filtered to recover the catalyst. The filtrate was washed with 10 mL of water, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel ( 60-120) with (PE:EA=9:1) as eluent to get pure 1,3,5-arylenzenes.
72% With para-dodecylbenzenesulfonic acid In neat (no solvent) at 130℃; for 4 h; Green chemistry General procedure: A mixture of acetophenone (3 mmol) and DBSA (0.6 mmol) was heated at 130 °C in a preheated oil bath for 3–8 hours. After completion of the reaction as indicated by thin layer chromatography (TLC), the reaction mixture was cooled to room temperature and diluted with equal volumes of saturated solution of NaHCO3 and brine (5 mL + 5 mL). The resulting solution was extracted with ethyl acetate (10 mL × 3) and the organic layers were combined, dried over anhydrous Na2SO4 and evaporated under reduced pressure to dryness. The crude product obtained was purified by silica gel (60–120 mesh size) column chromatography using 1–2percent ethyl acetate in heptane as the eluent to afford the desired products in pure form.
60% With ethylenediamine; trifluoroacetic acid In nitromethane for 48 h; Reflux General procedure: To a solution of aryl methyl ketone (1, 1.5mmol) in dry nitromethane (1.5mL) was added trifluoroacetic acid (0.045 mL, 0.6mmol) and ethylenediamine (0.020 mL, 0.3mmol). The mixture was stirred at reflux and detected by TLC. After completion of the reaction, the reaction mixture was cooled to room temperature, quenched with saturated NH4Cl, extracted with Ethyl acetate. Combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give product 2.
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  • 17
  • [ 13329-40-3 ]
  • [ 149104-90-5 ]
Reference: [1] Synlett, 2001, # 2, p. 266 - 268
  • 18
  • [ 13329-40-3 ]
  • [ 68-12-2 ]
  • [ 1008119-09-2 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 13, p. 5489 - 5494
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