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[ CAS No. 403-29-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 403-29-2
Chemical Structure| 403-29-2
Chemical Structure| 403-29-2
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Product Details of [ 403-29-2 ]

CAS No. :403-29-2 MDL No. :MFCD00040830
Formula : C8H6BrFO Boiling Point : -
Linear Structure Formula :- InChI Key :ZJFWCELATJMDNO-UHFFFAOYSA-N
M.W : 217.04 Pubchem ID :96749
Synonyms :
Chemical Name :2-Bromo-1-(4-fluorophenyl)ethanone

Calculated chemistry of [ 403-29-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.46
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) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.29
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.9
Solubility : 0.273 mg/ml ; 0.00126 mol/l
Class : Soluble
Log S (Ali) : -2.29
Solubility : 1.12 mg/ml ; 0.00518 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.89
Solubility : 0.028 mg/ml ; 0.000129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 403-29-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 403-29-2 ]

* 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 [ 403-29-2 ]
  • Downstream synthetic route of [ 403-29-2 ]

[ 403-29-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 403-42-9 ]
  • [ 403-29-2 ]
YieldReaction ConditionsOperation in experiment
97% With Oxone; ammonium bromide In methanol for 1.3 h; Reflux General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.
94.8% With bromine In cyclohexane at 0 - 40℃; for 0.5 h; 25 g of compound 1 (p-fluoroacetophenone) (0.18 mol) was dissolved in 50 mL of cyclohexane, and 2-3 drops of bromine were added dropwise, and the temperature was raised to 40 ° C.After the color of bromine was found to fade, the temperature was lowered to 0 ° C.29 g of liquid bromine (0.18 mol) was added dropwise, and the reaction was carried out for 0.5 hour.When GC was detected without Compound 1, it was washed successively with saturated aqueous sodium carbonate solution, 5percent by mass of sodium chloride solution and water.Dispensing, drying,The toluene was distilled off under reduced pressure to give 39 g of Compound 2,The purity was 95.0percent, and the yield was 94.8percent.
90% With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrileReflux; Inert atmosphere; Schlenk technique General procedure: N-bromosuccinimide (0.37 mmol) was added to the stirredsolution of acetophenone (2) (0.37 mol, 1 equiv) in acetonitrile(40 mL). The resulting reaction mixture was stirredfor 10–15 min. After that p-TsOH (0.74 mmol, 2 equiv) wasadded to the reaction mixture and refluxed for 4–5 h andmonitored by TLC. After completion of reaction, reactioncontent was brought to room temperature and washed withsaturated solution of sodium bicarbonate and extracted withethyl acetate (3 × 20 mL), organic layer was dried oversodium sulphate and concentrated under reduced pressure.The obtained residues were purified by column chromatographyusing silica 100–200 mesh size by ethyl acetate:hexane (4:96) mixture and pure compound was identified as2-bromo-1-phenyl-ethanone 3a–g.
90.8% With bromine In acetonitrile 10 g (72.4 mmol) of p-fluoroacetophenone was dissolved in 100 mL of acetonitrile, and 11.57 g (72.4 mmol)Br2 in acetonitrile, stirred overnight (8-10h). After the reaction was complete, the solvent was removed by steam under reduced pressure, the ethyl acetate was re-dissolved, washed with brineWashed three times, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by steaming under reduced pressure. The solvent was filtered through 50 mL of cyclohexane and a few drops of ether to obtainTo 14.2 g of white crystals, yield: 90.8percent.
89.2% With bromine In acetonitrile at 20℃; 20 g (144.7 mmol) of p-fluoroacetophenone was dissolved in 200 mL of acetonitrile, and 23.12 g (144.7 mmol)Br2 in 50 mL of acetonitrile was stirred at room temperature overnight. After completion of the reaction, the reaction solution was concentrated and concentrated with ethyl acetateWashed with brine three times, dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure. The resulting white oil was evaporated at low temperatureCuring, with 100mL n-hexane plus 1mL ethyl acetate beating, filter white solid 28g, the yield: 89.2percent,
87% at 70℃; for 3.5 h; Green chemistry The representative example of oxidative bromination is described as follows: A mixture of 1.2 g acetophenone 1a (10 mmol) and 0.121 g Cu(NO3)2•3H2O (0.5mmol) was stirred and an oxygen balloon (about 0.5–1 L) was attached to the reaction system. Then 8mol/L aqueous solution of hydrobromic acid (1.5mL, 12mmol) was added dropwise to the mixture. The reaction mixture was then stirred at 70°C and monitored by TLC or GC. After the completion of the reaction, the mixture was extracted with CH2Cl2. The organic extract was first washed with 5percent sodium sulfite, saturated sodium bicarbonate solution, and then water and finally dried over anhydrous magnesium sulfate. The solvent was removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/dichloromethane 3:1) to afford the product, α-bromoacetophenone (2a) in 1.81 g, yield: 91percent.
85% Microwave irradiation General procedure: Acetophenone (0.55 mmol) and 100 mL glacial acetic acid taken in beaker. Similarly, bromine (0.125 mmol) and 100 mL glacial acetic acid taken in another beaker and it added drop by drop in the solution of acetophenone and glacial acetic acid with occasionally shaking. Reaction mixture was transferred in an Erlenmeyer flask and irradiated under microwave irradiation for 15 min with a time interval of 35 s, after the completion of reaction indicated by TLC, poured in ice water, isolated the solid and recrystallized from ethanol (Scheme-I). Physico-chemical data of the synthesized compounds are given in Table-1.
85% With hydrogen bromide; potassium iodide; sodium nitrite In water at 0 - 20℃; for 10 h; General procedure: In a RBF cooled in ice bath at 0 C, HBr(12 mmol, in 2 ml of water) was taken. To this a solution of NaNO2(5 mmol, in 5ml of water) was added drop wise. The reaction was stirred for 15min maintaining the temperature at 0 °C and KI (5 mol percent) was added. After 10 min ketone(10 mmol) was added at once. After 15 min reaction temperature was brought to room temperature slowly. Reaction was monitored by TLC (ethyl acetate: pet ether, 1:9). After completion of reaction 50 ml of CHCl3 was added and organic layer separated. Aqueous layer was extracted with 25 ml of CHCl3 and combined organic layer was washed with 10percent NaHSO3 solution (2 x 20 ml) and 10percent NaHCO3 solution (2 x 20 ml).The organic layer was dried over sodium sulphate and concentrated under reduced pressure. Pure product was obtained after column chromatography (silica gel, 60-120, eluentethyl acetate: pet ether).
79% With bromine In diethyl ether Preparation Example 1
Preparation of 2-Bromo-4'-Fluoro-acetophenone
In 25 ml of diethyl ether was dissolved 5.00 g (36.2 mmol) of p-fluoroacetophenone and while stirring the solution on an ice bath, 5.8 g (36.2 mmol) of bromine was dropped.
After dropping, the mixture was stirred for 5 minutes and then the solvent was distilled off under reduced pressure.
The residue thus obtained was purified by silica gel column chromatography (chloroform 100percent).
The results of NMR measurement revealed that it contained the target compound, and in addition, the raw materials and a dibromo form as a side product.
Yield after adjustment was 6.21 g and percent yield was 79.0percent.
1H-NMR (CDCl3, ppm) 4.42 (s, 2 H), 7.12~8.18 (m, 4 H)
73% With N-Bromosuccinimide In ethyl acetate at 40℃; 10 mmol 4-fluoroacetophenone is added to a 100 mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS),Dissolve 35mL of ethyl acetate and 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 green crystals in 73percent yield.
69% With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 80℃; General procedure: A modified reaction route: NBS (1.2 equiv.) was added to a solution of appropriately substitutedacetophenones 9a–9l (1.0 equiv.) in CH3CN (15 mL) with p-TSA (0.2 equiv.). The solution washeated at 80 °C for 3-5 h until all the starting materials had been consumed (TLC monitored). Thereaction mass was poured in ice-cold water and extracted with DCM (3 × 20 mL). Anhydrous Na2SO4was added to the combined organic layer, filtered and the excess solvent was removed under reducedpressure. The resultant solid/ liquid obtained were washed with hexane to yield compounds 10a–10i.4,5 2-Bromo-1-(4-fluorophenyl)ethan-1-one (10a): Light brown solid, yield 69percent. M. p. 47-49 (°C).
44.56% at 15 - 50℃; for 12.3333 h; 1-(4-Fluorophenyl)ethanone (9.00 g, 65.15 mmol, 1.00 eq) was dissolved in acetic acid (100.00 mL), liquid bromine (10.41 g, 65.15 mmol, 1.00 eq) was added at 15 °C and the mixture was stirred for 20 minutes.
The resulting mixture was then stirred at 50 °C for 12 hours, concentrated under reduced pressure, and the pH of the mixture was adjusted to 9 with a sodium carbonate solution.
The mixture was extracted with ethyl acetate (200 mL * 2).
The combined organic layers were concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100 to 200 mesh silica gel, petroleum ether / ethyl acetate = 1/0) to deliver 2-bromo-1-(4-fluorophenyl)ethanone (6.30 g, 29.03 mmol, 44.56percent yield) as a white solid. LCMS (ESI) m / z: 218.8 (M + 1).
14 g With bromine In methanol at 0 - 20℃; for 2.5 h; Step 1 : Synthesis of 2-bromo-l -(4-fluorophenyl) ethan-l-one: [0234] To the stirred solution of 4-Fluoroacetophenone (10 g, 71.9 mmol) in 200 mL of MeOH at 0°C was added Bromine (3.7 mL, 23.1 mmol) (dropwise addition) and stirred for about 30 minutes and stirred for about 2 hours at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated and the crude product was dissolved in n-hexane and stirred for about 30 minutes. The obtained solid was filtered and washed with n-hexane then dried and proceeded for next step (wt: 14.0 g).

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  • 2
  • [ 95895-33-3 ]
  • [ 403-29-2 ]
YieldReaction ConditionsOperation in experiment
93% With tetrafluoroboric acid; water In 2,2,2-trifluoroethanol at 80℃; for 2 h; General procedure: A mixture of haloalkyne (0.2 mmol), tetrafluoroboric acid (20 molpercent, 40percent  aqueous solution ) in 2,2,2-trifluoroethanol (1 mL) was stirred at 80°C for 2 or 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.
87% at 40℃; for 6 h; Green chemistry General procedure: A mixture of haloalkyne (0.5 mmol), AgF (5molpercent) and water (1 equiv.) in TFA (1 mL) was stirred at 40°C for 6h, after which TFA was distilled out for reuse. The residue was separated by column chromatography to give the pure sample.
86% With indium(III) triflate; water In acetic acid at 100℃; Sealed tube General procedure: The reaction mixture of In(OTf)3 (16.8mg, 0.03mmol), 1-haloalkynes (0.3mmol), H2O (0.9mmol), HOAc (0.6mL), in a 5mL sealed tube was stirred at 100°C and monitored periodically by TLC. Upon completion, HOAc was removed under reduced pressure using an aspirator, and then the residue was purified by flash chromatography (PE/EA) on silica gel to afford corresponding carbonyl compounds 2a–2ad.
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[5] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 116 - 121
[6] Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1251 - 1254
  • 3
  • [ 405-99-2 ]
  • [ 403-29-2 ]
YieldReaction ConditionsOperation in experiment
81% With dibromamine-T; sodium thiosulfate In water; acetone at 20℃; for 2 h; General procedure: To a solution of olefin (1mmol) in acetone (3mL) and water (0.1mL), TsNBr2 (2.2mmol) was added at room temperature. After completion of reaction, sodium thiosulfate (200mg approx.) was added and the reaction mixture was stirred for another 10min. The reaction mixture was extracted with ethyl acetate, dried (Na2SO4) and concentrated. Purification of the crude product by flash chromatography on silica gel (230–400 mesh) with petroleum ether–EtOAc as eluent gave the pure product.
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[6] Tetrahedron, 2018, vol. 74, # 27, p. 3602 - 3607
  • 4
  • [ 766-98-3 ]
  • [ 403-29-2 ]
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[2] Green Chemistry, 2017, vol. 19, # 8, p. 1983 - 1989
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[4] Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158
  • 5
  • [ 7542-64-5 ]
  • [ 403-29-2 ]
YieldReaction ConditionsOperation in experiment
171 mg With water; sodium sulfite In ethyl acetate; acetone at 20℃; General procedure: To a stirred solution of alkyne (1 mmol) in ethyl acetate(1 mL), 0.1 mL of acetone:water (1:1) and TsNBr2 (2 mmol) wasadded. After 10 min Na2SO3 (8 mmol) was added and the reaction was stirred at room temperature till completion asmonitored by TLC. The organic layer was extracted with ethylacetate, washed with water, dried with Na2SO4 and concentrated.The crude product was purified by flash chromatographyon silica gel (230-400 mesh) using petroleum ethereethyl acetateas eluent.
Reference: [1] Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158
  • 6
  • [ 403-41-8 ]
  • [ 403-29-2 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 10, p. 3710 - 3714
  • 7
  • [ 403-42-9 ]
  • [ 7542-64-5 ]
  • [ 403-29-2 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 3, p. 291 - 293
  • 8
  • [ 22118-09-8 ]
  • [ 462-06-6 ]
  • [ 403-29-2 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 30, p. 4187 - 4196
  • 9
  • [ 350-35-6 ]
  • [ 403-29-2 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8206 - 8218
  • 10
  • [ 151-50-8 ]
  • [ 403-29-2 ]
  • [ 4640-67-9 ]
YieldReaction ConditionsOperation in experiment
6%
Stage #1: at 20℃; for 2 h;
Stage #2: With hydrogenchloride In ethanol; water
To a stirred suspension of 2.5 g (11.5 mmol) 2-bromo-l-(4-fiuoro-phenyl) -ethanone in 40 ml ethanol was added a solution of 0.90 g (23 mmol) potassium cyanide in 9 ml water. The mixture was then stirred at RT for 2 h, then acidified to ph=5-6 with aqueous HCl IM and then extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane / ethyl acetate 6:1) afforded 0.11 g (6 percent) 3-(4-fluoro-phenyl)-3-oxo-propionitrile as a yellow solid.
Reference: [1] Patent: WO2006/63732, 2006, A1, . Location in patent: Page/Page column 30
[2] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 17, p. 1953 - 1957
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  • [ 4640-67-9 ]
Reference: [1] Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 1, p. 33 - 36
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  • [ 143-33-9 ]
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  • [ 4640-67-9 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 20, p. 4429 - 4431
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  • [ 456-00-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With hexamethylenetetramine In chloroform at 20℃; for 16 h;
Stage #2: With hydrogenchloride In methanol; water for 4 h; Reflux
Intermediate 5A was synthesized according to the procedure described in PCT Publication No. WO 2009/137081 (PCT US2009/002845). To a solution of 2-bromo-l- (4-fluorophenyl)ethanone (6.57 g, 30.3 mmol) in CHC13 (65.5 mL) was added hexamethylenetetramine (4.37 g, 30.8 mmol). The reaction mixture was stirred at rt for 16 h and then filtered off. The white solid thus collected was suspended in MeOH (130 mL) and to it was added cone. HC1 (-8.6 mL). This homogenous reaction mixture was refluxed for 4 h. Upon cooling, the inorganics were filtered off and the filter cake was washed with MeOH (-30 mL). The combined filtrate was concentrated under reduced pressure to afford a solid that was dried on high vac for 2 h. It was then purified by silica gel chromatography (Thomson BIOTAGE® column, eluting with a gradient of 5percent to 20percent solution of MeOH in CH2C12) to provide the desired product as a red solid. This solid was suspended in min. amount of CH2C12 and filtered off to provide Intermediate 5A as a colorless solid (5.44 g, 95percent yield). HPLC Ret. Time: 0.90 min. (Method D). MS(ES): m/z= 136.05 [M+H]+.
76%
Stage #1: With hexamethylenetetramine In chloroform at 20℃; for 16 h;
Stage #2: With hydrogenchloride In ethanol; water at 20℃; for 12 h;
Preparation 45
2-amino-1-(4-fluorophenyl)ethan-1-one hydrochloride
2-Bromo-4'-fluoroacetophenone (1.5 g, 6.9 mmol) was added to a solution of HMTA (1.06 g, 7.59 mmol) in CHCl3 (25 mL).
The mixture was stirred at RT for 16 hrs.
The precipitate was filtered and the cake was suspended in EtOH (30 mL) and diluted with 37percent HCl (4.2 mL), then stirred at RT for 12 hrs.
The precipitate was filtered, the filtrate was concentrated in vacuum to provide an off-white solid that was triturated with isopropanol to afford 2-amino-1-(4-fluorophenyl)ethan-1-one hydrochloride (p45, 1 g, y=76percent) as white solid that was used as such in the next step. MS (m/z): 154.2 [MH]+.
Reference: [1] Patent: WO2014/100533, 2014, A1, . Location in patent: Page/Page column 72; 73
[2] Patent: US2018/297990, 2018, A1, . Location in patent: Paragraph 0244
[3] Journal of Medicinal Chemistry, 1982, vol. 25, # 9, p. 1045 - 1050
[4] Synlett, 2004, # 11, p. 2031 - 2033
[5] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 8, p. 628 - 635
[6] Patent: WO2016/40078, 2016, A1, . Location in patent: Page/Page column 6
[7] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 849 - 853
[8] Patent: WO2018/11746, 2018, A1, . Location in patent: Page/Page column 38
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Reference: [1] Tetrahedron Asymmetry, 2016, vol. 27, # 2-3, p. 91 - 100
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