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[ CAS No. 134-84-9 ] {[proInfo.proName]}

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Chemical Structure| 134-84-9
Chemical Structure| 134-84-9
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Product Details of [ 134-84-9 ]

CAS No. :134-84-9 MDL No. :MFCD00008553
Formula : C14H12O Boiling Point : -
Linear Structure Formula :CO(C6H5)(CH3C6H4) InChI Key :WXPWZZHELZEVPO-UHFFFAOYSA-N
M.W : 196.24 Pubchem ID :8652
Synonyms :

Calculated chemistry of [ 134-84-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.28
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 3.54
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 3.26
Log Po/w (SILICOS-IT) : 3.91
Consensus Log Po/w : 3.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.75
Solubility : 0.0351 mg/ml ; 0.000179 mol/l
Class : Soluble
Log S (Ali) : -3.58
Solubility : 0.0512 mg/ml ; 0.000261 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.25
Solubility : 0.00109 mg/ml ; 0.00000557 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.28

Safety of [ 134-84-9 ]

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 [ 134-84-9 ]

* 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 [ 134-84-9 ]
  • Downstream synthetic route of [ 134-84-9 ]

[ 134-84-9 ] Synthesis Path-Upstream   1~7

  • 1
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YieldReaction ConditionsOperation in experiment
72% With N-Bromosuccinimide In chloroform for 18 h; Reflux; 100W bulb shining A stirred mixture of 4-methyl benzophenone (1) (15.0 g, 76 mmol) and N-bromo succinimide (14.2 g, 80 mmoll) in chloroform (100 ml) was heated to reflux for 18 h. with a 100W bulb shining 2 cm from the flask. The reaction mixture was cooled, washed with water and concentrated in vacuo. The resulting solid was washed with diethyl ether to leave 2 (15.1 g, 72percent) as a white solid; δH (CDCl3) 4.55 (2H, s, CH2Br), 7.46-7.84 (9H, m, Ar-H).
71.5% With N-Bromosuccinimide In chloroform for 18 h; Heating / reflux; UV-irradiation A stirred mixture of 4-methylbenzophenone (15.02 g, 76.6 mmol) and N-bromosuccinimide (14.2 g, 79.8 mmol) in CHCl3 (100 cm3) was heated under gentle reflux for 18 h with a 100W bulb shining 2 cm from the flask. The reaction mixture was washed with water, dried (MgSO4) and solvent was removed in vacuo). The resulting solid was then washed with Et2O to remove any starting material to leave the product as a white solid (15.07 g, 71.5percent, mp 110-112° C.(lit. 110-111°); δH (200 MHz; CDCl3) 4.55 (2 H, s, CH2Br), 7 .46-7.70 (5 H, m, ArH), 7.80-7.90 (4 H, m, ArH o- to CO); m/z 277 ([M81Br+H]+, 25percent) and 275 ([M79Br+H]-, 25percent), 197 (100percent)
64% With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethaneReflux A solution of phenyl(p-tolyl)methanone (5.0 g, 25.5 mmol), 1-bromopyrrolidine-2,5-dione (4.99 g, 28.0 mmol), and (E)-2,2'-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (0.209 g, 1.27 mmol) in CCl4 (80.0 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was washed with water (3 x 50) mL, dried and concentrated under vacuum. The residue was applied to a silica gel column and eluted with ethyl acetate/hexane, 1:20 to give (4-(bromomethyl)phenyl)(phenyl)methanone (4.5 g, 16 mmol, 64percent yield) as a white solid. LCMS m/z = 275.0 [M+H]+.
60% With bromine In benzene90 watt (90 joule/sec) halogen spotlight; Heating / reflux 4-Methylbenzophenone (750 g; 3.82 moles) was added to a 5 liter Morton flask equipped with an overhead stirrer and dissolved in 2850 mL of benzene. The solution was then heated to reflux, followed by the dropwise addition of 610 g (3.82 moles) of bromine in 330 mL of benzene. The addition rate was approximately 1.5 mL/min and the flask was illuminated with a 90 watt (90 joule/sec) halogen spotlight to initiate the reaction. A timer was used with the lamp to provide a 10percent <n="45"/>duty cycle (on 5 seconds, off 40 seconds), followed in one hour by a 20percent duty cycle (on 10 seconds, off 40 seconds). At the end of the addition, the product was analyzed by gas chromatography and was found to contain 71percent of the desired 4- bromomethylbenzophenone, 8percent of the dibromo product, and 20percent unreacted 4- methylbenzophenone. After cooling, the reaction mixture was washed with 1O g of sodium bisulfite in 100 mL of water, followed by washing with 3X 200 mL of water. The product was dried over sodium sulfate and recrystallized twice from 1 :3 toluene:hexane. After drying under vacuum, 635 g of 4-bromomethylbenzophenone was isolated, providing a yield of 60percent, having a melting point of 1 120C - 1 140C. Nuclear magnetic resonance ("NMR") analysis (1H NMR (CDCl3)) was consistent with the desired product: aromatic protons 7.20-7.80 (m, 9H) and methylene protons 4.48 (s, 2H). All chemical shift values are in ppm downfield from a tetramethylsilane internal standard.
60% With bromine In benzeneHeating / reflux; illuminated with a 90 watt (90 joule/sec) halogen spotlight 4-Methylbenzophenone (750 g; 3.82 moles) was added to a 5 liter Morton flask equipped with an overhead stirrer and dissolved in 2850 mL of benzene. The solution was then heated to reflux, followed by the dropwise addition of 610 g (3.82 moles) of bromine in 330 mL of benzene. The addition rate was approximately 1.5 mL/min and the flask was illuminated with a 90 watt (90 joule/sec) halogen spotlight to initiate the reaction. A timer was used with the lamp to provide a 10percent duty cycle (on 5 seconds, off 40 seconds), followed in one hour by a 20percent duty cycle (on 10 seconds, off 40 seconds). At the end of the addition, the product was analyzed by gas chromatography and was found to contain 71percent of the desired 4-bromomethylbenzophenone, 8percent of the dibromo product, and 20percent unreacted 4-methylbenzophenone. After cooling, the reaction mixture was washed with 10 g of sodium bisulfite in 100 mL of water, followed by washing with 3.x.200 mL of water. The product was dried over sodium sulfate and recrystallized twice from 1:3 toluene:hexane. After drying under vacuum, 635 g of 4-bromomethylbenzophenone was isolated, providing a yield of 60percent, having a melting point of 112° C.-114° C. Nuclear magnetic resonance ("NMR") analysis (1H NMR (CDCl3)) was consistent with the desired product: aromatic protons 7.20-7.80 (m, 9 H) and methylene protons 4.48 (s, 2 H). All chemical shift values are in ppm downfield from a tetramethylsilane internal standard.
59% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 24 h; Reflux 4-Methylbenzophenone 10.0 g (0.05 mol) and azodiisobutyronitrile(AIBN, 0.075 g) was added to 150 ml CCl4 in a roundbottom flask with a condenser and a magnetic stirrer, and then N-bromosuccinimide(NBS, 9.0 g, 0.05 mol) was added. The mixturewas keep refluxing for 24 h, then was cooled to room temperature,the solvent was evaporated under vacuum in the end. The productwas further purified through recrystallization from benzene andcyclohexane to yield white solid (yield, ~59percent, m.p., 103.0-105.0 °C).1H NMR (500 MHz, CDCl3) δ (ppm): 4.456 (s, -CH2, 2H), 7.18-7.20(d, Ar-H, 2H), 7.532-7.534 (d, Ar-H, 2H), 7.425-7.434 (d, Ar-H,2H), 7.505-7.519 (t, Ar-H, 1H), 7.711-7.725 (d, Ar-H, 2H). 13C NMR(125 MHz, CDCl3) δ (ppm): 38.323, 124.652, 126.863, 129.832,130.083, 133.843, 135.083, 135.326, 139.093, 187.083. Elementaryanalysis, Anal. Calcd for C14H11BrO: C, 61.12; H, 4.03. Found: C,61.02; H, 3.97.

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YieldReaction ConditionsOperation in experiment
82% With N-Bromosuccinimide In tetrachloromethane Step A
Preparation of 4-bromomethylbenzophenone
1 To a solution of 4-methylbenzophenone (3.0 g, 15.3 mmol) in 60 ml CCl4 was added N-bromosuccinimide (3.0 g, 1.1 eq) and AlBN (30 mg).
The solution was refluxed for 4.5 h, then cooled to room temperature.
The succinimide were removed by filtration, and the filtrate was concentrated to dryness.
Recrystallization required large amounts of solvent and chromatography appeared a better alternative.
The residue was chromatographed on silica gel eluding with 5percent Ethyl Acetate/Hexane (3.44 g; 82percent yield).
1 NMR (300 MHz, CDCl3, ppm): δ4.55 (s, 2H); 7.5 (m, 4H, 7.6 (m, 1H); 7.8 (m, 4H).
Reference: [1] Patent: US5183810, 1993, A,
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YieldReaction ConditionsOperation in experiment
60% With bromine In benzene for 1 h; Heating / reflux; UV-irradiation EXAMPLE 3
Preparation of 4-bromomethylbenzophenone (BMBP)
4-Methylbenzophenone (750 g; 3.82 moles) was added to a 5 liter Morton flask equipped with an overhead stirrer and dissolved in 2850 mL of benzene.
The solution was then heated to reflux, followed by the dropwise addition of 610 g (3.82 moles) of bromine in 330 mL of benzene.
The addition rate was approximately 1.5 mL/min and the flask was illuminated with a 90 watt (90 joule/sec) halogen spotlight to initiate the reaction.
A timer was used with the lamp to provide a 10percent duty cycle (on 5 seconds, off 40 seconds), followed in one hour by a 20percent duty cycle (on 10 seconds, off 40 seconds).
At the end of the addition, the product was analyzed by gas chromatography and was found to contain 71percent of the desired 4-bromomethylbenzophenone, 8percent of the dibromo product, and 20percent unreacted 4-methylbenzophenone.
After cooling, the reaction mixture was washed with 10 g of sodium bisulfite in 100 mL of water, followed by washing with 3*200 mL of water.
The product was dried over sodium sulfate and recrystallized twice from 1:3 toluene:hexane.
After drying under vacuum, 635 g of 4-bromomethylbenzophenone was isolated, providing a yield of 60percent, having a melting point of 112° C.-114° C.
Nuclear magnetic resonance ("NMR") analysis (1H NMR (CDCl3)) was consistent with the desired product: aromatic protons 7.20-7.80 (m, 9H) and methylene protons 4.48 (s, 2H).
All chemical shift values are in ppm downfield from a tetramethylsilane internal standard.
Reference: [1] Patent: US2008/154241, 2008, A1, . Location in patent: Page/Page column 17
[2] Chemistry - A European Journal, 2014, vol. 20, # 40, p. 12750 - 12753
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YieldReaction ConditionsOperation in experiment
69% With bromine In benzene Example 8
Synthesis of 1,3-diethyl 2-[(4-benzoylphenyl)methyl]propanedioate
4-methylbenzophenone (10.0 g; 51.0 mmol) was dissolved in benzene (60 mL) and the solution was warmed to reflux.
Solution of bromine (8.39 g; 52.5 mmol) in benzene (15 mL) was added to the reaction mixture over 10 h.
The reaction was refluxed for a further 6 h until a light orange solution in obtained and all bromine is consumed.
The benzene solvent was evaporated and crude product was obtained as an off-white solid.
Recrystallisation from methanol (130 mL) provided 4-(bromomethyl)benzophenone (14.5 g; 69percent yield) as a white crystalline solid.
1H NMR (400 MHz, CDCl3): 7.80-7.76 (m, 4H), 7.59 (tt, J=7.4, 1.3 Hz, 1H), 7.51-7.46 (m, 4H), 4.52 (s, 2H).
Reference: [1] Patent: US2015/148441, 2015, A1, . Location in patent: Page/Page column
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YieldReaction ConditionsOperation in experiment
55% With N-Bromosuccinimide; water In chloroform for 3 h; Reflux General procedure: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl3 (4.0 mL). After refluxing for 3 h in the air, the reaction mixture was quenched withNa2S2O3·5H2O, cooled to roomtemperature, washed with 5mL CH2Cl2, dried with MgSO4,and filtered to get clear organic solution. The solvent was removed reduced pressure by a rotary evaporator, and the resulting residue was subjected to column chromatography on silica gel using co-solvent(ethyl acetate / petroleum ether, v/v) as eluent to give the corresponding diaryllketones.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 32, p. 4458 - 4462
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Reference: [1] Patent: US6166219, 2000, A,
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Reference: [1] Tetrahedron, 2007, vol. 63, # 20, p. 4284 - 4289