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[ CAS No. 585-74-0 ] {[proInfo.proName]}

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Chemical Structure| 585-74-0
Chemical Structure| 585-74-0
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Product Details of [ 585-74-0 ]

CAS No. :585-74-0 MDL No. :MFCD00008742
Formula : C9H10O Boiling Point : -
Linear Structure Formula :- InChI Key :FSPSELPMWGWDRY-UHFFFAOYSA-N
M.W : 134.18 Pubchem ID :11455
Synonyms :
Chemical Name :1-(m-Tolyl)ethanone

Calculated chemistry of [ 585-74-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.6
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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.529 mg/ml ; 0.00394 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 0.97 mg/ml ; 0.00723 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.09
Solubility : 0.11 mg/ml ; 0.000818 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 585-74-0 ]

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 [ 585-74-0 ]

* 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 [ 585-74-0 ]
  • Downstream synthetic route of [ 585-74-0 ]

[ 585-74-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 585-74-0 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
96% With Oxone; ammonium bromide In methanol for 0.666667 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.
80% With bromine In 1,4-dioxane; diethyl ether at 20℃; for 5 h; To a solution of 1-m-tolyl-ethanone (6.Og, 44.72mmol) in dioxane (5ml), bromine (7.14g, 44.72mmol) in dioxane (10ml) and ether (15ml) was added and stirred at room temperature for 5 hr. The reaction mixture was poured into ice water and the compound was extracted using ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and then evaporated to give crude 2- bromo- 1-m-tolyl-ethanone, 7.6g (80percent). The crude compound obtained was used in the next step without further purification.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8236 - 8247,12
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8236 - 8247
[4] Synthetic Communications, 2013, vol. 43, # 19, p. 2603 - 2614
[5] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 41
[6] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1170 - 1176
[7] Journal of Pharmaceutical Sciences, 1982, vol. 71, # 5, p. 556 - 561
[8] Chemical & Pharmaceutical Bulletin, 1995, vol. 43, # 9, p. 1497 - 1504
[9] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1291 - 1295
[10] Patent: WO2010/29119, 2010, A1, . Location in patent: Page/Page column 63
[11] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 954 - 971
[12] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 14 - 35
[13] MedChemComm, 2015, vol. 6, # 6, p. 1036 - 1042
[14] Chemical Biology and Drug Design, 2015, vol. 86, # 4, p. 849 - 856
[15] Chemical Communications, 2016, vol. 52, # 29, p. 5152 - 5155
[16] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 8, p. 1166 - 1173
[17] Organic Letters, 2017, vol. 19, # 11, p. 2877 - 2880
[18] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8134 - 8139
[19] Tetrahedron Letters, 2018, vol. 59, # 33, p. 3214 - 3219
[20] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
  • 2
  • [ 585-74-0 ]
  • [ 875815-03-5 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide; silica gel In methanol for 0.25 h; Reflux General procedure: The α-bromination reaction was carried out using acetophenone (1200 mg, 10 mmol), N-bromosuccinimide (2136 mg, 12 mmol), 10percent (w/w) silica gel (120mg) in 10 mL of methanol at reflux conditions until the disappearance of the substrate. (Note: 2136mg of N-bromosuccinimide was added portion wise i.e. 356 mg for each time in six portions). The progress of the reaction was monitored by TLC. The reaction mass was filtered after the completion of the reaction as per TLC and the catalyst was collected for reuse. The filtrate was concentrated under vacuum. Double distilled water was added to the reaction mixture and quenched with aqueous sodium thiosulfate and the product extracted with dichloromethane (Caution: Severe burning sensation of eyes was observed during the work-up process). The layers were separated and the organic layer was collected and washed thrice with distilled water (3×50mL). The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude product was purified by column chromatography over silica gel (60–120 mesh) using n-hexane–EtOAc (99:1 ratio). With the aim of studying the recycling of the catalyst, the isolated catalyst was washed with ethyl acetate (5mL) after its filtration from the reaction medium, collected and dried in vacuum at 70°C to a constant weight. Subsequently it was reused for the α-bromination of acetophenone and achieved 95percent, 86percent and 83percent yields of product (2a) for first, second and third reuse of catalyst respectively. All products gave spectroscopic data in agreement with the literature [15,21,27–30]. The method is also very practical for scale up in process development. We attempted large scale (100 gram scale) synthesis of 2-bromo-1-phenylethanone 2a and obtained fruitful results with isolated yields ranging from 93percent to 96percent.
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 179 - 182
  • 3
  • [ 105-58-8 ]
  • [ 585-74-0 ]
  • [ 33166-79-9 ]
YieldReaction ConditionsOperation in experiment
84% at 80℃; for 2 h; Sodium hydride (3.1g, 77.1mmol) and diethylcarbonate were added to 3- methyl acetophenone (4.5g, 33.54mmol). The reaction mixture was stirred for 2hrs with heating at 80°C. Once the reaction was completed, ice water and acetic acid were added thereto. The resulting mixture was washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgS04 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 5.8g of the titled compound (yield: 84 percent). @H-NMR (200MHz, CDC13) 8 7.83-7.63 (m, 2H) 7.42-7.28 (m, 2H) 4.27~4.18 (m, 2H) 3.97 (s, 2H) 2.40 (s, 3H) 1.36~1.23 (m, 3H)
84% at 80℃; for 2 h; Sodium hydride (3.1 g, 77.1 mmol) and diethyl carbonate were combined with 3-methylacetophenone (4.5 g, 33.54 mmol). The mixture was stirred for 2 hours at 80°C. After the reaction was completed, ice water and acetic acid were added thereto. Then, the mixture was extracted with ethyl acetate/saturated sodium chloride. The extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 3-oxo-3-m-tolylpropionate ethyl ester (5.8 g, yield 84 percent). 1H NMR (200MHz, CDCl3) : No. 7.83-7.63 (m, 2H), 7.42-7.28 (m, 2H), 4.27-4.18 (m, 2H), 3.97 (s, 2H), 2.40 (s, 3H), 1.36-1.23 (m, 3H).
46.9%
Stage #1: With sodium hydride In toluene for 0.5 h; Heating / reflux
Stage #2: With acetic acid In toluene at 20℃;
Example 10; Ethyl 3-methyl-benzoyl-acetate (1 -10-a); To a vigorously stirred suspension of NaH (564 mg, 48.5 mmol) and CO(OEt)2 (5.73 g, 48.5 mmol) in anhydrous toluene (50ml) was added dropwise a solution of 3-methylacetophenone (4.33 g, 32.3 mmole) in toluene under reflux. The mixture was allowed to reflux and was stirred for 30 min after the addition was complete. When cooled to room temperature, the mixture was acidified with glacial AcOH. After ice-cold water was added, the mixture was extracted with toluene. The organic layer was dried over MgSO4, and evaporated. The residue was further chromatographed over silica gel by elution with CH2CI2-/i-haxane (3:2) to afford l-10-b as light-yellow liquid (3.13g, 46.9percent) <n="35"/>1H-NMR (DMSO-t/6, 200 MHz): δ 7.68-7.72 (2H, m, H-4, H-6) , 7.32-7.36 (2H, m, H-2, H-3) , 4.16 (2H, q, J = 7, CH2CH3) , 3.94 (2H, s, H-10) , 2.38 (3H, s, CH3), 1.2 (3H, t, J = 7,CH2CHa) MS (m/z) 206 (El+) Anal, calcd for C12H14O3: C, 69.88; H, 6.84; Found: C, 69.72; H, 6.95.
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 6, p. 1910 - 1915
[2] Patent: WO2005/100297, 2005, A1, . Location in patent: Page/Page column 28-29
[3] Patent: WO2005/100303, 2005, A1, . Location in patent: Page/Page column 56
[4] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 7, p. 2590 - 2594
[5] Angewandte Chemie - International Edition, 2012, vol. 51, # 34, p. 8661 - 8664
[6] Patent: WO2008/70176, 2008, A1, . Location in patent: Page/Page column 32-33
[7] Journal of Medicinal Chemistry, 1997, vol. 40, # 19, p. 3049 - 3056
[8] European Journal of Organic Chemistry, 2015, vol. 2015, # 17, p. 3656 - 3660
[9] Organic and Biomolecular Chemistry, 2018, vol. 16, # 25, p. 4683 - 4687
  • 4
  • [ 585-74-0 ]
  • [ 1450-72-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 52, p. 13075 - 13079[2] Angew. Chem., 2012, vol. 124, # 52, p. 13252 - 13256,5
  • 5
  • [ 383-63-1 ]
  • [ 585-74-0 ]
  • [ 53764-99-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 5, p. 1531 - 1535
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 9, p. 1347 - 1365
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 499 - 504
[4] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3406 - 3413
  • 6
  • [ 585-74-0 ]
  • [ 766-82-5 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1981, # 9, p. 3216 - 3245
  • 7
  • [ 585-74-0 ]
  • [ 70138-19-1 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With titanium(IV) isopropylate; ammonia In ethanol at 20℃; for 24 h; Inert atmosphere
Stage #2: With sodium tetrahydroborate In ethanol for 24 h;
General procedure: A mixture of 1-(4-(trifluoromethyl)phenyl)ethanone (400 mg, 2.13 mmol), Ti(O-i-Pr)4 (1.25 mL, .similar.4.25 mmol) and ammonia in EtOH (2 M, 5.30 mL, .similar.10.6 mmol) was stirred under argon at room temperature for 24 h NaBH4 (120 mg, 3.19 mmol) was then added, and the resulting mixture was stirred for another 24 h. The pH of the reaction mixture was adjusted to pH 2 using HCl (6 M), and washed with tert-butyl methyl ether (TBME) (3 .x. 20 mL). Using NaOH (pellets) the pH was adjusted to ca 10, and the mixture was extracted with TBME (6 .x. 30 mL). The combined organic phase was dried over MgSO4, and the solvent was removed under reduced pressure to give 210 mg (1.11 mmol, 52percent) of a yellow oil.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 6002 - 6014
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 3, p. 358 - 363
[3] Chirality, 2018, vol. 30, # 7, p. 900 - 906
[4] Bulletin des Societes Chimiques Belges, 1963, vol. 72, p. 202 - 207
[5] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 441 - 446
[6] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 1996, # 12, p. 2615 - 2622
[7] Tetrahedron Asymmetry, 2006, vol. 17, # 6, p. 967 - 974
[8] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 7, p. 1339 - 1347
  • 8
  • [ 77287-34-4 ]
  • [ 585-74-0 ]
  • [ 70138-19-1 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1808,1810[2] Organic Syntheses, 1943, vol. Coll. Vol. II, p. 503,505