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[ CAS No. 20099-89-2 ] {[proInfo.proName]}

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Chemical Structure| 20099-89-2
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Product Details of [ 20099-89-2 ]

CAS No. :20099-89-2 MDL No. :MFCD00052931
Formula : C9H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 224.05 Pubchem ID :-
Synonyms :
Chemical Name :4-(2-Bromoacetyl)benzonitrile

Calculated chemistry of [ 20099-89-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.22
TPSA : 40.86 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) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 2.01
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 1.53
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.414 mg/ml ; 0.00185 mol/l
Class : Soluble
Log S (Ali) : -2.5
Solubility : 0.717 mg/ml ; 0.0032 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.7
Solubility : 0.0451 mg/ml ; 0.000201 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 20099-89-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 20099-89-2 ]

* 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 [ 20099-89-2 ]
  • Downstream synthetic route of [ 20099-89-2 ]

[ 20099-89-2 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 1443-80-7 ]
  • [ 20099-89-2 ]
YieldReaction ConditionsOperation in experiment
61% With N-Bromosuccinimide In ethyl acetate at 40℃; In a 100 mL round bottom flask, 10 mmol of 4-cyanoacetophenone 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,The filtrate was spin-dried and separated by column chromatography (eluent: petroleum ether/ethyl acetate) to give a white solid with a yield of 61percent.
61% With N-Bromosuccinimide In ethyl acetate at 40℃; In a 100 mL round bottom flask, 10 mmol of 4-cyanoacetophenone 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) afforded a white solid in 61percent yield.
38% With Oxone; ammonium bromide In methanol at 20℃; for 48 h; 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.
29% With hydrogen bromide; bromine In chloroform j)
Preparation of 2-Bromo-4'-cyanoacetophenone
To a mixture of para-cyanoacetophenone (52 g, 0.36 mol) in chloroform (520 ml) and 48percent HBr (5.2 ml), a solution of bromine (19.3 ml) in chloroform (52 ml) was added dropwise over a period of 20 min.
The mixture was stirred for 3 h at room temperature and neutralized to pH7 with sat. NaHCO3.
The organic layer was washed with sat.
NaCl and dried over anhydrous Na2SO4 and concentrated.
The residue was chromatographed on silica gel (AcOEt/n-hexane=1/3 as an eluent) and recrystallized to obtain 2-bromo-4'-cyanoacetophenone as a colourless plate (23.4 g, 29percent).
EI-MS(+): m/z 223 (M+)
1H-NMR(CDCl3): 4.43(2H,s), 7.80(2H,d,J=6.6 Hz), 8.09(2H,d,J=6.6 Hz)
29% With hydrogen bromide; bromine In chloroform g)
Preparation of 2-bromo-4'-cyanoacetophenone
To a mixture of para-cyanoacetophenone (52 g, 0.36 mol) in chloroform (520 ml) and 48percent HBr (5.2 ml), a solution of bromine (19.3 ml) in chloroform (52 ml) was added dropwise over a period of 20 min.
The mixture was stirred for 3 h at room temperature and neutralized to pH7 with sat. NaHCO3.
The organic layer was washed with sat.
NaCl and dried over anhydrous Na2SO4 and concentrated.
The residue was chromatographed on silica gel (AcOEt/n-hexane=1/3 as an eluent) and recrystallized to obtain 2-bromo-4'-cyanoacetophenone as a colourless plate (23.4 g, 29percent).
EI-MS(+): m/z 223 (M+)
1H-NMR(CDCl3) δ4.43(2H,s), 7.80(2H,d,J=6.6 Hz), 8.09(2H,d,J=6.6 Hz)

Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1980, vol. 313, # 4, p. 315 - 323
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 43, p. 6390 - 6400
[3] Helvetica Chimica Acta, 2013, vol. 96, # 5, p. 889 - 896
[4] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 4, p. 623 - 630
[5] Patent: CN107629023, 2018, A, . Location in patent: Paragraph 0135; 0138; 0139; 0140
[6] Patent: CN107629022, 2018, A, . Location in patent: Paragraph 0212; 0213; 0214; 0215
[7] RSC Advances, 2016, vol. 6, # 42, p. 35602 - 35608
[8] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[9] Patent: US6300353, 2001, B1,
[10] Patent: US6300353, 2001, B1,
[11] Patent: US2784194, 1954, ,
[12] Yakugaku Zasshi, 1952, vol. 72, p. 305,307[13] Chem.Abstr., 1953, p. 2133
[14] Journal of Medicinal Chemistry, 1971, vol. 14, # 10, p. 977 - 982
[15] Journal of Medicinal Chemistry, 1987, vol. 30, # 8, p. 1497 - 1502
[16] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 7, p. 1162 - 1168[17] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 7, p. 1472 - 1478
[18] Journal of Physical Chemistry, 1995, vol. 99, # 20, p. 8190 - 8195
[19] Patent: WO2004/85408, 2004, A1, . Location in patent: Page 285
[20] Patent: US5935776, 1999, A,
[21] Patent: US5648372, 1997, A,
[22] Patent: US4812470, 1989, A,
[23] Patent: EP1231210, 2002, A2, . Location in patent: Page 73
[24] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 5063 - 5070
[25] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 407 - 416
[26] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 2031 - 2034
[27] Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3570 - 3574
[28] Chemical Communications, 2014, vol. 50, # 51, p. 6726 - 6728
[29] Organic Letters, 2017, vol. 19, # 8, p. 1994 - 1997
[30] Letters in Drug Design and Discovery, 2017, vol. 14, # 5, p. 528 - 539
[31] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
[32] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8134 - 8139
[33] Advanced Synthesis and Catalysis, 2018, vol. 360, # 8, p. 1628 - 1633
[34] Tetrahedron Letters, 2018, vol. 59, # 33, p. 3214 - 3219
[35] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
  • 2
  • [ 157729-39-0 ]
  • [ 20099-89-2 ]
YieldReaction ConditionsOperation in experiment
72% 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.
66% 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.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 45, p. 4983 - 4986
[2] Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1251 - 1254
[3] Tetrahedron Letters, 2014, vol. 55, # 7, p. 1373 - 1375
  • 3
  • [ 1443-80-7 ]
  • [ 20099-89-2 ]
  • [ 21661-87-0 ]
YieldReaction ConditionsOperation in experiment
45% With N-Bromosuccinimide; silica gel In methanol for 0.3 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] Journal of Medicinal Chemistry, 2011, vol. 54, # 12, p. 4042 - 4056
[2] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 179 - 182
  • 4
  • [ 100-47-0 ]
  • [ 598-21-0 ]
  • [ 20099-89-2 ]
YieldReaction ConditionsOperation in experiment
80% at 0℃; for 4 h; The reactor was charged with 2.5 mL of 1,2-dichloroethane, AlCl3 (0.55 g, 4.14 mmol), 2-bromoacetyl bromide (1.21 g g, 6.0 mmol) was added dropwise at 0 ° C, followed by the dropwise addition of benzonitrile (0.52 g, 5.0 mmol) at one time. After the addition was complete, the cooling was stopped and stirring was continued for 4 h, the temperature was raised to room temperature, the deionized water was added to quench the excess of AlCl3, The organic layer was separated and evaporated to dryness, and the crude product was purified by column chromatography to give Compound 1-1 (0.9g, 80 percent).
Reference: [1] Patent: CN107033099, 2017, A, . Location in patent: Paragraph 0041; 0042; 0043; 0044
  • 5
  • [ 3435-51-6 ]
  • [ 20099-89-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9889 - 9894
[2] Tetrahedron, 2018, vol. 74, # 27, p. 3602 - 3607
  • 6
  • [ 25309-65-3 ]
  • [ 20099-89-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 20, p. 4701 - 4704
  • 7
  • [ 67-56-1 ]
  • [ 1443-80-7 ]
  • [ 20099-89-2 ]
  • [ 164594-65-4 ]
YieldReaction ConditionsOperation in experiment
35% for 16 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.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
  • 8
  • [ 25309-65-3 ]
  • [ 1443-80-7 ]
  • [ 20099-89-2 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 4, p. 784 - 787
  • 9
  • [ 67-56-1 ]
  • [ 1129-35-7 ]
  • [ 20099-89-2 ]
  • [ 52798-47-7 ]
  • [ 21661-87-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 5, p. 1490 - 1496
  • 10
  • [ 20099-89-2 ]
  • [ 241479-67-4 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydrogencarbonate In ethanol h)
Preparation of 4-{2-[(1R,2R)-2-(2,5-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-benzonitrile
A mixture of (2R,3R)-3-(2,5-Difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-ylthiobutyramide (26.7 g, 85.4 mmol) and a-bromo-4'-cyano-acetophenone (24.0 g, 0.107 mol) in EtOH (500 ml) was refluxed for 1 hr.
The reaction mixture was cooled down to r.t.
And the solvent was removed under reduced pressure down to 150 ml.
The residue was poured into in to cold (0° C.) saturated NaHCO3 aq. (400 ml).
The resulting mixture was extracted with EtOAc (300 ml+150 ml*2).
The combined organic layer was washed with brine (200 ml), dried over Na2SO4 and concentrated in vacuo.
The residue was chromatographed on silica gel (Wako-gel C-300, Hexane:EtOAc=1:2) to give 4-{2-[(1R,2R)-2-(2,5-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl }-benzonitrile (32.0 g, 86percent).
Physical form: colorless heavy syrup; ESI-MS: m/z 437 (M)+; 1H-NMR(CDCl3): 1.25(3H,d,J=7.3 Hz),4.12(1 H,q,J=7.3 Hz),4.26,4.96 (2H,Abq,J=14.5 Hz), 5.75(1H,s),6.89~7.07(2H,m),7.23~7.29(1 H,m),7.65 (1H,s),7.71(1H,s),7.75, 8.02(4H,Abq,J=8.6 Hz),7.85(1H,s).
77.4% at 78℃; for 3 h; The white solid obtained above (3.85 g, 12.75 mmol) was dissolved in absolute ethanol (60 ml), then add α-bromo-4-cyanoacetophenone (3.14g, 14.02mmol) to 78°C,The reaction was refluxed for 3 h. After cooling to room temperature, the reaction solution was concentrated and extracted with ethyl acetate.The ethyl acetate phase is washed with saturated sodium bicarbonate solution, the organic phase is dried and concentrated.Ice methyl tert-butyl ether washing, drying white solidIsoconazole4.31g(yield: 77.4percent, e.e. >99percent, d.e. >99percent).
Reference: [1] Patent: US6300353, 2001, B1,
[2] Patent: CN106317044, 2017, A, . Location in patent: Paragraph 0080; 0081
[3] Patent: WO2016/55918, 2016, A1, . Location in patent: Page/Page column 15
  • 11
  • [ 20099-89-2 ]
  • [ 241479-67-4 ]
YieldReaction ConditionsOperation in experiment
70% at 60℃; for 2 h; (D) is added in three-necked reaction bottle for product 1mol 3rd, the 1.05mol2-bromo-4-cyano-acetophenone and [...] 0.3L95percent of ethanol (i.e. 95 ethanol), the 60 °C stirring for 2 hours, TLC detection after the reaction is complete by adding volume ratio of the 1 [...] 1 of water and 95 mixed solvent of ethanol, heated to 55 °C, add triethylamine adjusted to pH 4, cooling to 50 °C stirring 0.5 hours, then 2 hours to about room temperature, stirring at room temperature for 10 hours, the cake uses volume ratio of the filter is characterized the 1 [...] 1 of water and 95 mixed solvent of ethanol washing, can be placed in an oven and dried, the yield is 70percent.
Reference: [1] Patent: CN105777740, 2016, A, . Location in patent: Paragraph 0019; 0026
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