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[ CAS No. 61150-57-0 ] {[proInfo.proName]}

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Chemical Structure| 61150-57-0
Chemical Structure| 61150-57-0
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Product Details of [ 61150-57-0 ]

CAS No. :61150-57-0 MDL No. :MFCD03840524
Formula : C7H5Br2F Boiling Point : -
Linear Structure Formula :- InChI Key :QPLUIZXBWYUFMY-UHFFFAOYSA-N
M.W : 267.92 Pubchem ID :10706977
Synonyms :

Calculated chemistry of [ 61150-57-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.94
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 3.27
Log Po/w (WLOGP) : 3.75
Log Po/w (MLOGP) : 4.25
Log Po/w (SILICOS-IT) : 3.93
Consensus Log Po/w : 3.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0308 mg/ml ; 0.000115 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.304 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.79
Solubility : 0.00439 mg/ml ; 0.0000164 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.69

Safety of [ 61150-57-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 UN#:3261
Hazard Statements:H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 61150-57-0 ]

* 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 [ 61150-57-0 ]
  • Downstream synthetic route of [ 61150-57-0 ]

[ 61150-57-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1422-53-3 ]
  • [ 61150-57-0 ]
YieldReaction ConditionsOperation in experiment
87% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 21 h; Heating / reflux Combine 2-bromo-4-fluoro-l -methyl-benzene (15 g, 79.3 mmol), N- bromosuccinimide (18.08 g, 101.6 mmol), and 2,2-azobisisobutyronitrile (3.9 g, 23.8 mmol) in carbon tetrachloride (150 mL) in a round bottom flask fitted with a reflux condensor. Heat the mixture at reflux for 21 h. Cool the mixture and remove the solvent under reduced pressure. Suspend the crude mixture in DCM and wash with water. Wash the organics with aqueous saturated sodium chloride and dry over sodium sulfate. Filter and remove the solvent under reduced pressure to obtain the crude product. Purify by column chromatography (1 percent ethyl acetate in hexane - > 10 percent ethyl acetate in hexanes) to give the title compound as an oily white solid (18.5 g, 87 percent). GCMS m/z 268 [M]+.
76% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2 h; Heating / reflux A mixture of 18.9 g (100 mmol) of 2-bromo-4-fluorotoluene, 17.8 g (100 mmol) of N-bromosuccinimide, 400 mg of benzoyl peroxide, and 200 ml of CCl4 were refluxed for 2 h. The reaction mixture was filtered through a glass frit (G2), and the precipitate was additionally washed with 3 x 50 ml of CCl4. The combined filtrate was evaporated to dryness. Fractional distillation of the residue (bp 92-960C/ 4 mm Hg) gave the title product as colorless oil. Yield 20.4 g (76percent). Anal. calc. for C7H5Br2F: C, 31.38; H, 1.88. Found: C, 31.49; H, 1.75.1H NMR (CDCl3): δ 7.43 (dd, J=8.6 Hz, J=5.8 Hz, IH, 6-H), 7.32 (dd, J=8.1 Hz, J=2.5 Hz, IH, 5-H), 7.02 (dt, J=8.6 Hz, J=5.8 Hz, IH, 3-H), 4.57 (m, 2H, CH2).
62% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane a)
Preparation of 2-Bromo-1-(Bromomethyl)-4-Fluorobenzene
A mixture of 2-Bromo-4-Fluorotoluene (46.6 g, 0.25 mol, Aldrich), N-bromosuccinimide (46.3 g, 0.26 mol, Aldrich) and benzoyl peroxide (0.5 g, 0.002 mol, Aldrich) in carbon tetrachloride (500 ml) was refluxed and illuminated (250 watt, infrared lamp) for 18 h.
After cooling to room temperature, the succinimide was filtered and the filtrate was concentrated in vacuo.
Chromatography on silica gel with hexanes as eluent gave 41.8 g (62percent) of 2-bromo-1-(bromomethyl)-4-fluorobenzene as a white solid: mp 47°-49° C.
100% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane A mixture of 2-bromo-4-fluorotoluene (37.4 g), N-bromosuccinimide (39 g), tetrachloromethane (120 ml) and benzoyl peroxide (0.25 g) is refluxed for 5 hours.
After standing overnight, the separated succinimide is filtered off and the filtrate is taken down under diminished pressure, yielding 52 g (100percent) of crude 2-bromo-4-fluorobenzyl bromide which can be used in the next step without purification.
In order to characterize the pure compound, a sample can be distilled; b.p. 127° C./20 Torr.

Reference: [1] Synlett, 2011, # 17, p. 2525 - 2528
[2] Patent: WO2008/144223, 2008, A2, . Location in patent: Page/Page column 28
[3] Patent: WO2007/70041, 2007, A1, . Location in patent: Page/Page column 126
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[5] Collection of Czechoslovak Chemical Communications, 1999, vol. 64, # 4, p. 649 - 672
[6] Organic Letters, 2015, vol. 17, # 19, p. 4654 - 4657
[7] Collection of Czechoslovak Chemical Communications, 1977, vol. 42, # 10, p. 3079 - 3093
[8] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 1, p. 57 - 64
[9] Patent: US5708033, 1998, A,
[10] Patent: US4238611, 1980, A,
[11] Patent: US2007/135595, 2007, A1,
[12] Heterocycles, 2010, vol. 80, # 1, p. 669 - 677
  • 2
  • [ 229027-89-8 ]
  • [ 61150-57-0 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 11, p. 3310 - 3313
  • 3
  • [ 1006-41-3 ]
  • [ 61150-57-0 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 11, p. 3310 - 3313
  • 4
  • [ 61150-57-0 ]
  • [ 61150-58-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 21, p. 5444 - 5448[2] Angew. Chem., 2014, vol. 126, # 21, p. 5548 - 5552,5
[3] Journal of the American Chemical Society, 2018, vol. 140, # 20, p. 6203 - 6207
[4] Organic Letters, 2018, vol. 20, # 14, p. 4223 - 4226
  • 5
  • [ 61150-57-0 ]
  • [ 333-20-0 ]
  • [ 61150-58-1 ]
Reference: [1] Chemistry Letters, 2018, vol. 47, # 7, p. 868 - 871
  • 6
  • [ 61150-57-0 ]
  • [ 143-33-9 ]
  • [ 61150-58-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1977, vol. 42, # 10, p. 3079 - 3093
  • 7
  • [ 61150-57-0 ]
  • [ 61150-59-2 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1977, vol. 42, # 10, p. 3079 - 3093
[2] Synlett, 2011, # 17, p. 2525 - 2528
[3] Journal of the American Chemical Society, 2018, vol. 140, # 20, p. 6203 - 6207
[4] Chemistry Letters, 2018, vol. 47, # 7, p. 868 - 871
  • 8
  • [ 61150-57-0 ]
  • [ 174603-56-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2015/36759, 2015, A1,
  • 9
  • [ 61150-57-0 ]
  • [ 174603-55-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2015/36759, 2015, A1,
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