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[ CAS No. 675109-26-9 ] {[proInfo.proName]}

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Chemical Structure| 675109-26-9
Chemical Structure| 675109-26-9
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Product Details of [ 675109-26-9 ]

CAS No. :675109-26-9 MDL No. :MFCD11848599
Formula : C8H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :HYTCKZQYVIURAW-UHFFFAOYSA-N
M.W : 212.04 Pubchem ID :22220919
Synonyms :

Calculated chemistry of [ 675109-26-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.1
TPSA : 29.1 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.71
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.16
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 1.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.705 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 4.46 mg/ml ; 0.021 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.75
Solubility : 0.0379 mg/ml ; 0.000179 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 675109-26-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 675109-26-9 ]

* 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 [ 675109-26-9 ]
  • Downstream synthetic route of [ 675109-26-9 ]

[ 675109-26-9 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 79670-17-0 ]
  • [ 675109-26-9 ]
YieldReaction ConditionsOperation in experiment
98% With ammonia In tetrahydrofuran; methanol at 20℃; for 0.666667 h; A solution of 5-bromo-2-bromomethyl-benzoic acid methyl ester (1 equiv) in a 1:1 THF/MeOH mixture was treated by gentle bubbling of ammonia gas for 40 minutes at room temperature. The reaction mixture was concentrated in vacuo. The residue was sonicated in CH2Cl2 for 15 minutes then filtered to give the desired product as a white solid.6-Bromo-2,3-dihydro-isoindol-l-one: (98 percent yield, 90 percent purity) m/z (LC-MS, ESP): 212.3/214.3 [M+H]+ R/T = 2.98 min
87% With ammonium hydroxide In methanol at 80℃; for 10 h; 3) The compound obtained in step (2) (150 g, 0.49 mol) was dissolved in 600 ml of methanol.The system then added 25percent of ammonia to 4.5 liters of ammonia and the system reacted at 70°C for 5 hours.It was cooled and filtered to give 90 g of a pale yellow powder in a yield of 87percent.
Reference: [1] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 117
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183
[3] Patent: CN107474006, 2017, A, . Location in patent: Paragraph 0050; 0051; 0054; 0056-0057; 0060; 0062-0063; 0066
[4] Patent: WO2008/20306, 2008, A2, . Location in patent: Page/Page column 38
[5] E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1108 - 1113
[6] Patent: US2004/58970, 2004, A1, . Location in patent: Page 8
  • 2
  • [ 79669-50-4 ]
  • [ 675109-26-9 ]
YieldReaction ConditionsOperation in experiment
71% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 85℃; for 2 h; Step 2 Compound 1251 B (1.219g, 5.32 mmol) was dissolved in CCI4 (30 mL). NBS (947 mg, 5.32 mmol) and benzoyl peroxide (66 mg, 0.27 mmol) was added. The solution was stirred at 850C for 2 hours. After cooling down, the solid was filtered and the organic layer was washed with water (10 mL). The organic layer was dried over Na2SO4, concentrated by rotary evaporator, dried under vacuum. The residue was then dissolved in NH3-MeOH (7N, 10 mL) and transferred into a 75 mL pressure bottle. The solution was stirred at 90 0C for over night. The product was purified by C18 chromatography (CH3CN/water: 5percent to 90percent, with addition of 0.1percent HCO2H) to give compound 1251C (800mg, 71percent).
Reference: [1] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 160
[2] E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1108 - 1113
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183
[4] Patent: CN107474006, 2017, A,
  • 3
  • [ 480-91-1 ]
  • [ 675109-26-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3091 - 3107
  • 4
  • [ 1200444-64-9 ]
  • [ 1972-28-7 ]
  • [ 675109-26-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 21, p. 3707 - 3712
  • 5
  • [ 79669-49-1 ]
  • [ 675109-26-9 ]
Reference: [1] E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1108 - 1113
[2] Patent: CN107474006, 2017, A,
[3] Patent: WO2007/84451, 2007, A1,
  • 6
  • [ 118-90-1 ]
  • [ 675109-26-9 ]
Reference: [1] E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1108 - 1113
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183
  • 7
  • [ 87384-76-7 ]
  • [ 675109-26-9 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 14, p. 2693 - 2701
  • 8
  • [ 87-41-2 ]
  • [ 675109-26-9 ]
Reference: [1] Patent: CN105153013, 2017, B,
[2] Patent: CN105153013, 2017, B,
  • 9
  • [ 675109-26-9 ]
  • [ 73183-34-3 ]
  • [ 1004294-80-7 ]
YieldReaction ConditionsOperation in experiment
82% With potassium acetate In 1,4-dioxane at 70 - 120℃; for 18 h; To a solution of 6-bromo-2,3-dihydro-isoindol-l-one (1 equiv) in dry dioxan (0.1 M) were added bis(pinacolato)diboron (1.1 equiv), potassium acetate (3.5 equiv) and dppf (0.05 equiv). The reaction mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added to the reaction mixture, which was degassed for a further 5 minutes. The reaction mixture was heated to 70°C for 2 hours under nitrogen then heated to 1200C for 16 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic phases dried (MgSO4), filtered and concentrated in vacuo. The residue was sonicated in EtOAc, the suspension was filtered onto a sintered funnel and the collected grey solid was dried and used without further purification. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-l-one: (82 percent yield, 29 percent purity, main impurity being the boronic acid 43 percent) m/z (LC-MS, ESP): 519.5 [2M+H]+ R/T = 3.38 min
Reference: [1] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 117
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9542 - 9555
[3] Patent: WO2017/107089, 2017, A1, . Location in patent: Page/Page column 37; 38
[4] Patent: WO2017/68412, 2017, A1, . Location in patent: Page/Page column 208; 209
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4978 - 4992
  • 10
  • [ 675109-26-9 ]
  • [ 919346-89-7 ]
Reference: [1] Patent: CN107474006, 2017, A, . Location in patent: Paragraph 0050; 0051; 0055; 0056; 0057; 0061-0063; 0067
  • 11
  • [ 675109-26-9 ]
  • [ 74-88-4 ]
  • [ 1254319-51-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With sodium iodide In N,N-dimethyl-formamide at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 1 h; Inert atmosphere
General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0°C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0°C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3x100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10percent acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80percent). ‘ H NMR [400 MHz, (CD3)2S0] ö 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J— 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.
Reference: [1] Patent: WO2014/28968, 2014, A1, . Location in patent: Page/Page column 64; 107
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9542 - 9555
[3] E-Journal of Chemistry, 2011, vol. 8, # 3, p. 1108 - 1113
  • 12
  • [ 675109-26-9 ]
  • [ 1313399-38-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9542 - 9555
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