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[ CAS No. 22265-36-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 22265-36-7
Chemical Structure| 22265-36-7
Chemical Structure| 22265-36-7
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Product Details of [ 22265-36-7 ]

CAS No. :22265-36-7 MDL No. :MFCD05662836
Formula : C7H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :JODFDXUBCBQKNC-UHFFFAOYSA-N
M.W : 199.05 Pubchem ID :4436571
Synonyms :

Calculated chemistry of [ 22265-36-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.41
TPSA : 49.87 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 0.88
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.96 mg/ml ; 0.00985 mol/l
Class : Soluble
Log S (Ali) : -1.51
Solubility : 6.13 mg/ml ; 0.0308 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.99
Solubility : 0.205 mg/ml ; 0.00103 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 22265-36-7 ]

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

Application In Synthesis of [ 22265-36-7 ]

* 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 [ 22265-36-7 ]
  • Downstream synthetic route of [ 22265-36-7 ]

[ 22265-36-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 623-00-7 ]
  • [ 22265-36-7 ]
YieldReaction ConditionsOperation in experiment
95.4%
Stage #1: With N-acetylcystein In ethanol at 45℃; for 20 h;
Stage #2: With ammonium carbamate In ethanol for 68 h;
In four flask equipped with a mechanical stirrer, thermometer, reflux condenser. takeFor bromoxynil 36.4g (0.2mol) was poured into a beaker, add 100ml of absolute ethanol, stirring to dissolve completely; then weighed 32.4gN- acetylcysteine (0.2mol), into another beaker was then added 150ml of absolute ethanol, stirring the mixture to complete dissolution, then a solution of ethanol will bromoxynil and N- acetylcysteine ethanol solution was poured into four flask, stirred and heated to 45 The reaction 20h . Weigh 8.6g ammonium carbamate (0.11 mol), was slowly added portionwise to a 4-neck flask, 20h, after complete dissolution the reaction, the reactionAfter completion of standing 48h, suction filtered, the filter cake was washed with ethanol, and drying, a white solid product was obtained 38g of bromobenzene formamidine (Compound ), yield 95.4percent, HPLC purity was 99.6percent.
Reference: [1] Patent: CN105669651, 2016, A, . Location in patent: Paragraph 0067; 0068
[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1946, vol. 133, p. 20,30
[3] Justus Liebigs Annalen der Chemie, 1975, p. 160 - 194
[4] Patent: WO2010/111483, 2010, A1, . Location in patent: Page/Page column 117
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2369 - 2375
[6] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
[7] Patent: EP2862856, 2015, A1,
[8] Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364
  • 2
  • [ 55368-42-8 ]
  • [ 22265-36-7 ]
YieldReaction ConditionsOperation in experiment
472 mg With sodium hydroxide In water 4-Bromobenzamidine hydrochloride (6a, 707 mg) was treated with 5 M aqueous sodium hydroxide (8 mL), and extracted with chloroform. The organic layer was dried, filtered and evaporated to give colorless solid (472 mg). To the solution of the obtained solid in ethanol (5 mL) was added ethyl propiolate (0.27 mL) and the mixture was warmed up to 60 °C, then potassium hydroxide (175 mg) in ethanol (4 mL) was added dropwise over 15 min. The mixture was warmed up to 80 °C and stirred for 6 h, then cooled down to room temperature. To the mixture was added 1 M hydrochloric acid (10 mL), and the precipitate was collected by filtration, washed with water, dried in vacuo at 50 °C overnight to give 7g (267 mg, 35percent) as a pale brown solid: 1H NMR (DMSO-d6) δ 6.25-6.50 (1H, m), 7.74 (2H, d, J = 8.3 Hz), 7.95-8.25 (3H, m), 12.50-13.20 (1H, br); FAB-MS m/z 251, 253 [(M+H)+].
9.58 g With sodium hydroxide In water at 20℃; for 3 h; Compound 3 (13.25 g) was suspended in water (40 mL), and a 5N aqueous sodium hydroxide solution (40 mL)was added, and the mixture was stirred at room temperature for 3 hours. The deposit was collected by filtration andwashed with water. The obtained white solid was dissolved in acetone, activated charcoal was added, and the mixturewas stirred for 10 minutes, and subsequently, filtered through Celite. The filtrate was concentrated under reducedpressure, and the obtained powder was washed with diethyl ether, collected by filtration and dried to obtain Compound4 (9.58 g) as a white powder.
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2369 - 2375
[2] Patent: EP2862856, 2015, A1, . Location in patent: Paragraph 0651; 0652
[3] Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364
  • 3
  • [ 19227-14-6 ]
  • [ 22265-36-7 ]
YieldReaction ConditionsOperation in experiment
68% for 96 h; Reflux; Inert atmosphere General procedure: Compound 44b (150 mg, 1.0 mmol) was boiled under reflux withHCOONH4 (403 mg, 6.3 mmol) and Pd/C (10percent, 150 mg) in AcOH (5 mL) for4 d under Ar. The cooled mixture was filtered (Celite®). Aq. NaOH(1.0 M, 20 mL) was added to the evaporation residue and the mixture wasextracted (EtOAc, 3 ). Drying andevaporation gave 44b (82 mg, 61percent) as a white powder.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
[2] ChemMedChem, 2015, vol. 10, # 2, p. 360 - 367
  • 4
  • [ 623-00-7 ]
  • [ 1147550-11-5 ]
  • [ 22265-36-7 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 390,391
  • 5
  • [ 623-00-7 ]
  • [ 19402-64-3 ]
  • [ 22265-36-7 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 147,149
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