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[ CAS No. 35590-37-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 35590-37-5
Chemical Structure| 35590-37-5
Structure of 35590-37-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35590-37-5 ]

CAS No. :35590-37-5 MDL No. :MFCD00174363
Formula : C6H3BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :FTFFHWWIPOQCBC-UHFFFAOYSA-N
M.W : 183.01 Pubchem ID :736793
Synonyms :

Calculated chemistry of [ 35590-37-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.65
TPSA : 36.68 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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.0 mg/ml ; 0.00547 mol/l
Class : Soluble
Log S (Ali) : -1.63
Solubility : 4.3 mg/ml ; 0.0235 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.199 mg/ml ; 0.00109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 35590-37-5 ]

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 [ 35590-37-5 ]

* 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 [ 35590-37-5 ]
  • Downstream synthetic route of [ 35590-37-5 ]

[ 35590-37-5 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 625-92-3 ]
  • [ 35590-37-5 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -15℃; for 0.25 h;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water at 20℃; for 2 h;
General procedure: To a flask containing dried LiCl (0.35 g, 8.24 mmol) was added iPrMgCl (2 M in THF, 4.1 mL) and THF (5 mL) at 15° C. After beingstirred for 15 min, 3-bromo-1-benzonitrile (1.46 g, 8.03 mmol) inTHF (1 mL) was added to the reaction mixture and the obtainedmixture was stirred for 15 min. Then, DMF (1.3 mL, 12 mmol) wasadded at 0° C and the mixture was stirred for 2 h. Then, aq NH3 (7 mL, 28-30percent) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After being stirred for 2 h at room temperature, the reactionmixture was poured into satd aq Na2SO3 solution and was extracted with CHCl3 (3∗30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue waspurified by short column chromatography on silica gel (eluent:hexane/ethyl acetate=9:1, v/v) to provide pure 1,3-dicyanobenzene (0.73 g) in 71percent yield. Most nitriles mentioned in this work are commercially availableand were identified by comparison with the authentic samples.
Reference: [1] Tetrahedron, 2013, vol. 69, # 5, p. 1462 - 1469
  • 2
  • [ 28733-43-9 ]
  • [ 35590-37-5 ]
YieldReaction ConditionsOperation in experiment
81% at 315℃; for 1 h; General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), the stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is almost complete. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic proteomics and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10 and A-11 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99percent).In these nitrile product preparation examples, 10 g of diphosphorus pentoxide was optionally added to the reaction vessel as a catalyst at the start of the reaction.
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 26, p. 7843 - 7853
[2] Patent: CN104557357, 2018, B, . Location in patent: Paragraph 0150; 0151; 0152; 0160
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3168 - 3185
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
  • 3
  • [ 28733-43-9 ]
  • [ 144-55-8 ]
  • [ 35590-37-5 ]
Reference: [1] Patent: US2003/125267, 2003, A1,
  • 4
  • [ 2402-97-3 ]
  • [ 7677-24-9 ]
  • [ 35590-37-5 ]
  • [ 55758-02-6 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 9942 - 9951
  • 5
  • [ 20826-04-4 ]
  • [ 35590-37-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3168 - 3185
[2] Patent: CN104557357, 2018, B,
  • 6
  • [ 113118-81-3 ]
  • [ 35590-37-5 ]
Reference: [1] Synlett, 2011, # 15, p. 2223 - 2227
  • 7
  • [ 35590-37-5 ]
  • [ 28733-43-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 18, p. 2889 - 2894
  • 8
  • [ 35590-37-5 ]
  • [ 98-80-6 ]
  • [ 10177-15-8 ]
YieldReaction ConditionsOperation in experiment
56% With pyridine; tetrakis(triphenylphosphine) palladium(0); ethanol In toluene for 20 h; Reflux (0.01 mmol, 11.5 mg) was dissolved in toluene / ethanol (V: & lt; RTI ID = 0.0 & gt; V). & Lt; / RTI & gt; A solution of 3-bromo-5- cyanopyridine (1 mmol, 0.183 g) V = 3: 1). After the reaction was allowed to proceed for 20 hours under refluxing, the reaction was stopped. The reaction mixture was allowed to stand at room temperature and washed with dichloromethane. The organic phase was collected and purified by silica gel column chromatography to give a white solid 0.11 g (yield: 56percent) of 3-phenyl-5-amidopyridine; Ms (M / Z): 198.2 (M +).
Reference: [1] Patent: CN104016914, 2016, B, . Location in patent: Paragraph 0034; 0035
  • 9
  • [ 35590-37-5 ]
  • [ 696-42-4 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3792 - 3795
  • 10
  • [ 2402-97-3 ]
  • [ 7677-24-9 ]
  • [ 35590-37-5 ]
  • [ 55758-02-6 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 9942 - 9951
  • 11
  • [ 35590-37-5 ]
  • [ 73183-34-3 ]
  • [ 497147-93-0 ]
YieldReaction ConditionsOperation in experiment
32% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 21 h; A 500 ml 2-neck flask was charged with 3-bromo-5-cyanopyridine (0.63 g, 2.5 mmol), 1,1 bis (diphenylphosphino) ferrocene palladiumdichloride (0.17 g, 0.21 mmol), potassiumacetate (0.61 g, 6.21 mmol) Was dissolved in 6 mL of 1,4-dioxane, and the mixture was heated and stirred at 90 DEG C for 21 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was distilled under reduced pressure and dried to obtain 0.1 g of compound F (yield: 32percent).
Reference: [1] Patent: KR2017/79357, 2017, A, . Location in patent: Paragraph 0300-0303
[2] Patent: WO2012/3283, 2012, A1, . Location in patent: Page/Page column 187
  • 12
  • [ 35590-37-5 ]
  • [ 5419-55-6 ]
  • [ 497147-93-0 ]
Reference: [1] Patent: WO2007/114771, 2007, A1, . Location in patent: Page/Page column 22-23
  • 13
  • [ 35590-37-5 ]
  • [ 73183-34-3 ]
  • [ 402718-29-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5473 - 5494
[2] Patent: US2007/78133, 2007, A1, . Location in patent: Page/Page column 29
[3] Patent: WO2013/43521, 2013, A1, . Location in patent: Page/Page column 38
[4] Patent: WO2014/32498, 2014, A1, . Location in patent: Page/Page column 17
  • 14
  • [ 35590-37-5 ]
  • [ 951624-83-2 ]
Reference: [1] Science, 2018, vol. 360, # 6392, p. 1010 - 1014
  • 15
  • [ 35590-37-5 ]
  • [ 951624-83-2 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 6, p. 2075 - 2084
  • 16
  • [ 35590-37-5 ]
  • [ 951624-83-2 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 6, p. 1744 - 1747
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