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[ CAS No. 112671-42-8 ] {[proInfo.proName]}

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Chemical Structure| 112671-42-8
Chemical Structure| 112671-42-8
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Product Details of [ 112671-42-8 ]

CAS No. :112671-42-8 MDL No. :MFCD11505492
Formula : C6H3BrINO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XLUAZLDTZYHVSO-UHFFFAOYSA-N
M.W : 327.90 Pubchem ID :13803666
Synonyms :

Calculated chemistry of [ 112671-42-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.68
TPSA : 45.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 3.09
Log Po/w (WLOGP) : 2.96
Log Po/w (MLOGP) : 3.35
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.16
Solubility : 0.0228 mg/ml ; 0.0000696 mol/l
Class : Moderately soluble
Log S (Ali) : -3.72
Solubility : 0.0625 mg/ml ; 0.000191 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0916 mg/ml ; 0.000279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.48

Safety of [ 112671-42-8 ]

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

Application In Synthesis of [ 112671-42-8 ]

* 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 [ 112671-42-8 ]
  • Downstream synthetic route of [ 112671-42-8 ]

[ 112671-42-8 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 112671-42-8 ]
  • [ 52415-29-9 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
  • 2
  • [ 875-51-4 ]
  • [ 112671-42-8 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With boron trifluoride diethyl etherate In tetrahydrofuran at -30℃; for 0.5 h;
Stage #2: With tert.-butylnitrite In tetrahydrofuran; diethyl ether at -30 - -5℃; for 1.25 h;
Stage #3: With iodine; potassium iodide In acetonitrile at 20℃; for 1.3 h;
To BF3·OEt2 (16.0 mL, 126.3 mmol) at –30 °C was added a solution of 4-bromo-2-nitroaniline (6.50g, 30.0 mmol) in THF (100 mL) dropwise over 20 min. The mixture was stirred at –30 °C for 10 min andthen a solution of tBuONO (13.0 mL, 90percent, 109.3 mmol) in THF (81 mL) was added dropwise over 15min. The reaction mixture was allowed to warm to –10 °C at which time Et2O (158 mL) was addeddropwise. The mixture was allowed to stir at –5 °C for 1 h until a white pale solid precipitated. The solidwas filtered and washed with Et2O to afford a white solid which was then added in one portion to a 500mL round-bottomed flask containing, KI (5.45 g, 26.53 mmol), iodine (7.16 g, 13.27 mmol), and MeCN(120 mL). The mixture was stirred at RT for 1.3 h, quenched with sat. aq Na2S2O3 (250 mL), and22extracted with CH2Cl2 (2 x 150 mL). The organic layers were combined, dried over Na2SO4, andconcentrated in vacuo to afford 4-bromo-1-iodo-2-nitrobenzene (8.61 g, 88percent yield) as a yellow solid.
Reference: [1] Biochemistry, 2018, vol. 57, # 18, p. 2733 - 2743
[2] Heterocycles, 2009, vol. 79, # C, p. 805 - 820
[3] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 13, p. 5547 - 5568
[5] Synthesis, 2008, # 13, p. 2039 - 2044
[6] Journal of Organic Chemistry, 2004, vol. 69, # 5, p. 1752 - 1755
[7] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[8] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
[9] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
[10] Patent: WO2017/20086, 2017, A1, . Location in patent: Page/Page column 62; 71
[11] Tetrahedron, 2017, vol. 73, # 34, p. 5072 - 5081
[12] Organic Letters, 2017, vol. 19, # 17, p. 4484 - 4487
  • 3
  • [ 88-74-4 ]
  • [ 112671-42-8 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
  • 4
  • [ 881-50-5 ]
  • [ 112671-42-8 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
  • 5
  • [ 103-88-8 ]
  • [ 112671-42-8 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
  • 6
  • [ 106-39-8 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 7
  • [ 106-37-6 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 8
  • [ 3460-18-2 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 9
  • [ 16588-24-2 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 10
  • [ 108-90-7 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 11
  • [ 106-40-1 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 12
  • [ 112671-42-8 ]
  • [ 64085-52-5 ]
YieldReaction ConditionsOperation in experiment
91% With iron; acetic acid In ethanol at 100℃; for 1.3 h; To a solution of 4-bromo-1-iodo-2-nitrobenzene (8.38 g, 109.6 mmol) in AcOH (45 mL) and EtOH(45 mL) at RT was added Fe (6.12 g, 109.6 mmol). The mixture was stirred at 100 °C for 1.3 h andcooled to RT. The reaction mixture was diluted with Et2O (90 mL) and washed with sat. aq. NaHCO3(200 mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3 x 60 mL).The organic layers were combined, washed with brine (300 mL), dried over Na2SO4, and concentrated invacuo. The residue was purified by flash chromatography (silica gel, hexane/AcOEt = 19:1) to afford 5-bromo-2-iodoaniline 30b (6.89 g, 91percent yield) as a light yellow solid.
39 g With tin(ll) chloride In methanol at 0 - 80℃; for 4 h; To a solution of 4-bromo-1 -iodo-2-nitrobenzene (66 g, 0.2 mol) in MeOH (700 mL) was added stannous chloride (226 g, 1 mol) at 0 °C. The resultant mixture was heated to reflux (80 °C) for 4 h. The solvent was removed under reduced pressure, and then the residue was diluted with ethyl acetate (1 L), washed with H2O (1 L), dried over sodium sulfate, concentrated to give a residue which was purified by column chromatography (eluent: petroleum ether: ethyl acetate= 20:1 ) to give 5-bromo-2-iodoaniline (39 g, 65percent) as a white solid. LCMS (Method B): 2.27 min m/z [MH]+=298.1 ; 300.1
Reference: [1] Heterocycles, 2009, vol. 79, # C, p. 805 - 820
[2] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
[3] Synthesis, 2008, # 13, p. 2039 - 2044
[4] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 5, p. 1823 - 1828
[5] Patent: WO2011/119860, 2011, A1, . Location in patent: Page/Page column 90
[6] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 68
[7] Patent: WO2017/20086, 2017, A1, . Location in patent: Page/Page column 62; 72
[8] Organic Letters, 2017, vol. 19, # 17, p. 4484 - 4487
[9] Biochemistry, 2018, vol. 57, # 18, p. 2733 - 2743
  • 13
  • [ 112671-42-8 ]
  • [ 94994-62-4 ]
Reference: [1] Patent: EP2930168, 2015, A1,
[2] Patent: KR101550768, 2015, B1,
[3] Patent: KR2015/98171, 2015, A,
[4] Patent: KR2015/87787, 2015, A,
[5] Patent: KR101614738, 2016, B1,
[6] Patent: KR2015/43669, 2015, A,
[7] Patent: KR2015/89427, 2015, A,
[8] Patent: KR101565039, 2015, B1,
[9] Patent: KR2015/102733, 2015, A,
  • 14
  • [ 112671-42-8 ]
  • [ 1001911-63-2 ]
Reference: [1] Patent: KR101565039, 2015, B1,
[2] Patent: KR2015/102733, 2015, A,
  • 15
  • [ 112671-42-8 ]
  • [ 1246669-45-3 ]
Reference: [1] Patent: EP2930168, 2015, A1,
[2] Patent: KR101550768, 2015, B1,
[3] Patent: KR2015/98171, 2015, A,
[4] Patent: KR2015/87787, 2015, A,
[5] Patent: KR2015/43669, 2015, A,
[6] Patent: KR2015/89427, 2015, A,
[7] Patent: KR101614738, 2016, B1,
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