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[ CAS No. 5228-61-5 ] {[proInfo.proName]}

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Chemical Structure| 5228-61-5
Chemical Structure| 5228-61-5
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Product Details of [ 5228-61-5 ]

CAS No. :5228-61-5 MDL No. :MFCD09056836
Formula : C6H5BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RMIFLIVHJLREFJ-UHFFFAOYSA-N
M.W : 217.02 Pubchem ID :5314766
Synonyms :

Calculated chemistry of [ 5228-61-5 ]

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 : 1.0
Molar Refractivity : 47.37
TPSA : 71.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : -0.33
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.413 mg/ml ; 0.0019 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.202 mg/ml ; 0.00093 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.28
Solubility : 1.14 mg/ml ; 0.00527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 5228-61-5 ]

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 [ 5228-61-5 ]

* 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 [ 5228-61-5 ]
  • Downstream synthetic route of [ 5228-61-5 ]

[ 5228-61-5 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 5228-61-5 ]
  • [ 51376-06-8 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 15, p. 4458 - 4461
  • 2
  • [ 5228-61-5 ]
  • [ 95-83-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
  • 3
  • [ 5228-61-5 ]
  • [ 95-54-5 ]
  • [ 1575-37-7 ]
Reference: [1] Synlett, 2014, vol. 25, # 10, p. 1403 - 1408
  • 4
  • [ 5228-61-5 ]
  • [ 1575-37-7 ]
Reference: [1] Chemische Berichte, 1873, vol. 6, p. 1544
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4367 - 4379
[3] Patent: EP1382603, 2004, A1, . Location in patent: Page 66; 67
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1939 - 1943
  • 5
  • [ 5228-61-5 ]
  • [ 102-51-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
  • 6
  • [ 68498-84-0 ]
  • [ 5228-61-5 ]
  • [ 96-96-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
  • 7
  • [ 5228-61-5 ]
  • [ 100-67-4 ]
  • [ 1552-17-6 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 24, p. 4817 - 4818
  • 8
  • [ 586-78-7 ]
  • [ 5228-61-5 ]
YieldReaction ConditionsOperation in experiment
84% With O-Methylhydroxylamin; potassium <i>tert</i>-butylate In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 0 - 20℃; for 4.83333 h; Example 14a; 7V-(2-Amino-5-(lH-pyrrol-2-yl)phenyl)-4-methoxybenzamide (147); Scheme 14;;Example 14a; ;<n="111"/>Step 1 : 5-Bromo-2-nitrobenzenamine (142); [0745] To a solution of potassium tert-butoxide (21.92 g, 195 mmol) and copper (I) chloride(2.36 g, 23.8 mmol) in ethyleneglycol dimethylether (170 mL), stirred at 0 0C under nitrogen, a solution of l-bromo-4-nitrobenzene (141, 8.69 g, 43.0 mmol) in DMF (45 mL) was added drop wise over 50 min. After complete addition the cooling bath was removed and the mixture was allowed to stir at room temperature for 4 h, diluted with DCM, washed with aqueous NH4Cl, dried over MgSO4, filtered and concentrated to give compound 142 (7.85 g, 84percent yield).[0746] 1H NMR (CDC13) δ (ppm): 7.98 (d, J= 9.2 Hz, IH), 7.02 (d, J= 2.0 Hz, IH), 6.82 (dd,J= 9.2, 2.0 Hz, IH), 6.12 (bs, 2H).
Reference: [1] Patent: WO2007/118137, 2007, A1, . Location in patent: Page/Page column 109-110
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444
[3] Patent: WO2016/89830, 2016, A1, . Location in patent: Page/Page column 43
[4] Patent: WO2016/89797, 2016, A1, . Location in patent: Page/Page column 65
[5] Patent: WO2016/89833, 2016, A1, . Location in patent: Page/Page column 42
  • 9
  • [ 51686-78-3 ]
  • [ 5228-61-5 ]
YieldReaction ConditionsOperation in experiment
94% With ammonium hydroxide In dimethyl sulfoxide at 100℃; for 20 h; Autoclave 13.53 g of 2,4-dibromonitrobenzene (2) dissolved in 20 mL of DMSO is put in a steal autoclave. 51 mL of an aqueous ammonium hydroxide solution (32 percent) is added, the autoclave is equipped with a magnetic stir bar, sealed and heated to 100 °C for 20 hours. After cooling to room temperature the reaction mixture is given into water, the precipitate is sucked off, washed several times with water and recrystallised from a mixture of DIPE/MeOH (1:1) to give 9.87 g (45.5 mmol) of the desired product as orange crystals (94 percent). Melting point: 148-150 °C. 1H-NMR (200 MHz, DMSO-d6): 7.89 (d, 3J = 9.2 Hz, 1H), 7.53 (s, 2H), 7.25 (d, 4J = 2.0 Hz, 1H), 6.76 (dd, 4J = 2.0 Hz, 3J = 9.2 Hz, 1H).
92% With ammonia In water; dimethyl sulfoxide at 100℃; for 18 h; In a sealed reaction tube, add cautiously 6 [ML] of an aqueous solution of ammonia [(32percent)] to a solution of 2,4-dibromonitrobenzene (1,6 g) in 2 [ML] of DMSO. Stir for 18 hours at [100°C] and cool to room temperature. Pour the heterogeneous mixture into water and filter the title compound (1.1 [G,, 92percent)] as a yellow solid.
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[2] Patent: WO2004/14900, 2004, A1, . Location in patent: Page 24; 58
[3] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[4] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
[5] Chemische Berichte, 1873, vol. 6, p. 1544
[6] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 179 - 183
  • 10
  • [ 321-23-3 ]
  • [ 5228-61-5 ]
YieldReaction ConditionsOperation in experiment
97% With ammonia In methanol at 20℃; for 18 h; 5-Bromo-2-nitro aniline
2-Fluoro-4-bromo-1-nitrobenzene (0.5 g, 2.2 mmol) was added to methanolic ammonia (10 mL) and stirred at r.t. for 18 h.
The reaction mixture was then concentrated in vacuo and the residue was triturated with isohexane, yielding the title compound (0.48 g, 97percent) as a yellow solid. δH (d6-DMSO) 7.88 (d, J 8.8 Hz, 1H), 7.53 (br s, 2H), 7.25 (d, J 3.0 Hz, 1H), 6.75 (dd, J 9.2, 2.0 Hz, 1H).
91% With ammonia In methanol at 0 - 20℃; for 12 h; Sealed tube To a solution of 4-bromo-2-fluoro-1-nitrobenzene (5 g, 22.7 mmol) in MeOH (5 mL), maintained at 0°C in a sealed tube, was added methanolic ammonia (15 mL). The reaction mixture was stirred at room temperature for 12 h, then concentrated. The crude residue was triturated with pentane and Et20 to afford the title compound (4.5 g, 91percent), which was used for the next step without any further purification. H (400 MHz, CD3OD) 7.93 (d,J9.1 Hz, 1H), 7.18 (d,J2.1 Hz, 1H), 6.74 (dd,J9.2, 2.1 Hz, 1H).
Reference: [1] Patent: US2015/152065, 2015, A1, . Location in patent: Paragraph 0498
[2] Patent: WO2015/86508, 2015, A1, . Location in patent: Page/Page column 75; 76
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1939 - 1943
  • 11
  • [ 593-56-6 ]
  • [ 586-78-7 ]
  • [ 5228-61-5 ]
YieldReaction ConditionsOperation in experiment
75% With potassium <i>tert</i>-butylate; copper(l) chloride In DMF (N,N-dimethyl-formamide); 1,2-dimethoxyethane at 0 - 20℃; for 4.71667 h; Step 1. 5-BromO-2-nitro-phenylamine (2); [0176] To a solution of potassium tert-butoxide (14.5 g; 129.2 MMOL) and copper (L) chloride (301 mg ; 3.04 MMOL) in ETHYLENEGLYCOL DIMETHYLETHER (120 mL), stirred at 0°C under nitrogen, a solution of 1-bromo-4-nitro-benzene (1,6. 141 g; 30.4 MMOL) and 0-methyl-hydroxylamine hydrochloride (3.174 g; 38 MMOL) in N, NDIMETHYLFORMAMIDE (65 mL) was added drop wise over 103 min, the cooling bath was removed and the mixture was allowed to react at room temperature for 3h, diluted with ethyl acetate (600 mL) and washed with saturated aqueous ammonium chloride. The organic layer was dried (MGS04), filtered and concentrated. After purification by flash chromatography (eluent 25percent ethyl acetate in hexane), 4.96 g (75percent yield) of compound 2 were obtained. [0177] H NMR: (400.2 MHz, CDCI3) 8 (ppm): 7.98 (d, J=9.24, 1H); 7.02 (d, J=1. 98,1H) ; 6.82 (dd, J=1.98 and 9.24, 1H); 6.12 (bs, 2H).
Reference: [1] Patent: WO2005/30704, 2005, A1, . Location in patent: Page/Page column 138
  • 12
  • [ 621-38-5 ]
  • [ 5228-61-5 ]
  • [ 40787-96-0 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 693
[2] Chem. Zentralbl., 1929, vol. 100, # I, p. 1683
[3] Journal of the American Chemical Society, 1937, vol. 59, p. 2381
  • 13
  • [ 108-36-1 ]
  • [ 5228-61-5 ]
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
[3] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
  • 14
  • [ 610-38-8 ]
  • [ 5228-61-5 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1902, vol. 21, p. 421
[2] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[3] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 15
  • [ 873983-28-9 ]
  • [ 5228-61-5 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2400
  • 16
  • [ 343864-78-8 ]
  • [ 7664-41-7 ]
  • [ 5228-61-5 ]
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
  • 17
  • [ 51686-78-3 ]
  • [ 7664-41-7 ]
  • [ 5228-61-5 ]
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
  • 18
  • [ 7664-93-9 ]
  • [ 591-19-5 ]
  • [ 5228-61-5 ]
  • [ 40787-96-0 ]
Reference: [1] Chem. Zentralbl., 1929, vol. 100, # I, p. 1683
  • 19
  • [ 5228-61-5 ]
  • [ 21745-41-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
  • 20
  • [ 5228-61-5 ]
  • [ 59483-54-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
  • 21
  • [ 5228-61-5 ]
  • [ 16293-12-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 17, p. 4790 - 4793
  • 22
  • [ 621-38-5 ]
  • [ 5228-61-5 ]
  • [ 40787-96-0 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 693
[2] Chem. Zentralbl., 1929, vol. 100, # I, p. 1683
[3] Journal of the American Chemical Society, 1937, vol. 59, p. 2381
  • 23
  • [ 7664-93-9 ]
  • [ 591-19-5 ]
  • [ 5228-61-5 ]
  • [ 40787-96-0 ]
Reference: [1] Chem. Zentralbl., 1929, vol. 100, # I, p. 1683
  • 24
  • [ 5228-61-5 ]
  • [ 147021-89-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4367 - 4379
  • 25
  • [ 5228-61-5 ]
  • [ 557-21-1 ]
  • [ 99512-10-4 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: at 20℃; for 0.75 h;
Stage #2: at 90℃; for 18 h;
Step 1: 3-Amino-4-nitrobenzonitrile (274) [0431] A suspension of bromoarene 2 (801mg; 3.7 MMOL) and zinc cyanide (570mg; 4. 85MMOL ; 1. 3eq. ) in degassed DIMETHYLFORMAMIDE (15 mL) was stirred at room temperature under nitrogen in the dark for 45 min and then treated with tetrakis (TRIPHENYLPHOSPHINE) PALLADIUM (O) (310mg, 1. 6MMOL). The mixture was stirred at 90°C for 18h; filtered through a celite pad, concentrated under reduced pressure and purified by flash chromatography on silica gel, eluent EtOAc-hexane (1 : 1) to afford the title compound 274 (380 mg, 63percent YIELD). H NMR: (400.2 MHz, CDCI3) 8 (ppm): 8.22 (d, J=8.6 Hz; 1H); 7.19 (d, J=1.8 Hz; 1H) ; 6.95 (dd, J=1.8, 8.6 Hz; 1H) ; 6.27 (bs; 2H). MS: CALC : 163.1 ; found: 164.1 (M+H)
Reference: [1] Patent: WO2005/30704, 2005, A1, . Location in patent: Page/Page column 243
  • 26
  • [ 5228-61-5 ]
  • [ 1256387-74-2 ]
Reference: [1] Patent: CN105399657, 2016, A,
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