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[ CAS No. 827-24-7 ] {[proInfo.proName]}

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Chemical Structure| 827-24-7
Chemical Structure| 827-24-7
Structure of 827-24-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 827-24-7 ]

CAS No. :827-24-7 MDL No. :MFCD00209452
Formula : C7H7BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VFPKZASVVCBVMG-UHFFFAOYSA-N
M.W :231.05 Pubchem ID :2775306
Synonyms :

Calculated chemistry of [ 827-24-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.33
TPSA : 71.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 0.1
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.26
Solubility : 0.126 mg/ml ; 0.000543 mol/l
Class : Soluble
Log S (Ali) : -3.84
Solubility : 0.0333 mg/ml ; 0.000144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.499 mg/ml ; 0.00216 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 827-24-7 ]

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 [ 827-24-7 ]

* 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 [ 827-24-7 ]
  • Downstream synthetic route of [ 827-24-7 ]

[ 827-24-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 827-24-7 ]
  • [ 113882-33-0 ]
Reference: [1] Journal of Antibiotics, 1994, vol. 47, # 12, p. 1456 - 1465
  • 2
  • [ 827-24-7 ]
  • [ 70733-25-4 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium chloride; zinc In tetrahydrofuran; methanol at 40℃; for 1 h; 2-bromo-4-methyl-6-nitroaniline (5.00 g, 21.64 mmol) was dissolved in MeOH(148 mL) and THF (18.50 mL). Ammonium chloride (23.15 g, 433 mmol) then zinc (14.15 g, 216 mmol) were added and the reaction mixture was heated to 40 °C for lh. The reaction mixture was cooled to ambient temperature, concentrated in vacuo, re-dissolved in EtOAc and saturated Na2CO3, and stirred vigorously for 10 minutes. The mixture was filtered through a sintered glass funnel and washed with more EtOAc. Theorganic layer was further washed twice with water, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to yield Intermediate I-iSA (4.35 g, 21.63 mmol, 100 percent yield). ‘H NMR (400MHz, CHLOROFORM-d) 6.81 (s, 1H), 6.48 (s, 1H), 3.66 (br. s., 2H), 3.46 (br. s., 2H), 2.19 (s, 3H). LC-MS: method H, RT = 0.93 mm, MS (ESI) m/z: 201.0 (M+H)
100% With ammonium chloride; zinc In tetrahydrofuran; methanol at 40℃; for 1 h; 2-bromo-4-methyl-6-nitroaniline (5.00 g, 21.64 mmol) was dissolved in MeOH (148 mL) and THF (18.50 mL). Ammonium chloride (23.15 g, 433 mmol) then zinc (14.15 g, 216 mmol) were added and the reaction mixture was heated to 40 °C for lh. The reaction mixture was cooled to ambient temperature, concentrated in vacuo, re-dissolved in EtOAc and saturated Na2CO3, and stirred vigorously for 10 minutes. Themixture was filtered through a sintered glass funnel and washed with more EtOAc. The organic layer was further washed twice with water, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to yield Intermediate I-iSA (4.35 g, 21.63 mmol, 100 percent yield). ‘H NMR (400MHz, CHLOROFORM-d) 6.81 (s, 1H), 6.48 (s, 1H), 3.66 (br. s., 2H), 3.46 (br. s., 2H), 2.19 (s, 3H). LC-MS: method H, RT = 0.93 mm,MS (ESI) m/z: 201.0 (M+H)
Reference: [1] Patent: WO2018/13776, 2018, A1, . Location in patent: Page/Page column 98
[2] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 139
[3] Organic Letters, 2006, vol. 8, # 22, p. 4989 - 4992
[4] Chemische Berichte, 1890, vol. 23, p. 1044
  • 3
  • [ 89-62-3 ]
  • [ 827-24-7 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 2 h; 4-Methyl-2-nitroaniline (131.2 g, 862 mmol) was suspended in glacial acetic acid (1.25 L) and bromine (54 mL, 1.05 mol) added over 1 h at ambient temperature. The reaction mixture was stirred for 1 h, poured into water (7.5 L) and the suspension stirred for 30 min. The solid was filtered, washed with water (5 .x. 1 L) and dried to give 21 (187.2 g, 94percent) as an orange solid: 1H NMR δ (CDCl3) 7.94 (1H, s), 7.56 (1H, s), 6.47 (2H, br s), 2.27 (3H, s).
83% With sodium chlorate; hydrogen bromide In water; acetic acid at 5 - 45℃; General procedure: To a stirring solution of 2-chloro-4-methylaniline or 4-methyl-2-nitroaniline (0.1 mol) in acetic acid (70 mL) cooled to 5 °C, 48percent aqueous HBr (0.3 mol, 33.6 mL) was added in one portion. A solution of sodium chlorate (33 mmol, 3.51 g) in water (18 mL) was added dropwise (the temperature of the mixture was kept below 45 °C), and the mixture was stirred at r.t. for 1 h. The precipitated product was filtered, washed with water (50 mL) and dried.
Reference: [1] Organic Letters, 2006, vol. 8, # 22, p. 4989 - 4992
[2] Chemistry - A European Journal, 2015, vol. 21, # 52, p. 18915 - 18920
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 3, p. 281 - 288
[4] Journal of Antibiotics, 1994, vol. 47, # 12, p. 1456 - 1465
[5] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 20, p. 6026 - 6032
[6] European Journal of Inorganic Chemistry, 2013, # 27, p. 4858 - 4866
[7] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 2, p. 597 - 599
[8] Inorganic Chemistry, 2018, vol. 57, # 16, p. 10028 - 10039
[9] Journal of Chemical Research, Synopses, 1997, # 11, p. 432 - 433
[10] Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 1040 - 1043
[11] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5568 - 5572
[12] Journal of Chemical Research, Synopses, 1995, # 11, p. 457
[13] Archiv der Pharmazie (Weinheim, Germany), 2002, vol. 335, # 1, p. 15 - 21
[14] Chemische Berichte, 1880, vol. 13, p. 963[15] Chemische Berichte, 1881, vol. 14, p. 417
[16] Helvetica Chimica Acta, 1988, vol. 71, p. 897 - 930
[17] Patent: US5633218, 1997, A,
[18] Patent: WO2003/72539, 2003, A1, . Location in patent: Page/Page column 78
  • 4
  • [ 614-83-5 ]
  • [ 827-24-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1878, vol. 192, p. 203
[2] Journal of the Chemical Society, 1914, vol. 105, p. 514
  • 5
  • [ 70733-24-3 ]
  • [ 827-24-7 ]
Reference: [1] Journal of the Chemical Society, 1914, vol. 105, p. 514
  • 6
  • [ 409321-38-6 ]
  • [ 64-19-7 ]
  • [ 98-11-3 ]
  • [ 827-24-7 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 918
  • 7
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 89-62-3 ]
  • [ 827-24-7 ]
Reference: [1] Chemische Berichte, 1880, vol. 13, p. 963[2] Chemische Berichte, 1881, vol. 14, p. 417
  • 8
  • [ 827-24-7 ]
  • [ 124289-22-1 ]
Reference: [1] Journal of Antibiotics, 1994, vol. 47, # 12, p. 1456 - 1465
[2] Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 1040 - 1043
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