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Chemical Structure| 102170-56-9
Chemical Structure| 102170-56-9
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Product Details of [ 102170-56-9 ]

CAS No. :102170-56-9 MDL No. :MFCD00053089
Formula : C7H7BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DCNWQCOXGLGSRC-UHFFFAOYSA-N
M.W :231.05 Pubchem ID :293073
Synonyms :

Calculated chemistry of [ 102170-56-9 ]

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 : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 0.1
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.279 mg/ml ; 0.00121 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.124 mg/ml ; 0.000537 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 : 2.1

Safety of [ 102170-56-9 ]

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 [ 102170-56-9 ]

* 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 [ 102170-56-9 ]
  • Downstream synthetic route of [ 102170-56-9 ]

[ 102170-56-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 102170-56-9 ]
  • [ 603-78-1 ]
Reference: [1] Chemische Berichte, 1880, vol. 13, p. 963[2] Chemische Berichte, 1881, vol. 14, p. 417
  • 2
  • [ 99-52-5 ]
  • [ 102170-56-9 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; for 1.16667 h; To a suspension of 2-methyl-4-nitroaniline (10.0 g, 65.7mrnol) in glacial acetic acid (100 rnL) at 20 °C was added bromine (3.4 mL, 66 rnmoi) dropwiseover 40 mm. The mixture was stirred at 20 °C for another 30 mm. Then water (100 rnL) was added, and the resulting precipitate was collected by filtration and dried in vaeuo at 80 °C for 6 h to yield the title compound (14.1 g, 99percent) as a yellow solid. MS (ESi): mass calcd. for C7HBrN2O2 23 0.0, m/z found 231 [M+Hft. ‘H NMR (300 MHz, DMSO-d6) ö 8.13 (d, J = 2.2 Hz, iH), 7.89 (d, J= 1.5 Hz, IH), 6.48 (s, 2H), 2.22 (s, 3H).
91% With N-Bromosuccinimide In acetonitrile at 60℃; for 3 h; To a solution of 2-methyl-4-nitroaniline (2.0 g, 13.2 mmol) inacetonitrile (40 mL) was added N-bromosuccinimide (2.8 g,15.8 mmol) at 60 C. The mixture was heated to reflux for 3 h andthen cooled to room temperature. The mixture was evaporated anddiluted with dichloromethane (50 mL). The organic layer waswashed with 2.5MNaOH and brine, dried over Na2SO4, filtered, andevaporated. The residue was purified by silica gel chromatography(n-hexane/ethyl acetate, 4/1, v/v) to give 2-bromo-6-methyl-4-nitroaniline as a yellow solid (2.75 g, 91percent). Mp: 178e179 C. Rf:0.40 (n-hexane/ethyl acetate, 5/1, v/v). 1H NMR (DMSO-d6,400 MHz) d 8.15 (d, J 2.5 Hz, 1H), 7.93 (d, J 2.1 Hz, 1H), 6.53 (s,2H), 2.23 (s, 3H). MS (ESI) m/z:228.5 [MH]-.
Reference: [1] Patent: WO2016/176460, 2016, A1, . Location in patent: Page/Page column 97
[2] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 2, p. 597 - 599
[3] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
[4] Journal of the Chemical Society, 1929, p. 1255
[5] Bulletin de la Societe Chimique de France, 1924, vol. <4>35, p. 1328
[6] Chemische Berichte, 1880, vol. 13, p. 963[7] Chemische Berichte, 1881, vol. 14, p. 417
  • 3
  • [ 139291-81-9 ]
  • [ 102170-56-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 4, p. 437 - 448
  • 4
  • [ 10035-10-6 ]
  • [ 7722-84-1 ]
  • [ 99-52-5 ]
  • [ 102170-56-9 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1924, vol. <4>35, p. 1328
  • 5
  • [ 102170-56-9 ]
  • [ 175610-68-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 4, p. 391 - 392
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 4, p. 437 - 448
  • 6
  • [ 102170-56-9 ]
  • [ 685109-10-8 ]
YieldReaction ConditionsOperation in experiment
49% With acetic acid; sodium nitrite In water at 20℃; for 1 h; Cooling with ice To a solution of 2-bromo-6-methyi-4-nitroaniline (14.1 g,61.0 mmol) in glacial acetic acid (162 mL) was added a solution of sodium nitrite (6.32 g, 91.Smmol) in water (14 mL) dropwise over 10 mm. During this time, the reaction solution was cooled in an ice bath to maintain an internal reaction temperature below 25 °C. The reaction was stirred at 20 °C for 1 hr. The reaction solution was concentrated in vaeuo, and the residue wastriturated with I : 1 methanoi:water, The resulting precipitate was collected by filtration, and dried in vaeuo at 80 °C for 6 hr to afford the title compound (10.4 g, 49percent) as a red solid. MS (ESI): mass calcd. for C71-L,BrN3O2 241.0. m/z found 242 [M±Hf, ‘H NMR (300 MHz, DMSO-d6) 15 8.84 (s. 1H), 8.53 (s, 1H), 8.37 (s, 11-i),
49% With acetic acid; sodium nitrite In water at 0 - 20℃; for 12.17 h; General procedure: To a 0 °C solution of 2-chloro-6-methyl-4-nitroaniline (15a)(0.9 g, 4.9 mmol) in glacial acetic acid (18 mL) was added a solutionof NaNO2 (0.40 g, 5.8 mmol) in 4 mL water dropwise over a periodof 10 min with stirring. The mixture was allowed to warm to roomtemperature and stirred for 12 h. The precipitate was removed byfiltration of the reaction mixture through a pad of Celite. The filtratewas poured into H2O (100 mL); the solid was collected by filtrationand purified by silica gel column chromatography (DCM/MeOH100:1 as eluent) to afford 16a as a light brown solid (0.50 g, 52percent).
Reference: [1] Patent: WO2016/176460, 2016, A1, . Location in patent: Page/Page column 97
[2] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
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