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[ CAS No. 180624-08-2 ] {[proInfo.proName]}

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Chemical Structure| 180624-08-2
Chemical Structure| 180624-08-2
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Product Details of [ 180624-08-2 ]

CAS No. :180624-08-2 MDL No. :MFCD11110560
Formula : C6H4BrIN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CUVSESOKQSEEHQ-UHFFFAOYSA-N
M.W : 342.92 Pubchem ID :10688709
Synonyms :

Calculated chemistry of [ 180624-08-2 ]

Physicochemical Properties

Num. heavy atoms : 12
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 : 60.09
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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 1.95
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.13
Solubility : 0.0251 mg/ml ; 0.0000733 mol/l
Class : Moderately soluble
Log S (Ali) : -4.13
Solubility : 0.0253 mg/ml ; 0.0000739 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.223 mg/ml ; 0.000652 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.75

Safety of [ 180624-08-2 ]

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 [ 180624-08-2 ]

* 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 [ 180624-08-2 ]
  • Downstream synthetic route of [ 180624-08-2 ]

[ 180624-08-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 875-51-4 ]
  • [ 180624-08-2 ]
YieldReaction ConditionsOperation in experiment
88% With iodine; silver sulfate In ethanol at 20℃; for 18 h; 4-Bromo-2-iodo-6-nitroaniline.4-Bromo-2-nitroaniline (14.3g, 0.0659 mol) was added in one portion to iodine (17.6g, 0.0692 mol) dissolved in ethanol (30OmI)1 followed by silver (I) sulphate (20.4g 0.0659 mol). After stirring at ambient temperature for 18 hours the reaction was <n="16"/>filtered and the solid obtained was washed with dichloromethane until all the orange product had dissolved. The combined filtrates were evaporated in vacuo and the resulting solid was washed with diethyl ether/ 40-60 Petroleum ether (1 :1 ) and filtered to give 4-bromo-2-iodo-6-nitroaniline as an orange solid (19.8 g, 88percent), which was used without further purification. 1H NMR (400MHz,δ,CDCI3): 6.15(2H,br s), 8.00(1 H,s), 8.42(1 H,s).
81% With iodine; silver sulfate In ethanol at 20℃; 4-bromo-2-nitroaniline (1.4 g, 6.45 mmol) was added to iodine (1.801 g, 7.10 mmol) in EtOH (30 mL), followed by silver sulfate (2.213 g, 7.10 mmol). The reaction mixture was stirred at room temperature overnight and filtered. The solid was washed with EtOAc. The filtrate was concentrated. The crude product was dissolved in a small amount of chloroform and charged to a 120 g silica gel cartridge which was eluted with 5percent for 3 min., then an 18 min gradient from 5percent to 40percent. The desired fractions were combined and concentrated to give Intermediate 1A (1.8 g, 5.25 mmol, 81percent yield) as a brown solid. H1 NMR (500 MHz, methanol-d4) δ 8.25(d, J=2.2 Hz, 1H), 8,04(d, J=2.2 Hz, 1H); LC-MS: method A, RT=2.08 min; No MS (ESI) was observed;
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5804 - 5812
[2] Patent: WO2007/148093, 2007, A1, . Location in patent: Page/Page column 14-15
[3] Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 10627 - 10635
[4] RSC Advances, 2018, vol. 8, # 54, p. 30761 - 30776
[5] Patent: WO2017/19828, 2017, A1, . Location in patent: Page/Page column 57
[6] Journal of the Chemical Society, 1928, p. 783
  • 2
  • [ 88-74-4 ]
  • [ 180624-08-2 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 783
[2] Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 10627 - 10635
  • 3
  • [ 180624-08-2 ]
  • [ 165669-16-9 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 17, p. 5804 - 5812
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