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[ CAS No. 15969-10-5 ] {[proInfo.proName]}

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Chemical Structure| 15969-10-5
Chemical Structure| 15969-10-5
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Product Details of [ 15969-10-5 ]

CAS No. :15969-10-5 MDL No. :MFCD00024243
Formula : C6H3BrClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :POBOBTAMSJHELX-UHFFFAOYSA-N
M.W : 252.45 Pubchem ID :291871
Synonyms :

Calculated chemistry of [ 15969-10-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.0
TPSA : 66.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 4.06
Log Po/w (WLOGP) : 2.72
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 0.58
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.27
Solubility : 0.0137 mg/ml ; 0.0000541 mol/l
Class : Moderately soluble
Log S (Ali) : -5.15
Solubility : 0.00178 mg/ml ; 0.00000706 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.532 mg/ml ; 0.00211 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 15969-10-5 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3077
Hazard Statements:H302-H315-H317-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 15969-10-5 ]

* 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 [ 15969-10-5 ]
  • Downstream synthetic route of [ 15969-10-5 ]

[ 15969-10-5 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 695-96-5 ]
  • [ 15969-10-5 ]
YieldReaction ConditionsOperation in experiment
95% With sodium nitrate; sulfuric acid; acetic acid In water at 25 - 30℃; Large scale The reaction flask was successively added with acetic acid (7.5 L) 4-chloro-2-bromophenol (1500.0 g, 7.2 mol) was stirred well;Sodium nitrate was added dropwise at room temperature(1229.0 g, 14.5 mol)And concentrated sulfuric acid(1418.0 g, 14.5 mol) in water (1.4 L);After the drop, the temperature control 25-30°C reaction about 20-30min;The reaction was stopped and poured into ice water (7.5 L) and stirred for 20 min.The filter cake was washed with water until the filtrate was near neutral (pH 6-7). The filter cake was dried to obtain a yellow solid: 1742 g, yield: 95percent.
80.1% With nitric acid In water; acetic acid (a)
2-bromo-4-chloro-6-nitro-phenol
A solution of 2-bromo-4-chloro-phenol (99.24 g, 480 mmol) in acetic acid (110 ml) and acetic anhydride (125 ml) was cooled to -10°C. Within 1 hour a solution containing 100percent nitric acid (33 ml) and acetic acid (40 ml) was added between -10° and -5°C, with stirring.
The mixture was stirred for an additional 1.5 hours at 0-5 °C, then the suspension poured onto 300 g of ice in 700 ml of water and stirred for a further 0.5 hour.
The solid was collected, washed, and dried to give 97.12 g (80.1percent) of the title compound (mp 121-2°C).
Reference: [1] Patent: CN106146330, 2016, A, . Location in patent: Paragraph 0062-0064
[2] Journal of the American Chemical Society, 1933, vol. 55, p. 2125,2129
[3] Journal of Organic Chemistry, 1946, vol. 11, p. 641,644
[4] Patent: EP1160247, 2001, A1,
  • 2
  • [ 89-64-5 ]
  • [ 15969-10-5 ]
YieldReaction ConditionsOperation in experiment
90.9% at 5 - 20℃; Example 116; 1-[6-Chloro-8-(1H-pyrazol-4-yl)-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbonyl]-4-(4-fluoro-benzyl)-piperidine-4-carbonitrile Step-1: 2-Bromo-4-chloro-6-nitro-phenolTo a solution of 4-chloro-2-nitrophenol (1 g, 5.76 mmol) in acetic acid was added bromine (0.32 ml, 6.3 mmol) at 5-10° C. and stirred at 10° C. for half an hour. The temperature of the reaction mixture was raised to room temperature and stireed at RT for 3 hours. The reaction mixture was diluted with ice-water and extracted with ethyl acetate. The organic layer was washed with ethyl acetate and dried over sodium sulfate. Concentration of organic layer was afforded 1.3 g (90.9percent) of 2-Bromo-4-chloro-6-nitro-phenol. GCMS [m/z]: 253.0. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 11.1 (s, 1H), 8.10 (d, 1H), 8.04 (d, 1H).
84% at 5 - 20℃; for 3.5 h; [0054] A solution of 4-chloro-2-nitrophenol (4) (3.12 g, 18.0 mmol) in acetic acid (25 mL) was cooled to 5-10 °C, and bromine (1.0 mL, 19.7 mmol) was added dropwise. The reaction mixture was stirred for half an hour at 10 °C and then for 3 hours at room temperature. The mixture was then diluted with ice- water and extracted with dichloromethane (DCM) (3x30 mL). The combined organic extracts were washed with brine (30 mL) and dried over anhydrous Na2S04. The solvent was then evaporated to give the crude product which was recrystallized from 96 percent ethanol to afford a yellow crystalline product (lb) (3.80 g, 84percent, purity 99percent, HPLC Method B). 1H NMR (600 MHz, DMSO-d6) δ: 8.02 (d, J= 2.6 Hz, 1H), 8.09 (d, J= 2.6 Hz, 1H) ppm; 1H NMR (300 MHz, CDC13) δ: 7.86 (d, J= 2.6 Hz, 1H), 8.11 (d, J= 2.6 Hz, 1H), 11.03 (1H, s, OH);13C NMR (150 MHz, DMSO-d6) δ: 114.90, 123,38, 123.97, 137.67, 137.77, 148.12 ppm; MS m/z [M-H]" 252.1.
76% at 20℃; for 4 h; Cooling with ice Step 1: 4-chloro-2-nitrophenol (1.0 equiv.) was dissolved in Acetic Acid (0.64 M) and cooled in an ice-bath. To the mixture was then added bromine (1.1 equiv.) and the mixture agitated for 3 h while gradually warming to room temperature. Additional bromine (0.3 equiv.) was added. Then, after additional hour, almost complete conversion to the desired product is observed. At this stage, ice-cold water was added and immediately, a yellowish suspension was observed. The mixture was vigirously agitated and then filtered. The yellowish orange precipitate was washed with water and then with heptane and the yellow powder was placed under high-vacuum for 3 days to afford 2-bromo-4-chloro-6- nilrophenol in 76percent yield. LCMS (rn/z) (M+H) = 291.9, Rt = 1.45 min.
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 14, p. 7388 - 7397
[2] Patent: US2010/152160, 2010, A1, . Location in patent: Page/Page column 111
[3] Patent: WO2013/49605, 2013, A1, . Location in patent: Paragraph 0054
[4] Patent: WO2016/38582, 2016, A1, . Location in patent: Paragraph 00335
[5] American Chemical Journal, 1904, vol. 32, p. 15
[6] Journal of the Chemical Society, 1887, vol. 51, p. 786[7] Journal of the Chemical Society, 1892, vol. 61, p. 577
  • 3
  • [ 106-48-9 ]
  • [ 15969-10-5 ]
Reference: [1] Organic Process Research and Development, 2004, vol. 8, # 4, p. 568 - 570
  • 4
  • [ 5324-13-0 ]
  • [ 15969-10-5 ]
Reference: [1] Journal of the American Chemical Society, 1933, vol. 55, p. 2125,2129
[2] Journal of Organic Chemistry, 1946, vol. 11, p. 641,644
  • 5
  • [ 92044-52-5 ]
  • [ 15969-10-5 ]
Reference: [1] Journal of the American Chemical Society, 1926, vol. 48, p. 2654
  • 6
  • [ 88-87-9 ]
  • [ 15969-10-5 ]
Reference: [1] Chem. News J. Ind. Sci., 1891, vol. 63, p. 222[2] Chem. Zentralbl., 1891, vol. 62, # I, p. 1031
  • 7
  • [ 573-56-8 ]
  • [ 15969-10-5 ]
Reference: [1] Chem. News J. Ind. Sci., 1891, vol. 63, p. 222[2] Chem. Zentralbl., 1891, vol. 62, # I, p. 1031
  • 8
  • [ 92044-52-5 ]
  • [ 7726-95-6 ]
  • [ 7553-56-2 ]
  • [ 15969-10-5 ]
Reference: [1] Journal of the American Chemical Society, 1926, vol. 48, p. 2654
  • 9
  • [ 695-96-5 ]
  • [ 7697-37-2 ]
  • [ 64-19-7 ]
  • [ 15969-10-5 ]
Reference: [1] Journal of Organic Chemistry, 1946, vol. 11, p. 641,644
  • 10
  • [ 88-87-9 ]
  • [ 7726-95-6 ]
  • [ 15969-10-5 ]
Reference: [1] Chem. News J. Ind. Sci., 1891, vol. 63, p. 222[2] Chem. Zentralbl., 1891, vol. 62, # I, p. 1031
  • 11
  • [ 89-64-5 ]
  • [ 7726-95-6 ]
  • [ 64-19-7 ]
  • [ 15969-10-5 ]
Reference: [1] American Chemical Journal, 1904, vol. 32, p. 15
[2] Journal of the Chemical Society, 1887, vol. 51, p. 786[3] Journal of the Chemical Society, 1892, vol. 61, p. 577
  • 12
  • [ 15969-10-5 ]
  • [ 376592-93-7 ]
Reference: [1] Patent: WO2013/49605, 2013, A1,
[2] Patent: CN106146330, 2016, A,
  • 13
  • [ 25487-66-5 ]
  • [ 15969-10-5 ]
  • [ 376592-58-4 ]
Reference: [1] Patent: WO2013/49605, 2013, A1, . Location in patent: Paragraph 0055
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