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[ CAS No. 116230-30-9 ] {[proInfo.proName]}

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Chemical Structure| 116230-30-9
Chemical Structure| 116230-30-9
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Product Details of [ 116230-30-9 ]

CAS No. :116230-30-9 MDL No. :MFCD00277644
Formula : C10H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :VWSBGGRCEQOTNU-UHFFFAOYSA-N
M.W : 223.07 Pubchem ID :613827
Synonyms :

Calculated chemistry of [ 116230-30-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.67
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 2.95
Log Po/w (WLOGP) : 3.31
Log Po/w (MLOGP) : 3.24
Log Po/w (SILICOS-IT) : 3.16
Consensus Log Po/w : 2.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0447 mg/ml ; 0.0002 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.205 mg/ml ; 0.000918 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.36
Solubility : 0.0098 mg/ml ; 0.000044 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 116230-30-9 ]

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 [ 116230-30-9 ]

* 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 [ 116230-30-9 ]
  • Downstream synthetic route of [ 116230-30-9 ]

[ 116230-30-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 582-17-2 ]
  • [ 116230-30-9 ]
YieldReaction ConditionsOperation in experiment
84% With bromine; triphenylphosphine In acetonitrile at 0 - 250℃; for 1.5 h; A synthetic procedure was based on the literature method [12]. To a vigorously stirred mixture of triphenylphosphine (31.5g, 120mmol) in acetonitrile (50.0mL), bromine (19.2g, 120mmol) was added dropwise at 0°C. The reaction mixture was allowed to reach room temperature, and 2,7-dihydroxynaphthalene 1 (16.0g, 100mmol) was added in one portion. The mixture was heated to 70°C for 30min, after which the solvent was removed by rotary evaporation. The flask was equipped with a gas trap, and the black residue was heated to 250°C for 1h. After cooling to room temperature, the mixture was dissolved in 200mL of dichloromethane and the viscous liquid was obtained after column chromatography (silica gel, petroleum ether/dichloromethane 1:1). The crude product was purified by column chromatography (silica gel, petroleum ether/dichloromethane 3:2) to give the compound 2 (18.8g, 84.3mmol, 84percent) as a beige powder. 1H NMR (400MHz, CDCl3) δ (ppm): 5.09 (s, 1H, –OH), 7.06 (d, 1H, J 2.4Hz, naphthalene-H), 7.10 (dd, 1H, J 8.8, 2.8Hz, naphthalene-H), 7.24 (dd, 1H, J 8.8, 2.0Hz, naphthalene-H), 7.63 (d, 1H, J 8.8Hz, naphthalene-H), 7.72 (d, 1H, J 8.8Hz, naphthalene-H), 7.84 (d, 1H, J 1.2Hz, naphthalene-H). 13C NMR (100MHz, CDCl3) δ (ppm): 108.7, 118.1, 120.8, 127.0, 127.3, 128.3, 129.4, 129.9, 135.7, 154.0. HR-ESI-MS m/z: [M−H] calcd. for C10H6BrO, 220.9602; found, 220.9601.
66% With bromine; triphenylphosphine In acetonitrile at 70℃; for 1 h; Schlenk technique To a stirring suspension of Triphenyl phosphine (31.5 g) in Acetonitrile (50 mL) in a 250 mL10 Schlenk-flaskwas added carefully Bromine (6.2 mL) at 0 00 with a syringe over 30 mm. The yellow solution was warmed to room temperature and 2,7-Dihydroxynaphthalene (16 g) was added in one portion. The reaction was refluxed at 70 00 for one hour. After cooling to room temperature, the solvent was removed under reduced pressure. The reaction flask was connected to a gas-washing bottle filled with a concentrated sodium hydroxide solution. The flask was heatedto 250 00 for two hours and the black residue dissolved in 100 mL Dichloromethane and purified via column chromatography (DCM:Pentan 1:1 to pure DCM). Product 101 was received as a beige powder (14.7 g, 66percent)DC: Dichloromethane:Pentane, 1:1, R=0,21H-NMR: (300 MHz, ODd3) = 7.76 (d, 1 H), 7.63 (d, 1 H), 7.54 (d, 1 H), 7.32 (dd, 1 H), 7.03 (dd, 1H), 6.98 (d, 1H), 4.98 (b, 1H)
43%
Stage #1: With bromine; triphenylphosphine In acetonitrile at 10℃; for 0.166667 h;
Stage #2: for 3 h; Heating / reflux
Stage #3: at 280 - 310℃; for 1.08333 h; Neat (no solvent)
Preparation 2 [0100] Preparation of 2-Bromo-7-methoxy-naphthalene. [CHEMMOL-00021] [0101] Preparation of 7-Bromo-2-naphthalenol. [0102] Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10° C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off under a water aspirator pressure over 2 hours, resulting in a grayish white solid. The solid was heated to 280° C. over 30 minutes giving a black liquid. The liquid was heated to 310° C. over 20 minutes and the temperature was maintained at 310° C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87percent pure by HPLC (43percent yield).
43%
Stage #1: With bromine; triphenylphosphine In acetonitrile for 3 h; Heating / reflux
Stage #2: at 280 - 310℃; for 1.08333 h;
Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10° C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280° C. over 30 minutes giving a black liquid. The liquid was heated to 310° C. over 20 minutes and the temperature was maintained at 310° C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87percent pure by HPLC (43percent yield).
43%
Stage #1: With bromine; triphenylphosphine In acetonitrile at 10 - 20℃;
Stage #2: for 3 h; Heating / reflux
Stage #3: at 20 - 310℃; for 1.08333 h; Neat (no solvent)
Triphenyl phosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were combined in a 1-L flask under N2 atmosphere. The mixture was cooled to 10 C. Bromine (17.6 mL, 0.342 mol) was added dropwise over 10 minutes. The cooling bath was removed and 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added along with 350 mL of CH3CN rinse. The resulting yellow tan mixture was heated at reflux for 3 hours. Acetonitrile was distilled off using a water aspirator over 2 hours resulting in a grayish white solid. The solid was heated to 280 C. over 30 minutes giving a black liquid. The liquid was heated to 310 C. over 20 minutes and the temperature was maintained at 310 C. for an additional 15 minutes until gas evolution ceased. The black mixture was cooled to room temperature. Chromatography yielded 34.5 g of the intermediate title compound as an off-white solid which was 87percent pure by HPLC (43percent yield).

Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 13, p. 4541 - 4552
[2] Dyes and Pigments, 2014, vol. 107, p. 174 - 181
[3] Patent: WO2015/121785, 2015, A1, . Location in patent: Page/Page column 32; 33
[4] Helvetica Chimica Acta, 1999, vol. 82, # 7, p. 981 - 1004
[5] Chemical Communications, 2012, vol. 48, # 5, p. 750 - 752
[6] Helvetica Chimica Acta, 2000, vol. 83, # 11, p. 2865 - 2883
[7] Patent: US2004/6229, 2004, A1, . Location in patent: Page/Page column 14
[8] Patent: US2003/232833, 2003, A1, . Location in patent: Page 13
[9] Patent: US2003/225281, 2003, A1, . Location in patent: Page 13
[10] European Journal of Organic Chemistry, 2000, # 3, p. 491 - 497
  • 2
  • [ 5060-82-2 ]
  • [ 116230-30-9 ]
YieldReaction ConditionsOperation in experiment
19%
Stage #1: With bromine; triphenylphosphine In acetonitrile for 2 h; Reflux
Stage #2: at 250℃; Sealed tube
  Triphenylphosphine (500 mg, 2.9 mmol) was dissolved in   MeCN (5 mL), and   bromine (0.15 mL, 2.9 mmol) was added at 0 °C whilst stirring. The solution was allowed to warm up to rt, and   7-methoxy-naphthalen-2-ol, 44 (490 mg, 2.8 mmol) was added portionwise. The solution was refluxed for 2 h, and the solvent removed in vacuo. The residue was heated to 250 °C in a sealed tube overnight. After cooling to rt, the residue was purified by chromatography using a stepped gradient of 10–20percent   EtOAc in   heptane to yield   45 as a beige solid. Yield: 120 mg (19percent). 1H NMR (CDCl3), δ: 5.17 (br, 1H, OH), 7.06 (d, J = 2.5, 1H, ArH), 7.11 (dd, J = 8.7, 2.4, 1H, ArH), 7.40 (dd, J = 8.7, 2.0, 1H, ArH), 7.63 (d, J = 8.9, 1H, ArH), 7.72 (d, J = 8.9, 1H, ArH), 7.84 (s, 1H, ArH). LC–MS: Rf = 2.01 min; m/z 221/223 ([M+H]+, 100).
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1284 - 1304
  • 3
  • [ 709667-62-9 ]
  • [ 116230-30-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, vol. 1, p. 253[2] Chem. Zentralbl., 1929, vol. 100, # II, p. 573
  • 4
  • [ 861072-57-3 ]
  • [ 116230-30-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, vol. 1, p. 253[2] Chem. Zentralbl., 1929, vol. 100, # II, p. 573
  • 5
  • [ 116230-30-9 ]
  • [ 130200-58-7 ]
YieldReaction ConditionsOperation in experiment
83% at 160℃; for 3 h; Inert atmosphere Weigh 7-bromo-2-naphthol (2.22g, 10mmol), CuCN (1.08g, 12mmol) was dissolved in 3ml of DMF. Under an argon atmosphere and heated to 160 reflux 3h, track after the reaction of the reaction was cooled to room temperature, 20ml of water, extracted with ethyl acetate. Ethanol - water system recrystallization brown powder 1.4g, 83percent yield.
Reference: [1] Patent: CN105566276, 2016, A, . Location in patent: Paragraph 0251; 0252; 0253; 0254
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