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[ CAS No. 580-13-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 580-13-2
Chemical Structure| 580-13-2
Chemical Structure| 580-13-2
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Product Details of [ 580-13-2 ]

CAS No. :580-13-2 MDL No. :MFCD00004051
Formula : C10H7Br Boiling Point : -
Linear Structure Formula :- InChI Key :APSMUYYLXZULMS-UHFFFAOYSA-N
M.W :207.07 Pubchem ID :11372
Synonyms :

Calculated chemistry of [ 580-13-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.65
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -4.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 3.65
Log Po/w (WLOGP) : 3.6
Log Po/w (MLOGP) : 4.05
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.1
Solubility : 0.0166 mg/ml ; 0.0000802 mol/l
Class : Moderately soluble
Log S (Ali) : -3.34
Solubility : 0.0949 mg/ml ; 0.000458 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.93
Solubility : 0.00243 mg/ml ; 0.0000117 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.28

Safety of [ 580-13-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P337+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 580-13-2 ]

* 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 [ 580-13-2 ]
  • Downstream synthetic route of [ 580-13-2 ]

[ 580-13-2 ] Synthesis Path-Upstream   1~27

  • 1
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 525,535
  • 2
  • [ 5438-13-1 ]
  • [ 10035-10-6 ]
  • [ 7705-08-0 ]
  • [ 580-13-2 ]
  • [ 90-11-9 ]
  • [ 13720-06-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 525,535
  • 3
  • [ 580-13-2 ]
  • [ 51934-39-5 ]
Reference: [1] Patent: WO2008/100480, 2008, A1,
  • 4
  • [ 580-13-2 ]
  • [ 50637-83-7 ]
Reference: [1] Patent: WO2011/54834, 2011, A1,
[2] Patent: WO2012/13643, 2012, A1,
[3] Patent: US2012/219594, 2012, A1,
[4] Patent: US2015/23913, 2015, A1,
[5] Patent: WO2015/5901, 2015, A1,
  • 5
  • [ 580-13-2 ]
  • [ 75-36-5 ]
  • [ 1590-25-6 ]
YieldReaction ConditionsOperation in experiment
49% With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h; 2-bromo-naphthalene (0.5 g, 2.41 mmol), AlCl3 (0.338 g, 2.53 mmol) and AcCl (0.172 mL, 2.41 mmol) weredissolved in 3.4 mL of nitrobenzene, and stirred at 100°C for 4 hours under reflux. After addition of water, the reactionsolution extracted with EtOAc. The organic layer was separated, dried with MgSO4 and purified by column chromatographyto obtain the title compound (0.3 g, 49percent).1H-NMR (CDCl3) δ 8.43 (1H, s), 8.06 (2H, m), 7.82 (2H, t), 7.63 (1H, m), 2.72 (3H, s).
42%
Stage #1: With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h;
Stage #2: With water In nitrobenzene
A mixture of 2-bromonaphthalene (950 g, 4589 mmol), acetyl chloride (260 mL,4589 mmol), nitrobenzene (6000 mL) and aluminum chloride (642.2 g, 4818 mmol) was stirred for 4 hours at 100°C. The mixture was poured onto ice water, the resulting slurry was filtrated and the organic phase separated from the filtrate. The organic phase was washed with water (2000 mL), dried over Na2S04 and filtrated. The solvent was removed by distillation. The residue was re-crystallized from a solution of hexane: ethyl acetate (10: 1) resulting in l-(6-bromonaphthalen-2-yl)ethanone (480 g, 42percent yield).
37% With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h; Into a four-necked flask of 500 ml,Then, 41.4 g of 2-bromonaphthalene, 15.7 g of acetyl chloride, 28 g of aluminum chloride and 250 mℓ of nitrobenzene were charged and stirred at 100 ° C. for 4 hours.Then, upon reaching below cooling to 30 ° C., the reaction mixture was poured into ice water, was removed and the precipitated precipitate was filtered off.The filtrate after washing twice with water 100 ml, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The residue is recrystallized from hexane to give 18.42g of 2-bromo-6-acetyl naphthalene. (Yield 37.0percent)1H-NMR (400 MHz, CDCl3): δH 2.71 (s, 3H), 7.63 (dd, 1H), 7.80 (d, 1H), 7.82 (d, 2H), 8.05 (M, 2 H), 8.42 (s, 1 H)
36%
Stage #1: With aluminum (III) chloride In nitrobenzene at 100℃; for 4 h;
Stage #2: With water In nitrobenzeneCooling with ice
Alternative for preparation of l-(6-bromonaphthalen-2-yl)ethanone; A mixture of 2-bromonaphthalene (41.4 g, 200 mmol), acetyl chloride (11.3 mL, 160 mmol), nitrobenzene (250 mL) and A1C13 (28g, 210 mmol) was stirred for 4 hours at 100°C (oil bath temperature). The resulting reaction mixture was cooled, poured onto ice /water (100 mL) and filtered. The filtrate was washed with water (100 mL). The solvent (nitrobenzene) was removed by distillation. The resulting residue was crystallized from hexane to afford 18 g of desired product (36percent yield).l-(6-bromonaphthalen-2-yl)ethanone: 1H NMR (400 MHz, ACETONITRILE- 3) δ ppm 2.66 (s, 3 H) 7.66 (dd, J=8.8, 2.0 Hz, 1 H) 7.86 (d, J=8.8 Hz, 1 H) 7.94 (d, J=8.8 Hz, 1 H) 8.02 (dd, J=8.8, 1.8 Hz, 1 H) 8.13 (d, J=2.0 Hz, 1 H) 8.53 (d, J=1.8 Hz, 1 H).
11 g With aluminum (III) chloride In nitrobenzene at 10 - 40℃; for 18 h; To a solution of 2-bromonaphthalene (25 g, 121 mmol) and AlCl3(19.32 g, 145 mmol) in nitrobenzene (227 mL) was added AcCl (10.78 mL, 152 mmol) at 10° C. The reaction mixture was heated to 40° C. for 18 h. Then the reaction mixture was cooled to rt and poured into ice containing con. HCl (400 mL). The reaction mixture was extracted with EtOAc and washed with 1.5 N HCl solution, brine, dried over Na2SO4and concentrated. The crude was purified by column chromatography (Silica gel 60-120, 3-5percent EtOAc/petroleum ether) to obtain bromide B-1a (11 g) as light brown solid.1H NMR (CDCl3), δ=7.26 ppm, 400 MHz): δ 8.43 (s, 1H), 8.08-8.04 (m, 2H), 7.84 (d, J=8.8, 1H), 7.81 (d, J=8.8, 1H), 7.64 (dd, J=8.8, 2.0, 1H), 2.72 (s, 3H).
11 g With aluminum (III) chloride In nitrobenzene at 10 - 40℃; for 10 h; To a solution of 2-bromonaphthalene (25 g, 121 mmol) and AICI3 (19.32 g,145 mmol) in nitrobenzene (227 mL) was added AcCl (10.78 mL, 152 mmol) at 10 °C. The reaction mixture was heated to 40 °C for 18 h. Then the reaction mixture was cooled to rt and poured into ice containing con. HCl (400 mL). The reaction mixture was extracted with EtOAc and washed with 1.5 N HCl solution, brine, dried over Na2S04and concentrated. The crude was purified by column chromatography (Silica gel 60-120, 3-5percent EtOAc/petroleum ether) to obtain bromide B-la (11 g) as light brown solid.XH NMR (CDC13), δ = 7.26 ppm, 400 MHz): δ 8.43 (s, 1 H), 8.08- 8.04 (m, 2 H), 7.84 (d, J = 8.8, 1 H), 7.81 (d, J = 8.8, 1 H), 7.64 (dd, J = 8.8, 2.0, 1 H), 2.72 (s, 3 H).

Reference: [1] Patent: EP3239143, 2017, A2, . Location in patent: Paragraph 0306
[2] Patent: WO2012/13643, 2012, A1, . Location in patent: Page/Page column 25-26
[3] Patent: JP2017/39655, 2017, A, . Location in patent: Paragraph 0044
[4] Patent: WO2011/54834, 2011, A1, . Location in patent: Page/Page column 39
[5] Chemical Communications, 2015, vol. 51, # 38, p. 8153 - 8156
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 26, p. 7530 - 7533[7] Angew. Chem., 2016, vol. 128, # 26, p. 7656 - 7659,4
[8] Chemische Berichte, 1891, vol. 24, p. 550
[9] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3356 - 3366
[10] Patent: US5877207, 1999, A,
[11] Patent: US5958954, 1999, A,
[12] Patent: US4766127, 1988, A,
[13] Patent: US2012/219594, 2012, A1,
[14] Patent: US2015/23913, 2015, A1, . Location in patent: Paragraph 0993-0994
[15] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 369
  • 6
  • [ 75-15-0 ]
  • [ 7446-70-0 ]
  • [ 580-13-2 ]
  • [ 75-36-5 ]
  • [ 1590-24-5 ]
  • [ 1590-25-6 ]
Reference: [1] Journal of the American Chemical Society, 1943, vol. 65, p. 239,241
[2] Journal of Organic Chemistry, 1948, vol. 13, p. 164,165
[3] Journal of Organic Chemistry, 1946, vol. 11, p. 163
[4] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1931, vol. <A>, p. 59,65
  • 7
  • [ 7446-70-0 ]
  • [ 580-13-2 ]
  • [ 98-95-3 ]
  • [ 75-36-5 ]
  • [ 1590-24-5 ]
  • [ 1590-25-6 ]
Reference: [1] Journal of the American Chemical Society, 1943, vol. 65, p. 239,241
[2] Journal of Organic Chemistry, 1948, vol. 13, p. 164,165
[3] Journal of Organic Chemistry, 1946, vol. 11, p. 163
[4] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1931, vol. <A>, p. 59,65
  • 8
  • [ 580-13-2 ]
  • [ 2243-83-6 ]
  • [ 613-56-9 ]
Reference: [1] Structural Chemistry, 2012, vol. 23, # 3, p. 771 - 790,20
[2] Structural Chemistry, 2012, vol. 23, # 3, p. 771 - 790
  • 9
  • [ 580-13-2 ]
  • [ 541-41-3 ]
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Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 26, p. 4554 - 4560
  • 10
  • [ 580-13-2 ]
  • [ 79-44-7 ]
  • [ 613-56-9 ]
Reference: [1] Russian Chemical Bulletin, 2012, vol. 61, # 7, p. 1456 - 1462[2] Izv. Akad. Nauk, Ser. Khim., 2012, # 7, p. 1441 - 1447,7
  • 11
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Reference: [1] Organic Letters, 2015, vol. 17, # 4, p. 912 - 915
[2] Patent: US9636670, 2017, B2,
  • 12
  • [ 5325-94-0 ]
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  • [ 613-56-9 ]
Reference: [1] Journal of Physical Chemistry A, 1999, vol. 103, # 17, p. 3155 - 3162
  • 13
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  • [ 1590-25-6 ]
  • [ 75-36-5 ]
  • [ 5773-80-8 ]
Reference: [1] Patent: US4454341, 1984, A,
  • 14
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  • [ 5773-80-8 ]
Reference: [1] Patent: EP3239143, 2017, A2,
  • 15
  • [ 930-68-7 ]
  • [ 580-13-2 ]
  • [ 6336-82-9 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 4, p. 1172 - 1175
  • 16
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  • [ 6336-82-9 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 5, p. 919 - 922
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 12, p. 3953 - 3979
  • 17
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  • [ 74866-28-7 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6504 - 6512
  • 18
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  • [ 74866-28-7 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 19, p. 10742 - 10749
  • 19
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  • [ 91270-69-8 ]
Reference: [1] Tetrahedron Asymmetry, 1996, vol. 7, # 1, p. 61 - 68
  • 20
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  • [ 523-27-3 ]
  • [ 122648-99-1 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4326 - 4329
  • 21
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  • [ 2243-58-5 ]
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 2994 - 3008
  • 22
  • [ 580-13-2 ]
  • [ 78871-05-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 22, p. 6604 - 6607[2] Angew. Chem., 2015, vol. 127, # 22, p. 6704 - 6707,4
[3] Organic Letters, 2018, vol. 20, # 9, p. 2778 - 2781
  • 23
  • [ 580-13-2 ]
  • [ 762-04-9 ]
  • [ 78871-05-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 17, p. 4549 - 4553[2] Angew. Chem., 2013, vol. 125, # 17, p. 4647 - 4651,5
[3] Green Chemistry, 2015, vol. 17, # 1, p. 314 - 319
  • 24
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  • [ 474688-73-8 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2007, vol. 66, # 3, p. 672 - 675
[2] Journal of Materials Chemistry, 2011, vol. 21, # 34, p. 12969 - 12976
[3] Dyes and Pigments, 2012, vol. 92, # 1, p. 588 - 595
[4] Patent: KR2015/22269, 2015, A,
[5] Patent: KR2015/22270, 2015, A,
[6] Patent: KR101502811, 2015, B1,
[7] Patent: KR2017/49295, 2017, A,
[8] Patent: WO2008/140208, 2008, A1,
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Reference: [1] Patent: US2008/299294, 2008, A1,
  • 26
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  • [ 918655-03-5 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 2 h; 2-bromo-naphthalene (2.07g, 10mmol), benzene-1,4-diBoronic acid(2.49g, 15mmol), Pd (PPh3) 4 (0.58 g, 0.5mmol), potassium carbonate (4.15g, 30mmol) and THF: H2O = 2:1 solution dissolved in 200ml 80 After 2 hours reflux agitation. Thereafter it was added and extracted three times with 40ml ethyl ether H2O40ml drying the obtained organic layer with magnesium sulfate, and separating the residue obtained by evaporating the solvent was subjected to silica gel column chromatography purification Intermediate B-1 (1.98g, 80percent yield) It was obtained.
Reference: [1] Patent: KR2016/30001, 2016, A, . Location in patent: Paragraph 0327-0330
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  • [ 934545-80-9 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 841 - 846
[2] Patent: WO2016/36207, 2016, A1,
[3] Patent: WO2016/64227, 2016, A1,
[4] Patent: KR2016/29399, 2016, A,
[5] Patent: KR2015/21171, 2015, A,
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A1440475[ 1262053-54-2 ]

2-Bromonaphthalene-1,2,3,4,4a,8a-13C6

Reason: Stable Isotope