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[ CAS No. 38303-35-4 ] {[proInfo.proName]}

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Chemical Structure| 38303-35-4
Chemical Structure| 38303-35-4
Structure of 38303-35-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 38303-35-4 ]

CAS No. :38303-35-4 MDL No. :MFCD00230868
Formula : C16H8Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :JBLQSCAVCHTKPV-UHFFFAOYSA-N
M.W : 360.04 Pubchem ID :181577
Synonyms :

Calculated chemistry of [ 38303-35-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 85.55
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.23
Log Po/w (XLOGP3) : 6.41
Log Po/w (WLOGP) : 6.11
Log Po/w (MLOGP) : 5.9
Log Po/w (SILICOS-IT) : 6.08
Consensus Log Po/w : 5.54

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.77
Solubility : 0.0000614 mg/ml ; 0.00000017 mol/l
Class : Poorly soluble
Log S (Ali) : -6.2
Solubility : 0.000226 mg/ml ; 0.000000627 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.24
Solubility : 0.00000207 mg/ml ; 0.0000000057 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.53

Safety of [ 38303-35-4 ]

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 [ 38303-35-4 ]

* 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 [ 38303-35-4 ]
  • Downstream synthetic route of [ 38303-35-4 ]

[ 38303-35-4 ] Synthesis Path-Upstream   1~12

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YieldReaction ConditionsOperation in experiment
71.1% With bromine In chloroform for 4 h; Inert atmosphere; Reflux 58 g (0.287 mol) of pyrene are initially introduced in 1750 ml of chloroform. A solution of 31 ml (0.609 mol) of Br2 in 250 ml of chloroform is subsequently added dropwise at RT with exclusion of light. The reaction mixture is heated under reflux for 4 h. After cooling, the precipitated solid is filtered off with suction and washed with ethanol and dried. The solid obtained is recrystallised 3 times from CHCI3. Yield: 1 ,6- dibromopyrene 73.4 g (0.201 mol), 71.1percent of theory, and 1 ,8-dibromopyrene 20.6 g (0.06 mol), 20percent of theory.
50% With bromine In tetrachloromethane at 20 - 25℃; for 54 h; The solution of 10 ml(31.19 g, 0.195 mol) of bromine in 500 ml of anhydrous CCl4 was addeddropwise to the solution of 20.2 g (0.1 mol) pyrene in 500 ml of anhydrousCCl4 for 6 h at 20–25 °C. Once the addition of bromine was completed,the mixture was kept at the same temperature for 48 h. The precipitate of1,6-dibromopyrene was filtered off, washed with hexane and methanoland dried in vacuo over P2O5, yield 9.02 g (25percent). The filtrate wasconcentrated, the solid residue was recrystallized from toluene–hexanegiving 1,8-dibromopyrene, yield 17.9 g (50percent).For 1,8-dibromopyrene: 1H NMR, δ: 7.97 (s, 2 H), 7.98 (d, 2H, J 8.5 Hz),8.22 (d, 2H, J 8.2 Hz), 8.46 (s, 2H). IR (ν/cm–1): 3102, 3038, 1936,1882, 1597, 1582 (C=C), 1481, 1455, 1427, 1416, 1310, 1295, 1234,1202, 1163, 1146, 1118, 1026, 976, 845, 836, 819, 784, 777, 768, 704.MS, m/z: 360 [M]+.For 1,6-dibromopyrene: 1H NMR, δ: 8.18 (d, 2H, J 8.2 Hz), 8.10 (d,2H, J 9.2 Hz), 8.26 (d, 2H, J 8.2 Hz), 8.44 (d, 2H, J 9.2 Hz). IR (ν/cm–1):3038, 1600, 1581 (C=C), 1482, 1453, 1427, 1417, 1287, 1234, 1202,1162, 1091, 1052, 1025, 979, 881, 852, 836, 818, 703. MS, m/z: 360 [M]+.
14% With bromine In chloroform at 20℃; for 5 h; Bromine (10.0 mL, 195 mmol) in CHCl3(500 mL) was dropped into a solution of pyrene (20.0 g, 98.9 mmol) inCHCl3 (500 mL) over 5 h while stirring. The precipitate was collectedafter 12 h and recrystallized from xylene to give compound 5 (5.01 g,14percent) and compound 6 (2.17 g, 6percent). Compound 5: 1H NMR (300 MHz,CDCl3): δ = 8.46 (d, 2H), 8.26 (d, 2H), 8.11 (d, 2H), 8.05 (d, 2H);EI + -Mass: 360. Compound 6: 1H NMR (300 MHz, CDCl3): δ= 8.56 (s,2H), 8.27 (d, 2H), 8.05 (m, 4H); EI + -Mass: 360.
Reference: [1] Dyes and Pigments, 2016, vol. 130, p. 106 - 115
[2] Journal of Molecular Structure, 2017, vol. 1127, p. 237 - 246
[3] Patent: WO2013/185871, 2013, A1, . Location in patent: Page/Page column 24
[4] Mendeleev Communications, 2016, vol. 26, # 5, p. 437 - 439
[5] Dyes and Pigments, 2018, vol. 158, p. 42 - 49
[6] Chemische Berichte, 1937, vol. 70, p. 926,929
[7] Chemistry Letters, 2004, vol. 33, # 1, p. 40 - 41
[8] Journal of the American Chemical Society, 2008, vol. 130, # 29, p. 9371 - 9379
[9] Journal of the American Chemical Society, 2008, vol. 130, # 46, p. 15285 - 15287
[10] Journal of Chemical Research, 2010, # 5, p. 278 - 282
[11] Tetrahedron Letters, 2011, vol. 52, # 47, p. 6284 - 6287
[12] Organic Electronics: physics, materials, applications, 2011, vol. 12, # 9, p. 1505 - 1511
[13] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 16000 - 16013
[14] Dyes and Pigments, 2014, vol. 103, p. 55 - 61
[15] Journal of Fluorescence, 2014, vol. 24, # 1, p. 153 - 160
[16] RSC Advances, 2014, vol. 4, # 37, p. 19538 - 19549
[17] Tetrahedron, 2014, vol. 70, # 34, p. 5100 - 5108
[18] Tetrahedron, 2014, vol. 70, # 34, p. 5100 - 5108
[19] New Journal of Chemistry, 2018, vol. 42, # 15, p. 12802 - 12810
[20] Chemistry - An Asian Journal, 2018,
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YieldReaction ConditionsOperation in experiment
28% With N2; bromine In tetrachloromethane First, pyrene (10 g, 0.0049 mol) is dissolved into CCl4 (300 mL) in a 3-necks-r.b.f.
And, Br2(17.38 g, 0.108 mol) CCl4(50 mL) are put into a dropping funnel provided at the round-floor flask and slowly dropped in the round-floor flask for 4 hours.
N2 is added to and HBr is removed from the solution.
When the process is finished, the solution is stirred under N2 current for one hour and formed sediment is filtered.
When the sediment is recrystallized by toluene, a green solid matter (6.05 g, 34percent) of 1,6-Dibromopyrene and a white solid matter of 1,8-Dibromopyrene (5 g, 28percent) are obtained.
Reference: [1] Patent: US2010/155714, 2010, A1,
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Reference: [1] Journal of Molecular Structure, 2013, vol. 1035, p. 19 - 26
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Reference: [1] Polyhedron, 2014, vol. 81, p. 436 - 441
[2] Physical Chemistry Chemical Physics, 2015, vol. 17, # 35, p. 22758 - 22769
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  • [ 1714-29-0 ]
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Reference: [1] Environmental Science and Technology, 2007, vol. 41, # 7, p. 2190 - 2195
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Reference: [1] Journal of Nanoscience and Nanotechnology, 2011, vol. 11, # 5, p. 4351 - 4356
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Reference: [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 1, p. 172 - 179
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 819 - 822[2] Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 4, p. 794 - 798
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 819 - 822[2] Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 4, p. 794 - 798
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  • [ 16400-51-4 ]
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Reference: [1] Patent: CN108586255, 2018, A,
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  • [ 42882-07-5 ]
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 819 - 822[2] Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 4, p. 794 - 798
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Reference: [1] Chemische Berichte, 1937, vol. 70, p. 926,929
[2] Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,38
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