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[ CAS No. 128-63-2 ] {[proInfo.proName]}

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Chemical Structure| 128-63-2
Chemical Structure| 128-63-2
Structure of 128-63-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 128-63-2 ]

CAS No. :128-63-2 MDL No. :MFCD00428682
Formula : C16H6Br4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZKBKRTZIYOKNRG-UHFFFAOYSA-N
M.W : 517.84 Pubchem ID :67188
Synonyms :

Calculated chemistry of [ 128-63-2 ]

Physicochemical Properties

Num. heavy atoms : 20
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 : 100.95
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.85
Log Po/w (XLOGP3) : 7.8
Log Po/w (WLOGP) : 7.63
Log Po/w (MLOGP) : 7.1
Log Po/w (SILICOS-IT) : 7.38
Consensus Log Po/w : 6.75

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -8.56
Solubility : 0.00000144 mg/ml ; 0.0000000028 mol/l
Class : Poorly soluble
Log S (Ali) : -7.65
Solubility : 0.0000117 mg/ml ; 0.0000000226 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.79
Solubility : 0.0000000836 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.98

Safety of [ 128-63-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 128-63-2 ]

* 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 [ 128-63-2 ]
  • Downstream synthetic route of [ 128-63-2 ]

[ 128-63-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 128-63-2 ]
  • [ 81-30-1 ]
Reference: [1] Patent: US2009596, 1933, ,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 1433
  • 2
  • [ 129-00-0 ]
  • [ 128-63-2 ]
YieldReaction ConditionsOperation in experiment
96% With bromine In nitrobenzene at 80 - 120℃; for 12 h; Bromine (8.75 g, 0.055 mol) was added dropwise, with vigorous stirring to a solution of   pyrene (2.5 g, 12.3 mmol) in   nitrobenzene (50 mL) at 80 °C [24]. Then the mixture was heated to 120 °C and kept for 12 h. After cooled to room temperature, the mixture was filtered, washed with ethanol (100 mL), and dried under vacuum to afford   5 (6.04 g, 96percent) as a pale-green solid; m.p. >300 °C (m.p. >300 °C) [21]. (Found C, 36.85; H, 1.23. C16H6Br4 (517.84) requires C, 37.11; H, 1.17percent). This compound was quite insoluble in all common organic solvents. The 1H NMR spectrum was not obtained in CDCl3 due to the limited solubility of this compound.
92% With bromine In nitrobenzene at 80℃; for 12 h; To a stirred nitrobenzene (120 mL) solution of pyrene (1, 4.048 g, 20 mmol) was slowly added nitrobenzene (40 mL) solution of Br2 (4.7 mL, 92 mmol). The solution was stirred at 80°C for 12 h. The solution was cooled to room temperature. Conc. NaOH aq (10 mL) was added to remove remaining Br2. The solid was collected by suction filtration with CHCl3 (100 mL) to give 1,3,6,8-tetrabromopyrene (11, light green solid, 9.6 g, 92percent yield). A stirred mixture of 1,3,6,8-tetrabromopyrene (11, 5.172 g, 10 mmol), trimethylsilylacetylene (6.7 mL, 48 mmol), (PPh3)2PdCl2 (353 mg), CuI (107 mg), PPh3 (263 mg), i-Pr2NH (50 mL), and THF (50 mL) was stirred at 80°C for 12 h. The solution was concentrated in vacuo. Purification by silica gel column chromatography (eluent; hexane) gave 1,3,6,8-tetrakis(trimethylsilylethynyl)pyrene (3, 4.936 g, 84percent yield).
76% With bromine In chloroform at 0 - 20℃; for 8 h; Synthesis of Intermediate 2-h [0156] Intermediate 2-h was synthesized according to Reaction Scheme 12 below: [0157] 50 g (0.247 mol) of pyrene was dissolved in 500 ml of chloroform in a 2 L round-bottom flask, and the temperature was decreased to 0° C. Then, a solution of 158 g (0.989 mol) of bromine dissolved in 150 ml of chloroform was slowly added to the flask, the temperature was slowly raised to room temperature, and the resultant mixture was reacted for 8 hours. After the reaction was complete, 100 ml of water was added and the bromine was removed using sodium thiosulfate, and the crystals formed therefrom were filtered and recrystallized. As a result, 97.5 g of Intermediate 2-h was obtained (76percent).
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[5] Chemistry - A European Journal, 2017, vol. 23, # 62, p. 15746 - 15758
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[17] Angewandte Chemie - International Edition, 2016, vol. 55, # 32, p. 9311 - 9315[18] Angew. Chem., 2016, vol. 128, p. 9457 - 9461,5
[19] Organic and Biomolecular Chemistry, 2011, vol. 9, # 12, p. 4558 - 4562
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[21] Organic Letters, 2013, vol. 15, # 6, p. 1318 - 1321
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[23] Patent: US4684753, 1987, A,
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[25] Patent: US2013/175509, 2013, A1, . Location in patent: Paragraph 0156; 0157
[26] Patent: US2009596, 1933, ,
[27] Patent: US2018935, 1933, ,
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[29] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 1433
[30] Justus Liebigs Annalen der Chemie, 1937, vol. 531, p. 1,38
[31] Tetrahedron, Supplement, 1966, vol. 8, p. 135 - 139
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  • 3
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  • [ 128-63-2 ]
YieldReaction ConditionsOperation in experiment
91% With sodium chlorate; bromine In water (a)
220 parts of technical-grade pyrene of 90percent purity are added to a solution of 84 parts of sodium chlorate and 350 parts of water.
370 parts of bromine are then added dropwise at 60°-65° C. in 2 hours.
This is followed by stirring at 60°-65° C. for 1 hour.
The temperature is then raised to 85° C., and 85°-95° C. is maintained with reflux cooling for 10 hours.
The tetrabromopyrene is worked up as described in Example 1a.
The 1,3,6,8-tetrabromopyrene (bromine content 61.8percent) is obtained in an amount of 557 parts and a purity of about 83percent, which corresponds to a yield of about 91percent of theory, based on 100percent pure pyrene, and on further processing 253 parts of napthalene-1,4,5,8-tetracarboxylic acid 1,4-monoanhydride are obtained.
Reference: [1] Patent: US4684753, 1987, A,
  • 4
  • [ 129-00-0 ]
  • [ 128-63-2 ]
YieldReaction ConditionsOperation in experiment
90% With sodium chlorate; ammonium hydroxide; bromine In water (a)
220 parts of technical-grade pyrene of 93percent purity (brazan content 4percent) are added to a solution of 84 parts of sodium chlorate in 340 parts of water.
375 parts of bromine are then added dropwise at 40°-50° C., with slight cooling, in 2 hours.
This is followed by stirring at 40°-50° C. for 1-2 hours.
The temperature is then gradually raised with reflux cooling to 85° C., which is followed by stirring at 85°-95° C. for 5 hours.
The suspension is then diluted with 200 parts of water, and the excess bromine is eliminated by gradual addition of 40percent strength aqueous sodium bisulfite solution.
This is followed by cooling down to 50°-60° C. and the dropwise addition of 25percent strength aqueous ammonia solution until a pH value of 9.5 is reached.
This is followed by stirring at 50°-60° C. for 4
hours and, finally, by filtration with suction, washing with water until salt-free and drying at 100° C.
The 1,3,6,8-tetrabromopyrene is obtained in an amount of 561 parts and purity of about 84percent, which corresponds to a yield of about 90percent of theory, based on 100percent pure pyrene, and on further processing to naphthalene-1,4,5,8-tetracarboxylic acid in accordance with the instructions of Example 1a 263 parts of naphthalene-1,4,5,8-tetracarboxylic acid 1,4-monoanhydride are obtained.
Reference: [1] Patent: US4684753, 1987, A,
  • 5
  • [ 129-00-0 ]
  • [ 128-63-2 ]
YieldReaction ConditionsOperation in experiment
2% With sodium chlorate; bromine In water (a)
220 parts of technical-grade pyrene of 90percent purity are added to a solution of 84 parts of sodium chlorate in 280 parts of water.
380 parts of bromine are then added dropwise at 40°-50° C. with slight cooling in 2 hours.
This is followed by stirring at 40°-50° C. for 1 hour.
The temperature is then gradually raised with reflux cooling to 85° C. and stirring at 85°-95° C. for 10 hours.
The suspension is worked up as described in Example 1a.
The 1,3,6,8-tetrabromopyrene is obtained in an amount of 564 parts and a purity of about 83percent, which corresponds to a yield of about 2percent of theory, based on 100percent pure pyrene, which on further processing to naphthalene-1,4,5,8-tetracarboxylic acid gives 258 parts of naphthalene-1,4,5,8-tetracarboxylic 1,4-monoanhydride.
Reference: [1] Patent: US4684753, 1987, A,
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  • [ 99768-12-4 ]
  • [ 933047-52-0 ]
Reference: [1] Patent: US2016/46738, 2016, A1,
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