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[ CAS No. 876-53-9 ] {[proInfo.proName]}

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Chemical Structure| 876-53-9
Chemical Structure| 876-53-9
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Product Details of [ 876-53-9 ]

CAS No. :876-53-9 MDL No. :MFCD00077218
Formula : C10H14Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :HLWZKLMEOVIWRK-UHFFFAOYSA-N
M.W : 294.03 Pubchem ID :265790
Synonyms :

Calculated chemistry of [ 876-53-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.66
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.71
Log Po/w (XLOGP3) : 3.68
Log Po/w (WLOGP) : 3.87
Log Po/w (MLOGP) : 4.36
Log Po/w (SILICOS-IT) : 3.9
Consensus Log Po/w : 3.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0307 mg/ml ; 0.000104 mol/l
Class : Soluble
Log S (Ali) : -3.37
Solubility : 0.125 mg/ml ; 0.000427 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.86
Solubility : 0.0405 mg/ml ; 0.000138 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 5.39

Safety of [ 876-53-9 ]

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 [ 876-53-9 ]

* 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 [ 876-53-9 ]
  • Downstream synthetic route of [ 876-53-9 ]

[ 876-53-9 ] Synthesis Path-Upstream   1~23

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Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
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Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
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Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 4
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Reference: [1] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2177 - 2194
[2] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[3] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[4] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[5] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[6] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[7] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[8] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[9] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 5
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 481 - 483[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 3, p. 540 - 542
[3] Dalton Transactions, 2014, vol. 43, # 22, p. 8530 - 8542
[4] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[5] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 2, p. 339 - 345
[6] Journal of Organic Chemistry, 1998, vol. 63, # 14, p. 4581 - 4586
[7] MedChemComm, 2017, vol. 8, # 1, p. 135 - 147
[8] Journal of the American Chemical Society, 1993, vol. 115, # 16, p. 7293 - 7299
[9] Asian Journal of Chemistry, 2012, vol. 24, # 4, p. 1756 - 1758
[10] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6938 - 6940
[11] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
[12] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2065 - 2071
[13] Synthetic Communications, 2006, vol. 36, # 15, p. 2113 - 2119
[14] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2177 - 2194
[15] Patent: US2004/127715, 2004, A1, . Location in patent: Page 11
  • 6
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YieldReaction ConditionsOperation in experiment
99% Sealed tube; Inert atmosphere General procedure: The reactions were carried out in glass ampoules (20 mL) or in a pressure microreactor of stainless steel (17 mL). The results of parallel experiments were identical. Into the microreactor (ampoule) in an argon atmosphere was charged 0.3 mmol of Fe(acac)3, 10 mmol of initial adamantane, 10 mmol of CBr4, and 150 mmol of CH2Br2. The reactor was hermetically closed (the ampoule was sealed) and heated while stirring. On the completion of the reaction the reactor (ampoule) was cooled to room temperature, opened, the solvent was distilled off, the residue was crystallized from hexane or ethanol. Yields are given in respect to converted adamantane (adamantine derivatives) (GLC procedure, internal reference decene; correction factor for adamantane 1.09, for bromoadamantane 1.53). The structure of compounds obtained was proved by comparison with known samples and published data.
Reference: [1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187[2] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[3] Tetrahedron Letters, 1986, vol. 27, # 12, p. 1399 - 1402
[4] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2041[5] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2239 - 2240
  • 7
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YieldReaction ConditionsOperation in experiment
35 %Spectr. With tert-butyl hypobromite; carbon tetrabromide In dichloromethane at 40℃; for 90 h; Darkness tert-Butyl hypobromite 50 (0.33 mL, freshly prepared and used immediately, 0.05 mmol, 0.1 eq.), adamantane 18 (68 mg, 0.5 mmol), carbon tetrabromide (166 mg, 0.5 mmol, 1 eq.) and dichloromethane (3.13 mL) were added to an oven-dried pressure tube and the reaction mixture was stirred at 40 °C for 90 h in the dark. The reaction mixture was cooled to RT and quenched with aqueous hydrochloric acid (1 M, 5 mL) and extracted with dichloromethane (4 x 10 mL). The organic phases were combined, dried over Na2SO4, filtered and concentrated in vacuo. The yield of adamantane 18 (29percent), 1-bromoadamantane 31 (35percent), 2-bromoadamantane 51 (14percent) and 1,3-bromoadamantane 52 (11percent) were determined by adding 1,3,5-trimethoxybenzene to the crude mixture as an internal standard for 1H-NMR.
Reference: [1] Molecules, 2018, vol. 23, # 5,
  • 8
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Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 13, p. 1013 - 1014
[2] Journal of the Chemical Society, Chemical Communications, 1987, # 13, p. 1013 - 1014
  • 9
  • [ 34913-44-5 ]
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5239 - 5243
  • 10
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Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[2] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 11
  • [ 768-93-4 ]
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Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
[2] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 12
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Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2428 - 2433
  • 13
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  • [ 1488928-52-4 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2013, vol. 49, # 9, p. 1358 - 1369[2] Khim. Geterotsikl. Soedin., 2013, vol. 49, # 9, p. 1457 - 1468,12
  • 14
  • [ 33388-08-8 ]
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Reference: [1] Journal of Physical Organic Chemistry, 1994, vol. 7, p. 610 - 614
[2] Journal of Organic Chemistry, 1997, vol. 62, # 13, p. 4260 - 4265
  • 15
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  • [ 52918-86-2 ]
  • [ 33803-54-2 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1991, vol. 40, # 12, p. 2528 - 2529[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1991, vol. 40, # 12, p. 2897 - 2898
  • 16
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Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1769,1771
  • 17
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Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1769,1771
  • 18
  • [ 62133-11-3 ]
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  • [ 2810-69-7 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 692 - 696[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 4, p. 776 - 780
  • 19
  • [ 768-95-6 ]
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Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1991, vol. 61, # 10, p. 2190 - 2191[2] Zhurnal Obshchei Khimii, 1991, vol. 61, # 10, p. 2360 - 2361
  • 20
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  • [ 5001-18-3 ]
Reference: [1] MedChemComm, 2017, vol. 8, # 1, p. 135 - 147
[2] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
[3] Patent: US2014/45779, 2014, A1, . Location in patent: Paragraph 0049
  • 21
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  • [ 39269-10-8 ]
Reference: [1] MedChemComm, 2017, vol. 8, # 1, p. 135 - 147
  • 22
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Reference: [1] Chemische Berichte, 1960, vol. 93, p. 1366 - 1371
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  • [ 103-84-4 ]
  • [ 58788-79-7 ]
Reference: [1] Patent: CN107673977, 2018, A,
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