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[ CAS No. 4101-68-2 ] {[proInfo.proName]}

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Chemical Structure| 4101-68-2
Chemical Structure| 4101-68-2
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Product Details of [ 4101-68-2 ]

CAS No. :4101-68-2 MDL No. :MFCD00000222
Formula : C10H20Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :GTQHJCOHNAFHRE-UHFFFAOYSA-N
M.W : 300.07 Pubchem ID :221483
Synonyms :

Calculated chemistry of [ 4101-68-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 9
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.92
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.68
Log Po/w (XLOGP3) : 5.83
Log Po/w (WLOGP) : 4.9
Log Po/w (MLOGP) : 4.76
Log Po/w (SILICOS-IT) : 4.79
Consensus Log Po/w : 4.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.78
Solubility : 0.00499 mg/ml ; 0.0000166 mol/l
Class : Moderately soluble
Log S (Ali) : -5.6
Solubility : 0.000752 mg/ml ; 0.00000251 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.62
Solubility : 0.000718 mg/ml ; 0.00000239 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.56

Safety of [ 4101-68-2 ]

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 [ 4101-68-2 ]

* 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 [ 4101-68-2 ]
  • Downstream synthetic route of [ 4101-68-2 ]

[ 4101-68-2 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 112-47-0 ]
  • [ 4101-68-2 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogen bromide In octane; water at 145℃; for 7 h; Dean-Stark General procedure: A one-neck rb flask was charged with diol (1equiv), 48percent aq HBr (~3 equiv/OH), octane (~7:1 v/w ratio vs diol), fitted tothe fractionating column/Dean-Stark trap, and heated inan oil bath (145-150 °C) w/rapid magnetic stirring. The aqueous (lower) layer of the initialazeotrope condensate (bp 89-92 °C) was tapped offuntil about half of the theoretical amount of H2O had been collected;the azeotrope temp (still head) then began to rise. The condenser was set to total reflux forseveral h, reopened, and aq material collected for 1h more (head temp 96-100°C). The final volume of aq distillatewas 90-100+percent of theory (higher-boiling distillate contained up to 24percent HBr). When the (pale tan) octane phase containedboth dibromide and bromoalkanol (6band 6c), washing with cold 85percent v/v H2SO4 (10 mL,then 5 mL) removed all color and all bromoalkanol. For all three dibromides (3b, 4b, 6b) the neutralized octane solutionwas stripped of solvent (vigreux column, reduced pressure), and the essentiallypure residue (1H NMR) was kugelrohr distilled. A trace of 4-methyltetrahydropyran was foundin 4b before distillation.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
[2] Green Chemistry, 2014, vol. 16, # 2, p. 836 - 843
[3] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5386 - 5394
[4] Journal of the American Chemical Society, 1936, vol. 58, p. 488
[5] Journal of the Chemical Society, 1958, p. 2068
[6] Monatshefte fuer Chemie, 1910, vol. 31, p. 181
[7] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1910, vol. 42, p. 1658[8] Chem. Zentralbl., 1911, vol. 82, # I, p. 1500
[9] Helvetica Chimica Acta, 1926, vol. 9, p. 265
[10] Journal of the American Chemical Society, 1930, vol. 52, p. 5281
[11] Organic Syntheses, 1940, vol. 20, p. 24
[12] Synthesis, 1987, # 5, p. 511 - 512
  • 2
  • [ 2834-05-1 ]
  • [ 4101-68-2 ]
YieldReaction ConditionsOperation in experiment
85% With bromine; dibromoisocyanuric acid In dichloromethane at 20℃; for 4 h; UV-irradiation EXAMPLE 12 (0564) Bromodecarboxylation of alkanoic acids (0565) bromoisocyanurate (0566) RC02H -1 · RBr (0567) hv (0568) [00169] A mixture of alkanoic acid RC02H (2 mmol), bromoisocyanurate, additive (optionally) and solvent (12 mL) was stirred under fluorescent room light irradiation (FL). The reaction mixture washed with 1 M aq Na2S03, dried over Na2S04, filtered through short silica gel pad and concentrated in vacuo to yield crude alkyl bromide RBr. Optionally, the crude bromide was purified by chromatography on silica gel. The results are presented in Table 11.
Reference: [1] Patent: WO2017/60905, 2017, A1, . Location in patent: Paragraph 00169; 00172
[2] Organic Letters, 2017, vol. 19, # 7, p. 1634 - 1637
[3] Chemistry - A European Journal, 2016, vol. 22, # 29, p. 9971 - 9974
[4] Journal of Physical Chemistry B, 2010, vol. 114, # 22, p. 7499 - 7508
  • 3
  • [ 112-47-0 ]
  • [ 53463-68-6 ]
  • [ 4101-68-2 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748
[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838
[3] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[4] Tetrahedron, 2004, vol. 60, # 24, p. 5237 - 5252
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220
[6] Organic Process Research and Development, 2011, vol. 15, # 3, p. 673 - 680
[7] Helvetica Chimica Acta, 1926, vol. 9, p. 226
[8] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
  • 4
  • [ 1647-16-1 ]
  • [ 4101-68-2 ]
YieldReaction ConditionsOperation in experiment
58 mol % With HBr gas; sodium hydrogencarbonate; dibenzoyl peroxide In diethyl ether; hexane; water EXAMPLE II
A 5 liter, 3-necked flask was equipped with a mechanical stirrer, a fritted bubbler and a gas outlet adapter.
A solution of 1,9-decadiene (500 g, 3.6 mol) and 5 g of benzoyl peroxide in 1 L of n-hexane was placed in the flask, which was chilled to about 5° C. and maintained at 5°-10° C. while HBr gas was bubbled through.
HBr gas was introduced over a 7 hour period, at which time the reaction mixture was poured into about 2 L of water, then neutralized by addition of NaHCO3.
About 200 mL of diethyl ether was added, the solution thoroughly mixed, then allowed to stand overnight.
After settling, the aqueous layer was separated and extracted with about 200 mL of ether.
The organic layers were then combined, dried over MgSO4, filtered, and stripped of solvent on a rotary evaporator.
Distillation of the crude product through a two foot packed glass column gave about 625 g (58 mol percent yield) of 1,10-dibromodecane.
Reference: [1] Synlett, 2010, # 13, p. 2014 - 2018
[2] Patent: US4540826, 1985, A,
  • 5
  • [ 112-47-0 ]
  • [ 497-19-8 ]
  • [ 4101-68-2 ]
YieldReaction ConditionsOperation in experiment
95 wt. % With concentrated aqueous HBr In water; chlorobenzene EXAMPLE I
A 5 liter jacketed 3-necked round bottom flask was equipped with a mechanical stirrer, a reflux condenser, and an addition funnel.
A quantity of 768 grams (1086 milliliters, 8.4 mole) of concentrated aqueous HBr (48 wt. percent) was placed in the reactor, followed by 696 g (4 mol) of 1,10-decanediol. 940 grams (532 milliliters, 8.4 mole) of concentrated H2 SO4 (96 wt. percent) was then added dropwise over several minutes.
Steam was then introduced through the vessel jacket, raising the temperature of the reaction contents to about 100°-105° C.
Steam was applied for about five hours, the reactor allowed to cool for about thirty minutes, then 2 L of water added, stirred briefly and allowed to stand overnight.
The aqueous layer was decanted and the reactor contents then washed with about 2 L of saturated sodium bicarbonate solution.
If necessary to assure neutral or slightly basic pH, Na2 CO3 was added.
Optionally, about 300-500 mL of chlorobenzene could be added to aid emulsion breaking.
The aqueous layer was discarded and the organic layer distilled to recover dibromide product boiling at 159°-163° C. at; 5-6 mm Hg. A 54 mol percent yield (640 g) of 1,10-dibromodecane (>95 wt. percent purity) was obtained.
Reference: [1] Patent: US4540826, 1985, A,
  • 6
  • [ 112-47-0 ]
  • [ 4101-68-2 ]
Reference: [1] Patent: US4540826, 1985, A,
  • 7
  • [ 1373139-23-1 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 8
  • [ 4224-70-8 ]
  • [ 4101-68-2 ]
Reference: [1] Naturwissenschaften, vol. 44>1957>89,
[2] Canadian Journal of Chemistry, 1962, vol. 40, p. 1846 - 1850
  • 9
  • [ 110-40-7 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of the American Chemical Society, 1930, vol. 52, p. 5281
  • 10
  • [ 112-47-0 ]
  • [ 13019-22-2 ]
  • [ 4101-68-2 ]
Reference: [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220
  • 11
  • [ 4224-70-8 ]
  • [ 818-88-2 ]
  • [ 26825-90-1 ]
  • [ 106-79-6 ]
  • [ 1472-93-1 ]
  • [ 4101-68-2 ]
Reference: [1] Canadian Journal of Chemistry, 1964, vol. 42, p. 1788 - 1791
  • 12
  • [ 1373139-23-1 ]
  • [ 140-88-5 ]
  • [ 29823-21-0 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 13
  • [ 4117-09-3 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 14
  • [ 4117-09-3 ]
  • [ 29823-21-0 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 15
  • [ 111-24-0 ]
  • [ 81726-81-0 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organometallic Chemistry, 1986, vol. 301, # 3, p. 391 - 400
  • 16
  • [ 112-47-0 ]
  • [ 10035-10-6 ]
  • [ 4101-68-2 ]
Reference: [1] Monatshefte fuer Chemie, 1910, vol. 31, p. 181
  • 17
  • [ 112-47-0 ]
  • [ 10035-10-6 ]
  • [ 856380-74-0 ]
  • [ 4101-68-2 ]
Reference: [1] Helvetica Chimica Acta, 1946, vol. 29, p. 1204,1207
  • 18
  • [ 749879-21-8 ]
  • [ 10035-10-6 ]
  • [ 64-19-7 ]
  • [ 120-80-9 ]
  • [ 4101-68-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 120,122 Anm. 2, 130
  • 19
  • [ 4101-68-2 ]
  • [ 10496-18-1 ]
Reference: [1] Synlett, 2005, # 12, p. 1901 - 1904
  • 20
  • [ 4101-68-2 ]
  • [ 124-18-5 ]
  • [ 112-29-8 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 19, p. 3909 - 3911
  • 21
  • [ 4101-68-2 ]
  • [ 646-25-3 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 4, p. 713 - 715
  • 22
  • [ 112-47-0 ]
  • [ 53463-68-6 ]
  • [ 4101-68-2 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748
[2] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5837 - 5838
[3] Tetrahedron, 2009, vol. 65, # 20, p. 3961 - 3966
[4] Tetrahedron, 2004, vol. 60, # 24, p. 5237 - 5252
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1215 - 1220
[6] Organic Process Research and Development, 2011, vol. 15, # 3, p. 673 - 680
[7] Helvetica Chimica Acta, 1926, vol. 9, p. 226
[8] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
  • 23
  • [ 1373139-23-1 ]
  • [ 140-88-5 ]
  • [ 29823-21-0 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 24
  • [ 4117-09-3 ]
  • [ 29823-21-0 ]
  • [ 4101-68-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 8, p. 4171 - 4176
  • 25
  • [ 4101-68-2 ]
  • [ 75-50-3 ]
  • [ 541-22-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 2998 - 3003
[2] Yakugaku Zasshi, 1954, vol. 74, p. 925[3] Chem.Abstr., 1955, p. 10962
[4] Journal of the American Chemical Society, 1959, vol. 81, p. 678
[5] Pharmaceutical Chemistry Journal, 1968, # 5, p. 247 - 250[6] Khimiko-Farmatsevticheskii Zhurnal, 1968, # 5, p. 15 - 18
[7] Journal of Physical Chemistry B, 2010, vol. 114, # 22, p. 7499 - 7508
  • 26
  • [ 593-81-7 ]
  • [ 4101-68-2 ]
  • [ 36707-88-7 ]
  • [ 541-22-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 8, p. 1448 - 1453
  • 27
  • [ 4101-68-2 ]
  • [ 62871-09-4 ]
YieldReaction ConditionsOperation in experiment
73% With potassium <i>tert</i>-butylate In tetrahydrofuran for 16 h; Inert atmosphere; Reflux General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product.
Reference: [1] Synthetic Communications, 2001, vol. 31, # 9, p. 1367 - 1371
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4047 - 4057
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2010, vol. 65, # 3, p. 414 - 424
[4] Molecular Crystals and Liquid Crystals, 2012, vol. 552, p. 33 - 42
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