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Chemical Structure| 91-13-4
Chemical Structure| 91-13-4
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Product Details of [ 91-13-4 ]

CAS No. :91-13-4 MDL No. :MFCD00000175
Formula : C8H8Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :KGKAYWMGPDWLQZ-UHFFFAOYSA-N
M.W :263.96 Pubchem ID :66665
Synonyms :

Calculated chemistry of [ 91-13-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.11
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 3.04
Log Po/w (WLOGP) : 3.17
Log Po/w (MLOGP) : 3.85
Log Po/w (SILICOS-IT) : 3.84
Consensus Log Po/w : 3.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0522 mg/ml ; 0.000198 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.52 mg/ml ; 0.00197 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.91
Solubility : 0.00323 mg/ml ; 0.0000122 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.71

Safety of [ 91-13-4 ]

Signal Word:Danger Class:6.1,8
Precautionary Statements:P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P403+P233 UN#:2928
Hazard Statements:H330-H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 91-13-4 ]

* 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 [ 91-13-4 ]
  • Downstream synthetic route of [ 91-13-4 ]

[ 91-13-4 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 95-47-6 ]
  • [ 89-92-9 ]
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YieldReaction ConditionsOperation in experiment
67% With N-Bromosuccinimide; tetrachlorosilane In acetonitrile at 20℃; for 11 h; General procedure: To a mixture of NXS and substrate (1 or 6) in CH3CN at room temperature was added SiCl4 and the mixture left to stir until TLC showed the disappearance of the starting material. The reaction was then poured onto H2O and the mixture extracted with CH2Cl2. The extracts were combined, dried over MgSO4 and evaporated. The residue was purified by recrystallization (pet. ether-Et2O, 3:1) to give pure 2b-2g, 3b, or by silica gel column chromatography (hexane-EtOAc 10:1 or 30:1) to give pure 2a,h,i, 3a-5 or 7-9, respectively
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 40, p. 7245 - 7247
[2] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[3] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[4] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[5] Chemistry Letters, 2004, vol. 33, # 7, p. 916 - 917
[6] Chemische Berichte, 1885, vol. 18, p. 1281[7] Chemische Berichte, 1882, vol. 15, p. 1747
[8] Helvetica Chimica Acta, 2009, vol. 92, # 3, p. 555 - 566
[9] Patent: WO2011/41349, 2011, A1, . Location in patent: Page/Page column 13; 19
  • 2
  • [ 95-47-6 ]
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Reference: [1] Heteroatom Chemistry, 2016, vol. 27, # 3, p. 173 - 183
  • 3
  • [ 95-47-6 ]
  • [ 583-71-1 ]
  • [ 576-23-8 ]
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Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 236 - 237
  • 4
  • [ 79985-01-6 ]
  • [ 118-90-1 ]
  • [ 86128-85-0 ]
  • [ 529-20-4 ]
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  • [ 91-13-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 10, p. 1857 - 1862
  • 5
  • [ 95-47-6 ]
  • [ 89-92-9 ]
  • [ 91-13-4 ]
YieldReaction ConditionsOperation in experiment
67% With N-Bromosuccinimide; tetrachlorosilane In acetonitrile at 20℃; for 11 h; General procedure: To a mixture of NXS and substrate (1 or 6) in CH3CN at room temperature was added SiCl4 and the mixture left to stir until TLC showed the disappearance of the starting material. The reaction was then poured onto H2O and the mixture extracted with CH2Cl2. The extracts were combined, dried over MgSO4 and evaporated. The residue was purified by recrystallization (pet. ether-Et2O, 3:1) to give pure 2b-2g, 3b, or by silica gel column chromatography (hexane-EtOAc 10:1 or 30:1) to give pure 2a,h,i, 3a-5 or 7-9, respectively
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 40, p. 7245 - 7247
[2] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[3] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[4] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[5] Chemistry Letters, 2004, vol. 33, # 7, p. 916 - 917
[6] Chemische Berichte, 1885, vol. 18, p. 1281[7] Chemische Berichte, 1882, vol. 15, p. 1747
[8] Helvetica Chimica Acta, 2009, vol. 92, # 3, p. 555 - 566
[9] Patent: WO2011/41349, 2011, A1, . Location in patent: Page/Page column 13; 19
  • 6
  • [ 95-47-6 ]
  • [ 91-13-4 ]
YieldReaction ConditionsOperation in experiment
80% With N-Bromosuccinimide; dibenzoyl peroxide In chloroform for 5 h; Reflux A mixture of compound 1 (40 g, 0.38 mol), NBS (140.8 g, 0.79 mol), benzoyl peroxide (0.91 g, 3.8 mmol) in CHCl3 (400 mL) was heated for 5 h under reflux. The reaction mixture was cooled to room temperature and CH2Cl2 (400 mL) was added to the mixture. The organic layer was washed with water (2×200 mL) and dried over Na2SO4, filtered, and the solvent were removed in vacuo. The residue was recrystallized from n-hexane–ethanol (30 : 1, 620 mL) to give compound 2 (79.0 g, 80percent) as white solid, mp 92–93°C. 1H-NMR (400 MHz, CDCl3) δ: 4.66 (4H,s), 7.29–7.38 (4H, m).
65% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 6.33333 h; Synthesis of the brominated compound was achieved in accordance with the literature. 20 For this purpose, o-xylene (5.80 g, 54.0 mmol) and N-bromosuccinimide(NBS) (20.00 g, 112.3 mmol) were dissolved in 25 ml of carbontetrachloride. A half amount of benzoyl peroxide (0.01 g, 0.04 mmol)was added and heterogeneous reaction mixture started to reflux. After 20 minutes, the other half of benzoyl peroxide (0.01 g, 0.04 mmol)was added and the mixture was refluxed for an additional 6 hoursand cooled down to room temperature. In the following step, succinimide solids precipitated during the reaction was separated fromthe solution under suction and the excess of carbon tetrachloride wasremoved by vacuum distillation. The crude mixture was chilled inthe refrigerator overnight, and the precipitated product was separatedby filtration. A white solid was obtained after recrystallization ofthe crude product from diethyl ether to yield 9.26 g (65percent) of 1,2-bis(bromomethyl)benzene (observed m.p: 97C, lit m.p: 99C). MS(EI) m/z (percent) calcd. for C8H8Br2: 264.0; found: 264.0 (M+, 11), 183.1(97), 104.2 (100), 78.2 (19).IR (ATR), νmax/cm−1: 3052–3021 (w, aromatic, C-H stretching),2965 (w, aliphatic C-H stretching), 1489 (m, aliphatic C-H bending),768 (s, aromatic C-H bending). Elemental analysis: anal. calcd. forC8H8Br2 (264.0): C 36.40 H 3.05 Br 60.54; found: C 35.20 H 2.41.
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 38, p. 7055 - 7056
[2] Journal of Organic Chemistry, 1986, vol. 51, # 6, p. 929 - 931
[3] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 1, p. 112 - 117
[4] Chemische Berichte, 1991, vol. 124, # 3, p. 645 - 654
[5] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865
[6] Organic Letters, 2000, vol. 2, # 25, p. 3979 - 3982
[7] RSC Advances, 2015, vol. 5, # 4, p. 2630 - 2639
[8] Journal of the Electrochemical Society, 2016, vol. 163, # 10, p. H896 - H905
[9] Synthetic Communications, 1999, vol. 29, # 23, p. 4079 - 4085
[10] Chemistry - A European Journal, 2017, vol. 23, # 69, p. 17463 - 17468
[11] Synthesis, 2009, # 11, p. 1807 - 1810
[12] Journal of the Indian Chemical Society, 1995, vol. 72, # 2, p. 133 - 136
[13] Bulletin de la Societe Chimique de France, 1982, vol. <2> 2, # 9-10, p. 327 - 328
[14] Pharmazie, 2001, vol. 56, # 10, p. 763 - 769
[15] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2561 - 2573
[16] Organic Syntheses, 1963, vol. Coll. Vol. IV, p. 984
[17] Chemische Berichte, 1885, vol. 18, p. 1277
[18] Journal of the Chemical Society, 1888, vol. 53, p. 7
[19] Journal of the Chemical Society, 1907, vol. 91, p. 1696
[20] Journal of Organic Chemistry, 1952, vol. 17, p. 523,527
[21] Bulletin de la Societe Chimique de France, 1961, p. 2225 - 2235
[22] Synthesis, 1983, # 6, p. 497 - 498
[23] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3521 - 3529
[24] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 5, p. 725 - 731
[25] Physical Chemistry Chemical Physics, 2012, vol. 14, # 11, p. 3909 - 3914
[26] Organic and Biomolecular Chemistry, 2015, vol. 13, # 8, p. 2399 - 2406
[27] Journal of Chemical Crystallography, 2016, vol. 46, # 4, p. 208 - 212
  • 7
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YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide; triphenylphosphine In dichloromethane at -78 - 20℃; for 12 h; Darkness General procedure: NBS (534 mg, 3 mmol) was dissolved in CH2Cl2 (10 mL) contained in a 50 mL flask. Ph3P (786 mg, 3 mmol) and 9 (1 mmol) were added sequentially dropwise into the NBS solution at –78 °C. The reaction mixture was stirred in the dark at r.t. for 12 h and the progression of the reaction was monitored by TLC (eluent: PE–EtOAc, 20:1). The mixture was then concentrated in vacuo and the product 11 was isolatedby flash chromatography on a silica gel column (eluent: PE–EtOAc, 30:1).
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 8, p. 1154 - 1162
[2] Organic Process Research and Development, 2002, vol. 6, # 2, p. 190 - 191
  • 8
  • [ 612-14-6 ]
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Reference: [1] Organic Letters, 1999, vol. 1, # 9, p. 1327 - 1329
  • 9
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Reference: [1] Heteroatom Chemistry, 2016, vol. 27, # 3, p. 173 - 183
  • 10
  • [ 95-47-6 ]
  • [ 583-71-1 ]
  • [ 576-23-8 ]
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Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 236 - 237
  • 11
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Reference: [1] Chemische Berichte, 1923, vol. 56, p. 2148
  • 12
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Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 272
  • 13
  • [ 89-95-2 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 436, p. 272
  • 14
  • [ 168971-56-0 ]
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Reference: [1] Chemische Berichte, 1923, vol. 56, p. 2148
  • 15
  • [ 79985-01-6 ]
  • [ 118-90-1 ]
  • [ 86128-85-0 ]
  • [ 529-20-4 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 10, p. 1857 - 1862
  • 16
  • [ 91-13-4 ]
  • [ 6425-66-7 ]
YieldReaction ConditionsOperation in experiment
68% at 0℃; for 4 h; Example 100 (3-Amino-1-oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]tria2in-7-yl)methanol (124). 1,2-Bis(brornornethyl)-4-nitrobenzene (118). KNO3 (33.0 g, 330 mmol) was added in small portions, over 1 h, to a stirred solution of 1 ,2-bis(bromomethyl)benzene (117) (72.2 g, 300 mmol) in CH2SO4 (600 ml_) at 0 0C. After the addition was completed, the mixture was stirred at 0 0C for 3 h. The mixture was poured onto ice and stirred at 0 0C for 2 h. The solid was filtered, washed with water several times and dried to give nitrobenzene 118 (63.1g, 68percent) as a white solid: mp (EtOAc/pet. ether) 73-74 0C; 1H NMR δ 8.25 (d, J = 2.3 Hz, 1 H, H-3), 8.15 (dd, J = 8.4, 2.3 Hz, 1 H, H-5), 7.56 (d, J = 8.4 Hz, 1 H, H-6), 4.67 (s, 2 H, CH2Br), 4.66 (S, 2 H, CH2Br); 13C NMR δ 148.0, 143.4 138.3, 132.1 , 125.9, 124.1 , 28.0, 27.5. Anal, calcd for C8H7NBr2O2: C, 31.1; H, 2.3; N, 4.5. Found: C, 31.1; H, 2.3; N, 4.5percent.
43% at 0℃; for 2 h; KNO3 (920 mg, 9.1 mmol) was slowly added to the solution of 1,2- bis(bromomethyl)benzene (25.1) 2.0 g, 7.6 mmol) in H2SO4 (10 mL) at 0 °C. The mixture was stirred at 0 °C for 2 hand then poured into ice water and filtered to afford 1,2-bis(bromomethyl)- 4-nitrobenzene (24.1) as a yellow solid (1.0 g, 43percent). [00476] 1H NMR (400 MHz, DMSO-d6): δ 4.92 (s, 2H), 4.96 (s, 2H), 7.79 (d, J = 8.52 Hz, 1H), 8.20 (dd, J = 8.49, 2.48 Hz, 1H), 8.41 (d, J = 2.45 Hz, 1H).
31%
Stage #1: for 0.25 h;
Stage #2: at 5℃; for 5 h; Cooling with ice
α,α-Dibromo-o-xylene (3.0 g, 11.4 mmol) was suspended in c.H2SO4 (25 mL) and stirred for 15 mins. After which time it was cooled in an ice bath. KNO3 (5.2 g, 51.4 mmol) was added in small portions over a period of 1 hour taking care to ensure the temperature of the reaction mixture did not exceed 5°C. After the addition the reaction was stirred for a further 4 hours before it was poured onto crushed ice (300 mL) and stirred. The precipitated crude solid was filtered and dried in vacuo. The crude material was purified over silica gel chromatography (ethyl acetate: hexane 1:9, Rf product 0.3) giving a white crystalline solid. Yield = 1.1 g (31percent). 1H NMR (400 MHz, CDCl3): δ 8.25 (1H, d, 4JHH = 2.3 Hz, ArH), 8.16 (1Η, dd, 3JHH = 8.4 Hz and 4JHH = 2.4 Hz, ArH), 7.56 (1Η, d, 3JHH = 8.4 Hz, ArH), 4.67 (2Η, s, CH2) and 4.66 ppm (2Η, s, CH2).
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6853 - 6865
[2] Patent: WO2006/104406, 2006, A1, . Location in patent: Page/Page column 109
[3] Patent: WO2016/90079, 2016, A1, . Location in patent: Paragraph 00475-00476
[4] Patent: WO2017/135897, 2017, A1, . Location in patent: Page/Page column 39
  • 17
  • [ 91-13-4 ]
  • [ 25177-85-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996
[2] Journal of Materials Chemistry A, 2014, vol. 2, # 44, p. 18823 - 18830
[3] Patent: US5047534, 1991, A,
  • 18
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  • [ 583-71-1 ]
  • [ 576-23-8 ]
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Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 236 - 237
  • 19
  • [ 91-13-4 ]
  • [ 73217-11-5 ]
Reference: [1] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1936, vol. 30, p. 180,188
  • 20
  • [ 91-13-4 ]
  • [ 37949-03-4 ]
Reference: [1] Drugs of the Future, 2018, vol. 43, # 9, p. 645 - 653
  • 21
  • [ 91-13-4 ]
  • [ 7500-53-0 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1986, vol. 137, p. 29 - 36
[2] Patent: WO2011/41349, 2011, A1,
  • 22
  • [ 91-13-4 ]
  • [ 4152-92-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1966, vol. 96, p. 1671 - 1695
  • 23
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  • [ 95335-46-9 ]
Reference: [1] Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1936, vol. 30, p. 180,188
  • 24
  • [ 612-14-6 ]
  • [ 74785-02-7 ]
  • [ 91-13-4 ]
Reference: [1] Organic Letters, 1999, vol. 1, # 9, p. 1327 - 1329
  • 25
  • [ 91-13-4 ]
  • [ 70654-85-2 ]
Reference: [1] Russian Chemical Bulletin, 2005, vol. 54, # 2, p. 437 - 440
[2] Patent: US2016/251376, 2016, A1,
  • 26
  • [ 91-13-4 ]
  • [ 1037624-75-1 ]
Reference: [1] Drugs of the Future, 2018, vol. 43, # 9, p. 645 - 653
[2] Drugs of the Future, 2018, vol. 43, # 9, p. 645 - 653
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