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[ CAS No. 69189-19-1 ]

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2D
Chemical Structure| 69189-19-1
Chemical Structure| 69189-19-1
Structure of 69189-19-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 69189-19-1 ]

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Product Details of [ 69189-19-1 ]

CAS No. :69189-19-1MDL No. :MFCD16620247
Formula : C8H7Br3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :342.85Pubchem ID :12496465
Synonyms :

Computed Properties of [ 69189-19-1 ]

TPSA : 0 H-Bond Acceptor Count : 0
XLogP3 : 3.7 H-Bond Donor Count : 0
SP3 : 0.25 Rotatable Bond Count : 2

Safety of [ 69189-19-1 ]

Signal Word:WarningClass
Precautionary Statements:P280-P305+P351+P338UN#:
Hazard Statements:H317-H319Packing Group:
GHS Pictogram:

Application In Synthesis of [ 69189-19-1 ]

  • Upstream synthesis route of [ 69189-19-1 ]
  • Downstream synthetic route of [ 69189-19-1 ]

[ 69189-19-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 171011-37-3 ]
  • [ 69189-19-1 ]
YieldReaction ConditionsOperation in experiment
95% With phosphorus tribromide In diethyl ether at 0℃; for 7.00 h; Reflux To a solution of 11 (103 mg, 0.474 mM) in Et2O (3 mL) was slowly added a solution of PBr3 (0.16 mL,1.66 mM) in Et2O (0.25 mL) at 0 °C. The whole was refluxed for 7 h, poured to ice (ca 30 mL), andextracted with Et2O (20 mL × 3). The organic solutions were washed with brine (10 mL), dried, andevaporated. Purification of the residue by column chromatography (SiO2, hexane) gave 12 (154 mg,95percent) as colorless plates, mp 42-44 °C (lit [20]. mp 40-44 °C).
84% With N-Bromosuccinimide In dichloromethane at 20℃; for 6.00 h; After dissolving Compound 3 (5.2 g, 23.9 mmol) in methylene chloride (50 milliliter), followed by adding N-bromosuccinimide (12.8 g, 71.7 mmol) at room temperature, and then the resultant solution was stirred for 6 hours. Water (200 milliliter) was poured in the resultant reaction solution, and the deposited solid was washed by ethanol, and as a result, Compound 4 was obtained. Product Amount: 6.9 g, Yield: 84 percent
Reference: [1] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514
[2] Patent: EP1659129, 2006, A1. Location in patent: Page/Page column 100-101
[3] Patent: US6025370, 2000, A
[4] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146
  • 2
  • [ 583-71-1 ]
  • [ 69189-19-1 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1.00 h; Heating / reflux 4-bromo-l,2-bis(bromomethyl)benzene (Q22). To a 1000 mL round bottom flask was added 4-brmo-oe-xylene <21) (0.0811 mol, 15.0Og), NBS (0.0426 mol, 7.580 g), 2,2 -azobisisobutyronitrile (0.00405 mol, 0.6650 g) and 500 mL of CCl4. The reaction mixture was then heated under reflux for Ih. After this time another amount of NBS and AIBN was added and repeated over four times in total. The precipitate was filtered off from the warm reaction mixture and the filtrate concentrated. Crude material was crystallized from hexanes to form white crystals (23 g, 93percent). 1H NMR (300 MHz, CDCl3) δ 7.53 (d, IH, ArH, J=2.0 Hz), 7.44 (dd, IH, ArH, J-8.1 Hz, J =2.0 Hz), 7.24 (d, IH, ArH, J=8.10), 4.60 (d, 4H, CH2, J=4.20 Hz)
56.7% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 1.00 h; Step A : 4-bromo-l,2-bis(bromomethyl)benzene A solution of 4-bromo-l,2-dimethylbenzene (2.0 g, 10.81 mmol) in carbon tetrachloride (70 mL) in a 250 mL round bottom flask was stirred at room temperature until all solids were dissolved. N-bromosuccinimide (4.81 g, 27.0 mmol) and 2,2'- azobis(2-methylpropionitrile) (0.044 g, 0.270 mmol) were added and mixture was heated to 70°C for 1 h. After cooling to room temperature, the mixture was filtered through celite bed. Celite bed was rinsed with carbon tetrachloride (3x50 mL). Combined filtrate was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by combi- flash column chromatography (Column: 120 gm Red- Sep; eluent: hexane). The fractions were collected and concentrated under reduced pressure to yield 4-bromo-l,2-bis(bromomethyl) benzene (2.1 g, 56.7percent yield) as colorless gummy oil. 1H NMR (400 MHz, CDC13): δ 7.56-7.51 (m, 1H), 7.44-7.41 (m, 1H), 7.25- 7.22 (m, 1H), 4.59 (s, 2H), 4.578 (s, 2H).
Reference: [1] Patent: WO2008/24435, 2008, A2. Location in patent: Page/Page column 98
[2] Journal of Organic Chemistry USSR (English Translation), 1985, p. 1418 - 1421[3] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 7, p. 1556 - 1560
[4] Patent: WO2015/103508, 2015, A1. Location in patent: Page/Page column 102
[5] Journal of Organic Chemistry, 1979, vol. 44, # 9, p. 1519 - 1533
[6] Patent: US2014/194386, 2014, A1. Location in patent: Paragraph 0460
  • 3
  • [ 86-90-8 ]
  • [ 69189-19-1 ]
Reference: [1] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146
[2] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514
  • 4
  • [ 171011-37-3 ]
  • [ 69189-19-1 ]
YieldReaction ConditionsOperation in experiment
95% With phosphorus tribromide In diethyl ether at 0℃; for 7.00 h; Reflux To a solution of 11 (103 mg, 0.474 mM) in Et2O (3 mL) was slowly added a solution of PBr3 (0.16 mL,1.66 mM) in Et2O (0.25 mL) at 0 °C. The whole was refluxed for 7 h, poured to ice (ca 30 mL), andextracted with Et2O (20 mL × 3). The organic solutions were washed with brine (10 mL), dried, andevaporated. Purification of the residue by column chromatography (SiO2, hexane) gave 12 (154 mg,95percent) as colorless plates, mp 42-44 °C (lit [20]. mp 40-44 °C).
84% With N-Bromosuccinimide In dichloromethane at 20℃; for 6.00 h; After dissolving Compound 3 (5.2 g, 23.9 mmol) in methylene chloride (50 milliliter), followed by adding N-bromosuccinimide (12.8 g, 71.7 mmol) at room temperature, and then the resultant solution was stirred for 6 hours. Water (200 milliliter) was poured in the resultant reaction solution, and the deposited solid was washed by ethanol, and as a result, Compound 4 was obtained. Product Amount: 6.9 g, Yield: 84 percent
Reference: [1] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514
[2] Patent: EP1659129, 2006, A1. Location in patent: Page/Page column 100-101
[3] Patent: US6025370, 2000, A
[4] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146
  • 5
  • [ 583-71-1 ]
  • [ 69189-19-1 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1.00 h; Heating / reflux 4-bromo-l,2-bis(bromomethyl)benzene (Q22). To a 1000 mL round bottom flask was added 4-brmo-oe-xylene <21) (0.0811 mol, 15.0Og), NBS (0.0426 mol, 7.580 g), 2,2 -azobisisobutyronitrile (0.00405 mol, 0.6650 g) and 500 mL of CCl4. The reaction mixture was then heated under reflux for Ih. After this time another amount of NBS and AIBN was added and repeated over four times in total. The precipitate was filtered off from the warm reaction mixture and the filtrate concentrated. Crude material was crystallized from hexanes to form white crystals (23 g, 93percent). 1H NMR (300 MHz, CDCl3) δ 7.53 (d, IH, ArH, J=2.0 Hz), 7.44 (dd, IH, ArH, J-8.1 Hz, J =2.0 Hz), 7.24 (d, IH, ArH, J=8.10), 4.60 (d, 4H, CH2, J=4.20 Hz)
56.7% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 70℃; for 1.00 h; Step A : 4-bromo-l,2-bis(bromomethyl)benzene A solution of 4-bromo-l,2-dimethylbenzene (2.0 g, 10.81 mmol) in carbon tetrachloride (70 mL) in a 250 mL round bottom flask was stirred at room temperature until all solids were dissolved. N-bromosuccinimide (4.81 g, 27.0 mmol) and 2,2'- azobis(2-methylpropionitrile) (0.044 g, 0.270 mmol) were added and mixture was heated to 70°C for 1 h. After cooling to room temperature, the mixture was filtered through celite bed. Celite bed was rinsed with carbon tetrachloride (3x50 mL). Combined filtrate was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude material was purified by combi- flash column chromatography (Column: 120 gm Red- Sep; eluent: hexane). The fractions were collected and concentrated under reduced pressure to yield 4-bromo-l,2-bis(bromomethyl) benzene (2.1 g, 56.7percent yield) as colorless gummy oil. 1H NMR (400 MHz, CDC13): δ 7.56-7.51 (m, 1H), 7.44-7.41 (m, 1H), 7.25- 7.22 (m, 1H), 4.59 (s, 2H), 4.578 (s, 2H).
Reference: [1] Patent: WO2008/24435, 2008, A2. Location in patent: Page/Page column 98
[2] Journal of Organic Chemistry USSR (English Translation), 1985, p. 1418 - 1421[3] Zhurnal Organicheskoi Khimii, 1985, vol. 21, # 7, p. 1556 - 1560
[4] Patent: WO2015/103508, 2015, A1. Location in patent: Page/Page column 102
[5] Journal of Organic Chemistry, 1979, vol. 44, # 9, p. 1519 - 1533
[6] Patent: US2014/194386, 2014, A1. Location in patent: Paragraph 0460
  • 6
  • [ 86-90-8 ]
  • [ 69189-19-1 ]
Reference: [1] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 139 - 146
[2] Synlett, 2013, vol. 24, # 19, p. 2510 - 2514
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