[ CAS No. 18014-00-1 ]

Name: 18014-00-1|Dimethyl 2,5-dibromoterephthalate|97%
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Quality Control of [ 18014-00-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 18014-00-1 ]

CAS No. :	18014-00-1	MDL No. :	MFCD00204592
Formula :	C₁₀H₈Br₂O₄	Boiling Point :	362°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	351.98 g/mol	Pubchem ID :	87401
Synonyms :

Safety of [ 18014-00-1 ]

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 [ 18014-00-1 ]

Upstream synthesis route of [ 18014-00-1 ]
Downstream synthetic route of [ 18014-00-1 ]

[ 18014-00-1 ] Synthesis Path-Upstream 1~7

1
[ 67-56-1 ]
[ 13731-82-3 ]
[ 18014-00-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	for 12 h; Reflux	Iodine (78 mg, 0.33 mmol) was added to p-xylene (6.13 mL, 50.0 mmol), the mixture was cooled to 0 °C, and bromine (5.20 mL, 101 mmol) was added dropwise over 10 min. The ice bath was removed and the reaction stirred at rt for 16 h in the absence of light. The reaction was quenched with 20percent aq. KOH and stirred for 15 min while the solution became colorless. The solid precipitate was filtered and rinsed 2 x with 100 mL of H₂O. The solids were recrystallized in ethanol to afford a white solid (9.19 g, 70percent). ¹H NMR (CDCl₃): δ 7.40 (s, 2H), 2.34 (s, 6H). 1,4–dibromo-2,5-dimethylbenzene (5.93 g, 22.5 mmol) and KMnO₄ (15.72 g, 99.5 mmol) were added to 80 mL of t-BuOH:H₂O (1:1). Celite (14 g) was added to the flask and the reaction was refluxed for 18 h. The reaction mixture was cooled to rt, filtered over celite and the filter was washed with hot H₂O (100mL) and EtOAc (50mL). The filtrate was then acidified to pH=1 with conc. HCl. The white suspension was then extracted 3x with 100 mL of EtOAc. The combined organic extracts were dried over MgSO₄ and excess solvent was removed under vacuum to obtain a white solid (3.06 g, 42percent) which was not purified further. ¹H NMR (DMSO-d6): δ 8.01 (s, 2H). 2,5–dibromoterephthalic acid (2.04 g, 6.30 mmol) dissolved in 35 mL of MeOH and refluxed for 30 min. Thionyl chloride (9.00 mL, 124 mmol) was then carefully added and the reaction was refluxed 12 hours. The reaction flask was cooled to room temperature, 50 mL of water was carefully added, and the reaction was extracted 3x with 75 mL of Et₂O. The combined organics were washed with 3 x with 50 mL of sat. NaHCO₃ and dried with MgSO₄. The solvent was removed under vacuum and the solids recrystallized in MeOH to yield a white crystalline solid (1.65g, 74percent), mp = 134-136 C (lit.³ mp 134-137 C). ¹H NMR (CDCl₃): δ 8.06 (s, 2H), 3.96 (s, 6H). The ¹H NMR matches the known spectrum.³

Reference： [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 5, p. 1781 - 1783
[2] Journal of the American Chemical Society, 1994, vol. 116, # 26, p. 11723 - 11736
[3] Tetrahedron, 2015, vol. 71, # 2, p. 283 - 292
[4] Journal of Organic Chemistry, 1959, vol. 24, p. 26
[5] Bulletin de la Societe Chimique de France, 1958, p. 1418,1420
[6] Journal of Organic Chemistry, 1959, vol. 24, p. 26
[7] Bulletin de la Societe Chimique de France, 1958, p. 1418,1420
[8] Macromolecules, 2004, vol. 37, # 21, p. 7945 - 7954

2
[ 1074-24-4 ]
[ 18014-00-1 ]

Reference： [1] Macromolecules, 2004, vol. 37, # 21, p. 7945 - 7954
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 5, p. 1781 - 1783
[3] Tetrahedron, 2015, vol. 71, # 2, p. 283 - 292

3
[ 67-56-1 ]
[ 18014-00-1 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2432 - 2440

4
[ 13731-82-3 ]
[ 18014-00-1 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2432 - 2440

5
[ 106-42-3 ]
[ 18014-00-1 ]

Reference： [1] Tetrahedron, 2015, vol. 71, # 2, p. 283 - 292

6
[ 67-56-1 ]
[ 1074-24-4 ]
[ 18014-00-1 ]

Reference： [1] Journal of the American Chemical Society, 1969, vol. 91, # 13, p. 3527 - 3533

7
[ 67-56-1 ]
[ 13731-82-3 ]
[ 18014-00-1 ]
[ 114537-99-4 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1958, p. 1418,1420

[ 18014-00-1 ] Synthesis Path-Downstream 1~25

1
2-(9,9-dioctyl-9H-fluoren-2-yl)-5-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-fluoren-2-yl]-terephthalic acid dimethyl ester [ No CAS ]
[ 18014-00-1 ]
C₁₄₆H₁₈₆O₁₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1520 - 1525

2
[ 18014-00-1 ]
[ 73183-34-3 ]
[ 302554-81-0 ]
[ 620624-92-2 ]
2-(9,9-dioctyl-9H-fluoren-2-yl)-5-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-fluoren-2-yl]-terephthalic acid dimethyl ester [ No CAS ]
[ 718640-08-5 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1520 - 1525

3
[ 18014-00-1 ]
[ 302554-81-0 ]
[ 620624-92-2 ]
2-(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)-5-(9,9-dioctyl-9H-fluoren-2-yl)-terephthalic acid dimethyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1520 - 1525

4
[ 18014-00-1 ]
[ 302554-81-0 ]
[ 620624-92-2 ]
2-(9,9-dioctyl-9H-fluoren-2-yl)-5-(9,9-dioctyl-7-trimethylsilanyl-9H-fluoren-2-yl)-terephthalic acid dimethyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1520 - 1525

5
[ 18014-00-1 ]
[ 302554-81-0 ]
2-bromo-5-(9,9-dioctyl-9H-fluoren-2-yl)-terephthalic acid dimethyl ester [ No CAS ]
[ 718640-08-5 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1520 - 1525

6
[ 872220-15-0 ]
[ 18014-00-1 ]
[ 872220-16-1 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 9933 - 9938

7
[ 1074-24-4 ]
[ 18014-00-1 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 7945 - 7954
[2]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 1781 - 1783
[3]Tetrahedron,2015,vol. 71,p. 283 - 292

8
[ 18014-00-1 ]
C₃₈H₄₄Br₂N₄O₄ [ No CAS ]

Reference： [1]Macromolecules,2004,vol. 37,p. 7945 - 7954

9
[ 18014-00-1 ]
[ 791717-67-4 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 7945 - 7954

10
[ 18014-00-1 ]
2,8-dibromo-6,6,12,12-tetrakis-(4-tert-butyl-phenyl)-6,12-dihydro-indeno[1,2-b]fluorene [ No CAS ]