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Chemical Structure| 89980-92-7 Chemical Structure| 89980-92-7

Structure of 89980-92-7

Chemical Structure| 89980-92-7

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Product Details of [ 89980-92-7 ]

CAS No. :89980-92-7
Formula : C8H9BrO2
M.W : 217.06
SMILES Code : BrC1=CC(CO)=CC=C1CO
MDL No. :MFCD25968595
Boiling Point : No data available
InChI Key :KYBPOEADFKOHSI-UHFFFAOYSA-N
Pubchem ID :18676617

Safety of [ 89980-92-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 89980-92-7 ]

* 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.

  • Downstream synthetic route of [ 89980-92-7 ]

[ 89980-92-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 18643-86-2 ]
  • [ 89980-92-7 ]
YieldReaction ConditionsOperation in experiment
91.8% With sodium tetrahydroborate; 1,2-dimethoxyethane; at 40℃; for 0.5h;Inert atmosphere; Large scale; In nitrogen atmosphere, at room temperature, 2-bromo dimethylterephthalate (30.0 kg, 109.9mol) in 2-dimethoxy ethane (259.8 kg) was added, sodium borohydride (24.9 kg, 659.4mol) was added, and stirred at 40 C for 30 minutes, methanol (60 kg) was dropped into the mixture, at this time, the internal temperature increases to 50 C. HPLC is confirmed for the end of reaction, the reaction mixture is then cooled to 10 C. Methanol (15.0 kg) was added, stirred at 5 C overnight. An aqueous solution of citric acid (33 wt %, 90.0 kg) was added to the reaction mixture. and concentrated under reduced pressure. Ethyl acetate (220.0 kg) was added to the resulting residue, and stirred at 35 C for 30 minutes, the mixture was washed with water (120.0 kg) , the separated aqueous layer was extracted with ethyl acetate (50.0 kg). The combined organic layer was washed with salt water (20 weight %, 100.0 kg) , dried using anhydrous magnesium sulfate (9.0 kg), concentrated under reduced pressure. Methanol (56.0 kg) was added to the residue, stirred at 40 C for 30 minutes to dissolve them. Water (280.0 kg) was added, stirred at 3-4 C for 1 hour, filtered, crystals were collected, washed with water (30 kg × 2 times) and heptane (30 kg × 2 times) , and dried under reduced pressure to obtain the title compound as white crystals (22.07 kg, yield 91.8%).
84% Crushed calcium chloride (14.55 g, 131.1 mmol) was added over a period of 20 minutes to a solution of sodium borohydride (6.61 g, 174.8 mmol) in ethanol (150 ml) with stirring at 0C, and then a solution of <strong>[18643-86-2]dimethyl 2-bromoterephthalate</strong> (described in J. Med. Chem., 13, 1235 (1970); 11.94 g, 43.7 mmol) in ethanol (20 ml) was added thereto. After the mixture was stirred at the same temperature for 30 minutes, sodium borohydride (5.3 g, 140 mmol) and calcium chloride (1 g, 9.0 mmol) were further added thereto. The resulting mixture was stirred for 40 minutes, and a 2N aqueous solution of hydrochloric acid (250 ml) was added thereto. The product was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride. The extract was concentrated under reduced pressure, and a solid residue was obtained. The residue was washed with a small amount of ethyl acetate to afford the title compound (7.98 g, 84% yield) as a colorless solid (mp. 104C). NMR spectrum (400 MHz, DMSO-d6) δ ppm: 4.48 (2H, d, J=5 Hz), 4.49 (2H, d, J=6 Hz), 5.27 (1H, t, J=6 Hz), 5.37 (1H, t, J=5 Hz), 7.31 (1H, d, J=7 Hz), 7.46-7.50 (2H, m) IR spectrum ν max KBr cm-1: 3332, 3244, 1435, 1404, 1201, 1058, 1018, 825 Mass spectrum m/z (EI): 216, 218 (M+).
76% With methanol; lithium borohydride; In tetrahydrofuran; at 0 - 20℃; To a solution of 1,4-dimethyl 2-bromobenzene-1,4-dicarboxylate (2.00 g, 7.324 mmol, 1.00 equiv) in THF (30.00 mL) was added LiBH4 (478.63 mg, 21.972 mmol, 3.00 equiv) slowly at 0 C. MeOH (5 mL) was added to the mixture. After stirring overnight at room temperature, the reaction mixture was quenched with 1 N HC1 to pH = 6~7. The resulting mixture was extracted with ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to afford 1.2 g (76%) of (3-bromo-4- (hydroxymethyl)phenyl)methanol as an off-white solid.
Dimethyl bromoterephthalate was reduced using a literature procedure. To a solution of <strong>[18643-86-2]dimethyl bromoterephthalate</strong> (2.0 g, 7.34 mmol) in THF (50 ml) was added powdered sodium borohydride (1 .7 g, 44.8 mmol) and the mixture heated at reflux for 1 hour. Methanol (20 ml) was then added dropwise (effervescence observed) and heating continued for another 1 hour. The mixture was allowed to cool to room temperature and aqueousconcentrated ammonium chloride (30 ml) added and stirring continued overnight. To the reaction mixture was added ethyl acetate and the organic phase washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was dissolved in a minimal amount of ethyl acetate and trituration with hexanes and dried under vacuum. 1 H NMR(CD30D, 400 MHz) d: 7.57 (br s, 1 H), 7.52 (d, J = 7.8 Hz, 1 H), 7.35 (d, J = 7.8 Hz, 1 H), 4.67 (s, 2H), 4.60 (s, 2H).

 

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