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Chemical Structure| 82386-90-1 Chemical Structure| 82386-90-1

Structure of 82386-90-1

Chemical Structure| 82386-90-1

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Product Details of [ 82386-90-1 ]

CAS No. :82386-90-1
Formula : C7H6ClIO
M.W : 268.48
SMILES Code : OCC1=CC(Cl)=CC=C1I
MDL No. :MFCD02684639

Safety of [ 82386-90-1 ]

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 [ 82386-90-1 ]

* 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 [ 82386-90-1 ]

[ 82386-90-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13421-00-6 ]
  • [ 82386-90-1 ]
YieldReaction ConditionsOperation in experiment
100% With Trimethyl borate; dimethylsulfide borane complex; In tetrahydrofuran; at 20℃; for 18h; To a 2 L flask with a mechanical stirrer, a thermometer, and an addition funnel at r.t. were added sequentially 124 g (0.4 mol) of the product of Step (i), 700 mL of THF, 500 g (4.85 mol) of (CH3O)3B, and 560 mL (1.12 mol) of 2.0 M BH3?Me2S. The reaction mixture was stirred at r.t. for 18 hrs., quenched with 500 mL of CH3OH and concentrated. The residue was dissolved with 1 L EtOAc, washed with brine, dried over MgSO4, and concentrated to give 121 g (>100%) of 2-iodo-5-chlorobenzyl alcohol as white solid. 1H NMR (CDCl3): delta 7.64 (d, J = 8.3 Hz, 1H), 7.41 (d, J = 2.5 Hz, 1H), 6.93 (dd, J = 8.3, 2.5, 1H), 4.57 (s, 2H).
With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 18h; EXAMPLE 64a Preparation of intermediate 5-chloro-2-Iodo-benzaldehyde To a solution of 5-chloro-2-iodo <strong>[13421-00-6]benzoic acid</strong> (4.92 g, 17 mmol) (TRANS) in anhydrous tetrahydrofuran (100 mL) at 0 C. was added borane tetrahydrofuran (1 M, 34 mL, 34 mmol) dropwise. The reaction mixture was then stirred at room temperature for 18 h. The mixture was concentrated and residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over MgSO4, and concentrated to give a colorless oil. The oil was dissolved into 1,2-dichloroethane (50 mL), and activated MnO2 (15 g) was added. The mixture was then heated at reflux for 2 h, cooled to room temperature, and filtered through a short pad of celite. The filtrated was concentrated and purified by chromatography (EtOAc:hexanes=1;8) to give 5-chloro-2-Iodo-benzaldehyde as a white solid (Yield 5.5 g, 25%).
9.5 g With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20℃; for 8h; Borane-dimethylsulfide complex (3.7 mL, 38.9 mmol) was added slowly to a cold (0C) solution of <strong>[13421-00-6]5-chloro-2-iodo-<strong>[13421-00-6]benzoic acid</strong></strong> (10 g, 35.4 mmol) in THF (20 mL). The reaction mixture was allowed to warm to rt, stirred for 8 h, quenched by addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The organic layer was dried (Na2S04), filtered, and concentrated to provide 9.5 g of the title compound. tR: 4.72 min (HPLC 2); Rf= 0.66 (hexane/EtOAc, 7:3).
  • 2
  • borane methylsulfide [ No CAS ]
  • [ 121-43-7 ]
  • [ 13421-00-6 ]
  • [ 82386-90-1 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; methanol; Step 1. Borane methylsulfide (7.3 mL, 73 mmol) was added to a stirred solution of <strong>[13421-00-6]5-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong></strong> (17.17 g, 60.79 mmol) in THF (40 mL) and trimethylborate (20 mL), maintaining the internal temperature at 20-25 C. After 16 h methanol (8.87 mL, 0.219 mol) was added cautiously and the solution was evaporated in vacuo, azeotroping with methanol (3*50 mL). The resulting solid was recrystallized (hexanes/ethyl acetate, 5:1, 120 mL) to give 5-chloro-2-iodobenzyl alcohol (12.2 g): 1H NMR (CDCl3, 400 MHz) delta 2.00 (br s, 1H), 4.64 (s, 2H), 7.00 (dd, J=2.6, 8.4 Hz, 1H), 7.49 (d, J=2.4, 1H), 7.72 (d, J=8.2 Hz, 1H).
  • 3
  • [ 13421-00-6 ]
  • [ 82386-96-7 ]
  • [ 82386-90-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium borohydrid; trifluoroborane diethyl ether; In tetrahydrofuran; C. The starting 2-chloro-11H-dibenz(b,f)-1,4-oxathiepin is a novel compound which may be prepared by the following procedure: A solution of 120 g of 5-chloro-2- iodo<strong>[13421-00-6]benzoic acid</strong> (K. Pelz et al., Collect.Czech.Chem.Commun. 33, 1852, 1968) in 145 ml of tetrahydrofuran is stirred and treated at 10-20 C. for 45 minutes with 16.1 g of sodium borohydride. The mixture is then stirred for 30 minutes at this temperature and treated with a solution of 80.3 g (71.4 ml) of boron trifluoride etherate in 40 ml of tetrahydrofuran. It is stirred for another 3 hours and while cooling with ice-cold water it is decomposed at a maximum temperature of 8 C. with 50 ml of 5% hydrochloric acid added dropwise. It is diluted with water and extracted with benzene. The extract is washed with a 5% sodium hydroxide solution and water, dried with magnesium sulfate and evaporated. There are obtained 100 g (96%) of crude 5-chloro-2-iodobenzyl alcohol with m.p. of 115-117 C. The analytically pure substance is obtained by crystallization from ethanol; m.p. 116-117 C.
  • 4
  • [ 201230-82-2 ]
  • [ 82386-90-1 ]
  • [ 54109-03-4 ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine; In acetonitrile; at 250℃; under 49403.3 Torr; for 16h;Autoclave; General procedure: A magnetic stirring bar, 2-iodobenzyl alcohol (1a, 116.0 mg, 0.5 mmol), NEt3 (251.6 mg, 2.5 mmol), and MeCN (10 mL) were placed in a stainless steel autoclave equipped with an inserted Pyrex glass liner. The autoclave was closed, purged three times with carbon monoxide, pressurized with 65 atm of CO and then heated at 250 °C by salt bath with stirring for 16 h. After the reaction, excess CO was discharged at room temperature. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (hexane/EtOAc = 3/1) to give 2a (60.4 mg, 91percent) as a white solid.
 

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