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Chemical Structure| 1334019-92-9 Chemical Structure| 1334019-92-9

Structure of 1334019-92-9

Chemical Structure| 1334019-92-9

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Product Details of [ 1334019-92-9 ]

CAS No. :1334019-92-9
Formula : C14H18BClO4
M.W : 296.55
SMILES Code : O=C(Cl)OCC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1
MDL No. :MFCD34168998
InChI Key :RRWXWRCAEZWWCE-UHFFFAOYSA-N
Pubchem ID :89410901

Safety of [ 1334019-92-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 1334019-92-9 ]

* 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 [ 1334019-92-9 ]

[ 1334019-92-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 32315-10-9 ]
  • [ 302348-51-2 ]
  • [ 1334019-92-9 ]
YieldReaction ConditionsOperation in experiment
Add anhydrous sodium carbonate (1.59 g, 10 mmol) to a three-necked flask. After removing the water at high temperature, it is cooled to room temperature, and after three times of gas exchange, Anhydrous toluene (5 mL) was added thereto under argon gas, Ice bath to around 0 C, A solution of triphosgene (592 mg, 2 mmol) in toluene (10 mL) was added dropwise. After stirring at 0 C for 30 min, A solution of 4-(hydroxymethyl)phenylboronic acid pinacol ester (234 mg, 1 mmol) in toluene (10 mL) was added dropwise. After the addition was completed, the mixture was slowly warmed to room temperature for 5 hours. Use argon to drive away the remaining phosgene for 1 h. After filtration, the solvent was evaporated under reduced pressure to give Intermediate 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxycarbonyl chloride. After drying in vacuo, it was dissolved in anhydrous dichloromethane (10 mL). Temperature-controlled 0 C slowly added dropwise to 2-[2-[2-benzylamino-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indole-2-ylidene) Ethylene]-1-cyclohexen-1-yl]vinyl]-1,3,3-trimethylphosphonium iodide (68 mg, 0.1 mmol) And N,N-diisopropylethylamine (132 muL, 0.8 mmol) In dichloromethane solution (20 mL), After the addition is completed, the reaction is slowly raised to room temperature for 12 to 18 hours.After the reaction was completed, it was washed twice with 0.1 N hydrochloric acid (20 mL). Wash once with saturated sodium carbonate solution (20 mL). Wash once with saturated sodium chloride solution (20 mL). The organic phase is dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give a crude material. Subsequent purification on a silica gel column (dichloromethane / 0-5% methanol). The green solid product is 2-[2-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-) Benzyloxycarbonyl]benzylamino]-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylene]-1-cyclo Hexen-1-yl]vinyl]-1,3,3-trimethylphosphonium iodide, 10% yield.
  • 2
  • [ 75-44-5 ]
  • [ 302348-51-2 ]
  • [ 1334019-92-9 ]
YieldReaction ConditionsOperation in experiment
91% In tetrahydrofuran; toluene; at 20℃; for 24h;Inert atmosphere; 4-(Hydroxymethyl)phenylboronic acid pinacol ester, compound 42 (800 mg, 3.4 mmol, 1 .0 equiv.) was dissolved in THF (7 mL). The resulting solution was then added dropwise into a phosgene solution (15 wt% in toluene, 7.5 mL, 1 0.3 mmol, 3.0 equiv.) under an argon atmosphere at room temperature and was stirred for 24 h. The residual phosgene and solvent were then removed by high vacuum to yield chloroformate 45 (920 mg, 91 %) as a pale brown liquid. Phosgene collected in the liquid nitrogen-cooled trap was then quenched with methanol (20 mL) and saturated sodium hydroxide solution (20 mL). 1H NMR (400 MHz, CDCI3): delta 7.86 (d, J = 8.2 Hz, 2H), 7.39 (d, J = 8.2 Hz, 2H), 5.32 (s, 2H), 1 .36 (s, 12H). Spectral data are consistent with published values.33
In 1,4-dioxane; toluene; at 21℃; for 20h;Inert atmosphere; A solution of (4-(4,4, 5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenyl)methanol (2.0 g, 8.54 mmol) in anhydrous dioxane (25 m L) was treated with phosgene (20percent in toluene, 22.6 mL, 42.7 mmol) and the reaction was stirred under a N2 atmosphere at 21 °C for 20 h . The mixture was concentrated in vacuo, redissolved, and co-evaporated with toluene (2x) to afford the crude product 1 (2.5 g, quantitative yield) as a clear oil . The crude chloroformate was used in subsequent reactions within few hours after its isolation . 1H NMR (400 MHz, CDCI3) delta 7.84 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 8.1 Hz, 2H), 5.31 (s, 2H), 1.35 (s, 12H) ; 13C N MR ( 101 MHz, CDCI3) delta 150.8, 136.2, 135.4, 128.0, 84.2, 73.4, 25.0.
  • 3
  • [ 7724-12-1 ]
  • [ 1334019-92-9 ]
  • [ 1422655-40-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 0℃; Triphosgen (0.26 g, 0.77 mmol) and 4-hydroxymethylphenylboronic acid, pinacol ester (0.5 g, 2.14 mmol) were dissolved in THF (20 ml) in an ice-water bath. Pyridine (0.35 ml, 4.28 mmol) was added dropwise, and the reaction mixture was stirred at 0°C until thin layer chromatography showed the disappearance of starting material. After bring the temperature to room temperature, the reaction mixture was extracted with dichloromethane/water. The organic layer was collected and dried over sodium sulfate. After filtration, solvent was removed and the residue was purified by flash chromatography to give the product as a white solid (0.1 g, 11percent). 1H NMR (300 MHz, CD2C12, delta): 8.43 (m, 1H), 8.10 (m, 1H), 7.78 (m, 2H), 7.41 (m, 2H), 7.26 (m, 1H), 5.25 (s, 2H), 1.32 (s, 12H); MS (ESI) m/z 436.1.
  • 4
  • [ 116-16-5 ]
  • [ 302348-51-2 ]
  • [ 1334019-92-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In tetrahydrofuran; at 0℃; Triphosgen (0.26 g, 0.77 mmol) and 4-hydroxymethylphenylboronic acid, pinacol ester (0.5 g, 2.14 mmol) were dissolved in THF (20 ml) in an ice-water bath. Pyridine (0.35 ml, 4.28 mmol) was added dropwise, and the reaction mixture was stirred at 0°C until thin layer chromatography showed the disappearance of starting material. After bring the temperature to room temperature, the reaction mixture was extracted with dichloromethane/water. The organic layer was collected and dried over sodium sulfate. After filtration, solvent was removed and the residue was purified by flash chromatography to give the product as a white solid (0.1 g, 11percent). 1H NMR (300 MHz, CD2C12, delta): 8.43 (m, 1H), 8.10 (m, 1H), 7.78 (m, 2H), 7.41 (m, 2H), 7.26 (m, 1H), 5.25 (s, 2H), 1.32 (s, 12H); MS (ESI) m/z 436.1.
 

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