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Chemical Structure| 34626-51-2 Chemical Structure| 34626-51-2
Chemical Structure| 34626-51-2

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Product Details of 5-Bromo-1-pentanol

CAS No. :34626-51-2
Formula : C5H11BrO
M.W : 167.04
SMILES Code : C(CCO)CCBr
MDL No. :MFCD00061101
InChI Key :WJVQJXVMLRGNGA-UHFFFAOYSA-N
Pubchem ID :118709

Safety of 5-Bromo-1-pentanol

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H302-H315-H318-H335
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312+P330-P303+P361+P353-P304+P340+P312-P305+P351+P338+P310-P332+P313-P370+P378-P403+P233-P403+P235-P405-P501
Class:3
UN#:1993
Packing Group:

Application In Synthesis of 5-Bromo-1-pentanol

* 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 [ 34626-51-2 ]

[ 34626-51-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1026737-34-7 ]
  • 2-(N-Phenylsulfonylindol-3-yl)ethyl 3-Deoxy-2,4-di-O-benzyl-b-D-glucopyranoside [ No CAS ]
  • [ 38222-83-2 ]
  • [ 34626-51-2 ]
  • [ 170220-11-8 ]
  • 2-(N-Phenylsulfonylindol-3-yl)-ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With trifluoromethylsulfonic anhydride; In dichloromethane; dimethyl sulfoxide; Z. 2-(N-Phenylsulfonylindol-3-yl)ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-beta-D-glucopyranoside (III-29a). A stirred solution of 5-bromo-1-pentanol (0.79 g, 4.7 mmol) in DMSO (15 ml) was treated with sodium azide (1.83 g, 28.2 mmol). The resultant mixture was stirred at room temperature for 2.5 h, diluted with water, and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The azide was used without purification in the next step. Crude 5-azido-1-pentanol (280 mg, equivalent to 2.17 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (441 mg, 2.17 mmol) were dissolved in dichloromethane (9 ml) and triflic anhydride (0.36 ml, 2.17 mmol) was added dropwise. After 10 min the mixture was poured into brine (40 ml) and extracted with dichloromethane (2*40 ml). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The triflate was used without purification in the next step. Sodium hydride (16 mg, 0.40 mmol, 60percent dispersion in oil) was added to a solution of alcohol III-28 (120 mg, 0.198 mmol) and azido triflate (105 mg, equivalent to 0.40 mmol) in dichloromethane (3 ml) at room temperature. The mixture was stirred for 24 h, diluted with dichloromethane (40 ml) and poured into saturated ammonium chloride (40 ml). The aqueous phase was extracted with dichloromethane and the combined organic solutions were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (15percent ethyl acetate/hexane) afforded III-29a (121 mg, 83percent yield) as a colorless oil: [alpha]D25 +4.0° (c 0.24, CHCl3); IR (CHCl3) 3022 (s), 2940 (s), 2880 (m), 2105 (s), 1455 (s), 1375 (s), 1270 (s), 1210 (m), 1180 (m), 1125 (m), 1090 (m), 725 (s), 599 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.1 Hz, 1H), 7.82 (dd, J=8.2, 0.9 Hz, 2H), 7.50-7.43 (m, 3H), 7.29-7.19 (m, 14H), 4.65 (d, J=12.0 Hz, 1H), 4.58 (d, J=11.4 Hz, 1H), 4.52 (d, J=12.0 Hz, 1H). 4.42 (d, J=11.5 Hz, 1H), 4.18 (dt, J=9.5, 6.7 Hz, 1H), 3.81 (dt, J=9.5, 7.1 Hz, 1H), 3.71 (d, J=10.6 Hz, 1H), 3.57 (dd, J=10.8, 4.7 Hz, 1H), 3.51-3.38 (m, 4H), 3.31-3.21 (m, 1H), 3.16 (t, J=6.9 Hz, 2H), 3.00 (t, J=6.9 Hz, 2H), 2.50-2.46 (dt, J=12.1, 4.5 Hz, 1H),1.63-1.50 (m, 5H), 1.48-1.32 (m, 3H); 13 C NMR (62.5 MHz, CDCl3) delta138.52, 138.23, 137.00, 135.07, 133.59, 131.09, 129.14, 128.43, 128.31, 127.78, 127.68, 127.50, 126.70, 126.69, 124.70, 123.54, 123.09, 119.71, 119.48, 113.70, 105.26, 78.01, 74.92, 72.67, 72.25, 71.38, 71.24, 69.96, 68.41, 34.97, 29.62, 29.15, 28.66, 25.65, 23.39; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 761.2973 (M+; calcd for C41 H46 N4 O7 S: 761.2985).
  • 2
  • [ 1026737-34-7 ]
  • 2-(N-Phenylsulfonylindol-3-yl) ethyl 3-Deoxy-2,4-di-O-benzyl-β-D-glucopyranoside [ No CAS ]
  • [ 38222-83-2 ]
  • [ 34626-51-2 ]
  • [ 170220-11-8 ]
  • 2-(N-Phenylsulfonylindol-3-yl) ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With trifluoromethylsulfonic anhydride; In dichloromethane; dimethyl sulfoxide; Z. 2-(N-Phenylsulfonylindol-3-yl) ethyl 2,4-Di-O-benzyl-3-deoxy-6-O-(5-azidopentyl)-beta-D-glucopyranoside (III-29a) A stirred solution of 5-bromo-1-pentanol (0.79 g, 4.7 mmol) in DMSO (15 ml) was treated with sodium azide (1.83 g, 28.2 mmol). The resultant mixture was stirred at room temperature for 2.5 h, diluted with water, and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The azide was used without purification in the next step. Crude 5-azido-1-pentanol (280 mg, equivalent to 2.17 mmol) and <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (441 mg, 2.17 mmol) were dissolved in dichloromethane (9 ml) and triflic anhydride (0.36 ml, 2.17 mmol) was added dropwise. After 10 min the mixture was poured into brine (40 ml) and extracted with dichloromethane (2*40 ml). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The triflate was used without purification in the next step. Sodium hydride (16 mg, 0.40 mmol, 60percent dispersion in oil) was added to a solution of alcohol III-28 (120 mg, 0.198 mmol) and azido triflate (105 mg, equivalent to 0.40 mmol) in dichloromethane (3 ml) at room temperature. The mixture was stirred for 24 h, diluted with dichloromethane (40 ml) and poured into saturated ammonium chloride (40 ml). The aqueous phase was extracted with dichloromethane and the combined organic solutions were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (15percent ethyl acetate/hexane) afforded III-29a (121 mg, 83percent yield) as a colorless oil: [alpha]D25 +4.0° (c 0.24, CHCl3); IR (CHCl3) 3022 (s), 2940 (s), 2880 (m), 2105 (s), 1455 (s), 1375 (s), 1270 (s), 1210 (m), 1180 (m), 1125 (m), 1090 (m), 725 (s), 599 (m) cm-1; 1 H NMR (500 MHz, CDCl3) delta7.96 (d, J=8.1 Hz, 1 H), 7.82 (dd, J=8.2, 0.9 Hz, 2 H), 7.50-7.43 (m, 3 H), 7.29-7.19 (m, 14 H), 4.65 (d, J=12.0 Hz, 1 H), 4.58 (d, J=11.4 Hz, 1 H), 4.52 (d, J=12.0 Hz, 1 H), 4.42 (d, J=11.5 Hz, 1 H), 4.18 (dt, J=9.5, 6.7 Hz, 1 H), 3.81 (dt, J=9.5, 7.1 Hz, 1 H), 3.71 (d, J=10.6 Hz, 1 H), 3.57 (dd, J=10.8, 4.7 Hzr 1 H), 3.51-3.38 (m, 4 H), 3.31-3.21 (m, 1 H), 3.16 (t, J=6.9 Hz, 2 H), 3.00 (t, J=6.9 Hz, 2 H), 2.50-2.46 (dt, J=12.1, 4.5 Hz, 1 H),1.63-1.50 (m, 5 H), 1.48-1.32 (m, 3 H); 13 C NMR (62.5 MHz, CDCl3) delta138.52, 138.23, 137.00, 135.07, 133.59, 131.09, 129.14, 128.43, 128.31, 127.78, 127.68, 127.50, 126.70, 126.69, 124.70, 123.54, 123.09, 119.71, 119.48, 113.70, 105.26, 78.01, 74.92, 72.67, 72.25, 71.38, 71.24, 69.96, 68.41, 34.97, 29.62, 29.15, 28.66, 25.65, 23.39; high resolution mass spectrum (FAB, m-nitrobenzyl alcohol) m/z 761.2973 (M+; calcd for C41 H46 N4 O7 S: 761.2985).
  • 3
  • [ 34626-51-2 ]
  • [ 407-97-6 ]
 

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