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[ CAS No. 116754-58-6 ] {[proInfo.proName]}

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Chemical Structure| 116754-58-6
Chemical Structure| 116754-58-6
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Product Details of [ 116754-58-6 ]

CAS No. :116754-58-6 MDL No. :MFCD00482035
Formula : C13H27BrO Boiling Point : -
Linear Structure Formula :- InChI Key :FJBCXJNCEVECEC-UHFFFAOYSA-N
M.W : 279.26 Pubchem ID :1636619
Synonyms :
Chemical Name :13-Bromotridecan-1-ol

Safety of [ 116754-58-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 116754-58-6 ]

* 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 [ 116754-58-6 ]

[ 116754-58-6 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 110-87-2 ]
  • [ 116754-58-6 ]
  • [ 116452-12-1 ]
YieldReaction ConditionsOperation in experiment
99% With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 18h; To a suspension of 41 (6.3 g, 22.2 mmol) and 2,3-dihydro-2H-pyran (3.80 g, 45.1 mmol) in DCM (80 mL) was added pyridinium p-toluenesulfonate (0.567 g, 2.26 mmol) at RT. The mixture turned into a solution and was stirred at RT for 18 hr. The reaction mixture was concentrated to remove DCM. The residue was treated with hexanes and water. The hexanes phase was washed by brine, dried over Na2S04, and evaporated to afford 42 (8.8 g, 99%) as an oil. 'H NMR (400 MHz, Chloroform-6/) 5 4.60 - 4.56 (m, 1H), 3.89 - 3.85 (m, 1H), 3.75 - 3.70 (m, 1H), 3.50 (dd, J= 7.7, 3.6 Hz, 1H), 3.42 - 3.36 (m, 3H), 1.89 - 1.81 (m, 3H), 1.71 (dd, J= 7.7, 4.3 Hz, 1H), 1.60 - 1.53 (m, 8H), 1.44 - 1.18 (m, 16H).
  • 2
  • [ 13362-52-2 ]
  • [ 116754-58-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen bromide; In water; toluene; for 48h;Reflux; Place a 1,13-tridecanol (21.6 g, 100 mmol) in a 500 mL round bottom flask,Toluene (analytical grade, 250 mL) and a 48 wt% aqueous solution of hydrobromic acid (13.5 mL, 120 mmol), the reaction mixture was stirred at reflux for 48 h.TLC detection until the material disappears. After the reaction solution was cooled to room temperature, it was diluted with n-hexane.The obtained organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and dried over anhydrous sodium sulfate. After the solvent was distilled off,13-bromo-1-tridecanol (27.5 g, 99%) was obtained.The obtained product 13-bromo-1-tridecanol has high purity and can be directly used in the next reaction.
99% With hydrogen bromide; In water; toluene; for 48h;Reflux; In a 500 mL round-bottom flask, place 1,13-tridecanediol (21.6 g, 100 mmol), toluene (analytical grade, 250 mL) and 48 wt% aqueous hydrobromic acid solution (13.5 mL, 120 mmol),The reaction mixture was stirred at reflux for 48h. TLC detection until the raw material disappears. After the reaction solution was cooled to room temperature, it was diluted with n-hexane.After washing the obtained organic phase with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and after evaporating the solvent,13-Bromo-1-tridecyl alcohol (27.5 g, 99%) was obtained.The resulting product 13-bromo-1-tridecyl alcohol has a higher purity and can be directly used in the next reaction
98% With hydrogen bromide; In water; toluene; for 22h;Dean-Stark; Reflux; To a suspension of 40 (5.0 g, 23.1 mmol) in toluene (130 mL) was added HBr (48% aq., 2.9 mL, 25.4 mmol). The mixture was refluxed for 17 hr, while trapping the water by using a Dean-Stark trap. An aliquot was taken and evaporated to dryness. NMR showed it still contained 40. Additional HBr (48% aq., 8.1 mL, 71 mmol) and toluene (60 mL) were added and continued to reflux for additional 5 hr, trapping the water by using a Dean-Stark trap. Stop the reaction. The reaction mixture was evaporated to dryness to leave the crude product 41 (6.3 g, 98%) as off-white solid. 'H NMR (500 MHz, Chloroform-ri) d 3.64 (t, J= 6.6 Hz, 2H), 3.41 (t, .7= 6.9 Hz, 2H), 1.85 (dt, J= 14.5, 7.0 Hz, 2H), 1.66 - 1.49 (m, 2H), 1.49 - 1.17 (m, 19H).
67% With hydrogen bromide; In cyclohexane; water; for 3h;Reflux; Inert atmosphere; Aqueous HBr (48%, 16 mL) was added under vigorous stirring to diol 11 (2.644 g, 12.22 mmol, 1.00 equiv) suspended in cyclohexane (32 mL). The mixture was stirred and heated to reflux for 3 h, and the aqueous phase was separated after cooling to r.t. and extracted with EtOAc (3 30 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The remainder was purified by column chromatography (cyclohexane/EtOAc, 3:1) to afford the title compound. Yield: 2.284 g (8.179 mmol, 67%); colourless solid; mp 54-55 C (lit.6b mp 56-57 C); Rf = 0.51 (cyclohexane/EtOAc, 3:1). IR (ATR): 3428, 2917, 2851, 1468, 1355, 1327, 1253, 1205, 1058, 1049, 1025, 1010, 995, 969, 722, 645, 604, 570 cm-1. 1H NMR (CDCl3, 500 MHz): δ = 3.64 (dt, J = 5.5, 6.5 Hz, 2 H, 1-H), 3.41 (t, J = 7.0 Hz, 2 H, 13-H), 1.85 (quin, J = 7.0 Hz, 2 H, 12-H), 1.57 (quin, J = 6.5 Hz, 2 H, 2-H), 1.46-1.24 (m, 18 H, 3-H to 11-H), 1.19 (t, J = 5.5 Hz, 1H, OH). 13C NMR (CDCl3, 125 MHz): δ = 63.3, 34.3, 32.98, 32.96, 29.74, 29.70, 29.67, 29.57, 28.92, 28.33, 25.9.
52% With hydrogen bromide; In water; toluene; at 0℃; for 18h;Inert atmosphere; Reflux; To a solution of 43 (7.2 g, 33 mmol) in toluene (105 mL) was added48% aq HBr (4.5 mL, 40 mmol) at 0 C. After stirring for 18 h underreflux conditions, the completion of the reaction was confirmed by TLC(1:1 n-hexane/EtOAc). The reaction mixture was diluted with EtOAcand washed with washed with 1m aq NaOH and brine. The organiclayer was subsequently dried over Na2SO4, filtered, and concentrated.The resulting residue was purified by silica gel column chromatography(4:1 n-hexane/EtOAc) to give 44 (4.9 g, 52%) as white powder. 1H NMR(500 MHz, CDCl3) δ 3.64 (near d, 2H, CH2OH), 3.41 (t, 2H,Jvic=7.0 Hz, CH2Br), 1.89-1.82 (m, 2H, CH2CH2Br), 1.60-1.54 (m,2H, CH2CH2OH), 1.42 (near t, 2H, CH2CH2CH2Br), 1.36-1.27 (m, 17H,-CH2-, OH); 13C NMR (125 MHz, CDCl3) δ 63.1, 34.1, 32.9, 32.8, 29.6,29.6, 29.6, 29.5, 29.4, 28.8, 28.3, 25.8. HRMS (ESI) m/z: found [M+Na]+ 301.1136, C13H27OBr calcd for [M+Na]+ 301.1137.

  • 3
  • [ 116452-11-0 ]
  • [ 116754-58-6 ]
  • [ 116452-12-1 ]
  • 4
  • [ 116754-58-6 ]
  • [ 83802-89-5 ]
  • 13-(7-Benzenesulfonyl-1,4-dioxa-spiro[4.5]dec-7-yl)-tridecan-1-ol [ No CAS ]
  • 5
  • [ 116754-58-6 ]
  • [ 220758-00-9 ]
  • 13-(7-Benzenesulfonyl-6-methyl-1,4-dioxa-spiro[4.5]dec-7-yl)-tridecan-1-ol [ No CAS ]
  • 6
  • [ 116754-58-6 ]
  • [ 220757-91-5 ]
  • 13-(7-Benzenesulfonyl-8-methyl-1,4-dioxa-spiro[4.5]dec-7-yl)-tridecan-1-ol [ No CAS ]
  • 7
  • [ 116754-58-6 ]
  • [ 220757-94-8 ]
  • 13-(7-Benzenesulfonyl-8,8-dimethyl-1,4-dioxa-spiro[4.5]dec-7-yl)-tridecan-1-ol [ No CAS ]
  • 8
  • [ 116754-58-6 ]
  • [ 56691-74-8 ]
  • [ 338389-14-3 ]
  • 10
  • [ 116754-58-6 ]
  • [ 98-59-9 ]
  • [ 885334-56-5 ]
  • 11
  • [ 116754-58-6 ]
  • C36H70O4 [ No CAS ]
  • 12
  • [ 116754-58-6 ]
  • C30H62Br2O8P2 [ No CAS ]
  • 13
  • [ 116754-58-6 ]
  • hexacosane-1,1'-diylbis[2-(2-trimethylammonio)ethylphosphate] [ No CAS ]
  • 14
  • [ 116754-58-6 ]
  • [ 15541-01-2 ]
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