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CAS No. : | 3344-70-5 | MDL No. : | MFCD00000226 |
Formula : | C12H24Br2 | Boiling Point : | - |
Linear Structure Formula : | Br(CH2)12Br | InChI Key : | ZJJATABWMGVVRZ-UHFFFAOYSA-N |
M.W : | 328.13 | Pubchem ID : | 18766 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | 1,12-Dibromododecane (0.20 g, 0.61 mmol) was dissolved in 4-methyl-2- pentanone (2.0 ml) and <strong>[1802-20-6]3-pentylpyridine</strong> (0.20 g, 1.34 mmol) was added. The mixture was 5 stirred at reflux for 20 h under a nitrogen atmosphere, and the solvent was removed under reduced pressure. The crude was triturated with Et2O (8 x 10 ml), and the solvent was removed under reduced pressure. The residue was purified by Al2O3 chromatography <n="32"/>(neutral, activity H-III)5 using gradient elution (starting with CHCl3/MeOH = 2 % to 10 %). The residue was passed down a column of Lewatit MP-64 anion resin (Cl"), eluting with EtOH. The resulting fractions were combined and the solvent removed under reduced pressure to give the above compound as a light yellow waxy oil (0.28 g, 85 %).5 1H NMR (300 MHz, CDCl3): delta 9.55 (4H, m, CH(2',6')), 8.20 (2H, d, J= 6.5 Hz, CH(4')), 8.07 (2H3 m, CH(3')), 5.00 (4H5 m5 CH2(I)), 3.10 (4H5 m, CH2(I")), 2.89 (4H5 m, CH2(2"))5 2.06 (4H5 m5 CH2(2))5 1.72 (4H5 m5 CH2(3"))5 1.33 (12H5 m, CH2(354,4")), 1.33 (8H5 m, CH2(5,6)), 0.96 (6H, m, CH3(5")). 13C NMR (300 MHz, CDCl3): 164.2, 144.2, 128.5, 61.2, 35.6, 32.2, 31.4, 29.5, 29.4, 29.1, 26.2, 22.4, 13.3, 1 signal obscured or io overlapping. MS: m/z ESI (positive ion) 233 [M-2C1"]2+ (18 %), 465 [M-2Cl"-H+]+ (10). Found [M-2C1"]2+ 233.2136, [C16H27N]2+ requires 233.2144. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In DMF (N,N-dimethyl-formamide); for 168h; | 4- (DIMETHYLAMINO) phenyldiphenylphosphine (1.73 mmoles, 0.529 g) and 1,12-dibromododecane (1.73 mmoles, 0.569 g) were dissolved in DMF (1 ml) and shaken for 1 week. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | General procedure: A solution of 8-T-cGMP (200 mM, 1 eq) and N.N-diisopropylethylamine (2 eq) in DMSO was added portionwise over 30 min to a solution of 1 , 12-dibromdodecane (1.5 M, 15 eq) in (0803) DMSO at 40 C. The reaction mixture was stirred until no further reaction progress was observed (< 10 % remaining starting material). The solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in (0804) MeCN/water (8:1 , v/v), washed with petroleum ether (3 x) and the aqueous phase evaporated to dryness using a rotary evaporator. The crude product was dissolved in DMF (115 mM). 4,4"-Thiobisbenzenthiol (0.5 eq) and Nu,Nu-diisopropylethylamine (2.2 eq) were added successively. The reaction mixture was stirred until the starting material was completely consumed. The solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in water (1 mL), washed with ethyl acetate (3 x 1 mL), subjected to preparative reversed phase hplc and desalted. (0805) Yield f Purity) :26 % (> 99 %). (0806) HPLC: (57 % MeCN, 30 mM NaH2PO* buffer, pH 6.8). (0807) UV-VIS: Amax = 275 nm (pH 7), epsilon = 24660 (est.). (0808) ESI- S (+): m/z calculated for C56H73N10O14P2S5 (P+H]+): 1337.39, found: 1337. (0809) ESS-MS (-): m/z calculated for C56H77N10O14P2S5 ([M-H] ): 1335.37, found: 1335. |