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Chemical Structure| 15715-58-9

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Product Details of Triethylammonium bicarbonate

CAS No. :15715-58-9
Formula : C7H17NO3
M.W : 163.21
SMILES Code : CC[NH+](CC)CC.OC([O-])=O
MDL No. :MFCD00466938
InChI Key :AFQIYTIJXGTIEY-UHFFFAOYSA-N
Pubchem ID :3082099

Safety of Triethylammonium bicarbonate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Triethylammonium bicarbonate

* 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 [ 15715-58-9 ]

[ 15715-58-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 15715-58-9 ]
  • [ 88683-57-2 ]
  • C35H43N2O9PSi2 [ No CAS ]
  • S-(2-cyanoethyl) 5'-O-(9-phenylxanthen-9-yl)thymidine 3'-(hydrogen-phosphorothioate) triethylammonium salt [ No CAS ]
  • 2
  • [ 15715-58-9 ]
  • [ 88683-57-2 ]
  • C41H48N3O7PSi2 [ No CAS ]
  • 4-N-benzoyl-5'-O-(9-phenylxanthen-9-yl)-2'-deoxycitidine S-(2-cyanoethyl) 3'-(hydrogen phosphorothioate) triethylammonium salt [ No CAS ]
  • 3
  • [ 15715-58-9 ]
  • [ 88683-57-2 ]
  • C40H50N5O7PSi2 [ No CAS ]
  • S-(2-cyanoethyl) 5'-O-(9-phenylxanthen-9-yl)-6-N-pivaloyl-2'-deoxyadenosine hydrogen 3'-phosphorothioate triethylammonium salt [ No CAS ]
  • 4
  • [ 15715-58-9 ]
  • [ 88683-57-2 ]
  • C43H48N5O8PSi2 [ No CAS ]
  • S-(2-cyanoethyl) 2-N-phenylacetyl-5'-O-(9-phenylxanthen-9-yl)-2'-deoxyguanosine 3'-(hydrogen phosphorothioate) triethylammonium salt [ No CAS ]
  • 5
  • [ 849042-95-1 ]
  • [ 7474-78-4 ]
  • [ 15715-58-9 ]
  • (x)C6H15N*C16H10N2O6S [ No CAS ]
  • 6
  • [ 15715-58-9 ]
  • [ 374750-30-8 ]
  • triethylammonium 2'-C-methylguanosine monophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% 2'-C-Methylguanosine (6-1, 0.5 g, 1.7 mmol) was dissolved in 8 mL of trimethylphosphate and cooled to 0C under nitrogen. Phosphorus oxy chloride (0.25 mL, 2.6 mmol) was added dropwise over 45 minutes and the resulting reaction mixture was stirred at 0C for 1 hour. An additional 0.12 mL of phosphorus oxy chloride was added dropwise and the resulting reaction mixture was stirred for an additional 1 hour at 0C. The reaction was quenched by addition of 4.0 mL of water and the product was isolated by weak anion exchange flash chromatography (Biotage Isolute NH2, 0-100% 1.0M triethylammonium bicarbonate/water) to provide the title compound as a white solid (0.69 g, 61% yield).
  • 7
  • C9H23NO7P2*3C9H21N [ No CAS ]
  • [ 15715-58-9 ]
  • [ 7075-11-8 ]
  • C18H35N4O14P3*3C6H15N [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% To the mixture of cytarabine-5' -phosphate (araCMP, 850 mg, 2.63 mmol) N, N- dimethylaniline (1.28 mL, 10.24 mmol) and Et3N (374 uL, 2.73 mmol) in anhydrous MeCN (10 ml) cooled on an ice bath under positive pressure of Ar (balloon) and stirring was added the cold solution of TFAA (1.02 mL, 13.6 mmol) in MeCN (10 ml) dropwise. The suspension became clear solution indicating formation of anhydride 7 (dark yellow solution). Reaction mixture stirred at RT for 15 minutes and then connected to vacuum line to remove the excess of (0106) TFAA/TFA. After 15 min mixture of NMI (629 uL, 14.14 mmol) and Et3N (1.84 mL, 23.8 mmol) in CH3CN (10 mL) was added at 0C and stirring. After 5 min, the ice bath was removed and the reaction mix was stirred at room temperature for 20 min (light yellow solution). Then the solution of ibandronate Bu3N salt (7g) in MeCN (35 ml, stored over molecular sieves for 1 h) was added via cannula and the reaction was stirred at room temperature for 10 minutes. (0107) [0068] The reaction was quenched by addition of water (40 mL) and extracted with DCM (2X40 mL) to remove organic bases. The aqueous layer was diluted with triethylammonium bicarbonate buffer (TEAB, 0.1M, pH 6.8) and loaded onto column with Amberchrome CG61M (113 mL). After the loading was complete, the column was eluted with TEAB (5 CV) and then DI water (8 CV). Finally, the conjugate was eluted out with CH3CN-H20 (1:4 to 1:3). (0108) Appropriate fractions were combined and concentrated in vacuo with bath temperature <30C to a volume less than 50 mL. The obtained concentrate was lyophilized, to provide conjugate as Et3N salt (9). Yield: 512 mg (33%)
  • 8
  • [ 1499-29-2 ]
  • [ 15715-58-9 ]
  • [ 1147-23-5 ]
  • 5-iodocytidine-5'-O-[(phosphonomethyl)phosphonic acid] triethylamine salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% General procedure: A solution of methylenebis(phosphonic dichloride) (3 eq.) in trimethyl phosphate (2 mL), cooled to 0C was added to a suspension of the corresponding nucleoside in trimethyl phosphate at 0C. The reaction mixture was stirred at 0C and samples were withdrawn at 10 min interval for LC-MS to check the disappearance of nucleosides. After 30 min, on the disappearance of a nucleoside, 7 mL of cold 1 M aqueous triethylammonium hydrogen carbonate buffer solution (pH 8.4-8.6) was added. It was stirred at 0 C for 15 min followed by stirring at rt for 30 min. Trimethyl phosphate was extracted using (2 x 100 mL) of tert- butyl methyl ether, and the aqueous layer was lyophilized. The mixture of nucleotide and dinucleotide was separated by ion-exchange chromatography on Source 15Q. Fractions containing the product were pooled and evaporated to dryness. The compound was then purified by RP-HPLC using a gradient of 10 mM triethylammonium acetate buffer - CH3CN from 80:20 to 20:80 in 40 min, then 10 mM triethylammonium acetate buffer - CH3CN from 100:0 to 90: 10 in 40 min, then 100:0 in 5 min, with a flow rate of 5 mL/min, suitable fractions were pooled and lyophilized to obtain final product as glassy solid
 

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