Gibbilimbol analogues as antiparasitic agents—Synthesis and biological activity against Trypanosoma cruzi and Leishmania (L.) infantum. Reproduction of any materials from the site is strictly forbidden without permission. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na(CH3COO)3BH. Browse other articles of this reference work: The full text of this article hosted at iucr.org is unavailable due to technical difficulties. Solubility: NaBH(OAc) 3 and related acyloxyborohydrides are rapidly destroyed by H 2 O and protic solvents; H 2 is liberated. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na(CH 3 COO) 3 BH. © 2020 Merck KGaA, Darmstadt, Germany and/or its affiliates. Sigma-Aldrich offers a number of Sodium triacetoxyborohydride products. Chem 2015, 23 (18), 6166-6172. Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH2Cl2, ClCH2CH2Cl. Eur. Remove contact lenses, if present and easy to do. Working off-campus? and you may need to create a new Wiley Online Library account. Applications Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines.
Disclaimer, Copyright © 2018 ChemSrc All Rights Reserved, Literature: Thermochimica Acta, , vol. The reaction is limited in use because of the low solubility of ammonium acetate in the common solvents used for STAB‐H such as ClCH 2 CH 2 Cl, THF, CH 3 CN, etc., which leads to formation of secondary amines since the initial primary amine product is more soluble and more reactive than ammonia.
If you do not receive an email within 10 minutes, your email address may not be registered, Store in a dry place. Sodium triacetoxyborohydride I want to do a reductive amination with sodium triacetoxyborohydride between aniline and a ketone with DCM as solvent. In this review posted before on this forum in scheme 3 they show a second ethylation after the first reaction when using straight NaBH4 and GAA at elevated temperatures, and this I want to avoid. MSDS/SDS Database Search | Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons. Moisture sensitive. Unlimited viewing of the article/chapter PDF and any associated supplements and figures. Sorry we cannot compare more than 4 products at a time. Sigma-Aldrich offers a number of Sodium triacetoxyborohydride products.
Type in Product Names, Product Numbers, or CAS Numbers to see suggestions. It reduces aldehydes but not most ketones. In contact with water releases flammable gases which may ignite spontaneously.
Chem. Causes skin irritation. [2][3][4], However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily, nor is it compatible with methanol.
Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.
Tetramethylammonium Triacetoxyborohydride are commercially available as colorless powders. TriAcetOxyBorohydride is a safer reducing agent than Sodium cyanoborohydride with comparable reactivity .
Sodium triacetoxyborohydride is a general, mild, and selective reducing agent for the reductive amination of various aldehydes and ketones. Hazard Statements: Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, By continuing to browse this site, you agree to its use of cookies as described in our, I have read and accept the Wiley Online Library Terms and Conditions of Use, https://doi.org/10.1002/9780470842898.rs112.pub2, 1S/C6H10BO6.Na/c1‐4(8)11‐7(12‐5(2)9)13‐6(3)10;/h7H,1‐3H3;/q‐1;+1, Tetramethylammonium Triacetoxyborohydride.
(Select up to %1% total). Store in a closed container. This item can also be found in the following categories: Manganese(IV) oxide, activated, tech., Mn 58% min.
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Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH2Cl2, ClCH2CH2Cl. Symp. For stereoselective reduction of ketones in AcOH, see: Tetrahedron Lett., 273 (1983). 112030-Sodium triacetoxyborohydride Version: 3 Revision date: 20/04/2016 Page 2 of 8 Print date: 20/04/2016 -Continued on next page.- P370+P378 In case of fire: Use appropriate elements to extinction. Form Supplied in: NaBH(OAc) 3 and the related Tetramethylammonium Triacetoxyborohydride are commercially available as colorless powders.
Med. Reduces aldehydes in the presence of ketones: J. Chem. Like other borohydrides, it is used as a reducing agent in organic synthesis.
Tahara, Y. K.; Ito, M.; Kanyiva, K. S.; Shibata, T. Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step.
1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran and occasionally in acetonitrile. BMS is soluble in most aprotic solvents. Encyclopedia of Reagents for Organic Synthesis.
112030-Sodium triacetoxyborohydride Version: 3 Revision date: 20/04/2016 Page 2 of 8 Print date: 20/04/2016 -Continued on next page.- P370+P378 In case of fire: Use appropriate elements to extinction.
Like other borohydrides, it is used as a reducing agent in organic synthesis.This colourless salt is prepared by protonolysis of sodium borohydride with acetic acid: Moisture Sensitive.
Encyclopedia of Reagents for Organic Synthesis. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Sodium TriAcetOxyBorohydride.
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Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH 2 Cl 2, ClCH 2 CH 2 Cl.
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One disadvantage of STAB is that it is H2O sensitive, not compatible with MeOH, and reacts slowly with EtOH and isopropanol.