sodium triacetoxyborohydride solubility

Ser., 641, 201 (1996). All Rights Reserved. Physical Data: mp 116–120 °C (dec); the related NaBH3OAc has not been fully characterized. Type in Product Names, Product Numbers, or CAS Numbers to see suggestions. If you do not receive an email within 10 minutes, your email address may not be registered, If you have previously obtained access with your personal account, please log in. Wear protective gloves/protective clothing/eye protection/face protection. This item can also be found in the following categories: Manganese(IV) oxide, activated, tech., Mn 58% min. Encyclopedia of Reagents for Organic Synthesis. Chem., 59, 5328 (1994); Tetrahedron: Asymmetry, 5, 1455 (1994). In contact with water releases flammable gases which may ignite spontaneously. Product Classification | TriAcetOxyBorohydride is a safer reducing agent than Sodium cyanoborohydride with comparable reactivity . The boron-hydrogen bond is stabilized by the steric and electron-withdrawing effects of the acetoxy groups, making sodium triacetoxyborohydride a mild reducing agent. Clear, Add the items to your existing shopping cart? Sodium triacetoxyborohydride (STAB) is a mild reducing agent that is commonly used in reductive aminations. THF requires sodium borohydride to inhibit reduction of THF to tributyl borate. [2][3][4], However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily, nor is it compatible with methanol. Solubility Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride. Causes skin irritation. Please remove at least one to add a new selection. How else can Product 316393, Sodium triacetoxyborohydride, be used as a reducing agent? 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. ; Carreira,E.M. Store in a closed container. "Oxindole Synthesis via Palladium-catalyzed C-H Functionalization", https://en.wikipedia.org/w/index.php?title=Sodium_triacetoxyborohydride&oldid=975314199, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, 116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes, This page was last edited on 27 August 2020, at 20:58. 40, p. 3453 - 3456, Evans,D.A. Sorry we cannot compare more than 4 products at a time. Moisture sensitive. Please check your email for instructions on resetting your password. Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride. sodiumtriacetoxyborohydride211945655360711, Pricing & availability is not currently available. Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride. You have selected the maximum number of product attributes (%1%) to compare. Analysis of Reagent Purity: NaBH(OAc)3 has been characterized by elemental analysis, IR, and 1H, 13C, and 11B NMR. About Us | Biologically Active Compounds | Handling, Storage, and Precautions: because H2 is liberated during the preparation of these reagents, all handling and storage of acyloxyborohydrides should take place under an inert atmosphere. Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH 2 Cl 2, ClCH 2 CH 2 Cl. and you may need to create a new Wiley Online Library account. Learn about our remote access options, Johnson & Johnson Pharmaceutical Research and Development, Spring House, PA, USA. and you may need to create a new Wiley Online Library account. Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. 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. Causes serious eye damage. Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. Keep away from any possible contact with water, because of violent reaction and possible flash fire. Physical Data: mp 116–120 °C (dec); the related NaBH3OAc has not been fully characterized. Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH2Cl2, ClCH2CH2Cl. 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. Bioorg. Solubility: NaBH(OAc) 3 and related acyloxyborohydrides are rapidly destroyed by H 2 O and protic solvents; H 2 is liberated. Incompatible with strong oxidizing agents, water, alcohols and acids. Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH2Cl2, ClCH2CH2Cl. [3], NaBH(OAc)3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts. Notes Moisture sensitive. View information & documentation regarding Sodium triacetoxyborohydride, including CAS, MSDS & more. Service | Preparative Method: NaBH(OAc)3 and NaBH3OAc can be easily prepared in situ from the appropriate amount of acetic acid and NaBH4. Form Supplied in: NaBH(OAc)3 and the related Preparative Method: NaBH(OAc)3 and NaBH3OAc can be easily prepared in situ from the appropriate amount of acetic acid and NaBH4. Am. Aqueous solutions are most stable in the presence of small amounts of sodium hydroxide (0.2% for a nearly saturated solution containing 44% sodium borohydride) and can be kept for several days. 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: Sodium TriAcetOxyBorohydride. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na(CH3COO)3BH. Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons. Commun., 535 (1975). © 2020  Merck KGaA, Darmstadt, Germany and/or its affiliates. Privacy Policy Selective reducing agent; review: Org. Bioorganic & Medicinal Chemistry Letters, 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. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran and occasionally in acetonitrile. If you do not receive an email within 10 minutes, your email address may not be registered, Working off-campus? Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na(CH3COO)3BH. For stereoselective reduction of ketones in AcOH, see: Tetrahedron Lett., 273 (1983). | Privacy. 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. Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH 2 Cl 2, ClCH 2 CH 2 Cl. 110, p. 3560, Shanghai Jizhi Biochemical Technology Co., Ltd, sodium,(Z)-4-[(2-amino-3-methylbutanoyl)amino]-3-chloro-5-hydroxy-5-oxopent-2-enoate, sodium 2-((p-tolylcarbamothioyl)thio)acetate, sodium,(1-oxo-1-propoxyoctadecan-9-yl) sulfate, sodium,4-(7-methoxy-1-benzofuran-4-yl)-4-oxobutanoate, Sodium tris(acetato-κO)(hydrido)borate(1-), Borate(1-), tris(acetato-κO)hydro-, sodium (1:1). Selling Leads | Soc., 110, 3560 (1988), and cyclic ß-enamino esters selectively to the cis-amino esters: J. Org. BMS is soluble in most aprotic solvents. All Rights Reserved. Sigma-Aldrich offers a number of Sodium triacetoxyborohydride products. Sigma-Aldrich offers a number of Sodium triacetoxyborohydride products. MSDS/SDS Database Search | (Select up to %1% total). Nitinol™ Nickel Titanium Shape Memory Alloys, Specpure® Inorganic Standards for Water Analysis, Specpure® Oil-Based Standards for Wear Metal Analysis, Specpure® XRF Standards for Petroleum Products, Cellular Growth & Attachment Factors - BT Products, POCO Electron Beam Crucibles & Hearth Shields (Carbon Graphite), Boron, Phosphorus, Silicon, and Sulfur Compounds, Sugars, Steroids, Amino Acids, and Nucleotides, Precious Metal Compounds - Homogeneous Catalysts. Chem. Chem 2015, 23 (18), 6166-6172. It also serves as a reducing agent in organic synthesis. Continue rinsing. A.; Lee, J. Y.; Rhim, H.; Yune, T. Y.; Choo, H. Y. P. 3-Benzamides and 3, 4, 5-trimethoxyphenyl amines as calcium channel blockers. It also serves as a reducing agent in organic synthesis. Proced. Customer Service. Form Supplied in: NaBH(OAc) 3 and the related Tetramethylammonium Triacetoxyborohydride are commercially available as colorless powders. Applications Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. Handling, Storage, and Precautions: because H2 is liberated during the preparation of these reagents, all handling and storage of acyloxyborohydrides should take place under an inert atmosphere. Sodium Triacetoxyborohydride MSDS(Chinese), Journal of Organic Chemistry, , vol.

Relationship Between Mathematics And Physics Dirac, Samsung M31 Vs A71, Kiwi Kalbi Marinade, South African Chelsea Bun Recipe, Armenian Lentils And Rice, How Does Patriarchy Affect Families, Soria Moria Painting,

Leave a comment

Your email address will not be published. Required fields are marked *