Sodium borohydride (NaBH4) is a mild reducing agent that is typically used to reduce aldehydes and ketones to their respective alcohols. The compound has a tetrahedral structure where boron is hybridized and its chemical structure could be given as below. The presence of sodium acetate prevents this problem if triphenyltin hydride is employed (Equation (170)) <1984JA8313, 1996CAR69>.
Sodium borohydride is a relatively selective reducing agent. It also reacts with these protic solvents to produce H2; however, these reactions are fairly slow. The heat of this reaction may be sufficient to ignite the hydrogen. Sodium borohydride is also popular as sodium tetrahydroborate and it is inorganic in nature and extensive used for organic synthesis process as the reducing agent. LAH has been used as the reducing agent in demercuration (Equation (171)) <1999JOC101, 1983JA6882, 1986JA2094, 1997JOC4653>.
Structure: CAS Number: 16940-66-2. Other examples of this phenomenon can be found in the literature <1981JOC563>. For the temperature greater than the 70 degree Celsius, it will ignite in the air and soluble in lower alcohols and insoluble in organic solvents. The chemical formula for the compound could be given as the NaBH4 with a molecular mass of 37.830 g mol-1 approx. Sodium borohydride is the borohydride that is produced on the largest scale industrially, estimated at 5000 tons/y in 2002. Sodium borohydride is relatively insoluble in ether solvents, so these are rarely used for borohydride reductions. NaBH4 is sometimes used to … Appearance: White solid. CopyCopied, Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module. In general, sodium borohydride is an excellent reagent for the reduction of ketones or aldehydes in the presence of esters,35 hydroxyl groups that are α to the carbonyl,36 a carbohydrate residue,37 or halogens in the α-position.38 Aryl ketones39 or aryl aldehydes40 are also easily reduced. Robert J. Ouellette, J. David Rawn, in Organic Chemistry (Second Edition), 2018.
Copyright © 2020 Andlearning.org ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780080523491002468, URL: https://www.sciencedirect.com/science/article/pii/B9780128007808000152, URL: https://www.sciencedirect.com/science/article/pii/B008044705800203X, URL: https://www.sciencedirect.com/science/article/pii/B9780080977423008120, URL: https://www.sciencedirect.com/science/article/pii/B9780080523491002316, URL: https://www.sciencedirect.com/science/article/pii/B9780128007204000076, URL: https://www.sciencedirect.com/science/article/pii/B978008044992000612X, URL: https://www.sciencedirect.com/science/article/pii/B0080446558000258, URL: https://www.sciencedirect.com/science/article/pii/B0080446558000027, URL: https://www.sciencedirect.com/science/article/pii/B9780128128381500165, Reduction of 7,7-dimethylbicyclo[2.2.1]heptan-2-one with, Synthesis: Carbon with Two Heteroatoms, Each Attached by a Single Bond, Comprehensive Organic Functional Group Transformations, Comprehensive Organic Synthesis II (Second Edition), Six-membered Rings with One Heteroatom, and their Fused Carbocyclic Derivatives, Synthesis: Carbon With One Heteroatom Attached by a Single Bond, Comprehensive Organic Functional Group Transformations II, Synthesis: Carbon With No Attached Heteroatoms, <1976JA5973, 1984TL5239, B-1985MI006, 1991COS(8)850>, <1984T2317, 1966JA993, 1983TL4923, 1997T2835, 2001T9915>, <1992CC428, 1992CC926, 1992T3835, 1993T2729>, <2002AG(E)2144, 2001TA597, 2001OL2567, 1996JOC2109, 1984T2317, 1983JA6882>, <1999JOC101, 1983JA6882, 1986JA2094, 1997JOC4653>, Colloids and Surfaces A: Physicochemical and Engineering Aspects.
Carboxylation of 1-phenylphosphorinane was achieved via deprotonation (BuLi)–carboxylation (CO2) to give 1-phenylphosphorinan-2-carboxylic acid <2001TL7303>.
However, unconjugated ketones and aldehydes are usually reduced in preference to a conjugated carbonyl elsewhere in the molecule.
It is used by pharmaceutical industries too as an antibiotic.