SODIUM CYANOBOROHYDRIDE

Sodium cyanoborohydride is the chemical compound with the formula NaBH3CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions

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Detailed Description for SODIUM CYANOBOROHYDRIDE

Sodium cyanoborohydride is the chemical compound with the formula NaBH3CN. It is a colourless salt, but commercial samples can appear tan. It is widely used in organic synthesis for the reduction of imines. The salt tolerates aqueous conditions

Hydride is the isolated atomic hydrogen anion, H- or any compound containing hydrogen and another element, more electropositive element or group. Hydride consists of a singly charged positive nucleus and two electrons of which one electron is weakly held and readily donative ¡°extra¡±. There are some types of hydrides according to their bonding.

Ionic hydrides (saline hydrides): the hydrogen obtains an electron from a more electropositive metal, usually one of the alkali metals, to be an anion, H- , and behaves like a halogen. Ionic hydrides  react vigorously with water with removing hydrogen gas (H2). Compounds that have hydrogen and one other element only is called binary hydrides with general form of MH or MH2 such as sodium hydride (NaH), lithium hydride (LiH), calcium hydride (CaH2), magnesium hydride (MgH2).

Covalent hydrides: The hydrogen shares one or more pairs of electrons with more electronegative elements (such as boron and aluminium) or nonmetallic elements. Water, ammonia, hydrogen sulfide (H2S), hydrocarbons (alkane, alkene and alkyne), and hydrazine belong to nonmetallic covalent hydrides which behave as molecules and are normally gas or volatile liquids. Hydrogen halides, boranes, silane, phosphines belong to covalent hydrides.

Metallic hydrides: They are alloy-like materials which have individual properties of metals. Their bondings are vary from element to element.

Polymeric hydrides: the hydrogen has bridges forming three center bond with other atoms such as boron, aluminum, and beryllium.

Hydrides which carry hydrogen can provide large amounts of heat when burned. They can be used as a component in jet fuels. They are less flammable and less volatile than hydrocarbon fuels. They are relatively environmentally friendly because they degrade quickly in the environment.  Hydrides and hydrido complexes containing this easily polarized ion are highly reactive, strongly basic and powerfully reducing in synthetic reactions. They are important reducing agents in industrial reactions though they are easily destroyed in the relatively acidic compound water (H2O) and in air containing dioxygen (O2).

Sodium Cyanoborohydride: Used as a selective amination reductant. It converts aldehydes (chemoselective), ketones (stereoselective) to the corresponding alcohols in the manufacture of pharmaceuticals and other fine chemicals. It is used in the reductive alkylation of amines, novel metals and oximes.

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystalline powder
MELTING POINT 241 - 243 C
BOILING POINT  
SPECIFIC GRAVITY

1.20

SOLUBILITY IN WATER Reacts
pH

 

VAPOR DENSITY  
AUTOIGNITION

 

NFPA RATINGS Health: 4; Flammability: 3; Reactivity: 2

REFRACTIVE INDEX

 

FLASH POINT

 

STABILITY Hygroscopic (dangerous when wet).

 

APPLICATIONS

Sodium borohydride is a milder reducing agent, can be used in aqueous solution. It converts selectively aldehydes and ketones the corresponding alcohols in the manufacture of pharmaceuticals and other fine chemicals. It will not react with esters, amides, or carboxylic acids, the more powerful reducing agent lithium aluminum hydride(LAH) is used to reduce these compounds. LAH is the more powerful reducing agent than sodium borohydride due to the weaker Al-H bond compared to the B-H bond. The reactivity of sodium borohydride can be modified by addition of iodine or methanol in BH3-THF to reduce esters into the corresponding alcohols like the reaction of benzyl benzoate to benzyl alcohol. Sodium borohydride is used as a hydrogen source for fuel cell systems and a foaming agent for rubbers. Sodium cyanoborohydride converts certain alcohol groups to methylene groups. Sodium Cyanoborohydride is used as a selective amination reductant. It converts aldehydes (chemoselective), ketones (stereoselective) to the corresponding alcohols in the manufacture of pharmaceuticals and other fine chemicals. It is used in the reductive alkylation of amines, novel metals and oximes. 


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