Pentaborane(9) is an inorganic compound with the formula B5H9. It is one of the most common boron hydride clusters, although it is a highly reactive compound. Because of its high reactivity toward oxygen, it was once evaluated as rocket or jet fuel. Like many of the smaller boron hydrides, pentaborane is colourless, diamagnetic, and volatile. It is related to pentaborane(11) (B5H11). Structure, synthesis, properties Its structure is that of five atoms of boron arranged in a square pyramid. Each boron has a terminal hydride ligand and four hydrides span the edges of the base of the pyramid. It is classified as a nido cage. It was first prepared by Alfred Stock by pyrolysis of diborane at about 200 °C. An improved synthesis starts from salts of octahydrotriborate (B3H8−), which is converted to the bromide B3H7Br− using HBr. Pyrolysis of this bromide gives pentaborane. 5 B3H7Br− → 3 B5H9 + 5 Br− + 4 H2 In the U.S., pentaborane was produced on a commercial scale by Callery Chemical Company. Above 150 °C, it decomposes, producing hydrogen. In storage, it decomposes negligibly, yielding a small amount of hydrogen and solid residue; when it occurs in a closed container, the consequent rise of pressure can be dangerous. It is much more stable in presence of water than diborane. Pentaborane is a nonpolar compound, so it is soluble in hydrocarbons like benzene, and cyclohexane, and in greases including those used in lab equipment. Reactions The chemistry of pentaborane is extensive. Halogenation give the symmetrical derivatives B5H8X, which can be isomerised to place the halide on the base of the square pyramid. With strong bases such as alkyl lithium reagents, it can be deprotonated and the resulting lithium salts react with diverse electrophiles to give substituted derivatives. It is Lewis acidic, forming double adducts with two equivalents of trimethylphosphine. Pentaborane is used for the synthesis of other boron hydride clusters. History of its use as a fuel Pentaborane was evaluated by both the U.S. and Russian armed services as a so-called "exotic fuel". Because simple boron compounds burn with a characteristic green flame, the nickname for this fuel in the U.S. industry was "Green Dragon". In terms of heat of combustion, pentaborane surpasses its equivalent carbon compounds because their self-linking element, carbon, weighs more than one atomic mass unit more than an atom of boron, and some boranes contain more hydrogen than the carbon equivalent.