Within this work, an aluminum dihydride complex ([((4-Me)Box(2)CH)AlH2]) (1) based on the bis(4-methyl-benzoxazol-2-yl)methanide ligand was synthesized and characterized by spectroscopic methods (NMR, ATR-IR, and fluorescence), DSC (differential scanning calorimetry), mass spectrometry (LIFDI), and single crystal X-ray diffraction. The reactivity of alane 1 was investigated toward the reducing agents [(Dip)NacNacAlI] and [(MesNacNacMgI)(2)], which gave the dialane compounds [(BoxCH)(HAlAlIIH)-Al-I((Dip)pNacNac)] (2) and [{(4-MeBox(2)CH)(AlH)-H-II}(2)] (4a), respectively. Furthermore, dialuminoxanes [{((Dip)BoxCH)AlH}2(mu-O)] (4b) and [({((Dip)NacNac)Mg}(2)(mu-H)){H3Al(II)AlIIH(4-MeBox(2)CH)}] (4c) were isolated as byproducts, with 4b co-crystallizing with 4a. The hydricity of both hydrides in the mixed-ligated dialane 2 were examined by a reaction with 1 equiv of trityl borate ([Ph3C][B(C6F5)4]), which resulted in [((Dip)Box(2)CH)(HAlAlII)-Al-I((Dipp)NacNac)][B(C(6)F5)4] (3). Due to the formation of 4b, complex 1 was reacted with 0.5 equiv of water, which causes the likely synthesis of insoluble oligomeric alumoxanes. To prevent this reaction and support the formation of well-defined dialumoxanes, 1 was initially converted to [((Dip)BoxH)((Dip)pO)AlH] (5) by the deprotonation of 2,6-diisopropylphenol (propofol). This sterically encumbered compound 5 was subsequently reacted with 0.5 equiv of water, which resulted in defined molecules of [{((Dip)BoxCH)(DippO)Al}2(mu-O)] (6). All these compounds exemplify the versatility of the (4-Me)Box(2)CH ligand in low-valent aluminum chemistry.