57186-59-1

Basic information

• Product Name: 2-Ethyl-5,5-dimethyl-1,3,2-dioxaborinane
• Synonyms: 2-Ethyl-5,5-dimethyl-1,3,2-dioxaborinane
• CAS NO: 57186-59-1
• Molecular Formula: C₇H₁₅BO₂
• Molecular Weight: 142
• Mol File: 57186-59-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 149.6±9.0 °C(Predicted)
• Appearance: /
• Density: 0.88±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-Ethyl-5,5-dimethyl-1,3,2-dioxaborinane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethyl-5,5-dimethyl-1,3,2-dioxaborinane(57186-59-1)
• EPA Substance Registry System: 2-Ethyl-5,5-dimethyl-1,3,2-dioxaborinane(57186-59-1)

Safety Data

• Hazardous Substances Data: 57186-59-1(Hazardous Substances Data)

Upstream product

• 4433-63-0 Ethyl boronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 55848-38-9 diethylborinic acid 2,2-dimethyl-propane-1,3-diyl ester 

Downstream Products

• 5554-65-4 1-(dimethylamino)-3-phenylpentan-3-ol 
• 1613405-38-1 (S)-4,4,5,5-tetramethyl-2-(3-methyl-1-phenylpentan-3-yl)-1,3,2-dioxaborolane 

Relevant articles and documents

Synthesis of enantioenriched tertiary boronic esters by the lithiation/borylation of secondary alkyl benzoates

Simple, secondary 2,4,6-triisopropyl benzoates (TIB esters) and secondary dialkyl N,N-diisopropyl carbamates have been reported to be resistant to deprotonation by strong bases. We have found that the combination of sBuLi (1.6 equiv) and TMEDA (6 equiv) in CPME at -60 C enables deprotonation of unactivated secondary dialkyl TIB esters, but not the carbamates. These carbanions were reacted with a range of neopentyl boronic esters which, after 1,2-metalate rearrangement and oxidation, gave a range of tertiary alcohols in high yield and universally high er. Further functional group transformations of the tertiary boronic esters were demonstrated (conversion to quaternary centers, C-tertiary amines) together with application of the methodology to the synthesis of the simplest unbranched hydrocarbon bearing a quaternary center, (R)-4-ethyl-4-methyloctane, validating the synthetic utility of the methodology.