594806

Butylboronic acid N,N,N′,N′-tetramethyl-D-tartaric acid diamide ester

97%

• Synonym(s): (4S,5S)-2-Butyl-N,N,N′N′-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide
• Empirical Formula (Hill Notation): C₁₂H₂₃BN₂O₄
• CAS Number: 161344-84-9
• Molecular Weight: 270.13
• MDL number: MFCD05663838
• UNSPSC Code: 12352103
• PubChem Substance ID: 24881537
• NACRES: NA.22

Properties

• assay: 97%
• optical activity: [α]20/D +106°, c = 1% in chloroform
• refractive index: n20/D 1.4780 (lit.)
• bp: 305-306 °C (lit.)
• density: 1.096 g/mL at 25 °C (lit.)
• SMILES string: CCCCB1O[C@@H]([C@H](O1)C(=O)N(C)C)C(=O)N(C)C
• InChI: 1S/C12H23BN2O4/c1-6-7-8-13-18-9(11(16)14(2)3)10(19-13)12(17)15(4)5/h9-10H,6-8H2,1-5H3/t9-,10-/m0/s1
• InChI key: AFQWQRBBIZKYTE-UWVGGRQHSA-N

Description

Application

Butylboronic acid N,N,N′,N′-tetramethyl-D-tartaric acid diamide is a dioxaborolane ligand that can be used to prepare:

• Enantioenriched spiropentanes via zinc catalyzed cyclopropanation of corresponding hydroxymethylallenes.
• 1,2,3-trisubstituted cyclopropane derivatives by asymmetric cyclopropanation of allylic alcohols in the presence of zinc reagents.
• Glycolipids plakosides A, B, and their derivatives by Sharpless asymmetric dihydroxylation and cyclopropanation reaction.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: >230.0 °F - closed cup
• flash_point_c: > 110 °C - closed cup
• ppe: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)