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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C12H23BN2O4
CAS Number:
161344-84-9
Molecular Weight:
270.13
NACRES:
NA.22
PubChem Substance ID:
24881537
UNSPSC Code:
12352103
MDL number:
MFCD05663838

Key Documents

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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

SMILES string

CCCCB1O[C@@H]([C@H](O1)C(=O)N(C)C)C(=O)N(C)C

InChI key

AFQWQRBBIZKYTE-UWVGGRQHSA-N

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.)

functional group

amide

Quality Level

100

Related Categories

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.

Storage Class

10 - Combustible liquids

wgk

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)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCF0335
MKCF0330
MKCC2179
MKCC0692
MKBV7719V

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Enantioselective synthesis of spiropentanes from hydroxymethylallenes
Charette AB, et al.
Organic Letters, 3(21), 3293-3295 (2001)
Enantioselective synthesis of 1, 2, 3-trisubstituted cyclopropanes using gem-dizinc reagents
Zimmer LE and Charette AB
Journal of the American Chemical Society, 131(43), 15624-15626 (2009)
Total synthesis and biological evaluation of glycolipids plakosides A, B and their analogs
Nicolaou KC, et al.
Helvetica Chimica Acta, 83(8), 1977-2006 (2000)

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