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Merck
CN

518379

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

Synonym(s):

(4R,5R)-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:
Molecular Weight:
270.13
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
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optical activity

[α]20/D -105°, c = 1.7% in chloroform

Quality Segment

refractive index

n20/D 1.478 (lit.)

bp

178-179 °C (lit.)

density

1.072 g/mL at 25 °C (lit.)

functional group

amide

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-/m1/s1

InChI key

AFQWQRBBIZKYTE-NXEZZACHSA-N

Application

Butylboronic acid N,N,N′,N′-tetramethyl-L-tartaric acid diamide ester can be used as a cyclopropanation ligand in one of the key steps for the total synthesis of:
  • (+)-Frondosin, a natural product from marine sponges.
  • Marine cyanobacterium natural products: coibacins A and B.

Reactant for:
Preparation of biologically and pharmacologically active molecules


Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)



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