Skip to Content
Merck
All Photos(2)

Key Documents

650897

Sigma-Aldrich

(4S,4′S)-(−)-2,2′-(3-Pentylidene)bis(4-isopropyloxazoline)

97%

Synonym(s):

(4S,4′S)-(−)-2,2′-(1-Ethylpropylidene)bis(4,5-dihydro-4-isopropyloxazole), [S-(R*,R*)]-(−)-2,2′-(1-Ethylpropylidene)bis(4,5-dihydro-4-isopropyloxazole)

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C17H30N2O2
CAS Number:
Molecular Weight:
294.43
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.4710 (lit.)

bp

120 °C/0.001 mmHg (lit.)

density

1.002 g/mL at 25 °C (lit.)

SMILES string

CCC(CC)(C1=N[C@H](CO1)C(C)C)C2=N[C@H](CO2)C(C)C

InChI

1S/C17H30N2O2/c1-7-17(8-2,15-18-13(9-20-15)11(3)4)16-19-14(10-21-16)12(5)6/h11-14H,7-10H2,1-6H3/t13-,14-/m1/s1

InChI key

PIJFQTUSLZLNOP-ZIAGYGMSSA-N

Application

(4S,4′S)-(−)-2,2′-(3-Pentylidene)bis(4-isopropyloxazoline) is a bisoxazoline that can be used as a ligand:
  • To prepare [11C]carboxylic acids, [11C]esters and [11C]amides using boronic acid esters and 11CO2.
  • In one of the key synthetic steps for the total synthesis of tatanan A and 3-epi-tatanan A.
  • To prepare copper(I) complex and used in a mass spectrometric method to study its chiral selectivity with different substrates.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

180.0 °F - closed cup

Flash Point(C)

82.22 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis
Noble A, et al.
Angewandte Chemie (International ed. in English), 55(51), 15920-15924 (2016)
CuI-catalyzed 11C carboxylation of boronic acid esters: A rapid and convenient entry to 11C-labeled carboxylic acids, esters, and amides
Riss PJ, et al.
Angewandte Chemie (International ed. in English), 51(11), 2698-2702 (2012)
A mass spectrometric method for rapidly assaying the chiral selectivities of the copper (I) complexes of C2-symmetric ligands.
Davis MC and Gronert S.
Journal of Mass Spectrometry : Jms, 50(11), 1279-1287 (2015)

Articles

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service