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388432

Sigma-Aldrich

2-Aminomethyl-18-crown-6

95%

Synonym(s):

1,4,7,10,13,16-Hexaoxacyclooctadecane-2-methanamine

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About This Item

Empirical Formula (Hill Notation):
C13H27NO6
CAS Number:
83585-61-9
Molecular Weight:
293.36
Beilstein:
4184588
MDL number:
MFCD00191741
UNSPSC Code:
12352005
PubChem Substance ID:
24864228
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.479 (lit.)

bp

135 °C/0.08 mmHg (lit.)

density

1.126 g/mL at 25 °C (lit.)

SMILES string

NCC1COCCOCCOCCOCCOCCO1

InChI

1S/C13H27NO6/c14-11-13-12-19-8-7-17-4-3-15-1-2-16-5-6-18-9-10-20-13/h13H,1-12,14H2

InChI key

BJUGHLWDFGGTGJ-UHFFFAOYSA-N

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Application

2-Aminomethyl-18-crown-6 (AM-18-C-6) can be used to prepare:
  • AM-18-C-6 bonded Merrifield peptide resin, which is used to study the absorption and the isotopic effect of magnesium.
  • Schiff base of gossypol with aminomethyl crown ether for complexation of monovalent cations.
  • Crown tagged triarylphosphine by reacting with triphenylphosphine carboxylic acid. These tagged triarylphosphine reagents are used in Mitsunobu and Heck reactions for the removal of phosphine derived by-products.
  • 1,16-hexadecanoyl-bis-(2-aminomethyl)-18-crown-6 (bola A-16), which is utilized as a vesicular carrier in a drug delivery system.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000017149
0000004146
0000004147
0000003407
BGBC5109V

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Adsorption and isotope effects by ion exchange with aqueous-2-aminomethyl-18-crown-6 bonded Merrifield resin
Kim DW, et al.
Journal of Colloid and Interface Science, 254(1), 190-194 (2002)
A new crown ether as vesicular carrier for 5-fluoruracil: synthesis, characterization and drug delivery evaluation
Muzzalupo R, et al.
Colloids and Surfaces. B, Biointerfaces, 58(2), 197-202 (2007)
Synthesis and application of crown ether tagged triarylphosphines
Jackson, Toby and Routledge, Anne
Tetrahedron Letters, 44(6), 1305-1307 (2003)
The Schiff base of gossypol with 2-(aminomethyl)-18-crown-6 complexes and H+, Li+, Na+, K+, Rb+, Cs+ cations studied by ESI MS, 1H NMR, FT-IR and PM5 semiempirical methods
Przybylski P, et al.
Journal of Molecular Structure, 699(1-3), 65-77 (2004)

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