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382655

Sigma-Aldrich

2-Hydroxymethyl-12-crown-4

95%

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Synonym(s):
(12-Crown-4)-2-methanol, 1,4,7,10-Tetraoxacyclododecan-2-methanol
Empirical Formula (Hill Notation):
C9H18O5
CAS Number:
Molecular Weight:
206.24
Beilstein/REAXYS Number:
4661968
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

liquid

refractive index

n20/D 1.480 (lit.)

bp

115 °C/0.04 mmHg (lit.)

density

1.192 g/mL at 25 °C (lit.)

SMILES string

OCC1COCCOCCOCCO1

InChI

1S/C9H18O5/c10-7-9-8-13-4-3-11-1-2-12-5-6-14-9/h9-10H,1-8H2

InChI key

NJIPEIQHUNDGPY-UHFFFAOYSA-N

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1 of 4

This Item
261645183431388440
vibrant-m

382655

2-Hydroxymethyl-12-crown-4

vibrant-m

261645

4-Aminophenethyl alcohol

vibrant-m

183431

4-Bromophenethyl alcohol

vibrant-m

388440

2-Hydroxymethyl-18-crown-6

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

refractive index

n20/D 1.480 (lit.)

refractive index

-

refractive index

n20/D 1.573 (lit.)

refractive index

n20/D 1.479 (lit.)

density

1.192 g/mL at 25 °C (lit.)

density

-

density

1.436 g/mL at 25 °C (lit.)

density

1.174 g/mL at 25 °C (lit.)

form

liquid

form

-

form

liquid

form

liquid

bp

115 °C/0.04 mmHg (lit.)

bp

-

bp

138 °C/9 mmHg (lit.)

bp

150 °C/0.5 mmHg (lit.)

Application

2-Hydroxymethyl-12-crown-4 can be used:
  • To prepare an ester of lasalocid with crown ether to study its complex formation with monovalent cations.
  • To prepare hydrogel adsorbents for potential usage in the recovery of lithium-ions from seawater.
  • As a starting material in the synthesis of metal-free phthalocyanines and metallophthalocyanines.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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The synthesis, using microwave irradiation and characterization of novel, organosoluble metal-free and metallophthalocyanines substituted with flexible crown ether moieties
Biyikliouglu Z and Kantekin H
Dyes and Pigments, 80(1), 17-21 (2009)
Hydrogel adsorbents of poly (N-isopropylacrylamide-co-methacryloyloxymethyl-12-crown-4) for Li+ recovery prepared by droplet microfluidics
Kim YS, et al.
Royal Society of Chemistry Advances, 5(14), 10656-10661 (2015)
NMR, FT-IR and ESI-MS study of new lasalocid ester with 2-(hydroxymethyl)-12-crown-4 and its complexes with monovalent cations
Pankiewicz R, et al.
Journal of Molecular Structure, 749(1-3), 128-137 (2005)

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