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2-(HYDROXYMETHYL)-12-CROWN 4-ETHER

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2-(HYDROXYMETHYL)-12-CROWN 4-ETHER Basic information

Product Name:
2-(HYDROXYMETHYL)-12-CROWN 4-ETHER
Synonyms:
  • 2-Hydroxymethyl-12-crown-4, tech., 93%
  • (12-Crown-4)-2-methanol, 1,4,7,10-Tetraoxacyclododecan-2-methanol
  • 2-(Hydroxymethyl)-1,4,7,10-tetraoxacyclododecane
  • 2-Hydroxymethyl-12-crown-4,93%,tech.
  • 2-HYDROXYMETHYL-12-CROWN-4
  • 2-(HYDROXYMETHYL)-12-CROWN 4-ETHER
  • (12-CROWN-4)-2-METHANOL
  • 12-CROWN-4-METHANOL
CAS:
75507-26-5
MF:
C9H18O5
MW:
206.24
EINECS:
278-224-5
Product Categories:
  • Crown Ethers
  • Functional Materials
  • Macrocycles for Host-Guest Chemistry
Mol File:
75507-26-5.mol
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2-(HYDROXYMETHYL)-12-CROWN 4-ETHER Chemical Properties

Boiling point:
115 °C/0.04 mmHg (lit.)
Density 
1.192 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.480(lit.)
Flash point:
>230 °F
form 
Liquid
pka
14.17±0.10(Predicted)
color 
Colorless to Light yellow
Specific Gravity
1.2
Water Solubility 
Miscible in water. Soluble in non-polar solvents. Insoluble in water.
BRN 
4661968
CAS DataBase Reference
75507-26-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
RIDADR 
UN 2810 6.1/PG 3
WGK Germany 
3
10
HS Code 
2932990090

MSDS

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2-(HYDROXYMETHYL)-12-CROWN 4-ETHER Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS VISCOUS LIQUID

Uses

Ethylene oxide is important or critical to the production of detergents, thickeners, solvents, plastics, and various organic chemicals such as ethylene glycol, ethanolamines, simple and complex glycols, polyglycol ethers and other compounds.

Uses

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.

Purification Methods

Purify it by chromatography on Al2O3 with EtOAc as eluent to give a hygroscopic colourless oil, which is distilled under high vacuum and is distilled in vacuo. It has IR: 3418 (OH) and 1103 (COC) cm-1, NMR: max 3.70s. [Kimura et al. J Chem Soc, Chem Commun 492 1983, Pugia et al. J Org Chem 52 2617 1987.] S -(-)-5-Hydroxymethyl -2(5 H )-furanone [78508-96 -0] M 114.1, 39 -42o, 40 -44o , b 1 3 0o/0.3mm, [ ] 546 -180o, [ ] D -148o (c 1.4, H2O). It is purified by chromatography on Silica gel using hexane/EtOAc (1:1) to give a colourless oil which is distilled using a Kügelrohr apparatus, and the distillate crystallises on cooling. It has RF 0.51 on Whatman No 1 paper using pentan-1-ol and 85% formic acid (1:1) and developing with ammoniacal AgNO3. [Boll Acta Chem Scand 22 3245 1968, NMR: Oppolzer et al. Helv Chim Acta 68 2100 1985, Beilstein 18 III/IV 56, 18/1 V 54.]

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