2-HYDROXYMETHYL-15-CROWN-5 Chemical Properties

Boiling point:

135 °C/1.5 mmHg (lit.)

Density 

1.175 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.479(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

Liquid

Specific Gravity

1.17

color 

Colorless to Light yellow to Light orange

Water Solubility 

Soluble in water(58 g/L) (25°C).

BRN 

3589706

InChI

1S/C11H22O6/c12-9-11-10-16-6-5-14-2-1-13-3-4-15-7-8-17-11/h11-12H,1-10H2

InChIKey

YHIQMMGCRYKJLB-UHFFFAOYSA-N

SMILES

OCC1COCCOCCOCCOCCO1

CAS DataBase Reference

75507-25-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10

HS Code 

29329990

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-HYDROXYMETHYL-15-CROWN-5 Usage And Synthesis

Chemical Properties

clear colorless to almost colorless liquid

Uses

2-Hydroxymethyl-15-crown-5 is used for chemical research.

Synthesis

In a four-necked flask equipped with a stirrer, reflux device, 200 mL of ethylene glycol dimethyl ether with 0.4 g of sodium hydroxide was added, stirred and heated to 75 ??C. Tetraethylene glycol-??-bromoalkyl ether 5 g was dissolved in 50 mL of ethylene glycol dimethyl ether and added dropwise to the reaction system. Then the reaction was stirred at 75-80??C for 22 h. After the reaction, the sodium bromide was filtered out and the solvent was evaporated to obtain a yellow viscous oily substance of 4.5 g. The bromine mass fraction was measured to be 0.71%. 80mL of oily material without separation directly added to 1 mol / L hydrochloric acid solution, reflux 4h, precipitated white solid. After cooling, the solid (triphenylmethanol) was filtered out and extracted with chloroform for 3-5 times, the extracts were combined, dried with anhydrous magnesium sulfate and evaporated with chloroform under reduced pressure. The residue was purified by chromatography with aluminum chloride (neutral), and the eluent was acetone-hexane (7:3, v/v). The solvent was removed by decompression evaporation to give 2-hydroxymethyl-15-crown-5 as a yellow oil, 2.03 g, in 87% yield.

2-HYDROXYMETHYL-15-CROWN-5(75507-25-4)Related Product Information

• Tetraphenylmethane
• Tetrakis(hydroxymethyl)phosphonium sulfate
• 1,2-Ethanedithiol
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• 1,1,1-Tris(hydroxymethyl)ethane
• 4-(HYDROXYMETHYL)BENZONITRILE
• methylol cellulose
• [12]Cycloparaphenylene
• 15-Crown-5
• 2-HYDROXYMETHYL-15-CROWN-5
• 3,6,9,12-tetraoxatetradecan-1-ol