4-Piperidinemethanol Chemical Properties

Melting point:

55-59 °C(lit.)

Boiling point:

118-120 °C10 mm Hg(lit.)

Density 

0,997 g/cm³

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Water Solubility 

Soluble in water

form 

Crystalline Powder, Chunks and/or Solid

pka

14.94±0.10(Predicted)

color 

White to off-white

Sensitive 

Hygroscopic

BRN 

103071

InChI

InChI=1S/C6H13NO/c8-5-6-1-3-7-4-2-6/h6-8H,1-5H2

InChIKey

XBXHCBLBYQEYTI-UHFFFAOYSA-N

SMILES

N1CCC(CO)CC1

CAS DataBase Reference

6457-49-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-22

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3263 8/PG 2

WGK Germany 

3

Hazard Note 

Irritant/Hygroscopic

HazardClass 

8

PackingGroup 

III

HS Code 

29333990

MSDS

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

4-Piperidinemethanol Usage And Synthesis

Chemical Properties

white to off-white crystalline powder, chunks

Uses

4-Piperidinemethanol may be used in the preparation of:

• N-tert-butoxycarbonyl-4-hydroxymethyl piperidine
• desferrioxamine B (DFO) containing third generation triazine dendrimer
• ethyl 3-(4-(hydroxymethyl)piperidin-1-yl)propanoate (EHMPP)
• 4-(hydroxymethyl)piperidine-1-carbodithioic acid (HL)
• 1-[[(1E)-2-(4-chlorophenyl)ethenyl]sulfonyl]-4-piperidinemethanol

General Description

4-Piperidinemethanol is a cyclic secondary amine. Its standard molar enthalpies of combustion, sublimation and formation have been determined.

Synthesis

The general procedure for the synthesis of 4-hydroxymethylpiperidine from ethyl 4-piperidinecarboxylate was as follows: lithium aluminum hydride (LiAlH4, 10.10 g, 0.266 mol) was suspended in tetrahydrofuran (THF, 150 mL) at 0 °C. Subsequently, a solution of ethyl 4-piperidinecarboxylate (18.13 g, 0.120 mol) dissolved in THF (300 mL) was slowly added. The reaction mixture was stirred at room temperature overnight. After the reaction was completed, it was cooled in an ice bath and a mixture of water (14 mL) and THF (28 mL) was slowly added. Next, a mixture of 15% aqueous sodium hydroxide (14 mL) and water (37 mL) was added and stirring was continued for 30 minutes at room temperature. The reaction mixture was filtered to remove the precipitate and the filtrate was concentrated to give 17.88 g of the target product 4-hydroxymethylpiperidine in quantitative yield.

References

[1] Patent: WO2004/76450, 2004, A1. Location in patent: Page 59
[2] Patent: WO2010/12611, 2010, A1. Location in patent: Page/Page column 27
[3] RSC Advances, 2016, vol. 6, # 22, p. 17929 - 17940
[4] European Journal of Medicinal Chemistry, 2019, p. 234 - 248
[5] European Journal of Medicinal Chemistry, 2017, vol. 139, p. 773 - 791

4-Piperidinemethanol(6457-49-4)Related Product Information

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