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HomeProduct name listNipecotic acid

Nipecotic acid

Synonym(s):(R)-(–)-Nipecotic acid;(±)-β-Homoproline;3-Carboxypiperidine;3-Piperidinecarboxylic acid;Hexahydronicotinic acid

  • CAS NO.:498-95-3
  • Empirical Formula: C6H11NO2
  • Molecular Weight: 129.16
  • MDL number: MFCD00005992
  • EINECS: 207-873-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-12 11:13:47
Nipecotic acid Structural

What is Nipecotic acid?

Chemical properties

off-white to pale yellow-beige powder

The Uses of Nipecotic acid

(+/-)-Nipecotic Acid (cas# 498-95-3) is a compound useful in organic synthesis.

Definition

ChEBI: A piperidinemonocarboxylic acid that is piperidine in which one of the hydrogens at position 3 is substituted by a carboxylic acid group.

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 602, 1963 DOI: 10.1021/jo01037a531

General Description

R(?)-Nipecotic acid is a potential inhibitor of uptake of γ-aminobutyric acid (GABA) in rat brain slices. Lipophilic derivatives of nipecotic acid are used as drugs for the treatment of epilepsy.

Synthesis

Firstly 3-piperidine formamides or their salts were reacted with concentrated hydrochloric acid which produces the (S)-3-piperidine carboxylic acid salt. Then the salt of (S)-3-piperidine carboxylic acid was converted to 3-piperidine carboxylic acid (final product) via stirring with potassium hydroxide in methanol. The synthesized final product was characterized using the 1HNMR technique with data as 1H NMR (401 MHz, D2O) δ 3.34 (dd, J = 12.6, 3.6 Hz, 1H), 3.29-3.19 (m, 1H), 3.15-2.98 (m, 2H), 2.66-2.55 (m, 1H), 2.06–1.96 (m, 1H), 1.95–1.82 (m, 1H), 1.82-1.63 (m, 2H).

synthesis of Nipecotic acid

Properties of Nipecotic acid

Melting point: 261 °C (dec.) (lit.)
Boiling point: 239.22°C (rough estimate)
Density  1.1426 (rough estimate)
refractive index  1.4587 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  water: soluble50mg/mL, clear, colorless to faintly yellow
form  Solid
pka pK1:3.35(+1);pK2:10.64(0) (25°C)
color  White
Water Solubility  Soluble in water
Merck  14,6560
BRN  81096
CAS DataBase Reference 498-95-3(CAS DataBase Reference)

Safety information for Nipecotic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Nipecotic acid

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