5261-99-4

Basic information

• Product Name: [(±)-(4-amino-2-hydroxy-4-oxobutyl)trimethylammonium] chloride
• Synonyms: [(±)-(4-amino-2-hydroxy-4-oxobutyl)trimethylammonium] chloride;DL-CARNITINAMIDE HYDROCHLORIDE;(3-Carbamoyl-2-hydroxypropyl)trimethylammonium chloride;(2R)-4-aMino-2-hydroxy-N,N,N-triMethyl-4-oxobutan-1-aMiniuM (carnitinaMide);Levocarnitine Impurity F
• CAS NO: 5261-99-4
• Molecular Formula: C₇H₁₇N₂O₂*Cl
• Molecular Weight: 197.68302
• EINECS: 226-073-0
• Mol File: 5261-99-4.mol

Chemical Properties

• Melting Point: 213-214℃
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0Pa at 25℃
• PKA: 8.026[at 20 ℃]
• Water Solubility: 762.8g/L at 20℃
• CAS DataBase Reference: [(±)-(4-amino-2-hydroxy-4-oxobutyl)trimethylammonium] chloride(CAS DataBase Reference)
• NIST Chemistry Reference: [(±)-(4-amino-2-hydroxy-4-oxobutyl)trimethylammonium] chloride(5261-99-4)
• EPA Substance Registry System: [(±)-(4-amino-2-hydroxy-4-oxobutyl)trimethylammonium] chloride(5261-99-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 5261-99-4(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H16N2O2.ClH/c1-9(2,3)5-6(10)4-7(8)11;/h6,10H,4-5H2,1-3H3,(H-,8,11);1H

Upstream product

• 18933-33-0 (R,S)-carnitinenitrile chloride 
• 51499-71-9 4-chloro-3-hydroxybutylamide 
• 75-50-3 trimethylamine 
• 2788-28-5 (2R)-(-)-3-cyano-2-hydroxypropyltrimethylammonium chloride 
• 226213-72-5 (R)-4-chloro-3-hydroxybutanamide 
• 1116-95-6 (D)-(+)-carnitinenitrile chloride 

Downstream Products

• 5261-99-4 (R)-(-)-carnitinamide chloride 
• 5261-99-4 (S)-(+)-Carnitinamid-Hydrochlorid 
• 461-06-3 CARNITINE 
• 541-15-1 L-carnitine 
• 406-76-8 (S)-carnitin 
• 161886-60-8 (S)-carnitine mesylate mesylate 
• 161886-59-5 (S)-carnitine mesylate isobutyl ester mesylate 

Relevant articles and documents

PROCESS FOR PRODUCTION OF BETAINE

According to the present invention, by using 4-halogeno-3-hydroxybutanamide as a substrate in quaternary amination reaction with trialkylamine which is an important step in betaine (such as carnitine) preparation processes, it becomes possible to reduce the production of crotonic acid derivatives (the major by-product) greatly compared to conventional processes. Consequently, it becomes possible to prepare a betaine, such as carnitine, at a high yield. The present invention also relates to a process for preparing a betaine represented by formula (1) below, comprising a step of quaternary aminating an amide represented by formula (2) below: wherein A1, A2 and A3 individually represent a C1-C20 hydrocarbon group which may have a substituent(s); and X1 is a halogen atom.

Entrainment resolution of carnitinamide chloride

The ready availability of (R)-carnitinamide, an immediate synthetic precursor of (R)-carnitine, is an ambitious goal and resolutions, due to the very low cost of racemic carnitinamide, can be the most convenient stereotechnology to reach it. We have efficiently resolved carnitinamide chloride by preferential crystallization from methanol according to simple entrainment procedure. The previous transformation of the chloride into other salts or the use of specific solvent systems was not required for successful resolution, as in the case of the reported entrainment of carnitinamide precursor, carnitine nitrile.

Enantiomeric resolution of a carnitinamide salt by preferential crystallization

A process for the resolution of (D,L)-carnitinamide (D,L-I) chloride in its enantiomers (D-I) and (L-I), characterized in that a supersaturated solution or suspension of (D,L-I) in a suitable solvent or mixture of solvents, optionally added with a surfactant, is used. A series of alternate preferential crystallizations is carried out after adding minimum amount of seeds of one of the two enantiomers, (D-I) or (L-I), that is to be precipitated, and subsequently restoring the supersaturation conditions by adding an appropriate amount of (D,L-I) racemate.

PROCESS FOR PRODUCING CARNITINAMIDE

[PROBLEMS] To provide a process in which in the production of carnitinamide as a production intermediate for L-carnitine, carnitine nitrile can be hydrated into carnitinamide with high selectivity so that high-purity carnitinamide excelling as a substrate for optical resolution or microbial stereoselective hydrolysis can be produced in high yield. [MEANS FOR SOLVING PROBLEMS] There is provided a process comprising hydrating carnitine nitrile into carnitinamide with the use of a catalyst containing manganese oxide to thereby realize production of carnitinamide containing substantially none of carnitine by-products in high yield. As a result, carnitinamide of extremely high purity can be produced through simple and easy crystallization operation.