2788-28-5

Basic information

• Product Name: D(+)-CARNITINENITRILE CHLORIDE
• Synonyms: D(+)-CARNITINENITRILE CHLORIDE;D-CARNITINENITRILE CHLORIDE;L-CARNITINENITRILE CHLORIDE;(3-cyano-2-hydroxypropyl)trimethyl-,chloride,l-ammoniu;3-cyano-2-hydroxy-n,n,n-trimethyl-,chloride,(r)-1-propanaminiu;l-(3-cyano-2-hydroxypropyl)trimethylammoniumchloride;l-carnitinnitrilchlorid;(R)-3-Cyano-2-hydroxy-N,N,N-trimethyl-1-propanaminium chloride
• CAS NO: 2788-28-5
• Molecular Formula: C₇H₁₅N₂O*Cl
• Molecular Weight: 178.66
• Mol File: 2788-28-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 249 °C
• Appearance: /
• CAS DataBase Reference: D(+)-CARNITINENITRILE CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: D(+)-CARNITINENITRILE CHLORIDE(2788-28-5)
• EPA Substance Registry System: D(+)-CARNITINENITRILE CHLORIDE(2788-28-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 2788-28-5(Hazardous Substances Data)

Usage

Uses

(2R)-Carnitinenitrile Chloride is used in biological studies to stud the action of carnitine and related compounds on acetylcholine receptors of neurons from Helix aspersa.

InChI:InChI=1/C7H15N2O.ClH/c1-9(2,3)6-7(10)4-5-8;/h7,10H,4,6H2,1-3H3;1H/q+1;/p-1/t7-;/m1./s1

Upstream product

• 18933-33-0 (R,S)-carnitinenitrile chloride 
• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 75-50-3 trimethylamine 
• 74-90-8 hydrogen cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 67843-74-7 (S)-epichlorohydrin 
• 84367-31-7 (R)-γ-chloro-β-hydroxybutyronitrile 
• 101396-91-2 (S)-N-(3-chloro-2-hydroxypropyl)-N,N,N-trimethylammonium chloride 
• 773837-37-9 sodium cyanide 
• 593-81-7 trimethylamine hydrochloride 

Downstream Products

• 541-15-1 L-carnitine 
• 6645-46-1 L-carnitine chloride 
• 5261-99-4 (R)-(-)-carnitinamide chloride 
• 56-99-5 (R)-carnitine hydrochloride 
• 5080-50-2 O-acetyl-L-carnitine hydrochloride 

Relevant articles and documents

Preparation method for synthesizing L-carnitine by using R-(-)-epichlorohydrin as starting material

The invention discloses a preparation method for synthesizing L-carnitine by using R-(-)-epichlorohydrin as a starting material, and belongs to the field of medicinal chemistry. The method comprises the steps: using R-(-)-epoxychlorohydrin and hydrocyanic acid as starting materials, performing a reaction for synthesis of R-4-chloro-3-hydroxybutyronitrile under the action of a basic catalyst, thensynthesizing L-carnitine hydrochloride through two routes, purifying the L-carnitine hydrochloride prepared through the two routes further through resin so as to remove chloride ions, and preparing the final product L-carnitine. The two process routes are simple, the reaction conditions are mild, the operation is simple and feasible, and industrial production is convenient; the whole process is green and environmentally friendly, the reaction yield is high, three waste is little, no sodium cyanide is used, and no solid waste sodium salt is generated; and the hydrolysis by-product ammonium chloride has good quality, and can be sold as a by-product, and great economic benefits and market competitiveness are achieved.

Novel method for preparing L-carnitine

The invention discloses a novel method for preparing L-carnitine and belongs to the technical field of medication chemistry. The method disclosed by the invention comprises the following steps: reacting quinine I and trimethylchlorosilane, thereby obtaining a quinine derivative II; reacting the quinine derivative II with racemic epoxy chloropropane, thereby obtaining quinine derivative quaternary ammonium salt III; reacting the quinine derivative quaternary ammonium salt III with a cyanide inorganic salt, and performing chiral ring opening to generate (R)-2-hydroxynitrile quaternary ammonium salt IV; carrying out an ion exchange reaction between the (R)-2-hydroxynitrile quaternary ammonium salt IV and trimethylamine, thereby obtaining (R)-2-hydroxynitrile trimethylamine salt, performing acidic hydrolysis, and performing ion exchange desalination, thereby obtaining the L-carnitine. The method provided by the invention is simple and feasible, the yield is greatly improved, and residues of heavy metal ions are avoided.

Asymmetric synthesis of l-carnitine from (R)-3-chloro-1,2-propanediol

A practical chemical synthesis of l-carnitine (1) has been accomplished from (R)-3-chloro-1,2-propanediol ((R)-4), which is a main by-product originated from (R,R)-Salen Co(III) catalyzed hydrolytic kinetic resolution (HKR) of (±)-epichlorohydrin. (R)-4 was utilized as a chiral starting material to prepare the key intermediate cyclic sulfite ((R)-5). The new synthetic approach demonstrated an efficient utilization of organic by-product for the asymmetric synthesis of bioactive compounds.