219897-36-6

Basic information

• Product Name: (R)-(-)-1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL TARTARATE
• Synonyms: (R)-(-)-1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL TARTARATE;(R)-(-)-1-(alpha-aminobenzyl)-2-naphthol (2R,3R)-2,3-dihydroxybutanedioate;R-(-)-1-(alpha-aminobenzyl)-2-naphthol tartarate (salt);(R)-(-)-1-(α-AMINOBENZYL)-2-NAPHTHOL TARTARATE (SALT)
• CAS NO: 219897-36-6
• Molecular Formula: C21H19NO6
• Molecular Weight: 381.37866
• Mol File: 219897-36-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(-)-1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL TARTARATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL TARTARATE(219897-36-6)
• EPA Substance Registry System: (R)-(-)-1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL TARTARATE(219897-36-6)

Safety Data

• Hazardous Substances Data: 219897-36-6(Hazardous Substances Data)

Usage

General Description

(R)-(-)-1-(alpha-aminobenzyl)-2-naphthol tartarate is a chemical compound with a molecular formula of C26H26N2O12. It is a tartaric acid salt of (R)-(-)-1-(alpha-aminobenzyl)-2-naphthol, and it is used in chemical synthesis as a chiral auxiliary. (R)-(-)-1-(ALPHA-AMINOBENZYL)-2-NAPHTHOL TARTARATE is commonly used in organic chemistry to facilitate the synthesis of enantiomerically pure compounds by controlling the stereochemistry of certain reactions. It is often utilized in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals where the stereochemistry of the molecule is critical to its function. This chemical is typically handled and stored in accordance with standard laboratory safety guidelines.

InChI:InChI=1/C17H15NO.C4H6O6/c18-17(13-7-2-1-3-8-13)16-14-9-5-4-6-12(14)10-11-15(16)19;5-1(3(7)8)2(6)4(9)10/h1-11,17,19H,18H2;1-2,5-6H,(H,7,8)(H,9,10)

Upstream product

• 87-69-4 L-Tartaric acid 
• 481-82-3 1-(α-aminobenzyl)-2-naphthol 
• 67-64-1 acetone 
• 53983-77-0 1,3-diphenyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine 
• 561052-90-2 1-(Phenyl-{[1-phenyl-meth-(E)-ylidene]-amino}-methyl)-naphthalen-2-ol 
• 860616-85-9 (+/-)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 869116-46-1 (R)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 147-71-7 D-tartaric acid 
• 219897-32-2 1-(α-aminobenzyl)-2-naphthol hydrochloride 

Downstream Products

• 667870-47-5 (7aR,11R,13S)-11-(4-phenylphenyl)-13-phenyl-8,9,10,11-tetrahydro-7aH,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 
• 667870-48-6 (7aR,11R,13S)-11-(1-naphthyl)-13-phenyl-8,9,10,11-tetrahydro-7aH,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 
• 667870-44-2 (7aR,11R,13S)-11,13-diphenyl-8,9,10,11-tetrahydro-7aH,13H-naphtho[1,2-e]pyrido[2,1-b][1,3]oxazine 

Relevant articles and documents

A new approach to the enantioseparation of Betti bases

An improved method for enantioseparation of racemic 1-(α-aminobenzyl) -2-naphthols has been developed by the reaction in situ of Betti base product mixtures with L-(+)-tartaric acid taken in a 1:1 ratio. The products of this reaction are (-)-1-(α-aminobenzyl)-2-naphthol tartrate, the acetal of benzaldehyde and tartaric acid as well as (+)-1,3-diaryl-2,3-dihydro-1H- naphth[1,2-e][1,3]oxazine, which can be easily separated by crystallization. Georg Thieme Verlag Stuttgart.

Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base

Racemic α-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H- naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-(α- aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.

An efficient kinetic resolution of racemic betti base based on an enantioselective N,O-deketalization

An efficient kinetic resolution of racemic Betti base with L-(+)-tartaric acid in acetone was developed based on a novel enantioselective N,O-deketalization, by which the enantiopure R- and S-enantiomers of Betti base were obtained as the corresponding N,