23357-46-2

Basic information

• Product Name: (R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine
• Synonyms: (R)-1,2,3,4-TETRAHYDRONAPHTHALEN-1-AMINE;(R)-(1,2,3,4-TETRAHYDRO-NAPHTHALEN-1-YL)AMINE;(R)-(-)-1-AMINOTETRALIN;(R)-(+)-1-AMINOTETRALIN;(R)-1-AMINOTETRALIN;(R)-(-)-1-AMINOTETRALINE;(R)-1-AMINOTETRALINE;(R)-(−)-1,2,3,4-Tetrahydro-1-naphthylamine
• CAS NO: 23357-46-2
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• EINECS: -0
• Product Categories: Tetrazoles
• Mol File: 23357-46-2.mol
• Article Data: 35

Chemical Properties

• Melting Point: 116-119 °C
• Boiling Point: 118-120°C 8mm
• Flash Point: >110°C
• Appearance: /
• Density: 1.002
• Refractive Index: 1.565
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.39±0.20(Predicted)
• Water Solubility: Soluble in water (6.91g/L at 25°C).
• Sensitive: Air Sensitive
• BRN: 4231302
• CAS DataBase Reference: (R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine(23357-46-2)
• EPA Substance Registry System: (R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine(23357-46-2)

Safety Data

• Hazard Codes: Xi,N,C
• Statements: 36/37-51/53-36/37/38-52/53-34-22
• Safety Statements: 26-36/37/39-61-45
• RIDADR: UN 3082
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅲ
• Hazardous Substances Data: 23357-46-2(Hazardous Substances Data)

Usage

Description

(R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine is an important organic intermediate with a unique molecular structure that features a naphthylamine core in a tetrahydro configuration. It is characterized by its chiral nature, which makes it a valuable compound in various chemical and pharmaceutical applications.

Uses

Used in Agrochemical Industry:
(R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine is used as a key intermediate for the synthesis of various agrochemicals, specifically in the development of pesticides and other crop protection agents. Its chiral properties allow for the creation of targeted and efficient products with minimal environmental impact.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine serves as a crucial building block for the development of chiral drugs. Its unique structure enables the creation of new medications with improved efficacy and reduced side effects, contributing to the advancement of stereoselective organic synthesis.
Used in Dyestuff Industry:
(R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine is also utilized as an intermediate in the production of dyes and pigments. Its chiral nature allows for the development of dyes with specific color properties and improved performance characteristics, such as enhanced stability and solubility.
Used in Chiral Amine Applications:
(R)-(-)-1,2,3,4-Tetrahydro-1-naphthylamine plays a significant role in stereoselective organic synthesis as a chiral amine. It is used directly as a resolving agent, building block, or chiral auxiliary, enabling the synthesis of enantiomerically pure compounds with high selectivity and efficiency. This contributes to the development of innovative and improved products across various industries.

InChI:InChI=1/C10H13N.ClH/c11-10-7-3-5-8-4-1-2-6-9(8)10;/h1-2,4,6,10H,3,5,7,11H2;1H/t10-;/m1./s1

Upstream product

• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 298-12-4 Glyoxilic acid 
• 104354-39-4 3,4-dihydro-naphthalen-1(2H)-one oxime O-methyl ether 
• 119-64-2 tetralin 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1055321-32-8 (R)-(+)-1-azido-1,2,3,4-tetrahydronaphthalene 
• 6094-36-6 N-benzoyl-L-glutamic acid 
• 61249-00-1 (S)-(1-naphthyl) glycidyl ether 
• 498542-91-9 (1S,2S)-N-acetyl-1,2-bis(trifluoromethanesulfonamido) cyclohexane 
• 68253-36-1 1-tetralone oxime 
• 53732-47-1 (S)-1-tetralol 
• 221179-29-9 (R,R)-(1-phenylethyl)-(1,2,3,4-tetrahydronaphthalen-1-yl)amine 
• 32908-39-7 (R)-1,2,3,4-tetrahydro-1-naphthylamine hydrogen L-tartrate 

Downstream Products

• 913359-59-8 4-benzyl 1-tert-butyl (2S)-2-{[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl-amino]carbonyl}-1,4-piperazinedicarboxylate 
• 1033000-39-3 (R)-[5-[(benzyloxycarbonyl)amino]-6-oxo-2-(phenyl)-1,6-dihydro-1-pyrimidinyl]-N-(tetrahydronaphthyl)acetamide 
• 960128-64-7 (R)-8-(diphenylphosphino)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 876625-06-8 [1-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-5-(toluene-4-sulfonylamino)-pentyl]-carbamic acid tert-butyl ester 
• 876624-78-1 [2-benzyloxy-1-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-ethyl]-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 876624-27-0 4-hydroxy-2-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 876624-29-2 4-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-oxazolidine-3-carboxylic acid benzyl ester 
• 913359-75-8 (S)-4-benzyl-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-piperazine-1-carboxylic acid tert-butyl ester 
• 922516-02-7 (R)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)formamide 
• 774222-30-9 8-benzyloxy-5-{R-1-hydroxy-2-[R-(1,2,3,4-tetrahydronaphthalen-1-yl)amino]-ethyl}-1H-quinolin-2-one 

Relevant articles and documents

Asymmetric synthesis of amines by the reductive amination of ketones using (+) and (-) norepinephrine followed by periodate oxidation

A new route for the synthesis of aralkyl primary amines is reported, where the commercially available (+) or (-) norepinephrine is condensed with aralkyl ketones followed by hydrogenation of the Schiff base using platinum catalyst. The chiral β-aminoalcohols thus obtained were oxidized by periodate to yield the aralkyl primary amines in 54-66% enantiomeric excess.

Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase

Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.

Enzymatic Primary Amination of Benzylic and Allylic C(sp3)-H Bonds

Aliphatic primary amines are prevalent in natural products, pharmaceuticals, and functional materials. While a plethora of processes are reported for their synthesis, methods that directly install a free amine group into C(sp3)-H bonds remain unprecedented. Here, we report a set of new-to-nature enzymes that catalyze the direct primary amination of C(sp3)-H bonds with excellent chemo-, regio-, and enantioselectivity, using a readily available hydroxylamine derivative as the nitrogen source. Directed evolution of genetically encoded cytochrome P411 enzymes (P450s whose Cys axial ligand to the heme iron has been replaced with Ser) generated variants that selectively functionalize benzylic and allylic C-H bonds, affording a broad scope of enantioenriched primary amines. This biocatalytic process is efficient and selective (up to 3930 TTN and 96percent ee), and can be performed on preparative scale.

Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization

In this study, we combined photo-organo redox catalysis and biocatalysis to achieve asymmetric C–H bond functionalization of simple alkane starting materials. The photo-organo catalyst anthraquinone sulfate (SAS) was employed to oxyfunctionalise alkanes to aldehydes and ketones. We coupled this light-driven reaction with asymmetric enzymatic functionalisations to yield chiral hydroxynitriles, amines, acyloins and α-chiral ketones with up to 99 % ee. In addition, we demonstrate functional group interconversion to alcohols, esters and carboxylic acids. The transformations can be performed as concurrent tandem reactions. We identified the degradation of substrates and inhibition of the biocatalysts as limiting factors affecting compatibility, due to reactive oxygen species generated in the photocatalytic step. These incompatibilities were addressed by reaction engineering, such as applying a two-phase system or temporal and spatial separation of the catalysts. Using a selection of eleven starting alkanes, one photo-organo catalyst and 8 diverse biocatalysts, we synthesized 26 products and report for the model compounds benzoin and mandelonitrile > 97 % ee at gram scale.