3886-70-2

Basic information

• Product Name: (R)-(+)-1-(1-Naphthyl)ethylamine
• Synonyms: (R) 1-(1-NAPTHYL)ETHYLAMINE;(R)-(+)-1-(1-NAPHTHYL)ETHYLAMINE;(R)-1-(1-NAPHTHYL)ETHYLAMINE;(R)-1-(NAPHTHALEN-1-YL)ETHANAMINE;(R)-(+)-1-(NAPHTHYL)ETHYLAMINE;(R)-(+)-A-(1-NAPHTHYL)ETHYLAMINE;(R)-(+)-ALPHA-(1-AMINOETHYL)NAPHTHALENE;(R)-(+)-ALPHA-(1-NAPHTHYL)ETHYLAMINE
• CAS NO: 3886-70-2
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• EINECS: 223-425-5
• Product Categories: chiral;Amines (Chiral);Analytical Chemistry;Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry;Miscellaneous;Cinacalcet Intermediate
• Mol File: 3886-70-2.mol
• Article Data: 54

Chemical Properties

• Melting Point: 135-136 °C
• Boiling Point: 153 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: brown/Liquid
• Density: 1.067 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00214mmHg at 25°C
• Refractive Index: n20/D 1.623(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 9.26±0.40(Predicted)
• Water Solubility: Soluble in water (<10/l).
• Sensitive: Air Sensitive
• Stability: Stable. Air-sensitive. Incompatible with acids, oxidizing agents, acid anhydrides, chloroformates, acid chlorides.
• BRN: 2208025
• CAS DataBase Reference: (R)-(+)-1-(1-Naphthyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-(1-Naphthyl)ethylamine(3886-70-2)
• EPA Substance Registry System: (R)-(+)-1-(1-Naphthyl)ethylamine(3886-70-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 2735
• WGK Germany: 3
• RTECS: QJ6963000
• F: 10-34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3886-70-2(Hazardous Substances Data)

Usage

Description

(R)-(+)-1-(1-Naphthyl)ethylamine is a chiral amine compound that plays a significant role in various organic reactions due to its unique stereochemistry. It is characterized by its naphthyl group attached to an ethylamine chain, which imparts specific properties that are valuable in the synthesis of complex organic molecules.

Uses

Used in Chiral Synthesis:
(R)-(+)-1-(1-Naphthyl)ethylamine is used as a chiral auxiliary in organic reactions for the synthesis of β-amino acids. Its presence helps in controlling the stereochemistry of the reaction, leading to the formation of enantiomerically pure products. This is particularly important in the pharmaceutical industry, where the stereochemistry of a drug can significantly affect its efficacy and safety.
Used in Enantioselective Transformations:
In the field of organic chemistry, (R)-(+)-1-(1-Naphthyl)ethylamine is also used in the enantioselective transformation of ketones to nitroolefins. This reaction is crucial for the synthesis of various biologically active compounds and pharmaceuticals, as it allows for the preparation of enantiomerically pure compounds with a high level of selectivity.
Used in Determination of Absolute Configuration:
(R)-(+)-1-(1-Naphthyl)ethylamine finds application in the determination of the absolute configuration of primary amines. It is used in conjunction with chiral (2-nitrophenyl)proline amides and H NMR spectroscopy to accurately determine the stereochemistry of primary amines. This technique is valuable in the field of stereochemistry and drug development, as it allows for the unambiguous assignment of the absolute configuration of chiral centers in molecules.

InChI:InChI=1/C12H13N/c1-9(13)11-8-4-6-10-5-2-3-7-12(10)11/h2-9H,13H2,1H3/p+1/t9-/m1/s1

Upstream product

• 123-66-0 Ethyl hexanoate 
• 42882-31-5 (RS)-1-(1-naphthyl)ethylamine 
• 1073144-62-3 (1R)-1-(naphthalen-1-yl)ethanamine (R)-mandelate 
• 23943-58-0 (R)-N-(1-naphthalen-1-ylethyl)-p,p-diphenylphosphinc amide 
• 82572-09-6 C₂₄H₂₀NOP 
• 1127-76-0 1-ethylnapthelene 
• 24227-47-2 2‐(1‐naphthalenyl)propanamide 
• 251957-73-0 1‐naphthalenylzinc bromide 
• 90-11-9 1-Bromonaphthalene 
• 703-55-9 1-naphthylmagnesiumbromide 
• 22561-77-9 2‐(1‐naphthalenyl)propanoic acid 
• 100430-65-7 (Z)-N-<1-(1'-naphthyl)ethylidene>-1-phenylethylamine 
• 15914-84-8 (S)-1-(1-Naphthyl)ethanol 

Downstream Products

• 74629-94-0 (1S,2R,R)-cis-1-(2-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)methyl N-<1-(1-naphthyl)ethyl>amide 
• 74629-95-1 (1R,2S,R)-cis-1-(2-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)methyl N-<1-(1-naphthyl)ethyl>amide 
• 147963-59-5 Benzoic acid (S)-2-cyano-1-[((R)-1-naphthalen-1-yl-ethylcarbamoyl)-methyl]-ethyl ester 
• 87691-43-8 Boc-Phe-His-Sta-Leu-(+)-α-naphthylethylamide 
• 87691-43-8 Boc-Phe-His-Sta-Leu-(-)-α-naphthylethylamide 
• 144271-30-7 (3R,1'R)-N-(1-naphthylethyl)-3-(4-methyl-1,3-cyclohexadienyl)butanamide 
• 74629-96-2 (1S,2S,R)-trans-1-(2-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)methyl N-<1-(1-naphthyl)ethyl>amide 
• 74629-97-3 (1R,2R,R)-trans-1-(2-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)methyl N-<1-(1-Naphthyl)ethyl>amide 
• 102779-14-6 (1R,2'R)-N-<1-(1-naphthyl)ethyl>-2-phenylbutanamide 
• 64187-98-0 (1R,2'S)-N-<1-(1-naphthyl)ethyl>-2-phenylbutanamide 
• 77732-38-8 (3S,1'R)-N-(1-naphthylethyl)-3-(4-methylphenyl)butanamide 
• 77732-39-9 (3R,1'R)-N-(1-naphthylethyl)-3-(4-methylphenyl)butanamide 
• 72165-50-5 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 3-hydroxy-3-methyl-4-((R)-1-naphthalen-1-yl-ethylcarbamoyl)-butyl ester 
• 78681-09-1 (+)-3-<1-(1-Naphthyl)ethylcarbamoyl>propionsaeure 

Relevant articles and documents

A METHOD FOR PREPARATION OF DIASTEREOMERIC LACTATE SALTS OF 1-(1-NAPHTHYL)ETHYL AMINE AND PURE ENANTIOMERS OF 1-(1-NAPHTHYL)ETHYL AMINE

The invention relates to method for preparation of pure enantiomers of 1-(1-naphthyl)ethyl amine by preparing lactate salt with chiral lactic acid as resolving agent. The method comprises reaction of L-lactic acid or D-lactic acid with racemic 1-(1-naphthyl)ethyl amine to form diastereomeric salts of (R/S)-1-(1-naphthyl)ethyl amine-(D/L)-lactate from which pure enantiomer is isolated. The invention also comprises method for preparation of compound with enriched enantiomers of 1-(1-naphthyl)ethyl amine from the mother liquor separated from the diastereomeric lactate salt. The enriched enantiomer is reacted with pure enantiomers of mandelic acid or lactic acid, preferably D-mandelic acid or L-mandelic acid and converted to diastereomeric mandelate salt. Pure (R)- or (S)-1-(1-naphthyl)ethyl amine is obtained from the diastereomeric mandelate salt. The chiral purity of pure enantiomer obtained is between 99% and 100%.

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.

Addition of Highly Polarized Organometallic Compounds to N-tert-Butanesulfinyl Imines in Deep Eutectic Solvents under Air: Preparation of Chiral Amines of Pharmaceutical Interest

Highly polarized organometallic compounds of s-block elements are added smoothly to chiral N-tert-butanesulfinyl imines in the biodegradable d-sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines after quantitatively removing the sulfinyl group. The practicality of the method is further highlighted by proceeding at ambient temperature and under air, with very short reaction times (2 min), enabling the preparation of diastereoisomeric sulfinamides in very good yields (74–98 %) and with a broad substrate scope, and the possibility of scaling up the process. The method is demonstrated in the asymmetric syntheses of both the chiral amine side-chain of (R,R)-Formoterol (96 % ee) and the pharmaceutically relevant (R)-Cinacalcet (98 % ee).