156942-67-5

Basic information

• Product Name: (R)-α-Methoxy-2-naphthaleneacetic acid, (R)-2-NMA
• Synonyms: (R)-α-Methoxy-2-naphthaleneacetic acid, (R)-2-NMA;(R)-α-Methoxy-2-naphthylacetic acid;(R)-2-NMA;(R)-alpha-Methoxy-2-naphthylacetic acid >=99.0%;(R)-ALPHA-METHOXY-2-NAPHTHYLACETIC ACID
• CAS NO: 156942-67-5
• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.235
• Mol File: 156942-67-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 101-104 °C
• Appearance: /
• CAS DataBase Reference: (R)-α-Methoxy-2-naphthaleneacetic acid, (R)-2-NMA(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-Methoxy-2-naphthaleneacetic acid, (R)-2-NMA(156942-67-5)
• EPA Substance Registry System: (R)-α-Methoxy-2-naphthaleneacetic acid, (R)-2-NMA(156942-67-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 156942-67-5(Hazardous Substances Data)

Usage

General Description

(R)-α-Methoxy-2-naphthaleneacetic acid, also known as (R)-2-NMA, is a chiral compound belonging to the class of naphthaleneacetic acids. It is an enantiomer of (S)-2-NMA and is commonly used as a plant growth regulator to promote the rooting of cuttings and the formation of adventitious roots in various plant species. (R)-2-NMA has been shown to have a high affinity for the auxin-binding protein, and it exhibits strong auxin activity, which makes it an effective tool for studying the hormonal control of plant growth and development. Additionally, it has potential applications in agriculture for enhancing crop yields and improving plant stress tolerance.

Upstream product

• 7362-01-8 (+/-)-α-Methoxy-α-(2-naphthyl)acetic acid 
• 160727-71-9 (+/-)-Methyl α-methoxy-α-(2-naphthyl)acetate 
• 475582-28-6 (R)-Methoxy-naphthalen-2-yl-acetic acid methyl ester 
• 537695-86-6 (R)-2-methoxy-2-naphthalen-2-ylethanol 
• 827-54-3 2-naphthylethylene 
• 49801-14-1 (S)-1-(2-naphthyl)-1,2-ethanediol 
• 537695-79-7 (R)-2-(tert-butyldimethylsilyloxy)-1-methoxy-1-naphthalen-2-ylethane 
• 537695-73-1 (R)-2-(tert-butyldimethylsilyloxy)-1-naphthalen-2-ylethanol 
• 77196-31-7 2-(dimethoxymethyl)naphthalene 
• 20862-03-7 2-naphthyl cyanohydrin 
• 103722-72-1 (+/-)-Methyl α-hydroxy-α-(21-naphthyl)acetate 
• 475582-26-4 (R)-α-hydroxy-2-naphthylacetamide 
• 475582-21-9 α-methoxy-2-naphthylacetamide 
• 126644-23-3 α-acetoxy-2-naphthylacetonitrile 

Relevant articles and documents

New Chiral Anisotropic Reagents, NMR Tools to Elucidate the Absolute Configuration of Long-chain Organic Compounds

Modified Mosher's method has been extended by use of 9-anthranylmethoxyacetic acid (9ATMA) and 2-naphthylmethoxynaphthylacetic acid (2NMA) instead of MTPA of the conventional method.Anisotropic effects of these reagents are much greater than that of MTPA, and the reagents have been shown to useful especially to determine the absolute configurations of the secondary alcohols involved in long-chain componds.

Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid

Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2-TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate with an e.e. of >99.9%. The resulting product of this enzyme-catalyzed hydrolysis, an (S)-cyanohydrin, spontaneously decomposed into naphthaldehyde, the starting material of this synthetic route, which could be recycled. The hydration of nitrile to amide as well as the hydrolysis of the acetate was performed with a microorganism, Rhodococcus rhodochrous, under very mild conditions without any loss of the enantiomeric purity. The amide group was hydrolyzed with nitrosylsulfuric acid, and the product was isolated as an α-hydroxy ester. The α-hydroxyl group was methylated with diazomethane-silica gel and the final task, hydrolysis of the ester, was accomplished under conditions as mild as neutral pH with an esterase from Krebsiella oxytoca to give enantiomerically pure 2-NMA.