26164-26-1

Basic information

• Product Name: (S)-(+)-alpha-Methoxyphenylacetic acid
• Synonyms: (S)-(+)-ALPHA-METHOXYPHENYLACETIC ACID 99%;(S)-(+)-ɑ-Methoxyphenylacetic acid, 99%;(2S)-2-Methoxy-2-phenylacetic acid;(S)-α-Methoxybenzeneacetic acid;(αS)-α-Methoxybenzeneacetic acid;[S,(+)]-α-Methoxybenzeneacetic acid;(S)-(+)-alpha-Methoxyphenylacetic acid,99%;Acetic acid, Methoxyphenyl-, (S)-
• CAS NO: 26164-26-1
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 247-492-5
• Product Categories: Analytical Chemistry;Carboxylic Acids (Chiral);Chiral Building Blocks;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;Synthetic Organic Chemistry;Chiral Reagents
• Mol File: 26164-26-1.mol
• Article Data: 34

Chemical Properties

• Melting Point: 64-66 °C(lit.)
• Boiling Point: 164-166°C 18mm
• Flash Point: 164-166°C/18mm
• Appearance: White/Fine Crystalline Powder or Crystals
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 0.00146mmHg at 25°C
• Refractive Index: 147 ° (C=0.5, EtOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethanol (Slightly)
• PKA: 3.10±0.10(Predicted)
• Water Solubility: Soluble
• BRN: 2361718
• CAS DataBase Reference: (S)-(+)-alpha-Methoxyphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-alpha-Methoxyphenylacetic acid(26164-26-1)
• EPA Substance Registry System: (S)-(+)-alpha-Methoxyphenylacetic acid(26164-26-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 26164-26-1(Hazardous Substances Data)

Usage

Description

(S)-(+)-alpha-Methoxyphenylacetic acid, with the CAS number 26164-26-1, is a white solid compound that plays a significant role in organic synthesis. It is characterized by its unique chemical structure, which allows it to be involved in the synthesis of various biologically active molecules.

Uses

1. Used in Organic Synthesis:
(S)-(+)-alpha-Methoxyphenylacetic acid is used as a reactant in organic synthesis for the production of different compounds.
2. Used in Pharmaceutical Industry:
(S)-(+)-alpha-Methoxyphenylacetic acid is used as a reactant for the synthesis of biologically active molecules, which have potential applications in the pharmaceutical industry. These molecules include:
a. Acyclonucleoside phosphonates: These are structural analogs of adefovir, an antiviral drug used to treat chronic hepatitis B infection.
b. Labeled discodermolide: (S)-(+)-alpha-Methoxyphenylacetic acid is used for studying binding to tubulin, which can provide insights into the development of new anti-cancer drugs.
c. 10-Isocyano-4-cadinene: This molecule is used for antifouling activity, which can be beneficial in the development of new materials and coatings to prevent biofouling.
d. Reactant in studies of immunostimulating chromanones gonytolides A-C: These compounds have potential applications in the development of new immunostimulating agents.
3. Used in Chemical Research:
(S)-(+)-alpha-Methoxyphenylacetic acid is also used as a reactant in various chemical reactions, such as:
a. Hydroxylations and epoxidations: These reactions are essential for the synthesis of various organic compounds and can provide valuable insights into the reactivity and selectivity of different functional groups.
b. Hydrogenations: This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and fine chemicals.

Purification Methods

Purify the acids by recrystallising from *C6H6/pet ether (b 80-100o). [Neilson & Peters J Chem Soc 1519 1962, Weizmann et al. J Am Chem Soc 70 1153 1948, Pirie & Smith J Chem Soc 338 1932, NMR: Dale & Mosher J Am Chem Soc 9 5 512 1973, for resolution: Roy & Deslongchamps Can J Chem 63 651 1985, Trost et al. J Am Chem Soc 1 0 8 4974 1986.] The racemic mixture has m 72o, b 121-122o/0.4mm, 165o/18mm (from pet ether) [Braun et al. Chem Ber 6 3 2847 1930]. [Beilstein 10 IV 566.]

InChI:InChI=1/C9H10O3/c1-12-8(9(10)11)7-5-3-2-4-6-7/h2-6,8H,1H3,(H,10,11)/p-1/t8-/m0/s1

Upstream product

• 3558-61-0 (S)-methyl 2-methoxy-2-phenylacetate 
• 86544-37-8 (S)-α-methoxyphenylacetaldehyde 
• 7021-09-2 rac-methoxyphenylacetic acid 
• 17199-29-0 (S)-Mandelic acid 
• 77-78-1 dimethyl sulfate 
• 3558-61-0 methyl 2-methoxy-2-phenylacetate 
• 115306-96-2 (3E,7Z)-3,7-dimethyl-2,5,6,9-tetrahydrooxonine 
• 31528-01-5 (S)-2-Methoxy-2-phenylessigsaeure-4-nitrophenylester 
• 146388-54-7 (2S,3R,4S)-(+)-4-methoxy-4-phenyl-2,3-butanediol 
• 611-71-2 (R)-Mandelic Acid 
• 4870-65-9 2-bromophenylacetic acid 
• 124-41-4 sodium methylate 
• 55137-68-3 (S)-(+)-O-methylmandeloyl chloride 
• 114027-88-2 (S)-N-(α-Methylbenzyl)-(S)-2-methoxy-2-phenylacetamide 

Downstream Products

• 149-95-1 D-noradrenaline 
• 360557-72-8 (2S)-2-methoxy-2-phenylacetamide 
• 3558-61-0 (S)-methyl 2-methoxy-2-phenylacetate 
• 31528-01-5 (S)-2-Methoxy-2-phenylessigsaeure-4-nitrophenylester 
• 123642-96-6 (S)-O-Methylmandelic acid derivative of (-)-menthol 
• 72565-52-7 (S)-Methoxy-phenyl-acetic acid (1S,2R)-1-ethyl-2-hydroxy-2-methyl-pent-3-ynyl ester 
• 72565-52-7 (S)-methoxy-phenyl-acetic acid (1R,2S)-1-ethyl-2-hydroxy-2-methyl-pent-3-ynyl ester 
• 135382-49-9 (S)-Methoxy-phenyl-acetic acid 2-oxo-2H-pyran-3-yl ester 
• 112893-81-9 (S)-Methoxy-phenyl-acetic acid (2S,6S)-2,6,10-trimethyl-undecyl ester 
• 107799-27-9 (+)-(3S,2'S)-ethyl 4-(dimethylamino)-3-<(2-methoxy-2-phenylacetyl)oxy>butanoate 
• 107799-26-8 (+)-(3R,2'S)-ethyl 4-(dimethylamino)-3-<(2-methoxy-2-phenylacetyl)oxy>butanoate 
• 114027-88-2 (S)-N-(α-Methylbenzyl)-(S)-2-methoxy-2-phenylacetamide 
• 112965-78-3 (S)-Methoxy-phenyl-acetic acid (2R,6R)-2,6,10-trimethyl-undecyl ester 
• 123643-00-5 (S)-O-Methylmandelic acid derivative of (2R,3R,4S,5R)-3-Hydroxy-2-methoxy-8-methyl-5-tetradecanoylnon-6-ene 1,4-lactone 

Relevant articles and documents

Enantioselective carboxylation of α-methoxybenzyllithium generated via asymmetric lithiation with a t-BuLi/chiral bis(oxazoline) complex

Treatment of benzyl methyl ether with a t-BuLi/chiral bis(oxazoline) complex followed by carboxylation is shown to afford α-methoxy phenylacetic acid in high % ee (up to 95%). The asymmetric induction was proved to occur at the post-lithiation step.

The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes by using chiral salen catalyst

The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes was established. The reaction was successfully achieved by using (R,R)-SalenAlCl as the chiral catalyst and LiI as an additive at 0°C in dichloromethane. Moderate to good yields and up to 62% ee were obtained. The new system showed a good substrate scope in which both aromatic aldehydes and aliphatic aldehydes can be employed. The reaction provided the first catalytic and enantioselective approach to chiral β-iodo Baylis-Hillman ester adducts.

The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation

A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).

Effect of the concentration of organic modifier in an aqueous-ethanol mobile phase on the chromatographic retention and thermodynamic characteristics of the adsorption of enantiomers of α-phenylcarboxylic acids on silica gel with immobilized eremomycin antibiotic

Regularities of the chromatographic retention and thermodynamics of the adsorption of enantiomers of α-phenylcarboxylic acids on a chiral stationary phase with immobilized macrocyclic antibiotic eremomycin under conditions of reversed-phase liquid chromatography with aqueous-ethanol mobile phases are studied. Relationships between the retention characteristics of the acids, the enantioselectivity of their separation, and the concentration of organic modifier in the mobile phase are found. It is shown that the sterical structure of substituents on the chiral atoms of the acids affect the mechanism of retention. The compensation effect in the studied systems is considered.