Mandelate

Base Information

• Chemical Name: Mandelate
• CAS No.: 769-61-9
• Molecular Formula: C8H7O3-
• Molecular Weight: 151.142
• DSSTox Substance ID: DTXSID90998189
• Nikkaji Number: J2.393.752B
• Wikidata: Q27109865
• Mol file: 769-61-9.mol

Synonyms:mandelate;Mandelate ion;2-hydroxy-2-phenylacetate;hydroxy(phenyl)acetate;769-61-9;Benzeneacetic acid, alpha-hydroxy-, ion(1-)-;alpha-hydroxybenzeneacetate;(+/-)-mandelate;C8H7O3;CHEBI:25147;DTXSID90998189;IWYDHOAUDWTVEP-UHFFFAOYSA-M;C8-H7-O3;alpha-hydroxybenzeneacetic acid, ion(1-);Q27109865

Chemical Property of Mandelate

Chemical Property:

• Vapor Pressure: 0.00012mmHg at 25°C
• Boiling Point: 321.8°Cat760mmHg
• Flash Point: 162.6°C
• PSA: 60.36000
• Density: g/cm³
• LogP: -0.53010
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.039519081
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)[O-])O
• General Description: Hydroxy(phenyl)acetate, also known as mandelate ion or 2-hydroxy-2-phenylacetate, is a key intermediate in pharmaceutical synthesis, notably for drugs like Plavix and Duloxetine. A recent study highlights an improved palladium-catalyzed method for its production from arylboronic acids and glyoxylate hemiacetals, offering a safer and more efficient alternative to conventional toxic or restrictive approaches. This method employs a cyclometalated NHC-palladium(II) catalyst, enabling high reactivity, broad functional group tolerance, and excellent yields of functionalized mandelate derivatives. The advancement provides a versatile and less hazardous route for synthesizing these pharmacologically important compounds.

Technology Process of Mandelate

There total 4 articles about Mandelate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phenylethane 1,2-diol (93-56-1) → hydroxyphenylacetate (769-61-9)

Guidance literature:

With hydrogen; sodium hydroxide; In water; at 105 ℃; for 24h;

DOI:10.1021/acscatal.1c04354

Reference yield:

2,2-dihydroxy-1-phenyl-ethanone (1075-06-5) → hydroxyphenylacetate (769-61-9)

Guidance literature:

In water; Rate constant; pH 12; isotope labelling experiments;

DOI:10.1039/P29880001345

Reference yield:

PhCH(OH)C(O)SCD3 (922498-88-2) → trideuteromethanethiol (7175-74-8) + hydroxyphenylacetate (769-61-9)

Guidance literature:

With [(bpta)Zn(CH₃CN)2(H₂O)](ClO₄)2; water; In acetonitrile; at 56.34 ℃; for 288h; pH=9; Reagent/catalyst; Temperature; pH-value; Concentration; Kinetics; aq. buffer;

DOI:10.1021/ic902322h

upstream raw materials:

2,2-dihydroxy-1-phenyl-ethanone

PhCH(OH)C(O)SCD₃

phenylethane 1,2-diol

Downstream raw materials:

NO₂(C₆H₄)B(OH)(C₆H₅CH(O)(COO))^(1-)

benzaldehyde

Refernces

Palladium catalyzed synthesis of mandelate derivatives from arylboronic acids and glyoxylate hemiacetals

10.1016/j.tetlet.2017.05.035

The research discusses the palladium-catalyzed synthesis of mandelate derivatives from arylboronic acids and glyoxylate hemiacetals, which are important intermediates for the production of various pharmaceuticals such as Plavix and Duloxetine. The study aims to develop a more efficient and less toxic method for synthesizing mandelate derivatives, addressing the limitations of traditional methods that involve the use of toxic cyano reagents or are restricted to specific types of aromatic compounds. The researchers utilized a cyclometalated N-heterocyclic carbene (NHC) palladium(II) complex as a highly reactive catalyst, which allowed for the arylation of glyoxylate hemiacetals using arylboronic acids. The process demonstrated good functional group tolerance and resulted in the formation of various functionalized methyl mandelate derivatives in good to excellent yields. The study concluded that it had successfully developed a palladium-catalyzed method for the synthesis of mandelate derivatives, offering a more versatile and safer alternative to traditional synthesis routes.