7021-04-7

Basic information

• Product Name: 4-BROMOMANDELIC ACID
• Synonyms: LABOTEST-BB LT00452571;Bromomandelicacid;(2R)-HYDROXY(5-BROMOPHENYL)ACETICACID;rac-(R*)-2-Hydroxy-2-(4-bromophenyl)acetic acid;rac-(R*)-α-Hydroxy-4-bromobenzeneacetic acid;rac-(αR*)-α-Hydroxy-4-bromobenzeneacetic acid
• CAS NO: 7021-04-7
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• EINECS: 230-085-1
• Mol File: 7021-04-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 116-118 °C(lit.)
• Appearance: /
• Density: 1.6494 (rough estimate)
• Refractive Index: 1.4730 (estimate)
• Merck: 1424
• CAS DataBase Reference: 4-BROMOMANDELIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMOMANDELIC ACID(7021-04-7)
• EPA Substance Registry System: 4-BROMOMANDELIC ACID(7021-04-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 7021-04-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromomandelic acid is used as a chiral building block for the synthesis of various biologically active compounds, contributing to the development of new pharmaceuticals with improved therapeutic effects.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 4-Bromomandelic acid is utilized for the creation of a range of chemical products, highlighting its importance in the chemical industry.
Used in Research and Development:
4-Bromomandelic acid is employed in research for its potential biological activities, such as anti-inflammatory and antibacterial properties, aiding in the discovery of novel treatments and applications in medicine.
Used in Drug Development:
4-Bromomandelic acid is used as a key component in the development of new drugs, particularly those targeting inflammation and bacterial infections, due to its demonstrated biological activities.

Upstream product

• 6940-50-7 4-bromo-DL-mandelic acid 
• 108-05-4 vinyl acetate 
• 102767-28-2 levetiracetam 
• 109050-30-8 (4-bromophenyl)(fluoro)acetic acid 
• 7099-87-8 4-bromophenylglyoxylic acid 
• 99-90-1 para-bromoacetophenone 
• 127709-20-0 α-hydroxy-(p-bromophenyl)-acetic acid methyl ester 

Downstream Products

• 154025-80-6 (R)-5-(4-bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one 

Relevant articles and documents

Resolution of halogenated mandelic acids through enantiospecific co-crystallization with levetiracetam

The resolution of halogenated mandelic acids using levetiracetam (LEV) as a resolving agent via forming enantiospecific co-crystal was presented. Five halogenated mandelic acids, 2-chloromandelic acid (2-ClMA), 3-chloromandelic acid (3-ClMA), 4-chloromandelic acid (4-ClMA), 4-bromomandelic acid (4-BrMA), and 4-fluoromandelic acid (4-FMA), were selected as racemic compounds. The effects of the equilibrium time, molar ratio of the resolving agent to racemate, amount of solvent, and crystallization temperature on resolution performance were investigated. Under the optimal conditions, the resolution efficiency reached up to 94% and the enantiomeric excess (%e.e.) of (R)-3-chloromandelic acid was 63%e.e. All five halogenated mandelic acids of interest in this study can be successfully separated by LEV via forming enantiospecific co-crystal, but the resolution performance is significantly different. The results showed that LEV selectively co-crystallized with S enantiomers of 2-ClMA, 3-ClMA, 4-ClMA, and 4-BrMA, while it co-crystallized with R enantiomers of 4-FMA. This indicates that the position and type of substituents of racemic compounds not only affect the co-crystal configuration, but also greatly affect the efficiency of co-crystal resolution.

Semirational Design of Fluoroacetate Dehalogenase RPA1163 for Kinetic Resolution of α-Fluorocarboxylic Acids on a Gram Scale

Here the synthetic utility of fluoroacetate dehalogenase RPA1163 is explored for the production of enantiomerically pure (R)-α-fluorocarboxylic acids and (R)-α-hydroxylcarboxylic acids via kinetic resolution of racemic α-fluorocarboxylic acids. While wild-type (WT) RPA1163 shows high thermostability and fairly wide substrate scope, many interesting yet poorly or moderately accepted substrates exist. In order to solve this problem and to develop upscaled production, in silico calculations and semirational mutagenesis were employed. Residue W185 was engineered to alanine, serine, threonine, or asparagine. The two best mutants, W185N and W185T, showed significantly improved performance in the reactions of these substrates, while in silico calculations shed light on the origin of these improvements. Finally, 10 α-fluorocarboxylic acids and 10 α-hydroxycarboxylic acids were prepared on a gram scale via kinetic resolution enabled by WT, W185T, or W185N. This work expands the biocatalytic toolbox and allows a deep insight into the fluoroacetate dehalogenase catalyzed C-F cleavage mechanism.

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

Mandelic acid and its derivatives are important chiral analogs which are widely used in the pharmaceutical synthetic industry. The present study investigated the enantiomeric separation of six mandelic acids (mandelic acid, 2-chloromandelic acid, 3-chloromandelic acid, 4-chloromandelic acid, 4-bromomandelic acid, 4-methoxymandelic acid) on the Chiralpak AD-3 column by supercritical fluid chromatography. The influences of volume fraction of trifluoroacetic acid, type and percentage of modifier, column temperature, and backpressure on the separation efficiency were investigated. And the enantiomer elution order was determined. The results show that, for a given modifier, the retention factor, the separation factor, and the separation resolution decreased gradually with increasing the volume ratio of the modifier. At the same volume ratio of modifier, the retention factor of the mandelic acid and its derivatives increased in the order of methanol, ethanol, and isopropanol, except 3-chloromandelic acid. The separation factor and the separation resolution decreased with the increase of column temperature (below the temperature limit). The backpressure affected the enantioseparation process: As the backpressure increased, a corresponding decrease in retention factor was observed. Under the same chiral column conditions, the SFC method exhibited faster and more efficient separation with better enantioselectivity than the HPLC method.

Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase

Enantiopure 2-hydroxy acids (2-HAs) are important intermediates for the synthesis of pharmaceuticals and fine chemicals. Deracemization of racemic 2-HAs into the corresponding single enantiomers represents an economical and highly efficient approach for synthesizing chiral 2-HAs in industry. In this work, a novel ketoacid reductase from Leuconostoc lactis (LlKAR) with higher activity and substrate tolerance towards aromatic α-ketoacids was discovered by genome mining, and then its enzymatic properties were characterized. Accordingly, an engineered Escherichia coli (HADH-LlKAR-GDH) co-expressing 2-hydroxyacid dehydrogenase, LlKAR, and glucose dehydrogenase was constructed for efficient deracemization of racemic 2-HAs. Most of the racemic 2-HAs were deracemized to their (R)-isomers at high yields and enantiomeric purity. In the case of racemic 2-chloromandelic acid, as much as 300 mM of substrate was completely transformed into the optically pure (R)-2-chloromandelic acid (> 99% enantiomeric excess) with a high productivity of 83.8 g L?1 day?1 without addition of exogenous cofactor, which make this novel whole-cell biocatalyst more promising and competitive in practical application.

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.).

One-pot, single-step deracemization of 2-hydroxyacids by tandem biocatalytic oxidation and reduction

A facile and efficient one-pot, single-step method for deracemizing a broad range of 2-hydroxyacids to (R)-2-hydroxyacids was established by combination of resting cells of an (S)-hydroxyacid dehydrogenase-producing microorganism and an (R)-ketoacid reductase-producing microorganism.

Robust enzymatic resolution of 3-fluoromandelic acid with lipase PS supported on celite

The resolution of different mandelic acids using the lipase PS Amano SD enzyme is described. By supporting the lyophilized enzyme over Celite, both the activity and the stability of lipase PS in organic media were significantly improved, enabling the robust resolution scale-up of 3-fluoromandelic acid. The methodology was extended to produce a range of optically pure (R)-mandelic acids, avoiding tedious extractions or chromatography.

Enantioselectivity of carbonic anhydrase catalyzed hydrolysis of mandelic methyl esters

We report the first enantioselective hydrolysis of esters catalyzed by caebonic anhydrase.We found that mandelic methyl esters are good substrates for carbonic anhydrase.The R enantiomers are better substrates and enantiomeric excess values are moderate (40-51percent).

Semisynthetic cephalosporins. Synthesis and structure activity relationships of 7 mandelamido 3 cephem 4 carboxylic acids

The synthesis, microbiological profile, and in vivo effectiveness in laboratory animals of a broad spectrum cephalosporin, 7(R) mandelamidocephalosporanic acid (1), are described. A number of derivatives and analogs of 1 were prepared and their structure activity relationships are discussed.