3972-41-6

Basic information

• Product Name: (R)-BROMOSUCCINIC ACID
• Synonyms: (R)-BROMOSUCCINIC ACID;(R)-2-broMosuccinic acid
• CAS NO: 3972-41-6
• Molecular Formula: C₄H₅BrO₄
• Molecular Weight: 196.98
• Mol File: 3972-41-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: 166-167 °C
• Boiling Point: 255.1°C at 760 mmHg
• Flash Point: 108.1°C
• Appearance: /
• Density: 2.022g/cm³
• Vapor Pressure: 0.00512mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Methanol (Slightly, Sonicated)
• PKA: 2.71±0.23(Predicted)
• CAS DataBase Reference: (R)-BROMOSUCCINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BROMOSUCCINIC ACID(3972-41-6)
• EPA Substance Registry System: (R)-BROMOSUCCINIC ACID(3972-41-6)

Safety Data

• Hazardous Substances Data: 3972-41-6(Hazardous Substances Data)

Usage

Description

(R)-Bromosuccinic Acid, also known as (R)-2-Bromosuccinic Acid, is an enantiomer of (S)-2-Bromosuccinic Acid. It is a chemical compound with the molecular formula C4H5BrO4 and is characterized by its distinct spatial arrangement of atoms. This enantiomer plays a crucial role in various chemical reactions and applications due to its unique stereochemistry.

Uses

Used in Chemical Synthesis:
(R)-Bromosuccinic Acid is used as a reagent for the synthesis of 3-mercaptopyrrolidine derivatives and alkanols. Its enantiomeric nature allows for the creation of specific chiral compounds, which are essential in various industries, including pharmaceuticals and agrochemicals.
Used in Chiral Stationary Phase Development:
(R)-Bromosuccinic Acid is utilized in the development of enantioselective high-performance liquid chromatography (HPLC) separations. These separations are crucial for distinguishing between enantiomers, which can have different biological activities and properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-Bromosuccinic Acid is used as a key intermediate in the synthesis of chiral drugs. The ability to produce pure enantiomers is vital for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Analytical Chemistry:
(R)-Bromosuccinic Acid is employed in the development of chiral stationary phases for HPLC, which are essential tools in analytical chemistry. These phases enable the separation and analysis of enantiomers, providing valuable information about their properties and potential applications.
Used with Ristocetin A:
(R)-Bromosuccinic Acid can be utilized in conjunction with ristocetin A, a macrocyclic glycopeptide, to develop enantioselective HPLC separations. This combination allows for the efficient separation and analysis of chiral compounds, which is particularly important in the development and quality control of pharmaceutical products.

InChI:InChI=1/C4H5BrO4/c5-2(4(8)9)1-3(6)7/h2H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1

Upstream product

• 1783-96-6 (2R)-aspartic acid 
• 56-84-8 L-Aspartic acid 
• 617-45-8 aspartic Acid 
• 10035-10-6 hydrogen bromide 
• 64-17-5 ethanol 
• 158706-00-4 diethyl (R)-bromosuccinate 

Downstream Products

• 20859-24-9 Dimethyl S-bromsuccinat 
• 197433-31-1 (S)-ethoxythiocarbonylmercapto-succinic acid 
• 197433-30-0 (R)-ethoxythiocarbonylmercapto-succinic acid 
• 22119-13-7 (S)-benzoylmercaptosuccinic acid 
• 22119-13-7 (R)-benzoylmercaptosuccinic acid 
• 904830-63-3 N-o-tolyl-L-aspartic acid 
• 158706-00-4 diethyl (R)-bromosuccinate 
• 158705-99-8 (S)-diethyl bromosuccinate 
• 97-67-6 (S)-Malic acid 
• 636-61-3 D-Malic acid 
• 10035-10-6 hydrogen bromide 
• 110-17-8 (2E)-but-2-enedioic acid 
• 16045-92-4 chlorosuccinic acid 

Relevant articles and documents

Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin

A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.

Stereoselective synthesis of resorcylic acid lactone Cochliomycin B

The total synthesis of 14-membered resorcylic acid lactone, Cochliomycin B has prescribed, in a convergent manner, from readily available starting materials, D-galactose, L-aspartic acid and ethyl acetoacetate. The key reactions involved in the synthesis are Julia-Kocienski olefination, E-selective Horner-Wadsworth-Emmons olefination and intramolecular lactonization.

Synthesis and Evaluation of Novel TLR2 Agonists as Potential Adjuvants for Cancer Vaccines

Cancer immunotherapy has gained increasing attention due to its potential specificity and lack of adverse side effects when compared to more traditional modes of treatment. Toll-like receptor 2 (TLR2) agonists are lipopeptides possessing the S-[2,3-bis(palmitoyloxy)propyl]-l-cysteine (Pam2Cys) motif and exhibit potent immunostimulatory effects. These agonists offer a means of providing "danger signals" in order to activate the immune system toward tumor antigens. Thus, the development of TLR2 agonists is attractive in the search of potential immunostimulants for cancer. Existing SAR studies of Pam2Cys with TLR2 indicate that the structural requirements for activity are, for the most part, very intolerable. We have investigated the importance of stereochemistry, the effect of N-terminal acylation, and homologation between the two ester functionalities in Pam2Cys-conjugated lipopeptides on TLR2 activity. The R diastereomer is significantly more potent than the S diastereomer and N-terminal modification generally lowers TLR2 activity. Most notably, homologation gives rise to analogues which are comparatively active to the native Pam2Cys containing constructs.