150521-30-5

Basic information

• Product Name: (R)-(+)-4-BROMOMANDELONITRILE
• Synonyms: (R)-(+)-4-BROMOMANDELONITRILE
• CAS NO: 150521-30-5
• Molecular Formula: C₈H₆BrNO
• Molecular Weight: 212.04
• Mol File: 150521-30-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(+)-4-BROMOMANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-4-BROMOMANDELONITRILE(150521-30-5)
• EPA Substance Registry System: (R)-(+)-4-BROMOMANDELONITRILE(150521-30-5)

Safety Data

• Hazardous Substances Data: 150521-30-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-4-BROMOMANDELONITRILE is used as a synthetic reagent for the production of pharmaceuticals, particularly for creating enantiomer-pure products. Its chirality allows for selective reactions with specific enantiomers, which is essential in the development of drugs with desired therapeutic effects and minimal side effects.
Used in Synthetic Tissue Production:
(R)-(+)-4-BROMOMANDELONITRILE is used as a key component in the synthesis of synthetic tissues, where its chiral properties contribute to the creation of biologically compatible materials. This is crucial for the development of advanced medical devices and implants that can be safely integrated into the human body.
Used in Laboratory Research:
(R)-(+)-4-BROMOMANDELONITRILE is used as a research tool in various laboratory settings, where its unique chemical properties can be explored for potential applications in the fields of chemistry, biology, and materials science. Its versatility as a synthetic reagent makes it a valuable asset in the development of new compounds and materials.

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen cyanide 
• 773837-37-9 sodium cyanide 
• 108-05-4 vinyl acetate 
• 58289-69-3 2-(4-bromophenyl)-2-hydroxyacetonitrile 
• 83575-55-7 2-(4-bromophenyl)-2-(trimethylsilyloxy)acetonitrile 

Relevant articles and documents

Controlled Exchange of Achiral Linkers with Chiral Linkers in Zr-Based UiO-68 Metal-Organic Framework

The development of highly robust heterogeneous catalysts for broad asymmetric reactions has always been a subject of interest, but it remains a synthetic challenge. Here we demonstrated that highly stable metal-organic frameworks (MOFs) with potentially acid-labile chiral catalysts can be synthesized via postsynthetic exchange. Through a one- or two-step ligand exchange, a series of asymmetric metallosalen catalysts with the same or different metal centers are incorporated into a Zr-based UiO-68 MOF to form single- and mixed-M(salen) linker crystals, which cannot be accomplished by direct solvothermal synthesis. The resulting MOFs have been characterized by a variety of techniques including single-crystal X-ray diffraction, N2 sorption, CD, and SEM/TEM-EDS mapping. The single-M(salen) linker MOFs are active and efficient catalysts for asymmetric cyanosilylation of aldehydes, ring-opening of epoxides, oxidative kinetic resolution of secondary alcohols, and aminolysis of stilbene oxide, and the mixed-M(salen) linker variants are active for sequential asymmetric alkene epoxidation/epoxide ring-opening reactions. The chiral MOF catalysts are highly enantioselective and completely heterogeneous and recyclable, making them attractive catalysts for eco-friendly synthesis of fine chemicals. This work not only advances UiO-type MOFs as a new platform for heterogeneous asymmetric catalysis in a variety of syntheses but also provides an attractive strategy for designing robust and versatile heterogeneous catalysts.

Multivariate Metal-Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions

The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural series of 2-fold interpenetrated MTV-MOFs that contain up to three different chiral metallosalen catalysts was constructed and used as efficient and recyclable heterogeneous catalysts for a variety of asymmetric sequential alkene epoxidation/epoxide ring-opening reactions. Interpenetration of the frameworks brings metallosalen units adjacent to each other, allowing cooperative activation, which results in improved efficiency and enantioselectivity over the sum of the individual parts. The fact that manipulation of molecular catalysts in MTV-MOFs can control the activities and selectivities would facilitate the design of novel multifunctional materials for enantioselective processes.

An orthogonal biocatalytic approach for the safe generation and use of HCN in a multistep continuous preparation of chiral O-acetylcyanohydrins

An enantioselective preparation of O-acetylcyanohydrins has been accomplished by a three-step telescoped continuous process. The modular components enabled an accurate control of two sequential biotransformations, safe handling of an in situ generated hazardous gas, and in-line stabilization of products. This method proved to be advantageous over the batch protocols in terms of reaction time (40 min vs 345 min) and ease of operation, opening up access to reactions which have often been neglected due to safety concerns.

Discovery and molecular and biocatalytic properties of hydroxynitrile lyase from an invasive millipede, Chamberlinius hualienensis

Hydroxynitrile lyase (HNL) catalyzes the degradation of cyanohy-drins and causes the release of hydrogen cyanide (cyanogenesis). HNL can enantioselectively produce cyanohydrins, which are valuable building blocks for the synthesis of fine chemicals and ph

Chemoenzymatic flow cascade for the synthesis of protected mandelonitrile derivatives

A chemoenzymatic two-step cascade process, with both steps having incompatible reaction conditions, was successfully performed in continuous flow. The chemoenzymatic aqueous formation of cyanohydrins was integrated with a subsequent organic phase protection step in a single flow process utilising a membrane-based phase separation module. The wider applicability of our setup was demonstrated with the synthesis of nine protected cyanohydrin derivatives, all obtained in good yields and high to excellent enantioselectivity.

Enantioselective cyanosilylation of aldehydes catalyzed by a multistereogenic salen-Mn(III) complex with a rotatable benzylic group as a helping hand

A multistereogenic salen-Mn(iii) complex bearing an aromatic pocket and two benzylic groups as helping hands was found to be efficient in the catalysis of asymmetric cyanosilylation. The salen-Mn catalyst partially mimics the functions of biocatalysts by

Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes

Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino- 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes

Investigation of lewis acid versus lewis base catalysis in asymmetric cyanohydrin synthesis

The asymmetric addition of trimethylsilyl cyanide to aldehydes can be catalysed by Lewis acids and/or Lewis bases, which activate the aldehyde and trimethylsilyl cyanide, respectively. It is not always apparent from the structure of the catalyst whether Lewis acid or Lewis base catalysis predominates. To investigate this in the context of using salen complexes of titanium, vanadium and aluminium as catalysts, a Hammett analysis of asymmetric cyanohydrin synthesis was undertaken. When Lewis acid catalysis is dominant, a significantly positive reaction constant is observed, whereas reactions dominated by Lewis base catalysis give much smaller reaction constants. [{Ti(salen)O}2] was found to show the highest degree of Lewis acid catalysis, whereas two [VO(salen)X] (X = EtOSO3 or NCS) complexes both displayed lower degrees of Lewis acid catalysis. In the case of reactions catalysed by [{Al(salen)}2O] and triphenyl- phosphine oxide, a non-linear Ham- mett plot was observed, which is indicative of a change in mechanism with increasing Lewis base catalysis as the carbonyl compound becomes more electron-deficient. These results suggested that the aluminium complex/tri- phenylphosphine oxide catalyst system should also catalyse the asymmetric addition of trimethylsilyl cyanide to ke- tones and this was found to be the case.

Asymmetric cyanohydrin formation from aldehydes catalyzed by manganese Schiff base complexes

The catalyst generated in situ from Mn(OAc)2 and a chiral Schiff base ligand exhibited excellent catalytic abilities in asymmetric cyanohydrin formation from aldehydes with sodium cyanide in up to 99% enantioselectivity and good yield.

Enzymatic kinetic resolution of racemic cyanohydrins via enantioselective acylation

Enzymatic kinetic resolution of a series of aromatic and aliphatic cyanohydrins in organic media has been investigated. The behavior of potential lipases, molecular sieves, acyl reagent, reaction temperature, and organic solvents on the kinetic resolution was studied. The influence of substrate structure, steric, and electronic nature and position of the aryl substituent on the enantioselectivity was discussed. Under the optimized reaction conditions, good enantioselectivity could be achieved for most of the investigated compounds. Specifically, substrates 1a, 1c, 1d, 1f, 1u could be resolved with the kinetic enantiomer ratio (E) higher than 200.