58289-69-3

Basic information

• Product Name: 2-(4-bromophenyl)-2-hydroxyacetonitrile
• Synonyms: 2-(4-bromophenyl)-2-hydroxyacetonitrile
• CAS NO: 58289-69-3
• Molecular Weight: 212.046
• Mol File: 58289-69-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 78-79 °C
• Boiling Point: 360.6±27.0 °C(Predicted)
• Density: 1.630±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-(4-bromophenyl)-2-hydroxyacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromophenyl)-2-hydroxyacetonitrile(58289-69-3)
• EPA Substance Registry System: 2-(4-bromophenyl)-2-hydroxyacetonitrile(58289-69-3)

Safety Data

• Hazardous Substances Data: 58289-69-3(Hazardous Substances Data)

Usage

Appearance

White to pale yellow solid The compound appears as a solid with a white to pale yellow color.

Usage

Intermediate in pharmaceuticals and agrochemicals It is commonly used as an intermediate in the production of pharmaceuticals and agrochemicals, serving as a starting material for further chemical reactions.

Functional groups

Hydroxy group, nitrile group, and benzene ring The compound has a hydroxy group (-OH) and a nitrile group (-C≡N) attached to a benzene ring, which is the aromatic part of the molecule.

Bromine atom position

Para position The bromine atom is attached to the benzene ring in the para position, which means it is located opposite to the hydroxy and nitrile groups on the ring.

Synthesis potential

Potent intermediate for various organic compounds The compound is known to be a potent intermediate for the synthesis of various organic compounds, making it useful in the production of pharmaceuticals and other chemical products.

Hazard classification

Hazardous chemical 2-(4-bromophenyl)-2-hydroxyacetonitrile is classified as a hazardous chemical, indicating that it may pose risks to human health and the environment.

Handling and storage

Handle and store with care Due to its hazardous nature, the compound should be handled and stored with care, following appropriate safety procedures and regulations.

Upstream product

• 83575-55-7 2-(4-bromophenyl)-2-(trimethylsilyloxy)acetonitrile 
• 1122-91-4 4-bromo-benzaldehyde 
• 623-49-4 ethyl cyanoformate 
• 74-90-8 hydrogen cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 773837-37-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 150521-30-5 2-hydroxy-2-(4-bromophenyl)acetonitrile 
• 6940-50-7 4-bromo-DL-mandelic acid 
• 586-76-5 4-Bromobenzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 6048-21-1 4-bromobenzoyl cyanide 
• 840511-77-5 2-(4-bromophenyl)-2-((4-methoxyphenyl)amino)acetonitrile 
• 167024-66-0 2-amino-2-(4-bromophenyl)acetonitrile 
• 57699-28-2 methyl 4-bromophenylglyoxalate 
• 54318-86-4 methyl (2E)-2-(4-bromophenyl)-3-phenylprop-2-enoate 
• 127709-20-0 α-hydroxy-(p-bromophenyl)-acetic acid methyl ester 

Relevant articles and documents

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

Highly chemoselective and efficient Strecker reaction of aldehydes with TMSCN catalyzed by MgI2 etherate under solvent-free conditions

Strecker reaction of various substituted aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and α,β-unsaturated aldehydes with trimethylsilyl cyanide (TMSCN) was realized in the presence of 5 mol % of MgI2 etherate in a mild, efficient and highly chemoselective manner under solvent-free conditions.

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.