139406-83-0

Basic information

• Product Name: (S)-(+)-4-METHOXY-MANDELONITRILE
• Synonyms: (S)-(+)-4-METHOXY-MANDELONITRILE
• CAS NO: 139406-83-0
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 0
• Mol File: 139406-83-0.mol
• Article Data: 53

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-(+)-4-METHOXY-MANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-4-METHOXY-MANDELONITRILE(139406-83-0)
• EPA Substance Registry System: (S)-(+)-4-METHOXY-MANDELONITRILE(139406-83-0)

Safety Data

• Hazardous Substances Data: 139406-83-0(Hazardous Substances Data)

Usage

General Description

(S)-(+)-4-Methoxy-mandelonitrile is a chemical compound with the molecular formula C9H9NO2. It is an enantiomer of 4-Methoxy-mandelonitrile, which is commonly found in natural products such as almonds and apricot kernels. (S)-(+)-4-Methoxy-mandelonitrile is a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is also used in organic synthesis as a chiral building block for the preparation of biologically active compounds. The compound has a variety of industrial applications and is often used as an intermediate in the production of fine chemicals. Its unique chemical properties make it a valuable and versatile molecule in the field of organic chemistry.

Upstream product

• 104-93-8 p-methylanizole 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 33646-40-1 4-methoxymandelonitrile 
• 773837-37-9 sodium cyanide 
• 99843-19-3 acetoxy-(4-methoxy-phenyl)-acetonitrile 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 108-05-4 vinyl acetate 
• 177186-34-4 (S)-2-(4-methoxyphenyl)-2-(trimethylsiloxy)acetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 66985-48-6 2-(4-methoxyphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 74-90-8 hydrogen cyanide 
• 591-31-1 3-methoxy-benzaldehyde 
• 151-50-8 potassium cyanide 

Downstream Products

• 65-85-0 benzoic acid 
• 127489-34-3 (4R,5S)-5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide 
• 127489-32-1 (4R,5S)-5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 344256-01-5 5-(4-Methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile 
• 82082-57-3 2,3-Dihydroxy-3-(4-methoxy-phenyl)-propionitrile 
• 103-82-2 phenylacetic acid 
• 147384-01-8 (S)-(+)-2-acetoxy-2-(4-methoxyphenyl)acetonitrile 

Relevant articles and documents

Topology-Based Functionalization of Robust Chiral Zr-Based Metal-Organic Frameworks for Catalytic Enantioselective Hydrogenation

The design and development of robust and porous supported catalysts with high activity and selectivity is extremely significant but very challenging for eco-friendly synthesis of fine chemicals and pharmaceuticals. We report here the design and synthesis of highly stable chiral Zr(IV)-based MOFs with different topologies to support Ir complexes and demonstrate their network structures-dependent asymmetric catalytic performance. Guided by the modulated synthesis and isoreticular expansion strategy, five chiral Zr-MOFs with a flu or ith topology are constructed from enantiopure 1,1′-biphenol-derived tetracarboxylate linkers and Zr6, Zr9, or Zr12 clusters. The obtained MOFs all show high chemical stability in boiling water, strongly acidic, and weakly basic aqueous solutions. The two flu MOFs featuring the dihydroxyl groups of biphenol in open and large cages, after sequential postsynthetic modification with P(NMe2)3 and [Ir(COD)Cl]2, can be highly efficient and recyclable heterogeneous catalysts for hydrogenation of α-dehydroamino acid esters with up to 98% ee, whereas the three ith MOFs featuring the dihydroxyl groups in small cages cannot be installed with P(NMe2)3 to support the Ir complex. Incorporation of Ir-phosphorus catalysts into Zr-MOFs leads to great enhancement of their chemical stability, durability, and even stereoselectivity. This work therefore not only advances Zr-MOFs as stable supports for labile metal catalysts for heterogeneous asymmetric catalysis but also provides a new insight into how highly active chiral centers can result due to the framework topology.

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.