126577-60-4

Basic information

• Product Name: (S)-3,4-DIHYDROXYBUTYRONITRILE
• Synonyms: (S)-3,4-DIHYDROXYBUTYRONITRILE;(R)-3,4-DIHYDROXYBUTYRONITRILE 99+%
• CAS NO: 126577-60-4
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.1
• Mol File: 126577-60-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 357.4°Cat760mmHg
• Flash Point: 170°C
• Appearance: /
• Density: 1.213g/cm³
• Vapor Pressure: 1.52E-06mmHg at 25°C
• Refractive Index: 1.476
• PKA: 13.07±0.20(Predicted)
• CAS DataBase Reference: (S)-3,4-DIHYDROXYBUTYRONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,4-DIHYDROXYBUTYRONITRILE(126577-60-4)
• EPA Substance Registry System: (S)-3,4-DIHYDROXYBUTYRONITRILE(126577-60-4)

Safety Data

• Hazardous Substances Data: 126577-60-4(Hazardous Substances Data)

Usage

General Description

(S)-3,4-Dihydroxybutyronitrile, also known as L-Tartaric acid nitrile, is an organic compound that belongs to the class known as cyanohydrins. (S)-3,4-DIHYDROXYBUTYRONITRILE contains a nitrile group (a carbon-nitrogen triple bond) and two hydroxyl groups. Cyanohydrins are known to be intermediary in several organic syntheses, and are often used in creating pharmaceuticals and organic materials. The “S” in its name denotes the stereochemistry of the compound, suggesting it has a specific spatial arrangement of its atoms. The compound itself can be synthesized using L-tartaric acid as a starting material.

InChI:InChI=1/C4H7NO2/c5-2-1-4(7)3-6/h4,6-7H,1,3H2/t4-/m0/s1

Upstream product

• 151-50-8 potassium cyanide 
• 96-24-2 3-monochloro-1,2-propanediol 
• 74889-59-1 (DL)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 
• 143-33-9 sodium cyanide 
• 556-52-5 oxiranyl-methanol 
• 74923-97-0 (R)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 
• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 131724-43-1 [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetonitrile 
• 890050-56-3 (R)-3-Hydroxy-4-trityloxy-butyronitrile 
• 852805-30-2 (R)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 129097-92-3 3-bromo-5-(hydroxymethyl)-Δ²-isoxazoline 

Downstream Products

• 137618-52-1 4-(benzyloxy)-3-hydroxybutanenitrile 
• 137618-66-7 2-benzyloxy-3-cyano propanol 

Relevant articles and documents

Glycerol kinase: substrate specificity.

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A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA1) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA1 agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA1 receptor agonist described so far (Emax = 118%, EC50 = 0.24 μM, KD = 19.6 nM; inactive at autotaxin and LPA2-6 receptors). This compound induces characteristic LPA1-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB

Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified cera

Highly regioselective conversion of epoxides to β-hydroxy nitriles with cyanide exchange resin

A simple and regioselective method is described for the efficient conversion of epoxides to β-hydroxy nitriles using Amberlite IRA-400 supported cyanide. The reactions occur in the absence of catalyst and furnish the corresponding β-hydroxy nitriles in high yields.