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

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

Uses

Used in Pharmaceutical Industry:
(S)-3,4-Dihydroxybutyronitrile is used as an intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex molecular structures.
Used in Organic Material Synthesis:
(S)-3,4-Dihydroxybutyronitrile is used as a building block in the creation of organic materials, leveraging its nitrile and hydroxyl groups for chemical reactions and bonding.

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 
• 143-33-9 sodium cyanide 
• 556-52-5 oxiranyl-methanol 
• 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 
• 105-33-9 4-chloro-3-hydroxybutyronitrile 
• 74923-97-0 (R)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 
• 57090-45-6 (2R)-3-chloro-1,2-propanediol 
• 129097-92-3 3-bromo-5-(hydroxymethyl)-Δ²-isoxazoline 
• 74889-59-1 (DL)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 

Downstream Products

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

Relevant articles and documents

Production of (S)-4-chloro-3-hydroxybutyronitrile using microbial resolution

A new production procedure of (S)-4-chloro-3-hydroxybutyronitrile was developed using microbial resolution. The resting cells of Pseudomonas sp. OS-K-29 preferentially converted (R)-4-chloro-3-hydroxybutyronitrile to the corresponding 1,2-diol by the dehalogenating activity so that (S)-4-chloro-3-hydroxybutyronitrile (94.5%ee) was obtained from the racemate in 40% yield at the microbial resolution step.

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-catalyzed enantiomer separation of 3-hydroxy-4-(tosyloxy) butanenitrile: Synthesis of (R)-GABOB (=(3R)-4-amino-3-hydroxybutanoic acid) and (R)-carnitine hydrochloride (= (2R)-3-carboxy-2-hydroxy-N,N,N-trimethylpropan- 1-aminium chloride)

Enzymatic resolution of racemic 3-hydroxy-4-(tosyloxy)butanenitrile ((±)-5) by using various lipases in different solvents were studied. The obtained optically pure (3R)-3-(acetyloxy)-4-(tosyloxy)-butanenitrile ((R)-6), upon treatment with aqueous ammonia followed by cone. HCl solution, provided (R)-GABOB (=(3R)-4-amino-3-hydroxybutanoic acid; (R)-1). Similarly, reaction of (R)-6 with aqueous trimethylamine solution followed by cone. HCl solution provided (R)-carnitine hydrochloride (=(2R)-3-carboxy-2-hydroxy-N,N,N- trimethylpropan-1-aminium chloride; (R)-2·HCl) in an expeditious manner.

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

New chemoenzymatic pathway for β-adrenergic blocking agents

The lipase mediated kinetic resolution of pharmaceutically important β-hydroxy nitriles is described in high enantiomeric excesses and good yields. Some of the chiral β-hydroxy nitriles have been employed in the synthesis of β-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-hydroxy-4-tosyloxybutanenitrile, chiral intermediates of high synthetic value.

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.

A new method for the preparation of β-hydroxy nitriles; Transformation of 3-bromo-2-isoxazolines to β-hydroxy nitriles by treatment of alkanethiolates

3-Bromo-2-isoxazolines are transformed to β-hydroxy nitriles in good yields by treatment with alkanethiolates under a very mild condition.

Method for preparing optically active 3,4-dihydroxy butyric acid derivatives

The present invention presents a method for preparation of S-3,4-dihydroxy butyronitrile expressed by the structural formula (II) STR1 characterized by causing R-3-chloro-1,2-propanediol expressed by the structural formula (I) STR2 to react with a cyanating agent. According to this invention, optically active 3,4-dihydroxy butyronitrile and 3,4-dihydroxy butyric acid derivatives may be manufactured economically and efficiently.

Total Synthesis of (R)-Glycerol Acetonide and the Antiepileptic and Hypotensive Drug (-)-γ-Amino-β-hydroxybutyric Acid (GABOB): Use of Vitamin C as a Chiral Starting Material

Ascorbic acid (Vitamin C) (9) is shown to be a useful, inexpensive chiral starting material for natural products synthesis.It is converted in high yield via two synthetic operations into (R)-glycerol acetonide (7), the more inaccessible enantiomer of glycerol acetonide.Since D-(R)-glyceraldehyde acetonide (4) and the corresponding alcohol 1 have been used in many total syntheses of a wide variety of compounds, the ready availability of the opposite enantiomers L-(S)-glyceraldehyde acetonide (6) and glycerol (7) should be of greate value.As one indication of this potential synthetic utility, the hypotensive, antiepileptic compound (R)-(-)-γ-amino-β-hydroxybutyric acid (GABOB) (8) has been synthesized from ascorbic acid (9) via nine steps in 10percent overall yield.As further evidence of the importance of these synthesis, several useful intermediates for the preparation of the highly active hypotensive agents, the aryloxypropanolamines (5), were prepared from Vitamin C.