125103-95-9

Basic information

• Product Name: (R)-(-)-3-HYDROXYBUTYRONITRILE
• Synonyms: (R)-(-)-3-HYDROXYBUTYRONITRILE;(3R)-3-Hydroxybutanenitrile;(R)-3-Hydroxybutanenitrile
• CAS NO: 125103-95-9
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.1
• Mol File: 125103-95-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 217℃
• Flash Point: 85℃
• Appearance: /
• Density: 0.991
• Vapor Pressure: 0.0286mmHg at 25°C
• Refractive Index: 1.425
• Solubility: DCM, Ethyl Acetate
• PKA: 13.89±0.20(Predicted)
• CAS DataBase Reference: (R)-(-)-3-HYDROXYBUTYRONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-3-HYDROXYBUTYRONITRILE(125103-95-9)
• EPA Substance Registry System: (R)-(-)-3-HYDROXYBUTYRONITRILE(125103-95-9)

Safety Data

• Hazardous Substances Data: 125103-95-9(Hazardous Substances Data)

Usage

Uses

(3R)-3-Hydroxybutanenitrile can be naturally extracted from Aspergillus sp. KJ-9 which is a fungal endophyte. (3R)-3-Hydroxybutanenitrile is found to be active against phytopathogenic fungi.

InChI:InChI=1/C4H7NO/c1-4(6)2-3-5/h4,6H,2H2,1H3/t4-/m1/s1

Upstream product

• 54529-88-3 3-acetoxy-butyronitrile 
• 132155-82-9 (+/-)-3-(phenoxyacetoxy)butyronitrile 
• 4368-06-3 3-hydroxybutanenitrile 
• 125136-88-1 (S)-3-(methylthioacetoxy)butyronitrile 
• 125103-89-1 (+/-)-3-<(methylthio)acetoxy>butyronitrile 
• 125103-90-4 (+/-)-3-<(butylthio)acetoxy>butyronitrile 
• 132155-81-8 (+/-)-3-(methoxyacetoxy)butyronitrile 

Relevant articles and documents

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomehtyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.

Enhanced reaction rate and enantioselectivity in lipase-catalyzed hydrolysis by addition of a crown ether

Both reaction rate and enantioselectivity in a lipase-catalyzed hydrolysis of β-acetoxybutyronitrile were significantly enhanced by addition of hydroxymethyl-12-crown-4.