4368-06-3

Basic information

• Product Name: 3-HYDROXYBUTYRONITRILE
• Synonyms: 3-HYDROXYBUTYRONITRILE;3-HYDROXYBUTYRONITRILE 95%;3-Hydroxybutanenitrile;3-Hydroxybutyronitrile,95%;3-Hydroxybutyronitrile, 1-Cyanopropan-2-ol
• CAS NO: 4368-06-3
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.1
• EINECS: 224-457-2
• Product Categories: C1 to C5;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C1 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4368-06-3.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 214 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear slightly yellow to amber liquid
• Density: 0.976 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0286mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• PKA: 13.89±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXYBUTYRONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYBUTYRONITRILE(4368-06-3)
• EPA Substance Registry System: 3-HYDROXYBUTYRONITRILE(4368-06-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4368-06-3(Hazardous Substances Data)

Usage

Description

3-Hydroxybutyronitrile, also known as β-Hydroxybutyronitrile, is a β-hydroxynitrile derivative that is characterized by its clear slightly yellow to amber liquid appearance. It undergoes thermolysis in the gas-phase through the formation of a six-membered cyclic transition state.

Uses

Used in Pharmaceutical Industry:
3-Hydroxybutyronitrile is used as an intermediate for the preparation of 2-Methylazetidine, which is a derivative of Azetidine (A813000). Azetidine serves as a useful building block in the synthesis of polypeptides and other nitrogen-containing compounds with potential biological properties, making it valuable in the development of new pharmaceuticals and therapeutic agents.
Used in Chemical Synthesis:
As a β-hydroxynitrile derivative, 3-Hydroxybutyronitrile can be utilized in various chemical synthesis processes, particularly in the creation of nitrogen-containing compounds. Its unique chemical properties allow it to be a versatile building block in the development of novel chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

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

Upstream product

• 19686-73-8 1-bromo-2-propanol 
• 151-50-8 potassium cyanide 
• 113429-86-0 (R)-1-bromo-2-propanol 
• 996-21-4 1-iodopropan-2-ol 
• 127-00-4 1-Chloro-2-propanol 
• 74-90-8 hydrogen cyanide 
• 75-56-9 methyloxirane 
• 156-62-7 calcium cyanamide 
• 143-33-9 sodium cyanide 
• 93554-80-4 2-aminobutyronitrile hydrochloride 
• 7677-24-9 trimethylsilyl cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 78-89-7 2-chloro-1-propanol 
• 141-78-6 ethyl acetate 

Downstream Products

• 5405-41-4 ethyl 3-hydroxybutyrate 
• 53778-71-5 3-chlorobutyronitrile 
• 4786-20-3 but-2-enenitrile 
• 1190-76-7 (Z)-2-butenenitrile 
• 4786-20-3 crotononitrile 
• 6168-83-8 (S)-3-Hydroxybutanoic Acid 
• 625-72-9 (R)-3-hydroxybutyric acid 
• 109-75-1 but-3-enenitrile 
• 300-85-6 3-Hydroxybutyric acid 
• 114963-62-1 4-amino-butan-2-ol 
• 75-07-0 acetaldehyde 
• 75-05-8 acetonitrile 
• 40482-53-9 β-Hydroxybutyramide 
• 123689-95-2 3-hydroxybutyronitrile 

Relevant articles and documents

AMIDITE COMPOUND AND METHOD FOR PRODUCING POLYNUCLEOTIDE USING SAID COMPOUND

The present invention provides an amidite compound represented by formula (1) which enables a synthesis of RNA with high purity, and the method for preparing a polynucleotide by using the same compound. (In the formula (1), wherein R represents the following formula (wherein Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, with the proviso that Ra and Rb does not represent a hydrogen atom, n is an integer of 1 to 5), and Ba represents a group containing optionally protected nucleobase structure, and G1 and G2 are identical to or different from each other and each represents a protecting group for a hydroxy group, and G3 are identical to or different from each other and each represents an alkyl group.

Ruthenium-catalyzed formation of pyrazoles or 3-hydroxynitriles from propargyl alcohols and hydrazines

Functionalized pyrazoles are generated from secondary propragyl alcohols and hydrazines in a ruthenium-catalyzed cascade process, consisting of redox isomerization, Michael addition, cyclocondensation and dehydrogenation steps. The same bifunctional catalyst mediates the conversion of tertiary propargyl alcohols with hydrazine to 3-hydroxynitriles via anti-Markovnikov hydroamination followed by elimination of ammonia.

Oxa-Michael Addition to α,β-Unsaturated Nitriles: An Expedient Route to γ-Amino Alcohols and Derivatives

Water addition to α,β-unsaturated nitriles would give facile access to the β-hydroxy-nitriles, which in turn can be hydrogenated to the γ-amino alcohols. We have previously shown that alcohols readily add in 1,4-fashion to these substrates using Milstein's Ru(PNN) pincer complex as catalyst. However, attempted water addition to α,β-unsaturated nitriles gave the 3-hydroxynitriles in mediocre yields. On the other hand, addition of benzyl alcohol proceeded in excellent yields for a variety of β-substituted unsaturated nitriles. Subsequent treatment of the benzyl alcohol addition products with TMSCl/FeCl3 resulted in the formation of 3-hydroxy-alkylnitriles. The 3-benzyloxy-alkylnitriles obtained from oxa-Michael addition also could be hydrogenated directly in the presence of acid to give the amino alcohols as their HCl salts in excellent yields. Hydrogenation under neutral conditions gave a mixture of the secondary and tertiary amines. Hydrogenation in the presence of base and Boc-anhydride gave the orthogonally bis-protected amino alcohols, in which the benzyl ether can subsequently be cleaved to yield Boc-protected amino alcohols. Thus, a variety of molecular scaffolds with a 1,3-relationship between O- and N-functional group is accessible starting from oxa-Michael addition of benzyl alcohol to α,β-unsaturated nitriles.