3-Hydroxypropionitrile

Base Information

• Chemical Name: 3-Hydroxypropionitrile
• CAS No.: 109-78-4
• Molecular Formula: C3H5NO
• Molecular Weight: 71.0788
• Hs Code.: 29269095
• European Community (EC) Number: 203-704-8
• ICSC Number: 1026
• NSC Number: 2598
• UN Number: 2810
• UNII: 7V8108WN46
• DSSTox Substance ID: DTXSID1025433
• Nikkaji Number: J5.090C
• Wikidata: Q904204
• Mol file: 109-78-4.mol

Synonyms:2-cyanoethanol;hydracrylonitrile

Chemical Property of 3-Hydroxypropionitrile

Chemical Property:

• Appearance/Colour: Colourless or straw-coloured liquid
• Vapor Pressure: 0.0132mmHg at 25°C
• Melting Point: -46 °C
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 229.6 °C at 760 mmHg
• Flash Point: 92.7 °C
• PSA: 44.02000
• Density: 1.04 g/cm³
• LogP: -0.10762
• Water Solubility.: >=10 g/100 mL at 20℃
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 71.037113783
• Heavy Atom Count: 5
• Complexity: 51.2
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(CO)C#N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin.

Technology Process of 3-Hydroxypropionitrile

There total 37 articles about 3-Hydroxypropionitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

acrylonitrile (107-13-1,25014-41-9) → 3,3'-thiobis-propanenitrile (111-97-7) + 3-Hydroxypropionitrile (109-78-4)

Guidance literature:

With sodium sulfide; benzyltri(n-butyl)ammonium chloride; In water; for 0.166667h;

Reference yield: 97.3%

oxirane (75-21-8,99932-75-9) + hydrogen cyanide (74-90-8) → 3-Hydroxypropionitrile (109-78-4)

Guidance literature:

With aluminum oxide; boron trifluoride diethyl etherate; In propylene glycol; at -10 - 10 ℃; for 28h; Reagent/catalyst; Temperature;

Reference yield: 92.0%

acrylonitrile (107-13-1,25014-41-9) → 3-Hydroxypropionitrile (109-78-4)

Guidance literature:

With sodium hydroxide; at 50 ℃; for 0.2h;

upstream raw materials:

oxirane

hydrogen cyanide

acrylonitrile

sodium cyanide

Downstream raw materials:

3-Methoxypropionitrile

3-(piperidin-1-yl)propionitrile

3-Morpholin-4-yl-propionitrile

3-indol-1-yl-propionic acid

Refernces

Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides

10.1021/ol0521432

The research focuses on the selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides using solid-phase synthesis. The purpose of this study was to develop a method for the selective synthesis of these compounds, which are challenging to produce due to the lack of regioselectivity in traditional solution-phase methods. The researchers used aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol, which were subjected to reactions with diphosphitylating and triphosphitylating reagents to yield polymer-bound reagents. These were then reacted with unprotected carbohydrates and nucleosides to produce monosubstituted nucleoside and carbohydrate diphosphates, dithiodiphosphates, triphosphates, and trithiotriphosphates with high regioselectivity. The conclusions of the research highlight the advantages of the solid-phase approach, including the production of monosubstituted derivatives, high selectivity, facile isolation and purification of products, and the trapping of byproducts on resins. The chemicals used in the process included phosphorus trichloride, 3-hydroxypropionitrile, diisopropylamine, water, and 1H-tetrazole, among others, to synthesize the diphosphitylating and triphosphitylating reagents, as well as various unprotected nucleosides and carbohydrates for the reactions.

Facile synthesis of hydroxymethylcytosine-containing oligonucleotides and their reactivity upon osmium oxidation

10.1039/c1ob05247k

The research aims to develop a facile synthesis method for hydroxymethylcytosine (hmC)-containing oligonucleotides (ODNs) and investigate their reactivity upon osmium oxidation. The study synthesizes hmC-containing ODNs using a straightforward route starting from thymidine and involving protection, bromination, and amination steps, ultimately converting the nucleoside into phosphoramidite form for DNA autosynthesizer use. The synthesized ODNs form stable duplexes with complementary DNA, exhibiting similar melting temperatures and enzymatic digestion properties to methylated counterparts. Osmium oxidation, a method previously used for detecting 5-methylcytosine (mC), is tested on hmC-containing ODNs under specific reaction conditions, revealing that hmC is oxidized as efficiently as mC, forming a stable ternary complex. The study concludes that osmium oxidation is a viable method for detecting hmC in DNA, potentially advancing epigenetic studies. Key chemicals used include thymidine, acetic anhydride, N-bromosuccinimide, 3-hydroxypropionitrile, phosphorus oxychloride, ammonia, di(n-butyl)formamidine, potassium osmate, potassium hexacyanoferrate(III), and bipyridine.