3-Hydroxypentanenitrile

Base Information

• Chemical Name: 3-Hydroxypentanenitrile
• CAS No.: 13635-05-7
• Molecular Formula: C5H9NO
• Molecular Weight: 99.1326
• DSSTox Substance ID: DTXSID20431791
• Nikkaji Number: J1.927.619H
• Mol file: 13635-05-7.mol

Synonyms:3-hydroxypentanenitrile;13635-05-7;3-hydroxyvaleronitrile;3-hydroxy-valeronitrile;DTXSID20431791;FXHRDEQPODSZQL-UHFFFAOYSA-N;AKOS009391057;CS-0258400;EN300-70004;F83351

Chemical Property of 3-Hydroxypentanenitrile

Chemical Property:

• PSA: 44.02000
• LogP: 0.67098
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 99.068413911
• Heavy Atom Count: 7
• Complexity: 81.3

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxypentanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC#N)O

Technology Process of 3-Hydroxypentanenitrile

There total 1 articles about 3-Hydroxypentanenitrile 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:

1-chloro-2-hydroxy-3-butene (671-56-7) + sodium cyanide (143-33-9,25596-52-5) → 3-hydroxyvaleronitrile (13635-05-7)

Guidance literature:

With water; at 50 - 60 ℃; Hydrieren des Reaktionsprodukts an Palladiumschwarz in Dioxan bei 25grad;

Reference yield: 77.0%

3-hydroxyvaleronitrile (13635-05-7) → 5-ethyl-1,2-oxazol-3-amine (19754-80-4)

Guidance literature:

3-hydroxyvaleronitrile; With hydroxylamine hydrochloride; ammonia; In water; at 20 - 70 ℃; for 5h;

With manganese(IV) oxide; boron trifluoride diethyl etherate; In toluene; for 3h; Reagent/catalyst; Temperature; Reflux;

Reference yield:

3-hydroxyvaleronitrile (13635-05-7) → (R)-octan-3-ol (589-98-0,20296-29-1,22658-92-0,70492-66-9)

Guidance literature:

Multi-step reaction with 6 steps

1: CH₂Cl₂; pyridine / 3 h / Ambient temperature

2: 49 percent / 1,4,8,11-tetrathiacyclotetradecane, lipase PS / acetone; H₂O / 8 h / 35 °C

3: 97 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

4: 315 mg / DIBAL / CH₂Cl₂; toluene / 4 h / -78 °C

5: n-BuLi / diethyl ether / 4 h / Ambient temperature

6: 88 percent / H₂ / PtO₂ / ethanol / 48 h / 760 Torr / Ambient temperature

With 1H-imidazole; 1,4,8,11-tetrathiacyclotetradecane; n-butyllithium; Lipase PS; hydrogen; diisobutylaluminium hydride; platinum(IV) oxide; In pyridine; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo971288m

upstream raw materials:

1-chloro-2-hydroxy-3-butene

sodium cyanide

Downstream raw materials:

3-hydroxyvaleric acid

(R)-3-hydroxypentanenitrile

(S)-3-hydroxypentanenitrile

(R)-1-(cyanomethyl)propyl acetate