164472-78-0

Basic information

• Product Name: (S)-TETRAHYDROFURAN-2-CARBONITRILE
• Synonyms: (S)-TETRAHYDROFURAN-2-CARBONITRILE;(R)-Tetrahydrofuran-2-carbonitrilepurum;sumofenantiomersgc;(R)-TETRAHYDROFURAN-2-CARBONITRILE PURUM 98+% (SUM OF ENANTIOMERS GC);(R)-Tetrahydrofurfurylnitrile, (R)-Tetrahydrofuroic nitrile
• CAS NO: 164472-78-0
• Molecular Formula: C₅H₇NO
• Molecular Weight: 97.12
• Mol File: 164472-78-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 207.4 °C at 760 mmHg
• Flash Point: -17℃
• Appearance: /
• Density: 1.04 g/cm³
• Vapor Pressure: 0.226mmHg at 25°C
• Refractive Index: 1.445
• Storage Temp.: 2-8°C
• BRN: 7197285
• CAS DataBase Reference: (S)-TETRAHYDROFURAN-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-TETRAHYDROFURAN-2-CARBONITRILE(164472-78-0)
• EPA Substance Registry System: (S)-TETRAHYDROFURAN-2-CARBONITRILE(164472-78-0)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 3273 3/PG 2
• WGK Germany: 2
• Hazardous Substances Data: 164472-78-0(Hazardous Substances Data)

Usage

Description

(S)-TETRAHYDROFURAN-2-CARBONITRILE, also known as (S)-THF-2-CN, is a chemical compound characterized by the molecular formula C5H7NO. It is a colorless liquid with a slightly sweet odor and is recognized for its role as an intermediate in the production of pharmaceuticals and agrochemicals. Additionally, it serves as a building block in organic synthesis for the creation of various fine chemicals.

Uses

Used in Pharmaceutical Industry:
(S)-TETRAHYDROFURAN-2-CARBONITRILE is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-TETRAHYDROFURAN-2-CARBONITRILE is utilized as an intermediate in the production of agrochemicals, which are essential for enhancing crop protection and yield.
Used in Organic Synthesis:
(S)-TETRAHYDROFURAN-2-CARBONITRILE is employed as a building block in organic synthesis for the production of a wide range of fine chemicals, which have diverse applications across different industries.

InChI:InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h5H,1-3H2/t5-/m0/s1

Upstream product

• 1393708-93-4 (R)-4-bromo-1-cyanobutyl acetate 
• 38694-47-2 4-bromobutyraldehyde 
• 631-57-2 Acetyl cyanide 
• 539820-25-2 (R)-2-tetrahydrofuran amide 
• 98-59-9 p-toluenesulfonyl chloride 
• 164472-76-8 (R)-(+)-5-bromo-2-hydroxypentanenitrile 

Downstream Products

• 1134785-42-4 rac-bis-1,1'-(5,6,7,8-tetrahydro-3-phenylisoquinoline)-N,N'-dioxide 
• 1134188-79-6 bis-1,1'-(5,6,7,8-tetrahydro-3-phenyl-isoquinoline) 
• 1198363-94-8 3-[(R)-tetrahydrofuran-2-yl]-3'-phenyl-(5,5',6,6',7,7',8,8'-octahydro-1,1'-biisoquinoline) 

Relevant articles and documents

Enantioenriched ω-bromocyanohydrin derivatives. Improved selectivity by combination of two chiral catalysts

Highly enantioenriched (R)-4-bromo-1-cyanobutyl acetate and (R)-5-bromo-1-cyanopentyl acetate were prepared by acetylcyanation of 4-bromobutanal and 5-bromopentanal, respectively, catalyzed by (S,S)-[(4,6-bis(t-butyl)salen)Ti(μ-O)]2 and triethylamine followed by enzymatic hydrolysis of the minor enantiomer. A cyclic procedure employing the same two chiral catalysts provided inferior results due to a slowly reached steady state and, in reactions with the former substrate, to ring-closure of the free cyanohydrin formed as an intermediate in the reaction. Hydrolysis of the acylated cyanohydrins followed by AgClO4-promoted cyclization provided (R)-2-cyanotetrahydrofuran and (R)-2-cyanotetrahydropyran in essentially enantiopure form.

Method of preparing optically pure (R)- or (S)- tetrahydrofuranyl ketone

Disclosed is a method of preparing an optically pure (R)-or (S)-tetrahydrofuranyl ketone. By such a method, (R)-or (S)-2-tetrahydrofuran amide is converted to (R)- or (S)-2-tetrahydrofuran nitrile through dehydration in the presence of a dehydrating agent and an amine base. Then, thus prepared (R)- or (S)-2-tetrahydrofuran nitrile is nucelophilic addition-reacted with a nucleophile, followed by hydrolyzing, thereby produce (R)- or (S)-tetrahydrofuranyl ketone having high optical purity, while minimizing production of other by-products.