7202-43-9

Basic information

• Product Name: (R)-(-)-Tetrahydrofurfurylamine
• Synonyms: (R)-(-)-TETRAHYDROFURFURYLAMINE;(R)-TETRAHYDROFURFURYLAMINE;(R)-2-(AMINOMETHYL)TETRAHYDROFURAN;(R)-(-)-2-(AMINOMETHYL)TETRAHYDROFURANE;RARECHEM AL BW 2434;(R)-(tetrahydrofuran-2-yl)methanamine;(R)-2-TETRAHYDROFURFURYLAMINE;-(-)-TCTRAHYDROFURFURYLAMINC
• CAS NO: 7202-43-9
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.15
• Product Categories: Amines;Chiral Compounds;chiral;Furans;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry
• Mol File: 7202-43-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 55 °C18 mm Hg(lit.)
• Flash Point: 114 °F
• Appearance: Clear colorless/Liquid
• Density: 0.98 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.95mmHg at 25°C
• Refractive Index: n20/D 1.455(lit.)
• Storage Temp.: Flammables area
• PKA: 9.47±0.29(Predicted)
• Water Solubility: miscible
• Sensitive: Hygroscopic
• BRN: 4652873
• CAS DataBase Reference: (R)-(-)-Tetrahydrofurfurylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-Tetrahydrofurfurylamine(7202-43-9)
• EPA Substance Registry System: (R)-(-)-Tetrahydrofurfurylamine(7202-43-9)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39-37/39
• RIDADR: UN 2943 3/PG 3
• WGK Germany: 3
• F: 10-34
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 7202-43-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

(R)-(-)-Tetrahydrofurfurylamine is used in the synthesis of novel topoisomerase I targeting anti-cancer agents with mild to potent cytotoxic activity. Also used in the discovery and synthesis of orally bioavailable stearoyl-CoA desaturase 1 inhibitors.

InChI:InChI=1/C5H11NO/c6-4-5-2-1-3-7-5/h5H,1-4,6H2/t5-/m1/s1

Upstream product

• 98-01-1 furfural 
• 4795-29-3 TETRAHYDROFURFURYLAMINE 

Downstream Products

• 767291-74-7 (R)-(+)-N,N-dimethyltetrahydrofurfurylamine 
• 874888-92-3 (S)-(4-nitro-benzyl)-(tetrahydro-furan-2-ylmethyl)-amine 

Relevant articles and documents

Preparation method of chiral 2 - aminomethyltetrahydrofuran (by machine translation)

The invention provides a preparation method of chiral 2 -aminomethyl tetrahydrofuran, which comprises the following steps: (1) reaction of chiral epichlorohydrin with 2 - chloroethyl magnesium bromide to generate chiral 1-chloro 5 -pentanol; (-2 -) chiral 2-benzamido 1-chloro 5 - pentanol to react under the action of a palladium catalyst to generate chiral -2 -benzamidomethyl tetrahydrofurane in the presence of a basic substance to form chiral 5 - 1 - dichloro -5 -1-pentanol and a 4 chiral 2 -2 - 1 -dichloro 3 pentanol in -2 - the presence of a basic substance to form -5 - an intramolecular ring-closing reaction in the presence of a 2 - basic substance to 2 - 2 - form chirality of 5 - chloro-5 -1 and 2 -methylene tetrahydrofurfuryl alcohol in the presence of a basic substance. The synthetic method is short in route, low in production cost, less in three wastes and suitable for industrial production. (by machine translation)

Preparative separation of tetrahydrofurfurylamine enantiomers

Tetrahydrofurfurylamine enantiomers were separated on a preparative scale by fractional crystallization of diastereoisomeric salts with natural L-tartaric acid. (R)-Tetrahydrofurfurylamine was isolated in 68% yield with an optical purity of more than 98.5% according to the HPLC data.

Resolution of certain asymmetric primary amines using lasalocid

Racemic modifications of optically active primary or tertiary amines are treated with lasalocid to form diastereomeric salts. The so-formed diastereomeric salts are separated and, subsequently, can be chemically decomposed to give the desired enantiomers of the amine. The resolving agent, lasalocid, is recovered in this process by precipitation or evaporation from organic solvents.