Tetrahydrofurfurylamine

Base Information

• Chemical Name: Tetrahydrofurfurylamine
• CAS No.: 4795-29-3
• Deprecated CAS: 13346-01-5
• Molecular Formula: C5H11NO
• Molecular Weight: 101.148
• Hs Code.: 29321900
• European Community (EC) Number: 225-351-9
• NSC Number: 76037
• UN Number: 2943
• DSSTox Substance ID: DTXSID40863454
• Nikkaji Number: J1.830I
• Mol file: 4795-29-3.mol

Synonyms:Tetrahydrofurfurylamine;4795-29-3;2-Tetrahydrofurfurylamine;2-Furanmethanamine, tetrahydro-;(Tetrahydrofuran-2-yl)methanamine;2-Aminomethyltetrahydrofuran;Furfurylamine, tetrahydro-;2-(Aminomethyl)tetrahydrofuran;oxolan-2-ylmethanamine;Tetrahydro-2-furanmethanamine;USAF Q-2;NSC 76037;EINECS 225-351-9;UN2943;BRN 0102729;AI3-25429;(oxolan-2-yl)methanamine;Tetrahydro-2-furanylmethylamine;5-18-09-00488 (Beilstein Handbook Reference);1-(tetrahydrofuran-2-yl)methanamine;C-(tetrahydrofuran-2-yl)methylamine;MFCD00005373;C-(Tetrahydro-furan-2-yl)methylamine;C-(Tetrahydro-furan-2-yl)-methylamine;Tetrahydrofurfurylamine [UN2943] [Flammable liquid];MFCD00085303;MFCD00192476;tetrahydofurfurylamine;tetrahydro-furfurylamine;tetrahydrofurfuryl amine;tetrahydrofurfuryl-amine;rac-tetrahydrofurfurylamine;2-tetrahydrofuranmethanamine;2-tetrahydrofurylmethylamine;WLN: T5OTJ B1Z;(?)-Tetrahydrofurfurylamine;Oprea1_644974;SCHEMBL31558;tetrahydrofuran-2-methylamine;Tetrahydrofuran-2-methanamine;Tetrahydrofurfurylamine, 97%;(2S)-oxolan-2-ylmethanamine;tetrahydrofuran-2-ylmethanamine;tetrahydrofuran-2-ylmethylamine;2-Furanmetanamina, tetrahidro-;(tetrahydro-2-furanylmethyl)amine;(tetrahydrofuran-2-yl)methylamine;(tetrahydrofuran-2-ylmethyl)amine;DTXSID40863454;(.+/-.)-Tetrahydrofurfurylamine;NSC76037;STR02270;1-(tetrahydro-2-furanyl)methanamine;NA2943;NSC-76037;STL194280;1-(tetrahydrofuran-2-yl)methaneamine;C-(tetrahydrofuran-2-yl)-methylamine;AKOS000119103;AKOS016039383;AB00408;PB47481;UN 2943;(+/-)-(tetrahydro-2-furanylmethyl)amine;BP-10719;LS-70652;SY012534;SY012535;BB 0240764;FT-0601949;FT-0604482;FT-0605079;T1072;EN300-18062;S10918;A827404;J-502112;J-502330;J-502561;Tetrahydrofurfurylamine [UN2943] [Flammable liquid];F2190-0384;(tetrahydrofuran-2-yl)methanamine

Chemical Property of Tetrahydrofurfurylamine

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 2.95mmHg at 25°C
• Melting Point: 156 °C at 760 mmHg
• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 45.6 °C
• PKA: 9.47±0.29(Predicted)
• Flash Point: 114 °F
• PSA: 35.25000
• Density: 0.967 g/cm³
• LogP: 0.82440
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: Chloroform, Methanol
• Water Solubility.: miscible
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 101.084063974
• Heavy Atom Count: 7
• Complexity: 56
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.9% ^*data from raw suppliers

Tetrahydro-2-furanmethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(OC1)CN
• Uses: Chemical intermediate, fine-grain photographic development, vulcanization accelerator. Tetrahydro-2-furanmethanamine 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

Technology Process of Tetrahydrofurfurylamine

There total 50 articles about Tetrahydrofurfurylamine 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: 94.0%

(2-furyl)methyl alcohol (98-00-0,25212-86-6,93793-62-5) → TETRAHYDROFURFURYLAMINE (4795-29-3)

Guidance literature:

With ammonia; hydrogen; In tetrahydrofuran; at 180 ℃; for 48h; Autoclave;

DOI:10.1002/cctc.201900304

Reference yield: 91.0%

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + TETRAHYDROFURFURYLAMINE (4795-29-3)

Guidance literature:

With ammonia; hydrogen; In tetrahydrofuran; at 180 ℃; for 12h; Autoclave;

DOI:10.1002/cctc.201900304

Reference yield: 53.8%

furfural (98-01-1) → TETRAHYDROFURFURYLAMINE (4795-29-3) + furan-2-ylmethanamine (617-89-0)

Guidance literature:

With ammonia; hydrogen; In tetrahydrofuran; at 180 ℃; for 12h; Autoclave;

DOI:10.1002/cctc.201900304

upstream raw materials:

Tetrahydrofurfuryl chloride

Tetrahydrofurfuryl alcohol

furfural

furan-2-ylmethanamine

Downstream raw materials:

tetrahydrofurfuryl isothiocyanate

N-tetrahydrofurfuryl-N'-(toluene-4-sulfonyl)-urea

N-tetrahydrofurfuryl-acetamide

2-chloro-N-[(tetrahydrofuran-2-yl)methyl]acetamide

Refernces

Preparative separation of tetrahydrofurfurylamine enantiomers

10.1134/S1070428007120123

D. M. Musatov et al. detail a method for separating the enantiomers of tetrahydrofurfurylamine on a preparative scale using fractional crystallization of diastereoisomeric salts with natural L-tartaric acid. Tetrahydrofurfurylamine is a significant compound used in the synthesis of various medical agents, including diuretics, enzyme inhibitors, analgesics, neurotropic drugs, and anticarcinogenic agents. The study reports the isolation of (R)-tetrahydrofurfurylamine with a yield of 68% and an optical purity of over 98.5% as determined by HPLC. The separation process involved dissolving L-tartaric acid and racemic tetrahydrofurfurylamine in a mixture of water and acetone, followed by crystallization and recrystallization steps. The (R)-enantiomer was obtained with high purity, while the mother liquor yielded the (S)-enantiomer with 79% enantiomeric purity.

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