2-(Chloromethyl)-5-nitrofuran

Base Information

• Chemical Name: 2-(Chloromethyl)-5-nitrofuran
• CAS No.: 4098-31-1
• Molecular Formula: C5H4 Cl N O3
• Molecular Weight: 161.54
• Hs Code.: 2932190090
• European Community (EC) Number: 809-457-8
• NSC Number: 74621
• DSSTox Substance ID: DTXSID70291266
• Wikidata: Q82029160
• Mol file: 4098-31-1.mol

Synonyms:2-(chloromethyl)-5-nitrofuran;4098-31-1;NSC74621;2-chloromethyl-5-nitrofuran;SCHEMBL6729712;DTXSID70291266;NSC 74621;NSC-74621;AKOS006221695

Chemical Property of 2-(Chloromethyl)-5-nitrofuran

Chemical Property:

• Vapor Pressure: 0.015mmHg at 25°C
• Boiling Point: 265.5°C at 760 mmHg
• Flash Point: 114.4°C
• PSA: 58.96000
• Density: 1.445g/cm³
• LogP: 2.44980
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 160.9879707
• Heavy Atom Count: 10
• Complexity: 135

Purity/Quality:

99% ^*data from raw suppliers

2-(chloromethyl)-5-nitrofuran 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(OC(=C1)[N+](=O)[O-])CCl

Technology Process of 2-(Chloromethyl)-5-nitrofuran

There total 6 articles about 2-(Chloromethyl)-5-nitrofuran 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: 71.0%

(5-nitrofuran-2-yl)methanol (2493-04-1) → 2-(chloromethyl)-5-nitrofuran (4098-31-1)

Guidance literature:

With thionyl chloride; at 20 ℃;

Reference yield:

5-nitrofurane-2-carboxaldehyde (698-63-5) → 2-(chloromethyl)-5-nitrofuran (4098-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Al(O-i-Pr)3 / propan-2-ol / 4 h / Heating

2: 16 percent / SOCl₂, pyridine / CHCl₃ / 3 h / -10 °C

With pyridine; thionyl chloride; aluminum isopropoxide; In chloroform; isopropyl alcohol;

DOI:10.1039/a607202j

Reference yield:

furfural (98-01-1) → 2-(chloromethyl)-5-nitrofuran (4098-31-1)

Guidance literature:

Multi-step reaction with 3 steps

1: nitric acid; acetic anhydride / 2 h / -30 °C

2: water; sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C

3: thionyl chloride / 20 °C

With sodium tetrahydroborate; thionyl chloride; water; nitric acid; acetic anhydride; In tetrahydrofuran;

upstream raw materials:

2-Chloromethylfuran

(5-nitrofuran-2-yl)methanol

5-nitrofurane-2-carboxaldehyde

furfural

Downstream raw materials:

C₂₁H₂₂FN₇O₅

Refernces

• 1、 Berry, Jane M.,Watson, Corrine Y.,Whish, William J. D.,Threadgill, Michael D.. "5-Nitrofuran-2-ylmethyl group as a potential bioreductively activated pro-drug system". . p. 1147 - 1156. Retrieved 2007/10/03.