4-Nitrobut-1-ene

Base Information

• Chemical Name: 4-Nitrobut-1-ene
• CAS No.: 32349-29-4
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.105
• DSSTox Substance ID: DTXSID30447080
• Nikkaji Number: J1.301.109E
• Wikidata: Q82265862
• Mol file: 32349-29-4.mol

Synonyms:4-nitrobut-1-ene;32349-29-4;4-nitro-1-butene;1-Butene, 4-nitro-;SCHEMBL2608475;DTXSID30447080;MFCD22493386;AKOS022183287;AT37472;SY266513

Chemical Property of 4-Nitrobut-1-ene

Chemical Property:

• Boiling Point: 144 °C(Press: 670 Torr)
• PSA: 45.82000
• Density: 0.986±0.06 g/cm3(Predicted)
• LogP: 1.36240
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 101.047678466
• Heavy Atom Count: 7
• Complexity: 74.2

Purity/Quality:

4-Nitrobut-1-ene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC[N+](=O)[O-]

Technology Process of 4-Nitrobut-1-ene

There total 4 articles about 4-Nitrobut-1-ene 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: 84.0%

1-bromo-4-butene (5162-44-7) → 4-nitrobut-1-ene (32349-29-4)

Guidance literature:

With sodium nitrite; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2013.06.004

Reference yield: 72.0%

trans-2-[(triethylsilyl)methyl]-1-nitrocyclopropane → hexaethyl disiloxane (994-49-0) + 4-nitrobut-1-ene (32349-29-4)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 25 ℃; for 12h; Further Variations:; Reagents; Product distribution;

DOI:10.1016/S0040-4020(00)00008-9

Reference yield: 35.0%

bromonitromethane (563-70-2) + allyltributylstanane (24850-33-7) → 4-nitrobut-1-ene (32349-29-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); at 100 ℃; for 24h;

DOI:10.1246/bcsj.58.1069

upstream raw materials:

1-bromo-4-butene

bromonitromethane

allyltributylstanane

Downstream raw materials:

(3R,4S)-N,N-dimethyl-4-nitro-3-(p-tolyl)hept-6-enethioamide

(3R,4S)-3-(4-methoxyphenyl)-N,N-dimethyl-4-nitrohept-6-enethioamide

(3R,4S)-N,N-dibenzyl-3-(4-chlorophenyl)-4-nitrohept-6-enethioamide

(3R,4R)-N,N-dibenzyl-3-(4-chlorophenyl)-4-nitrohept-6-enethioamide

Refernces

Practical synthesis of sinigrin

10.1080/07328309608005429

The study presents a practical synthesis of sinigrin, a naturally occurring glucosinolate found in the Cruciferae plant family, suitable for preparation on a ten-gram scale. The key step involves the preparation of hydroxamoyl chloride, followed by condensation with 1-mercaptoglucose. The authors modified existing methods to improve yield, using an ethyl ether solution of HCl instead of gaseous HCl and avoiding water in subsequent steps to prevent contamination. The final product, sinigrin monohydrate, was obtained with an overall yield of 42%, and its spectral and analytical data matched those of natural sinigrin. The chemicals involved include 4-nitrobut-1-ene, sodium methoxide, ethyl ether, thiol (1-mercaptoglucose), sulfuric acid, pyridine, sulfur trioxide, potassium bicarbonate, methanolic ammonia, and activated charcoal, each playing specific roles in the synthesis, such as reagents for functional group transformations and catalysts for reactions.