Dinoseb

Base Information

• Chemical Name: Dinoseb
• CAS No.: 88-85-7
• Deprecated CAS: 152212-20-9,39403-80-0,39403-80-0
• Molecular Formula: C10H12 N2 O5
• Molecular Weight: 240.216
• Hs Code.: 2908910000
• European Community (EC) Number: 201-861-7
• ICSC Number: 0149
• NSC Number: 202753
• UN Number: 2779,2902
• UNII: YD44ZEM22M
• DSSTox Substance ID: DTXSID3020207
• Nikkaji Number: J3.909H
• Wikipedia: Dinoseb
• Wikidata: Q415111
• Metabolomics Workbench ID: 45604
• ChEMBL ID: CHEMBL1892987
• Mol file: 88-85-7.mol

Synonyms:2,4-dinitro-6-sec-butylphenol;2-sec-butyl-4,6-dinitrophenol;dinitrobutylphenol;dinoseb;dinoseb ammonium salt;dinoseb ethanolamine salt;dinoseb sodium salt;dinoseb triethanolamine salt;DNBP

Chemical Property of Dinoseb

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 0.000198mmHg at 25°C
• Melting Point: 55.5 ºC
• Refractive Index: 1.6620 (estimate)
• Boiling Point: 318.1oC at 760 mmHg
• PKA: 4.62(at 25℃)
• Flash Point: >100°C
• PSA: 111.87000
• Density: 1.29
• LogP: 3.76850
• Storage Temp.: 2-8°C
• Water Solubility.: 0.0052 g/100 mL
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 240.07462149
• Heavy Atom Count: 17
• Complexity: 298
• Transport DOT Label: Poison

Purity/Quality:

97% ^*data from raw suppliers

Dinoseb ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T;N,N,T,Xn
• Statements: 24/25-44-50/53-61-62-36-63-43-36/37/38-23/24/25-45-67-40-41-38
• Safety Statements: 45-53-60-61-36/37-24/25-23-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Nitroaromatic
• Canonical SMILES: CCC(C)C1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])O
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the central nervous system. Exposure at high levels could cause death.
• Effects of Long Term Exposure: The substance may have effects on the hematopoetic system. May cause reproductive toxicity in humans.
• Description: Dinoseb, also known as dinitrophenol, can adversely affect the energy generating reaction in a cell. No cell will live very long under the influence of high concentrations of dinitrophenol. It makes the body burn enough energy to result in weight loss. During the 1930s, physicians unwittingly prescribed certain types of dinitrophenol as diet pills. Dow Chemical changed the basic structure of dinitrophenol slightly to produce dinoseb, which was marketed in 1948. Dinoseb was widely used as a contact herbicide against broadleaf weeds. Dinoseb causes toxicity the same way in plants, animals, and fungi because all cells contain very similar biochemical pathways for creating energy from the breakdown of sugars. Furthermore, photosynthesis in plants relies on an energy transfer system that is also inhibited by dinitrophenol. Given the high toxicity, EPA concluded that the doses causing the birth defects and the endocrine-disrupting effects were close to worker exposure levels. Thus, under an emergency order issued in 1986, EPA suspended dinoseb’s registration. In August 1990, the EPA banned the burying of dinoseb-contaminated soils in EPA-approved landfills, making incineration the only EPA-approved disposal method for dinoseb-contaminated soil. Incineration is expensive and incomplete, leaving a noncombustible residue as a further hazardous waste and some combustion products that could remain toxic. Therefore, an ex situ soil bioremediation process was developed by the Sabre Processing company. This process is known as the SABRE process; it uses an anaerobic consortium and supplemental carbon source at the field scale to successfully remediate contaminated soils.
• Uses: The amine, ammonium salt or acetate ester is used as a contact herbicide for postemergence weed control in cereals, cotton, peas, beans, potatoes, pumpkins, soybeans and strawberries. Dinoseb is used as an herbicide andinsecticide. Dinoseb is used as an herbicide, corn yield enhancer, insecticide, and miticide. It is used as a herbicide in soybeans, a variety of vegetables, fruits, nuts, citrus trees, and with other field crops for control of grasses and broadleaf weeds. It is used as an insecticide in grapes.

Technology Process of Dinoseb

There total 7 articles about Dinoseb 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: 92.9%

2-sec-butylphenol (89-72-5) → dinoseb (88-85-7)

Guidance literature:

With nitric acid; at 40 ℃; for 7h; under 4560.31 Torr; Temperature; Autoclave; Inert atmosphere;

Reference yield:

2-sec-butylphenol (89-72-5) → 2-hydroxy-3-sec-butyl-5-nitrobenzenesulfonic acid + 4-hydroxy-5-sec-butyl-3-nitrobenzenesulfonic acid + dinoseb (88-85-7)

Guidance literature:

2-sec-butylphenol; With sulfuric acid; at 84 ℃;

With nitric acid; In water; Product distribution / selectivity;

Reference yield:

→ dinoseb (88-85-7)

Guidance literature:

Phenol, Buten 1.) (2-sec.-Butylphenol), HNO3 / H2SO4;

upstream raw materials:

2-sec-butylphenol

(-)-(R)-2-sec-butylphenol

(+)-(S)-2-sec-butylphenol

Downstream raw materials:

1-((S)-sec-butyl)-2-chloro-3,5-dinitro-benzene

(+/-)-1-sec-butyl-2-chloro-3,5-dinitro-benzene

2-Butoxy-1-sec-butyl-3,5-dinitro-benzene

1-sec-Butyl-2-(4-chloro-benzyloxy)-3,5-dinitro-benzene

Refernces

• 1、 -. "SULFONATED NITROPHENOLS AS POLYMERIZATION INHIBITORS". Page/Page column 22-24. . Retrieved 2008/06/13.
• 2、 -. "Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide". . . Retrieved 2008/06/13.