Bromoxynil

Base Information

• Chemical Name: Bromoxynil
• CAS No.: 1689-84-5
• Molecular Formula: C7H3Br2NO
• Molecular Weight: 276.915
• Hs Code.: 2926909032
• European Community (EC) Number: 216-882-7
• UN Number: 2811,2588
• UNII: J46EK95K0P
• DSSTox Substance ID: DTXSID3022162
• Nikkaji Number: J7.557D
• Wikipedia: Bromoxynil
• Wikidata: Q408345
• Metabolomics Workbench ID: 50808
• ChEMBL ID: CHEMBL453905
• Mol file: 1689-84-5.mol

Synonyms:3,5-dibromo-4-hydroxybenzonitrile;bromoxynil;bromoxynil, potassium salt;bromoxynil, sodium salt

Chemical Property of Bromoxynil

Chemical Property:

• Appearance/Colour: Off-white to salmon crystalline powder
• Vapor Pressure: 0.00552mmHg at 25°C
• Melting Point: 189-191 °C(lit.)
• Refractive Index: 1.71
• Boiling Point: 265.6 °C at 760 mmHg
• PKA: 4.06(at 25℃)
• Flash Point: 114.4 °C
• PSA: 44.02000
• Density: 2.24 g/cm³
• LogP: 2.78888
• Storage Temp.: 0-6°C
• Water Solubility.: 0.13 G/L (25 ºC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 276.85609
• Heavy Atom Count: 11
• Complexity: 176
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Bromoxynil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,N
• Statements: 25-26-43-50/53-63
• Safety Statements: 27/28-36/37-45-60-61-63-28A-28-27

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Herbicides, Other
• Canonical SMILES: C1=C(C=C(C(=C1Br)O)Br)C#N
• Uses: Bromoxynil is a nitrile herbicide. Bromoxynil is effective in post-emergent control of broad leaf weeds in cereal, corn, sorghum, onions, flax, mint, turf, and on non-cropland. Selective contact foliage-applied herbicide used to control many broad-leaved weeds in cereals.

Technology Process of Bromoxynil

There total 10 articles about Bromoxynil 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: 99.0%

4-cyanophenol (767-00-0) → Bromoxynil (1689-84-5)

Guidance literature:

With hydrogenchloride; bromide; bromate; In water; at 28 ℃; Product distribution / selectivity;

Reference yield: 98.0%

→ Bromoxynil (1689-84-5)

Guidance literature:

Reference yield: 91.0%

3-bromo-4-hydroxybenzonitrile (2315-86-8) → Bromoxynil (1689-84-5)

Guidance literature:

With iron(III) chloride; N-Bromosuccinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; at 40 ℃; for 2.5h; regioselective reaction;

DOI:10.1002/chem.201605671

upstream raw materials:

(2,6-dibromo-4-cyanophenyl) acetate

4-cyanophenol

3,5-dibromo-4-hydroxybenzaldehyde

diethyl ether

Downstream raw materials:

3,5-Dibrom-4-(methyl-propyl-acetoxy)benzonitril

2,6-dibromo-4-cyanophenyl N-(2,6-dibromo-4-cyanophenoxycarbonyl)sulfamate

2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-chloroacetyl-α-D-glucopyranoside

2,6-dibromo-4-cyanophenyl 2,3,4,6-tetra-O-chloroacetyl-β-D-glucopyranoside

Refernces

• 1、 Elumalai, Vijayaragavan,Hansen, J?rn H.. "A scalable and green one-minute synthesis of substituted phenols". . p. 40582 - 40587. Retrieved 2020/11/18.
• 2、 Mostafa, Mohamed A. B.,Calder, Ewen D. D.,Racys, Daugirdas T.,Sutherland, Andrew. "Intermolecular Aryl C?H Amination through Sequential Iron and Copper Catalysis". supporting information. p. 1044 - 1047. Retrieved 2017/02/05.