Bromoxynil Chemical Properties

Melting point:

189-191 °C(lit.)

Boiling point:

265.6±40.0 °C(Predicted)

Density 

2.0926 (rough estimate)

refractive index 

1.6400 (estimate)

storage temp. 

0-6°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.06(at 25℃)

color 

Buff, Creamy

Water Solubility 

0.13 G/L (25 ºC)

Merck 

13,1426

BRN 

2364039

CAS DataBase Reference

1689-84-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzonitrile, 3,5-dibromo-4-hydroxy-(1689-84-5)

EPA Substance Registry System

Bromoxynil (1689-84-5)

Safety Information

Hazard Codes 

T+,N

Risk Statements 

25-26-43-50/53-63

Safety Statements 

27/28-36/37-45-60-61-63-28A-28-27

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DI3150000

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

1689-84-5(Hazardous Substances Data)

Toxicity

LD50 orally in mice: 111 mg/kg (Carpenter, 1964)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Bromoxynil Usage And Synthesis

Chemical Properties

Off-white to salmon crystalline powder

Chemical Properties

Bromoxynil is a colorless to white crystalline solid or tan powder. Odorless (pure).

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.

Uses

Selective contact foliage-applied herbicide used to control many broad-leaved weeds in cereals.

Definition

ChEBI: A dibromobenzene that is 2,6-dibromophenol substituted by a cyano group at position 4.

General Description

Colorless solid. Melting point 382-384°F (194-195°C). Sublimes at 275°F (135°C) under pressure of 0.15 mm Hg. Used as a herbicide.

Reactivity Profile

Bromoxynil is a weak acid.

Hazard

Toxic.

Agricultural Uses

Herbicide: A U.S. EPA restricted Use Pesticide (RUP). For post-emergent control of broadleaf weeds. Used on alfalfa, garlic, corn, sorghum, flax, cereals, turf and on pasture and rangelands.

Trade name

BRIOTRIL®; BRUCIL®; BRITTOX®; BROMINAL®; BROMINEX®; BROMINAL®; BROMINAL ME-4®; BROMINIL®; BROMILIL PLUS®; Bromox 2E; BROMOTRIL®; BROMOXYNIL NITRILE HERBICIDE®; BRONATE®; BROXYNIL®; BUCTRIL® Bromoxynil; BUCTRIL® GEL HERBICIDE (octanoate); BUCTRIL® 4EC GEL (mixture of bromoxynil octanoate + bromoxynil heptanoate); BUCTRIL INDUSTRIAL®; CHIPCO BUCTRIL®; CHIPCO CRAB-KLEEN®; FLAGON®, 400 EC; HOBANE®; LABUCTRIL®; LITAROL®; M&B 10064®; MB 10064®; MB 10731® (octanoate); M&B 10731®; ME4 BROMINAL®; MERIT®; MEXTROL-BIOX®; MOXY 2E®; NCR CE EE DOV7® (octanoate); NU-LAWN WEEDER®; OXYTRIL M®; PARDNER®; SABRE®; TORCH®

Potential Exposure

Bromoxynil is a hydroxybenzonitrile herbicide used for postemergent control of broadleaf weeds; on alfalfa, garlic, corn, sorghum, flax, cereals, turf and on pasture and rangelands. A United States Environmental Protection Agency RUP.

Environmental Fate

Biological. Duke et al. (1991) reported that bromoxynil can be converted to 3,5- dibromo-4-hydroxybenzoic acid by a microbial nitrolase.
Soil. In soils, Klebsiella pneumoniae metabolized bromoxynil to 3,5-dibromo-4- hydroxybenzoic acid and ammonia (McBride et al., 1986). In soil, bromoxynil undergoes nitrile and then amide hydrolysis yielding 3,5-dibromo-4-hydroxybenzoic acid and
Nitrification in soils is inhibited when bromacil is applied at a concentration of <50 ppm (Debona and Audus, 1970). The half-life in soil is approximately 10 days (Hartley and Kidd, 1987).
Plant. In plants, the cyano group is hydrolyzed to an amido group which is subsequently oxidized to a carboxylic acid. Hydrolyzes to hydroxybenzoic acid (Hartley and Kidd, 1987). In plants, bromoxynil may hydrolyze to a benzoic acid (Humburg et al., 1989). Bromoxynil-resistant cotton was recently developed by inserting a bxn gene cloned from the soil bacterium Klebsiella ozaenae. This gene, which encodes a specific nitrolase, converted bromoxynil to its primary metabolite 3,5-dibromo-4-hydroxybenzoic acid (Stalker et al., 1988).
Chemical/Physical. Emits toxic fumes of nitrogen oxides and bromine when heated to decomposition (Sax and Lewis, 1987). Reacts with bases forming water-soluble salts (Worthing and Hance, 1991). Bromacil is stable to UV light (Hartley and Kidd, 19

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.

Incompatibilities

A weak acid; keep away from bases and alkalies. React with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Keep away from oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.) and strong acids.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Incineration with effluent gas scrubbing is recommended. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. If allowed, Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Bromoxynil(1689-84-5)Related Product Information

• 4-Cyanophenol
• 4-Methoxyphenol
• 4-Ethyl-5-fluoro-6-hydroxypyrimidine
• 2-Hydroxyphenylacetic acid
• 1,3-Dibromo-5,5-dimethylhydantoin
• 4,6-Dihydroxypyrimidine
• 4-Nitrobenzonitrile
• 4-Hydroxybenzaldehyde
• 4-Hydroxybenzoic acid
• Triclosan
• 2-Cyanophenol
• Benzonitrile
• Salicylic acid
• Methylparaben
• Ammonium bromide
• 1-Bromobutane
• (2-HYDROXYETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
• BROMOACETONE