Chloramben Chemical Properties

Melting point:

200 °C

Boiling point:

312 °C

Density 

1.4062 (rough estimate)

refractive index 

1.6100 (estimate)

storage temp. 

0-6°C

solubility 

Acetonitrile (Slightly), DMSO (Sparingly), Metahnol (Slightly)

pka

2.75±0.25(Predicted)

form 

Powder

color 

Pale Beige

Water Solubility 

700 mg/L (25 ºC)

Merck 

13,2082

BRN 

2365906

Exposure limits

An experimental carcinogen.

CAS DataBase Reference

133-90-4(CAS DataBase Reference)

NIST Chemistry Reference

3-Amino-2,5-dichlorobenzoic acid(133-90-4)

EPA Substance Registry System

Chloramben (133-90-4)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

45-36/37/38-40

Safety Statements 

53-22-26-36/37/39-45-36

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

DG1925000

HS Code 

29224999

Hazardous Substances Data

133-90-4(Hazardous Substances Data)

Toxicity

Nontoxic to fish (Hartley and Kidd, 1987); acute oral LD50 for rats 5,620 mg/kg (Hartley and Kidd, 1987), 3,500 mg/kg (RTECS, 1985).

MSDS

• Language:English Provider:3-Amino-2,5-dichlorobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Chloramben Usage And Synthesis

Description

Chloramben is a colorless, odorless, crystallinesolid. Molecular weight=206.03; Freezing/Meltingpoint=200-201℃; Vapor pressure=6.8 3 1023 mmHg at100℃. Hazard Identification (based on NFPA 704 MRating System): Health 3, Flammability 0, Reactivity 0.Soluble in water; solubility=690 ppm at 25℃.

Chemical Properties

Off-white to beige powder

Chemical Properties

Chloramben is a colorless, odorless, crystalline solid.

Uses

Preemergence or preplant herbicide used in many vegetable and field crops to control annual broad-leaved weeds and grasses. Also for postemergent control of common ragweed, redroot pigweed, smartweed and velvet-leaf.

Uses

Chloramben may be used as an analytical reference standard for the determination of the analyte in water samples using liquid chromatography with electrochemical detection (LC-EC).

Uses

Herbicide or plant growth regulator.

Definition

ChEBI: Chloramben is a chlorobenzoic acid.

General Description

Purplish white powder or light purple solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chloramben reacts with sodium hypochlorite solutions .

Health Hazard

ACUTE/CHRONIC HAZARDS: Chloramben emits toxic fumes when heated to decomposition.

Fire Hazard

Flash point data for Chloramben is not available, but Chloramben is probably combustible.

Agricultural Uses

Herbicide: A herbicide for grasses, and broadleaf weeds. Mostly used on soybeans, and also on corn, beans, asparagus, pumpkins, peanuts, sunflowers, peppers, cotton, sweet potatoes, squash, melons, hardwood trees, and some conifers. Not approved for use in EU countries. Not registered for use in the U.S. There are 51 global suppliers

Trade name

ACP-M-728®; AMBEN®; AMBIBEN®; AMIBEN®[C]; AMIBIN®; AMOBEN®; ORNAMENTAL WEEDER®[C]; VEGABEN®; VEGIBEN®[C]; WEEDONE® GARDEN WEEDER

Potential Exposure

A General Use Pesticide (GUP) that is no longer produced or sold in the United States. It is used as an herbicide for grasses, broadleaf weeds, soybeans, beans, and some vegetables. Workers involved in the manufacture, formulation, or application of this reemergence herbicide.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

Environmental Fate

Soil. In soils, chloramben was degraded by microorganisms but no products were identified (Humburg et al., 1991). The main degradative pathway of chloramben in soil is decarboxylation and subsequent mineralization to carbon dioxide. The calculated halflives in Ella loamy sand, Kewaunee clay and Poygan silty clay were 120–201, 182–286 and 176–314 days, respectively (Wildung et al., 1968). Persistence in soil is 6–8 weeks (Hartley and Kidd, 1987).
Groundwater. According to the U.S. EPA (1986) and Ashton and Monaco (1991), chloramben has a high potential to leach to groundwater, especially in sandy soils during heavy rains. Plant. Degrades in plants to N-glucoside, glucose ester, conjugates and insoluble residues (Ashton and Monaco, 1991).
Photolytic. Plimmer and Hummer (1969) studied the irradiation of chloramben in water (2–4 mg/L) under a 450-W mercury vapor lamp (λ >2,800 ?) for periods of 2 to 20 hours. Chloride ion was released and a complex mixture of colored products was observed. It was postulated that amino free radicals reacted with each other via polymerization and oxidation processes. The experiment was repeated except the solution contained sodium bisulfite as an inhibitor under a nitrogen atmosphere. Oxidation did not occur and loss of the 2-chloro substituent gave 3-amino-5-chlorobenzoic acid (Plimmer and Hummer, 1969).
Chloramben (sodium salt) in aqueous solutions (100 mg/L) was rapidly photodegraded in outdoor sunlight and under a 360-W mercury arc lamp (Crosby and Leitis, 1969).
In sunlight, the solution became yellow-brown. Subsequent analysis by gas-liquid chromatography did not resolve any compounds other than chloramben. However, analysis by TLC indicated at least 12 unidentified products. These products were reportedly formed via replacement of chlorine by a hydroxy group, reductive dechlorination and abstraction of hydrogen from the amine group (oxidation). No photodegradation products could be identified in the solutions irradiated with the mercury arc lamp (Crosby and Leitis, 1969).
Chemical/Physical. Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Sax and Lewis, 1987). Forms water-soluble salts with alkalies.

Metabolism

Chloramben is generally stable to hydrolytic degradation; however, it will decompose in sodium hypochlorite solutions. It is also very sensitive to light and under oxidative conditions aqueous solutions will rapidly undergo photolysis. The predominant reaction in oxidative photolysis is unclear but appears to involve the formation of amino radicals. Photolysis also occurs under reductive conditions by dechlorination at the 2 position, i.e., when appropriate reducing agents are present, e.g., sodium bisulfite.

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with chloramben you should be trained on its proper handling and storage. Store in a cool, dry place, or a refrigerator, and avoidcontact with strong acids, acid fumes, and light. A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with OSHAStandard 1910.1045.

Shipping

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

Toxicity evaluation

Although limited studies are available, those that have been conducted, for example, on cows and dogs, indicate that the majority of ingested chloramben is quickly excreted through the urine and feces and does not accumulate in tissues. An interesting interaction between caffeine and chloramben suggests that they can form an insoluble complex in the intestinal tract and thus decrease the amount of chloramben absorbed into the blood stream. The acute oral LD₅₀ in rat is >5000 mg/kg.

Incompatibilities

Rapidly decomposed by light. Strong acids and acid fumes

Waste Disposal

Chloramben is stable to heat, oxidation, and hydrolysis in acidic or basic media. The stability is comparable to that of benzoic acid. Wet oxidation or incineration are recommended disposal methods.

Chloramben(133-90-4)Related Product Information

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