2,2-Dichloropropionic acid CAS 75-99-0
Introduction：Basic information about 2,2-Dichloropropionic acid CAS 75-99-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2,2-Dichloropropionic acid Basic information
| Product Name: | 2,2-Dichloropropionic acid |
| Synonyms: | dowponm;Kenapon;Kyselina 2,2-dichlorpropionova;kyselina2,2-dichlorpropionova;Liropon;Propionic acid, 2,2-dichloro-;Proprop;s1315 |
| CAS: | 75-99-0 |
| MF: | C3H4Cl2O2 |
| MW: | 142.97 |
| EINECS: | 200-923-0 |
| Product Categories: | DA - DH;Herbicides;Pesticides&Metabolites;Aliphatic halogenatedAlphabetic;D;API intermediates |
| Mol File: | 75-99-0.mol |
2,2-Dichloropropionic acid Chemical Properties
| Melting point | 166°C (dec.) |
| Boiling point | 202°C |
| density | 1.4014 |
| refractive index | 1.4544 |
| Fp | >110°C |
| storage temp. | 0-6°C |
| solubility | Acetonitrile (Slightly), Chloroform (Sparingly), Methanol (Slightly) |
| form | Liquid |
| pka | pK1:2.06 (25°C) |
| color | Colorless to Light yellow |
| Water Solubility | 50.2 g/100 mL |
| Sensitive | Moisture Sensitive |
| Merck | 14,2802 |
| BRN | 1750149 |
| Stability: | Hygroscopic |
| Major Application | agriculture environmental |
| InChI | 1S/C3H4Cl2O2/c1-3(4,5)2(6)7/h1H3,(H,6,7) |
| InChIKey | NDUPDOJHUQKPAG-UHFFFAOYSA-N |
| SMILES | CC(Cl)(Cl)C(O)=O |
| CAS DataBase Reference | 75-99-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Propanoic acid, 2,2-dichloro-(75-99-0) |
| EPA Substance Registry System | Dalapon (75-99-0) |
Safety Information
| Hazard Codes | Xn,Xi,F |
| Risk Statements | 22-38-41-52/53-40-36/37/38-11 |
| Safety Statements | 26-39-61-36-16-24-9 |
| OEB | B |
| OEL | TWA: 1 ppm (6 mg/m3) |
| RIDADR | 3265 |
| WGK Germany | 3 |
| RTECS | UF0690000 |
| TSCA | TSCA listed |
| HazardClass | 8 |
| PackingGroup | III |
| HS Code | 29159000 |
| Storage Class | 8A - Combustible corrosive hazardous materials |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 3 Eye Dam. 1 Skin Irrit. 2 |
| Hazardous Substances Data | 75-99-0(Hazardous Substances Data) |
| Toxicity | LD50 in male, female rats (mg/kg): 7126, 6936 orally (Gaines, Linder) |
| Description | Dalapon is a commonly used herbicide for the control ofannual and perennial grasses in croplands. The US EnvironmentalProtection Agency (EPA) has listed dalapon asa general use pesticide and categorized dalapon as a Class IItoxic agent (moderately toxic). As such, any product thatcontains dalapon would be labeled with ‘warning.’ Themoderate toxicity associated with dalapon is confinedprimarily to workers around dalapon and those individualswho are applying dalapon. Contact with the herbicide canbe caustic to human skin, damaging to the conjunctiva ofthe human eye, and irritating/damaging to the upperrespiratory system of humans. When used to control grassesin cropland as well as noncropland, dalapon is distributedvia either aerial or ground equipment for foliage application.Some of the common croplands that have benefittedfrom dalapon application include corn, potatoes, legumecrops, citrus, fruit, and nut trees. It is used extensively in thewestern United States to control a variety of grasses such asBermuda, Johnson, Crab, and Quack grasses. Dalapon istranslocated to the roots where it acts as a growth regulator.Although highly soluble with the ability to readily movethrough the environment, dalapon is relative safe andinstances of dalapon intoxication are rare. The primarysources of toxicity are contact with the sodium or magnesiumsalt of dalapon, which is an irritant to the eyes, skin,and respiratory system. Cases of elevated levels of dalaponin drinking water or groundwater have also been rare, andlittle toxicity has been reported following dalapon exposurein water. Individuals who were exposed to high levels forextended periods of time can experience kidney dysfunction.Collectively, dalapon is a relatively safe herbicide forthe control of many annual and perennial grasses. |
| Chemical Properties | clear yellow liquid |
| Uses | Dalapon is used as an herbicide primarily to control annualand perennial grasses, including Bermuda grass and Johnsongrass. Use of dalapon on food crops is primarily with sugarcaneand sugar beets. Dalapon is also used on fruits, potatoes,carrots, asparagus, alfalfa, and flax, and in forestry, homegardening, and to control reed and sedge growth in aquaticenvironments. |
| Uses | Dalapon is used primarily for the selective control of annual and perennial grass weeds in cropland and noncropland. Dalapon is also used as a selective aquatic herbicide. It is acidic in nature and are not strongly sorbed by soils, and reported to be rapidly degraded in both soil and water by microbial processes. |
| Uses | Herbicide marketed as the sodium saltor a mixture of the sodium and magnesium saltsused to control grasses in a wide variety ofcrops and in a number of noncrop applications,such as along drainage ditches and railroadsand in industrial areas. |
| Definition | ChEBI: Dalapon is a carboxylic acid and an organohalogen compound. |
| General Description | A colorless liquid. Soluble in water. Density 11.6 lb /gal. Corrosive to metals and tissue. Used as a herbicide. |
| Air & Water Reactions | Soluble in water. Reacts slowly in water to form hydrochloric and pyruvic acids. |
| Health Hazard | VAPOR: Irritating to eyes, nose and throat. LIQUID: Will burn skin and eyes. Harmful if swallowed. |
| Fire Hazard | Combustible. Irritating fumes of hydrochloric acid may form in fire. Volatilizes with steam. |
| Safety Profile | A corrosive with low toxicity by skin contact. A skin irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl- |
| Synthesis | 2,2-Dichloropropionic acid was prepared as follows: 1.7 ml (2.3 g, 1 mass%) of 60% nitric acid was added dropwise with stirring to 100 ml of 2,2-Dichloropropionic acid of density d4201.393 and purity not less than 98.5%, and the product was then maintained in isothermal conditions until the gas release had completely ceased followed by the addition of a ?? 2SeO3 solution. The resulting solution was stirred at a temperature of 50-60??C for 12 hours to give 151.5 g of a transparent yellow semi-finished solution. Quality parameters: d4201.386, content of 2,2-dichloropropionic acid - 91.7%, water - 7.8%, selenium - 0.68%, nitrate ion - 0.04%. |
| Potential Exposure | AgriculturalChemical; Mutagen. Those involved in the manufacture,formulation, and application of the herbicide. Used againstquack grass, bermuda grass, johnson grass, cattails, rushes,etc. |
| 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. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. If victim is conscious, administer water ormilk. Do not induce vomiting. |
| Environmental Fate | The mechanism of action of dalapon is the same as for mostacids. The acid denatures tissue proteins upon contact. At lowerconcentrations, the dalapon causes nonlethal yellowing ofsensitive plants, which clearly distinguished them from resistantplants. The mode of action of chlorinated aliphatic acids isnot known but they probably affect many enzyme pathways.Dalapon is readily absorbed into roots and leaves of plants andthen translocated. Lower concentrations will inhibit plantgrowth and cause leaf chlorosis, followed by necrosis anddeath. Higher concentrations of dalapon will result in significantnecrosis of areas of the plant in contact with dalapon.Although the direct mechanism of these effects has remainedelusive, it is thought that dalapon may affect lipid, carbohydrate,and nitrogen metabolism as secondary effects. Oneprevailing hypothesis for the primary dalapon affect is thatdalapon exerts direct effects on plant structural proteins leadingto these secondary metabolic outcomes. |
| storage | Color Code—White: Corrosive or Contact Hazard;Store separately in a corrosion-resistant location. Prior toworking with this chemical you should be trained on itsproper handling and storage. Store in tightly closed containers in a cool, well-ventilated area away from metals andmoisture. |
| Shipping | Acids, liquid, n.o.s. must carry a “CORROSIVE”label. They fall in DOT Hazard Class 8 and Packing GroupII. |
| Toxicity evaluation | Dalapon is somewhat persistent in soil but does not readilyadsorb to soil particles. It can remain active in soil for severalmonths when applied at high rates. In general, dalapon isconsidered to have low to moderate persistence with detectionin soil for 2–8 weeks. Due to its inability to bind to soilparticles, dalapon has a relatively high mobility in soil, withleaching possible. Microorganisms in the soil are very efficientat degrading dalapon. The herbicide is usually not found belowthe first 6 inches of soil layer. Breakdown is relatively rapid andcomplete, leading to the production of compounds that are notnaturally occurring. Soil microorganisms are efficient atdegrading dalapon, however, such that dalapon is not typicallyfound in groundwater. High temperatures and increasedmoisture accelerate dalapon degradation in soil. Dalapon canalso be degraded by ultraviolet light. In aquatic environments,dalapon is degraded by microorganisms (most important),hydrolysis, and photolysis. In the absence of microbial degradation,the half-life of dalapon is several months or longer ifthe water temperature is below 25°C, with the primaryhydrolysis product being pyruvate. Dalapon is absorbed byboth plant roots and leaves followed by translocation. Withhigh applications, dalapon precipitates and leads to localcorrosive effects on plants. Due to the ability of dalapon to berapidly metabolized and degraded by microorganisms,hydrolyzed to pyruvate, rapidly translocated to plants, andquickly moved through the environment, it is not expected thatdalapon will constitute any bioaccumulation hazard. |
| Incompatibilities | Metals: Highly corrosive to aluminumand copper alloys. Reacts slowly in water to form hydrochloric and pyruvic acids. |
2,2-Dichloropropionic acid Preparation Products And Raw materials
| Preparation Products | Pyruvic acid-->DALAPON-METHYL ESTER-->3-ETHOXYACRYLIC ACID |
