2,2-Dichloropropionic acid

Base Information

• Chemical Name: 2,2-Dichloropropionic acid
• CAS No.: 75-99-0
• Molecular Formula: C3H4Cl2O2
• Molecular Weight: 142.97
• Hs Code.: 29159000
• European Community (EC) Number: 200-923-0
• ICSC Number: 1509
• NSC Number: 56352
• UN Number: 1760
• UNII: VO6PY8ZMRW
• DSSTox Substance ID: DTXSID2021575
• Nikkaji Number: J2.399J
• Wikipedia: 2,2-Dichloropropionic_acid
• Wikidata: Q3012266
• ChEMBL ID: CHEMBL445525
• Mol file: 75-99-0.mol

Synonyms:dalapon;dalapon, ammonium salt;dalapon, calcium salt;dalapon, magnesium salt;dalapon, sodium salt;dalapon-magnesium;dalapon-sodium

Chemical Property of 2,2-Dichloropropionic acid

Chemical Property:

• Appearance/Colour: A colorless liquid.
• Vapor Pressure: 0.282mmHg at 25°C
• Melting Point: 166 °C (dec.)
• Refractive Index: 1.4544
• Boiling Point: 187.5 °C at 760 mmHg
• PKA: pK1:2.06 (25°C)
• Flash Point: 76.1 °C
• PSA: 37.30000
• Density: 1.497 g/cm³
• LogP: 1.26480
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: 50.2 g/100 mL
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 141.9588348
• Heavy Atom Count: 7
• Complexity: 88.9
• Transport DOT Label: Corrosive

Purity/Quality:

98% ^*data from raw suppliers

2,2-DichloropropanoicAcid(~90%purity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,F
• Statements: 22-38-41-52/53-40-36/37/38-11
• Safety Statements: 26-39-61-36-16-24-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Other
• Canonical SMILES: CC(C(=O)O)(Cl)Cl
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Description: Dalapon is a commonly used herbicide for the control of annual and perennial grasses in croplands. The US Environmental Protection Agency (EPA) has listed dalapon as a general use pesticide and categorized dalapon as a Class II toxic agent (moderately toxic). As such, any product that contains dalapon would be labeled with ‘warning.’ The moderate toxicity associated with dalapon is confined primarily to workers around dalapon and those individuals who are applying dalapon. Contact with the herbicide can be caustic to human skin, damaging to the conjunctiva of the human eye, and irritating/damaging to the upper respiratory system of humans. When used to control grasses in cropland as well as noncropland, dalapon is distributed via either aerial or ground equipment for foliage application. Some of the common croplands that have benefitted from dalapon application include corn, potatoes, legume crops, citrus, fruit, and nut trees. It is used extensively in the western United States to control a variety of grasses such as Bermuda, Johnson, Crab, and Quack grasses. Dalapon is translocated to the roots where it acts as a growth regulator. Although highly soluble with the ability to readily move through the environment, dalapon is relative safe and instances of dalapon intoxication are rare. The primary sources of toxicity are contact with the sodium or magnesium salt of dalapon, which is an irritant to the eyes, skin, and respiratory system. Cases of elevated levels of dalapon in drinking water or groundwater have also been rare, and little toxicity has been reported following dalapon exposure in water. Individuals who were exposed to high levels for extended periods of time can experience kidney dysfunction. Collectively, dalapon is a relatively safe herbicide for the control of many annual and perennial grasses.
• 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. Herbicide marketed as the sodium salt or a mixture of the sodium and magnesium salts used to control grasses in a wide variety of crops and in a number of noncrop applications, such as along drainage ditches and railroads and in industrial areas. Dalapon is used as an herbicide primarily to control annual and perennial grasses, including Bermuda grass and Johnson grass. Use of dalapon on food crops is primarily with sugarcane and sugar beets. Dalapon is also used on fruits, potatoes, carrots, asparagus, alfalfa, and flax, and in forestry, home gardening, and to control reed and sedge growth in aquatic environments.

Technology Process of 2,2-Dichloropropionic acid

There total 34 articles about 2,2-Dichloropropionic acid 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: 95.0%

2,2-dichloropropanal (27313-32-2) → 2,2-Dichloropropionic acid (75-99-0)

Guidance literature:

With hydrogenchloride; picoline hydrochloride; chlorine; In chloroform; at 65 - 70 ℃; for 24h;

Reference yield: 92.0%

4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate → Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3) + 2,2-Dichloropropionic acid (75-99-0) + dinitrogen monoxide (10024-97-2)

Guidance literature:

With water; In methanol; aq. phosphate buffer; at 20 ℃; for 24h; pH=7.4; Reagent/catalyst; Kinetics; Sealed tube;

DOI:10.1016/j.bmc.2015.04.023

Reference yield: 68.23%

propionic acid (802294-64-0,79-09-4) → 2,2-Dichloropropionic acid (75-99-0) + (R,S)-2-chloropropionic acid (598-78-7)

Guidance literature:

With chlorine; pyrographite; propionic acid anhydride; at 130 ℃; for 2.5h; under 760.051 Torr;

DOI:10.14233/ajchem.2014.15520

upstream raw materials:

(R,S)-2-chloropropionic acid

2,2-dichloro-propionic acid anilide

(1,1,2,2-tetrachloro-propyl)-phosphorimidic acid trichloride

1,1,3,3-tetrachloro-butan-2-one

Downstream raw materials:

2,2-dichloro-propionic acid-(4-chloro-benzyl ester)

3-ethoxyprop-2-enoic acid

propionic acid

2,3-Dimethylmaleic anhydride

Refernces

• 1、 Xue, Jianwei,Qi, Beibei,Wen, Xiaoguang,Wang, Yingying,Lv, Zhiping,Li, Fuxiang. "Promotive effects in α-monochloropropionic acid catalytic synthesis with propionic anhydride". . p. 481 - 485. Retrieved 2014/06/09.
• 2、 Seoud, Omar A. E.I.,Ruasse, Marie-Francoise,Possidonio, Shirley. "pH-independent hydrolysis of 4-nitrophenyl 2,2-dichloropropionate in aqueous micellar solutions: Relative contributions of hydrophobic and electrostatic interactions". . p. 526 - 532. Retrieved 2007/10/03.