127-20-8

Basic information

• Product Name: 2,2-DICHLOROPROPIONIC ACID SODIUM SALT
• Synonyms: 2,2-Dichloropropionic acid sodium;2-2-Dichloropionic acid sodium salt;2,2-Dichloropropionic acid salt (Na);dalapon-Na;2,2-Dichloropropionic acid sodium salt for synthesis;DPA SODIUM;DALAPONE-NA;DALAPON-SODIUM
• CAS NO: 127-20-8
• Molecular Formula: C₃H₃Cl₂O₂*Na
• Molecular Weight: 164.95
• EINECS: 204-828-5
• Product Categories: Organics
• Mol File: 127-20-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 166.5°C
• Boiling Point: 187.5°Cat760mmHg
• Flash Point: 76.1°C
• Appearance: /
• Density: 1.497g/cm³
• Vapor Pressure: 0.282mmHg at 25°C
• Storage Temp.: +4°C
• Solubility: 450g/l
• CAS DataBase Reference: 2,2-DICHLOROPROPIONIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DICHLOROPROPIONIC ACID SODIUM SALT(127-20-8)
• EPA Substance Registry System: 2,2-DICHLOROPROPIONIC ACID SODIUM SALT(127-20-8)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-34-36/37/38
• Safety Statements: 26-27-28-36/37/39-36
• RIDADR: UN 3261 8/PG 2
• WGK Germany: WGK 1 slightly water endangering
• RTECS: UF1225000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 127-20-8(Hazardous Substances Data)

Usage

Uses

2,2-Dichloropropionic acid sodium salt is a selective, systemic herbicide used to control perennial and annual grasses on noncrop land, fruits, vegetables and some aquatic weeds.

Safety Profile

Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of Na2O and Cl-.

Environmental Fate

Soil. Undergoes dechlorination and the liberation of carbon dioxide in soil. The residual activity is limited to approximately 3–4 months (Hartley and Kidd, 1987). The average half-life for dalapon-sodium in soil incubated in the laboratory under aerobic conditions was 15 days (Namdeo, 1972)Photolytic. Dalapon (free acid) is subject to photodegradation. When an aqueous solution (0.25 M) was irradiated with UV light at 253.7 nm at 49°C, 70% degraded in 7 hours. Pyruvic acid is formed which is subsequently decarboxylated to acetaldehyChemical/Physical. Slowly reacts with moisture at room temperature forming pyruvic acid (Frank and Demint, 1969; Kenaga, 1974), hydrochloric acid and sodium chloride (Kenaga, 1974; Wolfe et al., 1990). The reported hydrolysis half-life of dalaponProducts reported from the combustion of the free acid (dalapon) at 900°C include carbon monoxide, carbon dioxide, chlorine and hydrochloric acid (Kennedy et al., 1972a)

InChI:InChI=1/C3H4Cl2O2.Na/c1-3(4,5)2(6)7;/h1H3,(H,6,7);/q;+1/p-1

Synthetic route

sodium 2,2-dichloropropionate (127-20-8) → 2,2-dichloropropionyl chloride (26073-26-7)

Conditions	Yield
With oxalyl dichloride In pyridine; dichloromethane at 25℃; for 2h;	70%
With dmap; oxalyl dichloride In dichloromethane

sodium 2,2-dichloropropionate (127-20-8) → α,α-Dichloropropionic anhydride (107905-50-0)

Conditions	Yield
With thionyl chloride In dichloromethane for 2h; Heating;	43%

C3H2Cl6NOP (5179-82-8) + sodium 2,2-dichloropropionate (127-20-8) → C12H11Cl9NO7P (36076-45-6)

Conditions	Yield
In acetone

Isopropyl-N-chloromethyl-N-(3-chlorophenyl)-carbamate (39074-64-1) + sodium 2,2-dichloropropionate (127-20-8) → 2,2-Dichloro-propionic acid [(3-chloro-phenyl)-isopropoxycarbonyl-amino]-methyl ester (40151-75-5)

(5-Chloro-2-methoxy-phenyl)-chloromethyl-carbamic acid isopropyl ester (39073-78-4) + sodium 2,2-dichloropropionate (127-20-8) → 2,2-Dichloro-propionic acid [(5-chloro-2-methoxy-phenyl)-isopropoxycarbonyl-amino]-methyl ester (50887-80-4)

sodium 2,2-dichloropropionate (127-20-8) → 2,2-dichloropropionyl hypofluorite (125973-26-4)

Conditions	Yield
With water; fluorine In various solvent(s) at -78℃;

sodium 2,2-dichloropropionate (127-20-8) + methyl iodide (74-88-4) → methyl 2,2-dichloropropionate (17640-02-7)

2-(5-chloro-2-hydroxy-phenyl)-propan-2-ol (73050-78-9) + sodium 2,2-dichloropropionate (127-20-8) → 6-chloro-2,4,4-trimethyl-[4H]-1,3-benzodioxin-2-carboxylic acid (73050-93-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane

chloro-5 hydroxy-2 α-methyl α-phenyl benzene methanol (74271-47-9) + sodium 2,2-dichloropropionate (127-20-8) → 6-chloro-2,4-dimethyl-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid

Conditions	Yield
In water; toluene

sodium 2,2-dichloropropionate (127-20-8) + copper(II) sulfate (7758-99-8) → Copper(II); 2,2-dichloro-propionate

Conditions	Yield
In water a soln. of Cu comp. added to a soln. of acid (pH 4.5-5, 1:2 molar ratio), left to stand at room temp.;

Downstream Products

• 17640-02-7 methyl 2,2-dichloropropionate 
• 50887-80-4 2,2-Dichloro-propionic acid [(5-chloro-2-methoxy-phenyl)-isopropoxycarbonyl-amino]-methyl ester 
• 40151-75-5 2,2-Dichloro-propionic acid [(3-chloro-phenyl)-isopropoxycarbonyl-amino]-methyl ester 

Relevant articles and documents

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.