2,4-Dichlorophenoxyacetic acid

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

2,4-Dichlorophenoxyacetic acid
Names
Preferred IUPAC name
(2,4-Dichlorophenoxy)acetic acid
Other names
2,4-D
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.147
KEGG
PubChem CID
UNII
  • InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12) Y
    Key: OVSKIKFHRZPJSS-UHFFFAOYSA-N Y
  • InChI=1/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12)
    Key: OVSKIKFHRZPJSS-UHFFFAOYAM
SMILES
  • Clc1cc(Cl)ccc1OCC(=O)O
Properties
C8H6Cl2O3
Molar mass 221.04 g/mol
Appearance white to yellow powder
Melting point 140.5 °C (284.9 °F; 413.6 K)
Boiling point 160 °C (320 °F; 433 K) 0.4 mm Hg
900 mg/L
Hazards
GHS labelling:
H302, H317, H318, H335, H412
P261, P273, P280, P305+P351+P338
Flash point nonflammable
Lethal dose or concentration (LD, LC):
LD50 (median dose)
500 mg/kg (oral, hamster)

100 mg/kg (oral, dog)
347 mg/kg (oral, mouse)
699 mg/kg (oral, rat)

NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 mg/m3
REL (Recommended)
TWA 10 mg/m3
IDLH (Immediate danger)
100 mg/m3
Safety data sheet (SDS) ICSC 0033
Related compounds
Related compounds
2,4,5-T, Dichlorprop
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2,4-D is one of the oldest and most widely available herbicides and defoliants in the world, having been commercially available since 1945, and is now produced by many chemical companies since the patent on it has long since expired. It can be found in numerous commercial lawn herbicide mixtures, and is widely used as a weedkiller on cereal crops, pastures, and orchards. Over 1,500 herbicide products contain 2,4-D as an active ingredient.

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