2,4-D 114

CHAPTER 4. CHEMICAL AND PHYSICAL INFORMATION

4.1 CHEMICAL IDENTITY

2,4-D is a free acid, phenoxy herbicide belonging to the phenoxyacetic acid chemical family, which is
widely used in the United States. While the free acid is itself used as an herbicide, there are nine forms of
2,4-D registered as active ingredients in end use products. These include salts, amines, and esters of
2,4-D (EPA 2005a). Derivatives include the sodium salt, diethanolamine salt, dimethyl amine salt,
isopropylamine salt, triisopropanolamine salt, butoxyethyl ester, ethylhexyl ester, and isopropyl ester.
Almost 90–95% of total 2,4-D global use is accounted for by the dimethyl amine salt and ethylhexyl ester
(Charles et al. 2001).

Formulations of 2,4-D and its derivatives vary in their chemical properties and behavior in the
environment. However, most quantified analyses of 2,4-D and its derivatives are expressed in terms of
the free acid (EPA 2005a).

Information regarding the chemical identity of 2,4-D and its derivatives are provided in Tables 4-1 and
4-2, respectively.

Table 4-1. Chemical Identity of 2,4-Da

Characteristic Information
Chemical name 2,4-Dichlorophenoxyacetic acid
Synonym(s) 2,4-D; 2,4-D Acid; Acetic acid, (2,4-dichlorophenoxy)-
Registered trade name(s)b Aqua-Kleen; Citrus Fix; Pyresta; Cimarron; Restore; Rush 24; 240;
AMINO; Amoxone; Chloroxone; Crop Rider; Dinoxol; Dormone;
Emulsamine; Fernimine; Fernoxone; Gesapax-H; Rilof-H; Target; Arena;
Campeon; Fenix; Fenix Gold; Stockton; Talion; Turuna; Valsamba;
Valsamin; Barrage; Brush-Rhap; Double Up; EndRun; HardBall; Opti-
Amine; Trump-Card; Unison; Broadrange; Foundation; Weco Max; Brash;
Phenoxy 088; Rugged; Strike; Charge; Dacomin; Chaser; Clean amine;
Colt; Crossbow; Rifle; Saber; Salvo; Savage; Shotgun; Whiteout; Defy;
Dical; Harvade; Willomine; Duplosan; Dyvel; Lotus; Topshot; U 46;
Weedmaster; Speed-Mix; Gen-Amin; Gen-Ester; Grotex Complex; Grox;
Trago
2,4-D 115

4. CHEMICAL AND PHYSICAL INFORMATION

Table 4-1. Chemical Identity of 2,4-Da

Characteristic Information
Chemical formula C8H6Cl2O3
Chemical structure Cl Cl

OH
O
O
CAS Registry Number 94-75-7

aAll information obtained from HSDB (2015), unless otherwise noted.

bMeister et al. 2014.

2,4-D = 2,4-dichlorophenoxyacetic acid; CAS = Chemical Abstracts Services; HSDB = Hazardous Substance Data
Bank

Table 4-2. Chemical Identity of 2,4-D Derivatives

Characteristic Informationa
Chemical name 2,4-D Sodiumb 2,4-D Diethanolaminec
2,4-D Dimethylamine
Synonym(s) Acetic acid, 2,4-Diolamine; Acetic
Acetic acid,
(2,4-dichlorophenoxy)-, acid, (2,4-dichlorophenoxy)-,
sodium salt; Sodium (2,4-dichlorophenoxy)-,
dimethylamine (1:1);
2,4-dichlorophenoxy- diethanolamine salt;
(2,4-Dichlorophenoxy)
acetate; 2,4-D Bis(2- acetic acid
2,4-Dichlorophenoxy- hydroxyethyl)dimethylamine salt;
acetic acid, sodium salt; ammonium; 2,4-D
Dimethylammonium
2,4-D Nab DEAb,c (2,4-dichlorophenoxy)
acetate; 2,4-D DMA
Registered trade name(s) See 2,4-D in Table 4-1 See 2,4-D in Table 4-1 See 2,4-D in Table 4-1
Chemical formula C8H5Cl2O3.Nab C8H6Cl2O3.C4H11NO2b C8H6Cl2O3.C2H7N
Chemical structurec
Cl Cl Cl Cl
Cl Cl
+
O [NH2(CH3)2] +
O [NH2(CH2CH2OH)2]
+ O
O Na O
O
O O
O

CAS Registry Number 2702-72-9 5742-19-8 2008-39-1

2,4-D 116

4. CHEMICAL AND PHYSICAL INFORMATION

Table 4-2. Chemical Identity of 2,4-D Derivatives

Characteristic Informationa
Chemical name 2,4-D Isopropylaminec 2,4-D 2,4-D Butoxyethyl ester
Triisopropanolaminec
Synonym(s) 2,4-D- Acetic acid, Acetic acid,
isopropylammonium; (2,4-dichlorophenoxy)-, (2,4-dichlorophenoxy)-,
Acetic acid, triisopropanolamine 2-butoxyethyl ester;
(2,4-dichlorophenoxy)-, salt; 2,4-D- 2,4-Dichlorophenoxy-
isopropylamine salt; tris(2-hydroxypropyl) acetic acid, butoxyethyl
2-Propanamine, ammonium; 2-Propanol, ester; 2,4-D BEE
(2,4-dichlorophenoxy) 1,1’,1’’-nitrilotris-,
acetate; 2,4-D IPAb,c (2,4-dichlorophenoxy)
acetate; 2,4-D TIPAb,c
Registered trade name(s) See 2,4-D in Table 4-1 See 2,4-D in Table 4-1 See 2,4-D in Table 4-1
Chemical formula C8H6Cl2O3.C3H9Nb C8H6Cl2O3.C9H21NO3b C14H18Cl2O4
Chemical structurec
Cl Cl Cl Cl Cl Cl
+
+ O NH (CH2CHOHCH3)3 O
O [NH3CH(CH3)2] O O O CH3
O
O O
O

CAS Registry Number 5742-17-6 32341-80-3 1929-73-3

Chemical name 2,4-D Ethylhexyl ester 2,4-D Isopropyl ester
Synonym(s) Isooctyl(2-ethylhexyl) Acetic acid, (2,4-dichlorophenoxy)-, isopropyl
2,4-dichlorophenoxy- ester; Acetic acid, (2,4-dichlorophenoxy)-,
acetate; 2,4-D, 1-methylethyl ester; 2,4-Dichlorophenoxyacetic
2-ethylhexyl; acid isopropyl ester; Isopropyl
2-Ethylhexyl (2,4-dichlorophenoxy)acetate; Isopropyl 2,4-D
(2,4-dichlorophenoxy) ester; 2,4-D IPE
acetate; Acetic acid,
(2,4-dichlorophenoxy)-,
2-ethylhexyl ester;
2,4-D EHE
Registered trade name(s) See 2,4-D in Table 4-1 See 2,4-D in Table 4-1
Chemical formula C16H22Cl2O3 C11H12Cl2O3
Chemical structurec
Cl Cl CH3
Cl Cl
O CH3
O
O O CH3
O
O CH3

CAS Registry Number 1928-43-4 94-11-1

aAll
information obtained from HSDB (2015), unless otherwise noted.
bMeisteret al. 2014.
cEPA 2005a.

2,4-D = 2,4-dichlorophenoxyacetic acid; CAS = Chemical Abstracts Services; EPA = Environmental Protection
Agency; HSDB = Hazardous Substance Data Bank
2,4-D 117

4. CHEMICAL AND PHYSICAL INFORMATION

4.2 PHYSICAL AND CHEMICAL PROPERTIES

Information regarding the physical and chemical properties of 2,4-D and its derivatives are provided in
Tables 4-3 and 4-4, respectively.

Table 4-3. Physical and Chemical Properties of 2,4-Da

Property Information
Molecular weight 221.03
Color White to yellow
Physical state Crystalline powder
Melting point 138°C
Boiling point 160°C (at 4 mm Hg)
Density/specific gravity:
at 25°C 1.42
Odor Odorless; slightly phenolic
Odor threshold 3.13 mg/kg
Solubility:
Water at 20°C 540 mg/L
Water at 25°C 677 mg/L
Organic solvents at 20°C:
Ethanol 1,250 g/kg
Diethyl ether 243 g/kg
Heptane 1.1 g/kg
Toluene 6.7 g/kg
Xylene 5.8 g/kg
Octanol 120 g/L (25°C)
Partition coefficients:
Log Kow 2.81
Log Koc 19.6–135.7
Vapor pressure at 20°C 1.40x10-7 mm Hg
Henry's law constant at 20°C 9.75x10-8 atm-m3/mol
Autoignition temperature No data
Flashpoint Not combustible
Flammability limits No data
Conversion factors No data
Explosive limits No data

aAll information obtained from HSDB (2015).

2,4-D = 2,4-dichlorophenoxyacetic acid

2,4-D 118

4. CHEMICAL AND PHYSICAL INFORMATION

Table 4-4. Physical and Chemical Properties of 2,4-D Derivativesa

Property 2,4-D Sodium 2,4-D Diethanolamine

Molecular weight 243.03b 326.18b
Color Whiteb Creamb
Physical state Powderb Powderb
Melting point 200°Cc 83°Cc
Boiling point No data No data
Density:
at 25°C 42.2 pounds/feet3 (0.676 g/cm3) 0.762 g/cm3 (bulk)c
(bulk)c
Odor No data No data
Odor threshold:
Water No data No data
Air No data No data
Solubility:
Water at 25°C 4.5x104 mg/L (unbuffered solution)b 8.06x105 mg/L (unbuffered
solution)b
Organic solvents No data No data
Partition coefficients:
Log Kow Not applicableb,d 0.0224–1.65b
Log Koc No data No data
Vapor pressure at 25°C Not applicableb,d 9.98x10-8 mm Hgb
Henry's law constant at 25°C No data No data
Autoignition temperature No data No data
Flashpoint No data No data
Flammability limits No data No data
Conversion factors No data No data
Explosive limits No data No data
2,4-D 119

4. CHEMICAL AND PHYSICAL INFORMATION

Table 4-4. Physical and Chemical Properties of 2,4-D Derivativesa

Property 2,4-D Dimethylamine 2,4-D Isopropylamine

Molecular weight 266.1 280.04b
Color White (pure); amber (technical)b Amberb
Physical state Crystals (pure); aqueous liquid Aqueous liquidb
(technical)b
Melting point 85–87°C 121°Cc
Boiling point Decomposition No data
Density/specific gravity:
at 20°C 1.23c 1.15c
Odor Odorless No data
Odor threshold:
Water No data No data
Air No data No data
Solubility:
Water at 25°C 3.0x106 g/mL (20°C) 1.74x105 g/mL (pH 5)
4.36x105 g/mL (pH 7)
3.31x105 g/mL (pH 9)
(unbuffered solutions)b
Organic solvents Soluble in methyl, ethyl, and No data
isopropyl alcohols, and acetone;
insoluble in kerosene and diesel oil
Organic solvents at 20°C
Acetonitrile 1.06 g/100 mL
Methanol >50 g/100 mL
Toluene 0.165 g/100 mL
n-Hexane 0.00357 g/100 mL
Octanol 5.41 g/100 mL
Partition coefficients:
Log Kow 0.65 Not applicableb,d
Log Koc 1.85–2.13 No data
Vapor pressure at 25°C 1 x10-7 mm Hgb Not applicableb,d
Henry's law constant at 25°C 1.4×10-16 atm-m3/molb No data
Autoignition temperature No data No data
Flashpoint No data No data
Flammability limits Not flammable No data
Conversion factors No data No data
Explosive limits No data No data
2,4-D 120

4. CHEMICAL AND PHYSICAL INFORMATION

Table 4-4. Physical and Chemical Properties of 2,4-D Derivativesa

Property 2,4-D Triisopropanolamine 2,4-D Butoxyethyl ester

Molecular weight 412.31b 321.2
Color Amberb Amber; colorless
Physical state Aqueous liquidb Liquid
Melting point 87–110°Cc <25°C
Boiling point No data 89°Cc
Density/specific gravity:
at 20°C 1.21 1.232 g/cm3
Odor No data Odorless (pure); fuel oil-like
(technical)
Odor threshold:
Water No data No data
Air No data No data
Solubility:
Water at 25°C 4.61x105 g/mL (pH 5) 12 mg/L
4.61x105 g/mL (pH 7)
1.04x105 g/mL (pH 9)
(unbuffered solutions)b
Organic solvents No data Miscible in acetone, acetonitrile,
n-hexane, and methanol; soluble in
oils
Partition coefficients:
Log Kow Not applicableb,d 4.1b
Log Koc No data No data
Vapor pressure at 25°C Not applicableb,d 4.5x10-6 mm Hg
Henry's law constant at 25°C No data No data
Autoignition temperature No data No data
Flashpoint No data >79°C (open cup)
Flammability limits No data No data
Conversion factors No data No data
Explosive limits No data No data
2,4-D 121

4. CHEMICAL AND PHYSICAL INFORMATION

Table 4-4. Physical and Chemical Properties of 2,4-D Derivativesa

Property 2,4-D Ethylhexyl ester 2,4-D Isopropyl ester

Molecular weight 333.28 263.12
Color Golden yellow Colorless
Physical state Liquid Liquid
Melting point <-37°C 5–25°C
Boiling point >300°C (decomposition) 240°Cc
Density:
at 20°C 1.148 No data
at 25°C/25°C No data 1.255–1.270
Odor Sweet, slightly pungent Fuel oil-like (technical)
Odor threshold:
Water No data No data
Air No data No data
Solubility:
Water at 25°C 0.086 mg/L 37.3 mg/L
Organic solvents No data Soluble in alcohols and most oils
Partition coefficients:
Log Kow 5.78 253.8c
Log Koc No data 2.78b
Vapor pressure at 25°C 3.6x10-6 mm Hgb 2.32x10-4 mm Hg
Henry's law constant at 25°C 1.8×10-5 atm-m3/mol 2.2×10-6 atm-m3/molb
Autoignition temperature No data No data
Flashpoint 171°C (open cup) >79°C (open cup)
Flammability limits No data No data
Conversion factors No data No data
Explosive limits No data No data

aAll
information obtained from HSDB (2015), unless otherwise noted.
bNPIC 2008.
cEPA 2005a.
dThe salt dissociates to acid in water; therefore, this endpoint does not apply.

2,4-D = 2,4-dichlorophenoxyacetic acid