2,4-Dichlorophenoxyacetic acid

Base Information

• Chemical Name: 2,4-Dichlorophenoxyacetic acid
• CAS No.: 94-75-7
• Deprecated CAS: 15183-39-8
• Molecular Formula: C8H6Cl2O3
• Molecular Weight: 221.04
• Hs Code.: 29189090
• European Community (EC) Number: 220-290-4,202-361-1
• ICSC Number: 0033
• NSC Number: 2925
• UN Number: 3077,2811,2765
• UNII: 2577AQ9262
• DSSTox Substance ID: DTXSID0020442
• Nikkaji Number: J3.947K
• Wikipedia: 2,4-dichlorophenoxyacetic acid
• Wikidata: Q209222
• Metabolomics Workbench ID: 49541
• ChEMBL ID: CHEMBL367623
• Mol file: 94-75-7.mol

Synonyms:Aceticacid, (2,4-dichlorophenoxy)- (7CI,8CI,9CI);(2,4-Dichlorophenoxy)acetic acid;2,4-Dichlorophenoxyacetic acid ester;2,4-Dichlorophenoxyethanoic acid;2,4-PA;2-(2,4-Dichlorophenoxy)acetic acid;Aminopielik 50SL;Amoxone;B-Selektonon;Barrage HF;Barrage hydrofluoride;Basalcoat;Deherban;Desormone;Dezormon;Diclordon;Dicopur;Esterone;Fernimine;Foredex 75;HM 2010;Hedonal;Hedonal(herbicide);Huragan;Ipaner;Isadiamineyeom;Monosan herbi;Mota Maskros;NSC190751;NSC 2925;Netagrone;Pielik;Tiller S;Unison;Verton 2D;Vidon638;2,4-D series;

Chemical Property of 2,4-Dichlorophenoxyacetic acid

Chemical Property:

• Appearance/Colour: light yellow crystalline powder
• Vapor Pressure: 0.4 mm Hg ( 160 °C)
• Melting Point: 137 °C
• Refractive Index: 1.576
• Boiling Point: 345.6 °C at 760 mmHg
• PKA: pK1:2.64 (25°C)
• Flash Point: 162.8 °C
• PSA: 46.53000
• Density: 1.488 g/cm^>3
• LogP: 2.45680
• Storage Temp.: APPROX 4°C
• Solubility.: 0.3g/l
• Water Solubility.: Slightly soluble. Decomposes. 0.0890 g/100 mL
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 219.9693994
• Heavy Atom Count: 13
• Complexity: 186
• Transport DOT Label: Class 9,Poison

Purity/Quality:

99% ^*data from raw suppliers

RASA4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,T,F
• Hazard Codes: Xn,Xi,T,F
• Statements: 22-37-41-43-52/53-39/23/24/25-23/24/25-36/37/38-11-36-20/21/22-67-66
• Safety Statements: 24/25-26-36/37/39-46-61-2-45-36/37-27-16-7-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Chlorophenoxy
• Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)OCC(=O)O
• Recent ClinicalTrials: Effect of Different Ovarian Stimulation Protocols on Endometrial Receptivity
• Recent EU Clinical Trials: A multicenter, double-blind, randomized study comparing the efficacy of combination therapy of Eprosartan respectively Ramipril with low-dose Hydrochlorothiazide and Moxonidine on blood pressure levels in patients with hypertension and associated diabetes mellitus type 2
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the skin, respiratory tract and eyes. Exposure at high levels could cause effects on the nervous system.
• Description: As one of the most inexpensive and oldest weed killers, 2,4-Dichlorophenoxyacetic acid (usually called 2,4-D) is a systemic herbicide that is widely applied all over the world. It is effective to selectively kill a variety of terrestrial and aquatic broadleaf weeds without affecting most grasses, such as cereals, lawn turf, and grassland. Nowadays, 2,4-D is widely used to treat unwanted vegetation in various areas. In the field of forestry, it is used for stump treatment, trunk injection, selective control of brush in conifer forests and used to kill weeds and brush along roadways, railways, and power lines which probably damage equipment or interfere with safe operation. Besides, it is applied to control aquatic weeds for the safety of boating, fishing and swimming or protection of hydroelectric equipment. It is also used to control the spread of invasive, noxious and non-native weed species by government and control various poisonous weeds such as poison ivy and poison oak. In addiction to the forestry use, 2,4-D can also be used as a supplement in plant cell culture media in laboratories as a dedifferentiation hormone. 2,4-D free acids, esters, amines, and salts are formulated in water suspensions or solutions, or in various organic solvents, for application as systemic herbicides that are used postemergence for selective control of broadleaf weeds.
• Physical properties: Odorless, white to pale yellow, powder or prismatic crystals. Impure formulations containing 2,4- D as the main component may have a phenolic odor.
• Uses: 2,4-D is registered with the US Environmental Protection Agency (EPA) for use on a variety of food/feed sites, turf, lawn, aquatic sites, and forestry applications, and as a growth regulator in citrus crops. Residents and professional applicators may use 2,4-D on home lawns. 2,4-Dichlorophenoxyacetic acid is often formulated as various forms of inorganic salts or esters. 2,4-D was first registered as a herbicide in 1948, and its annual production was estimated at 52–67 million lb in 1990. The primary use of 2,4-D is for control of broadleaf weeds, and as such, it is used for a large spectrum of applications in agriculture, forestry, and lawn care. 2,4-D also is used along right-ofways, on rangelands, parks, and in aquatic environments. 2,4-D is one of the most widely used herbicides. It is a chlorine-substituted phenoxyacetic acid herbicide used for postemergence control of annual and perennial broad-leaved weeds in fruits, vegetables, turfs and ornamentals.Exposure to this chemical may arisein the garden, farm, or plantation setting,where it is sprayed for weed control andto enhance the plant growth. Its residueshave been detected in soils, sediments, andgroundwater, as well as in tissues of corals(Crockett et al. 1986; Glynn et al. 1984).

Technology Process of 2,4-Dichlorophenoxyacetic acid

There total 64 articles about 2,4-Dichlorophenoxyacetic 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: 99.8%

bromoacetic acid (79-08-3) + 2,4-dichlorophenol (120-83-2,40477-79-0) → 2,4-Dichlorophenoxyacetic acid (94-75-7,89300-30-1)

Guidance literature:

bromoacetic acid; With water; potassium hydroxide; at 110 ℃; for 2h; Green chemistry;

2,4-dichlorophenol; With water; sodium hydroxide; at 100 - 130 ℃; for 4.5h; Green chemistry;

With sulfuric acid; at 140 ℃; for 2h; under 3000.3 Torr; Green chemistry;

Reference yield: 99.7%

(2-chlorophenoxy)acetic acid (614-61-9) → 2,4-Dichlorophenoxyacetic acid (94-75-7,89300-30-1)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; In acetonitrile; at 20 - 25 ℃; for 0.0833333h; Green chemistry;

DOI:10.1016/j.tetlet.2020.152689

Reference yield: 99.6%

methyl 2,4-dichlorophenoxyacetate (1928-38-7) → 2,4-Dichlorophenoxyacetic acid (94-75-7,89300-30-1) + methylene chloride (74-87-3)

Guidance literature:

With hydrogenchloride; zinc(II) chloride; In water; at 140 ℃; for 4h; Reagent/catalyst; Temperature;

upstream raw materials:

(2-chlorophenoxy)acetic acid

4-Chlorophenoxyacetic acid

2-(2,4-dichlorophenoxy)acetonitrile

2,4-dichlorophenoxyacetic acid amine

Downstream raw materials:

(2,4-dichloro-phenoxy)-acetic acid tetrahydrofurfuryl ester

methyl 2,4-dichlorophenoxyacetate

(2,4-dichloro-phenoxy)-acetic acid-(2-methoxy-ethyl ester)

Aqua-Kleen

Refernces

• 1、 Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh. "Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)". supporting information. . Retrieved 2021/01/04.
• 2、 D'Oca, Caroline R. M.,D'Oca, Marcelo G. M.,Nachtigall, Fabiane M.,Orth, Elisa S.,Porciuncula, Larissa M.,Santos, Leonardo S.,Santos, Maria F. C.,Teixeira, Alex R.. "Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies". . . Retrieved 2020/07/10.