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2,4-Dichlorobenzoic acid

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Name

2,4-Dichlorobenzoic acid

EINECS 200-067-8
CAS No. 50-84-0 Density 1.517 g/cm3
PSA 37.30000 LogP 2.69160
Solubility Insoluble in water Melting Point 157-160 °C(lit.)
Formula C7H4Cl2O2 Boiling Point 309.5 °C at 760 mmHg
Molecular Weight 191.014 Flash Point 141 °C
Transport Information N/A Appearance White to slightly yellowish powder
Safety 26-36-37/39-22 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 50-84-0 (2,4-Dichlorobenzoic acid) Hazard Symbols IrritantXi, HarmfulXn
Synonyms

Benzoic acid, 2,4-dichloro-;2,4-Dichlorobenzoate;2,4-dichloro-benzoic acid;

Article Data 83

2,4-Dichlorobenzoic acid Synthetic route

6319-33-1

1,2-bis(2,4-dichlorobenzylidene)hydrazine

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 240h; Heating;100%
With [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃; for 4h; Green chemistry;77%
1747-47-3

2,4-Dichlor-1--benzol

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 48h; Heating;100%
56843-28-8

2,4-dichlorobenzaldoxime

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 145h; Heating;98%
650598-43-9

2-bromo-4,6-dichlorobenzoic acid

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With zinc In sodium hydroxide at 25℃; for 2h;98%
874-42-0

2,4-dichlorobenzaldeyhde

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide for 0.0361111h; Microwave irradiation;96%
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 18h; Heating;94%
With polysterene-bound phenylseleninic acid; dihydrogen peroxide In tetrahydrofuran for 12h; Heating;93%
153147-35-4

2-oxo-2-(2,4-dichlorophenyl)ethanal

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With pyrrolidine; dihydrogen peroxide In toluene at 25℃; for 2h;96%
With iodine; dimethyl sulfoxide at 180℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;92%
32768-54-0

2,3-dichlorotoluene

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With hydrogen bromide In water95.1%

C7H4Cl2O2*C8H11N

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 60℃;94%
650598-47-3

2,4-dichloro-3-(triethylsilyl)benzoic acid

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 2h; Heating;92%
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

50-84-0

2,4 dichlorobenzoic acid

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)ethan-1-one With tert.-butylhydroperoxide; sodium hydroxide; tungsten(VI) oxide In water at 80℃; for 8h;
Stage #2: With hydrogenchloride In water
92%
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 5h;87%
With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry;80%
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 12h;60%
With dihydrogen peroxide In water at 22 - 25℃; for 11688h;

2,4-Dichlorobenzoic acid Consensus Reports

Reported in EPA TSCA Inventory.

2,4-Dichlorobenzoic acid Specification

The 2,4-Dichlorobenzoic acid, with the CAS registry number 50-84-0, is a kind of white to slightly yellowish powder. This chemical is soluble in ethanol, diethyl ether, benzene, acetone, chloroform while insoluble in water and normal heptane and it is stable chemically while incompatible with strong oxidizing agents. In addition, its product categories are including Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic acids; C7; Carbonyl Compounds; Carboxylic Acids; Alpha sort; D; DAlphabetic; DIA - DIC; Pesticides&Metabolites.

The physical properties of this chemical are as follows: (1)ACD/LogP: 2.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.15; (4)ACD/LogD (pH 7.4): -0.33; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.79; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 42.97 cm3; (15)Molar Volume: 125.8 cm3; (16)Polarizability: 17.03×10-24 cm3; (17)Surface Tension: 53.9 dyne/cm; (18)Density: 1.517 g/cm3; (19)Flash Point: 141 °C; (20)Enthalpy of Vaporization: 58.1 kJ/mol; (21)Boiling Point: 309.5 °C at 760 mmHg; (22)Vapour Pressure: 0.000275 mmHg at 25°C; (23)Exact Mass: 189.958835; (24)MonoIsotopic Mass: 189.958835; (25)Topological Polar Surface Area: 37.3; (26)Heavy Atom Count: 11; (27)Complexity: 161.

Use of this chemical: 2,4-dichloro-benzoic acid could react to produce 2-amino-4-chloro-benzoic acid. This reaction could happen in the presence of the reagent of copper powder & ammonia, and it needs the reaction temperature of 120 ℃.

Production method of this chemical: 2,4-dichloro-benzaldehyde could react to produce 2,4-dichloro-benzoic acid. This reaction could happen in the presence of the reagent of sodium perborate tetrahydrate and the solvent of acetic acid, and it needs the reaction temperature of 45 - 50 ℃ with the yield of 87 %.

As to its usage, it is widely applied in many ways. It could be used as the intermediate of bacteriacide pyrifenox and also the intermediate of phytocide pyrazoxyfen; It could also be the intermediate of pharmaceutics, dye and pesticide.

When you are dealing with this chemical, you should be much more cautious. For one thing, it is irritant to eyes, respiratory system and skin, which also may cause inflammation to the skin or other mucous membranes. For another thing, it is harmful which may cause damage to health. If swallowed, it will be dangerous. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and do remember not to breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)C(=O)O
(2)InChI: InChI=1S/C7H4Cl2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,(H,10,11)
(3)InChIKey: ATCRIUVQKHMXSH-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 830mg/kg (830mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 20, Pg. 332, 1979.
mouse LD50 subcutaneous 1200mg/kg (1200mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Biochemical Pharmacology. Vol. 13, Pg. 1538, 1964.
 

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