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4-Chlorophenoxyacetic acid

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Name

4-Chlorophenoxyacetic acid

EINECS 204-581-3
CAS No. 122-88-3 Density 1.367 g/cm3
PSA 46.53000 LogP 1.80340
Solubility Slightly soluble in water Melting Point 157-159 °C
Formula C8H7ClO3 Boiling Point 315.151 °C at 760 mmHg
Molecular Weight 186.595 Flash Point 144.399 °C
Transport Information N/A Appearance white to light beige powder
Safety 22 Risk Codes 22
Molecular Structure Molecular Structure of 122-88-3 (4-Chlorophenoxyacetic acid) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

4-Chlorophenoxyacetic Acid(4-Cpa);Aceticacid, (4-chlorophenoxy)- (9CI);Acetic acid, (p-chlorophenoxy)- (8CI);(4-Chlorophenoxy)acetic acid;(p-Chlorophenoxy)acetic acid;4-CP;4-CPA;BI 12;HP 55;NSC 8769;NSC 9213;PCPA;Tomatone;Tomatotone;p-CPA;Aceticacid, 2-(4-chlorophenoxy)-;

Article Data 121

4-Chlorophenoxyacetic acid Synthetic route

106-48-9

4-chloro-phenol

79-11-8

chloroacetic acid

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
With sodium hydroxide Irradiation;98%
With sodium hydroxide; dodecyltriethylammonium bromide for 0.0833333h; Irradiation;96%
Stage #1: 4-chloro-phenol; chloroacetic acid With sodium hydroxide In water at 60 - 70℃; for 3h;
Stage #2: With hydrogenchloride In water
88%
14426-42-7

ethyl p-chlorophenoxyacetate

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
Stage #1: ethyl p-chlorophenoxyacetate With sodium hydroxide In tetrahydrofuran for 2h; Reflux;
Stage #2: With hydrogenchloride In water pH=1;
91%
With sodium hydroxide In ethanol Reflux;88%
With sodium hydroxide In ethanol; water Reflux;88%
3926-62-3

sodium monochloroacetic acid

106-48-9

4-chloro-phenol

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 105℃; for 5h;85%
Stage #1: 4-chloro-phenol With sodium hydroxide In ethanol; water at 20℃; for 0.333333h;
Stage #2: sodium monochloroacetic acid In ethanol; water at 102℃; for 5h;
77%
With sodium hydroxide In ethanol; water for 1h; Reflux;74.6%
4841-22-9

(4-chloro-phenoxy)-acetic acid methyl ester

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 0℃; for 2.5h; Reflux;95.6%
With water; sodium hydroxide In ethanol at 0℃; for 2.58333h; Reflux;95.6%
With water; sodium hydroxide In ethanol at 0℃; Reflux;95.6%
79-08-3

bromoacetic acid

106-48-9

4-chloro-phenol

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane; mineral oil at 0 - 100℃; for 3h; Inert atmosphere; Cooling with ice;60.3%
96-32-2

bromoacetic acid methyl ester

106-48-9

4-chloro-phenol

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
Stage #1: bromoacetic acid methyl ester; 4-chloro-phenol With caesium carbonate In acetone at 20℃; for 12h;
Stage #2: With potassium hydroxide; water In tetrahydrofuran at 20℃; for 12h;
Stage #1: bromoacetic acid methyl ester; 4-chloro-phenol With caesium carbonate In acetone at 20℃; for 12h;
Stage #2: With potassium hydroxide In tetrahydrofuran; water at 20℃; for 12h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;
Stage #1: bromoacetic acid methyl ester; 4-chloro-phenol With potassium phosphate In acetone at 60 - 95℃; for 18h;
Stage #2: With sodium hydroxide In acetone for 1h;
1892-43-9

2-(4-chlorophenoxy)ethanol

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
With oxygen; molybdenum(VI) oxide In water at 80℃; under 750.075 Torr;187.16 g

isooctyl 4-chlorophenoxyacetate

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
With phosphoric acid at 120℃; for 3h;186.29 g
Stage #1: isooctyl 4-chlorophenoxyacetate With phosphoric acid at 120℃; for 3h;
Stage #2: With water
185.92 g
With phosphoric acid at 120℃; for 3h; Large scale;1821.1 g
With phosphoric acid at 120℃; for 3h; Large scale;1857.9 g
105-39-5

chloroacetic acid ethyl ester

106-48-9

4-chloro-phenol

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
Stage #1: chloroacetic acid ethyl ester; 4-chloro-phenol With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 0.0666667h; Microwave irradiation;
Stage #2: With sodium hydroxide In water; N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;
Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; pH=6;
91%
Stage #1: chloroacetic acid ethyl ester; 4-chloro-phenol With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 0.0666667h; Microwave irradiation;
Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide for 0.0833333h; Microwave irradiation;
91%
106-48-9

4-chloro-phenol

122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH solution; isopropyl alcohol
2: aq. NaOH solution
View Scheme
Multi-step reaction with 2 steps
1: K2CO3 / acetone
2: aq. KOH
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetone / 14 h / Reflux
2.1: sodium hydroxide / tetrahydrofuran / 2 h / Reflux
2.2: pH 1
View Scheme

4-Chlorophenoxyacetic acid Uses

 4-Chlorophenoxyacetic acid (CAS NO.122-88-3) is plant growth hormone. It is used as growth regulators, fruit drop prevention and herbicides. It also can be used as pharmaceutical intermediates.

4-Chlorophenoxyacetic acid Consensus Reports

Reported in EPA TSCA Inventory.

4-Chlorophenoxyacetic acid Specification

The 4-Chlorophenoxyacetic acid, with the CAS registry number 122-88-3, is also known as (p-Chlorophenoxy)acetic acid. It belongs to the product categories of Pharmaceutical Raw Materials; Phenoxyacetic Acids and Alcohols (substituted); Organic acids; Auxins; Biochemistry; Plant Growth Regulators. Its EINECS number is 204-581-3. This chemical's molecular formula is C8H7ClO3 and molecular weight is 186.59. What's more, its systematic name is (4-Chlorophenoxy)acetic acid. Its classification codes are: (1)Agricultural Chemical; (2)Drug / Therapeutic Agent; (3)Growth regulator / Fertilizer; (4)Mutation data. This chemical is harmful if swallowed. When using it, you should not breathe dust. It is a synthetic pesticide similar to chemicals in a group of plant hormones called auxins. Esterized with dimethylethanolamine (DMAE) it forms centrophenoxine.

Physical properties of 4-Chlorophenoxyacetic acid are: (1)ACD/LogP: 1.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.73; (4)ACD/LogD (pH 7.4): -1.99; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 46.53 Å2; (13)Index of Refraction: 1.558; (14)Molar Refractivity: 44.024 cm3; (15)Molar Volume: 136.519 cm3; (16)Polarizability: 17.452×10-24cm3; (17)Surface Tension: 49.1 dyne/cm; (18)Density: 1.367 g/cm3; (19)Flash Point: 144.399 °C; (20)Enthalpy of Vaporization: 58.741 kJ/mol; (21)Boiling Point: 315.151 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 4-chloro-phenol and chloroacetic acid by irradiation. This reaction will need reagent aq. NaOH with the reaction time of 5 min. This reaction will also need catalyst n-C12H25N(C2H5)3Br. The yield is about 96%.

4-Chlorophenoxyacetic acid can be prepared by 4-chloro-phenol and chloroacetic acid by irradiation

Uses of 4-Chlorophenoxyacetic acid: it can be used to produce 2-(4-chloro-phenoxy)-N-(4-methyl-pent-3-enyl)-acetamide. It will need reagents POCl3, Et3N and solvent CH2Cl2. The yield is about 68.5%.

4-Chlorophenoxyacetic acid can be used to produce 2-(4-chloro-phenoxy)-N-(4-methyl-pent-3-enyl)-acetamide

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc(OCC(=O)O)cc1
(2)Std. InChI: InChI=1S/C8H7ClO3/c9-6-1-3-7(4-2-6)12-5-8(10)11/h1-4H,5H2,(H,10,11)
(3)Std. InChIKey: SODPIMGUZLOIPE-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 680mg/kg (680mg/kg)   Chimica Therapeutica. Vol. 5, Pg. 211, 1970.
rat LD50 oral 850mg/kg (850mg/kg)   Residue Reviews. Vol. 10, Pg. 97, 1965.

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