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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 | Hazard Symbols | Xn,Xi | ||
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 |
Conditions | Yield |
---|---|
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% |
ethyl p-chlorophenoxyacetate
4-Chlorophenoxyacetic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium hydride In 1,4-dioxane; mineral oil at 0 - 100℃; for 3h; Inert atmosphere; Cooling with ice; | 60.3% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With oxygen; molybdenum(VI) oxide In water at 80℃; under 750.075 Torr; | 187.16 g |
4-Chlorophenoxyacetic acid
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 (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.
Reported in EPA TSCA Inventory.
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%.
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%.
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. |