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| CAS No.: | 122-88-3 | |
|---|---|---|
| Name: | 4-Chlorophenoxyacetic acid | |
| Article Data: | 121 | |
| Molecular Structure: | ||
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| Formula: | C8H7ClO3 | |
| Molecular Weight: | 186.595 | |
| 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)-; | |
| EINECS: | 204-581-3 | |
| Density: | 1.367 g/cm3 | |
| Melting Point: | 157-159 °C | |
| Boiling Point: | 315.151 °C at 760 mmHg | |
| Flash Point: | 144.399 °C | |
| Solubility: | Slightly soluble in water | |
| Appearance: | white to light beige powder | |
| Hazard Symbols: |
 Xn, Xi
|
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| Risk Codes: | 22 | |
| Safety: | 22 | |
| PSA: | 46.53000 | |
| LogP: | 1.80340 | |
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| 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% |
- 14426-42-7
ethyl p-chlorophenoxyacetate
- 122-88-3
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 |
- 122-88-3
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 |
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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.
Consensus Reports
Reported in EPA TSCA Inventory.
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%.
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. |