94-81-5

Basic information

• Product Name: MCPB
• Synonyms: 2m4khm;2m-4kh-m;2M-4XM;2-methyl-4-chlorophenoxybutyricacid;2-methyl-4-chlorophenoxygamma-butyricacid;3-Phenoxybutyric acid;4-((4-chloro-o-tolyl)oxy)-butyricaci;4-(2-Methyl-4-chlorphenoxy)-buttersaeure
• CAS NO: 94-81-5
• Molecular Formula: C₁₁H₁₃ClO₃
• Molecular Weight: 228.67
• EINECS: 202-365-3
• Product Categories: Miscellaneous
• Mol File: 94-81-5.mol

Chemical Properties

• Melting Point: 101-102℃ (ligroine )
• Boiling Point: 327.31°C (rough estimate)
• Flash Point: 191.5°C
• Appearance: /
• Density: 1.2076 (rough estimate)
• Vapor Pressure: 2.39E-05mmHg at 25°C
• Refractive Index: 1.4530 (estimate)
• Storage Temp.: 0-6°C
• PKA: 4.58±0.10(Predicted)
• Water Solubility: 44mg/L(room temperature)
• BRN: 2215202
• CAS DataBase Reference: MCPB(CAS DataBase Reference)
• NIST Chemistry Reference: MCPB(94-81-5)
• EPA Substance Registry System: MCPB(94-81-5)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• RTECS: ES8575000
• Hazardous Substances Data: 94-81-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless crystal; melts at 100 °C (212 °F);practically insoluble in water (44 mg/L at25 °C/77 °F); readily dissolves in most organicsolvents.

Uses

Different sources of media describe the Uses of 94-81-5 differently. You can refer to the following data:
1. MCPB is used for research regarding herbicides to control weed in crop field.
2. Herbicide.

Definition

ChEBI: A monocarboxylic acid that is butyric acid substituted by a 2-methyl-4-chlorophenoxy group at position 4.

Hazard

Toxic by ingestion.

Health Hazard

MCPB is structurally similar to 2,4-DB,except one methyl group substituting a Clatom in the ring. Toxic properties and thesymptoms are similar to 2,4-DB. It is mod-erately toxic by ingestion and possibly otherroutes of exposure. Skin contact can causeirritation.LD50 oral (rat): 680 mg/kgLD50 oral (mouse): 800 mg/kg.

Agricultural Uses

Herbicide: A metabolite of MCPA (see above). MCPB is a phenoxy herbicide produced as a sodium salt and an acid. Herbicide registered for use on peas prior to flowering. There are no residential uses of MCBP. Target organisms: post-emergence control of Canadian thistle, buttercup, mustard, purslane, ragweed, common lambsquarters, pigweed, smartweed, sowthistle, morning glory and other broad leaf weeds[83] .

Trade name

2 M-4Kh-M; 2M4KhM; 2 M-4XM; 4MCPB; BEXANE; BEXONE; U46 MCPB; LEGUMEX; PDQ; THITROL; TRIFOLEX; TRITROL; TROTOX

InChI:InChI=1/C11H13ClO3/c1-3-9(11(13)14)15-10-5-4-8(12)6-7(10)2/h4-6,9H,3H2,1-2H3,(H,13,14)

Upstream product

• 96-48-0 4-butanolide 
• 52106-86-2 sodium 4-chloro-2-methyl-phenolate 
• 95-48-7 ortho-cresol 
• 56359-11-6 4-o-tolyloxybutyric acid ethyl ester 
• 93840-66-5 4-chloro-2-methylphenoxybutyric acid isooctyl ester 
• 10443-70-6 ethyl 4-(4-chloro-2-methylphenoxy)butyrate 
• 1570-64-5 2-methyl-4-chlorophenol 
• 124-38-9 carbon dioxide 
• 50912-62-4 1-(3-bromopropoxy)-4-chloro-2-methylbenzene 
• 584-08-7 potassium carbonate 

Downstream Products

• 1617-90-9 vincamin 
• 84596-52-1 5-(4-chlorophenyl)-2-pyridylamine-1-oxide 

Relevant articles and documents

A method for preparing chloro-benzene oxygen carboxylic acid (by machine translation)

The invention provides a method for preparing carboxylic acid chloro-benzene oxygen, comprising the following steps: S1) phenoxy fatty alcohol in the catalyst B A and under the action of the catalyst, and the chlorinating agent to 2 bit and/or 4 bit selective chlorination reaction, to obtain chloro-benzene oxygen fatty alcohol; said catalyst A is Lewis acid; said catalyst B is C5 - 22 of the thioether, thiazole, isothiazole, thiophene or their halogenated derivatives; S2) [...] fatty alcohol and water, under the action of a catalyst, and an oxidizing agent for the selective catalytic oxidation reaction, get chloro-benzene oxygen carboxylic acid. The invention through the re-design of the process route, the catalyst and the chlorinating agent fine screening, effectively reduces the energy consumption, the selectivity of the dichloride to improve at the same time avoiding the losses of the active ingredient, the resulting chloro-benzene oxygen carboxylic acid content can be up to 98.5% or more, the total yield can be up to 99% or more. (by machine translation)

A phenoxy carboxylic acid herbicide preparation method (by machine translation)

The invention provides a phenoxy carboxylic acid herbicide preparation method, including: S1, will be [...], alkaline substance mixed with the chlorinated carboxylic acid ester, in the one-pot condensation reaction in anhydrous system, phenoxy carboxylic acid ester obtained; the ClR states the chloro- carboxylic acid ester of the formula is1 COOR, R1 Is C1 - 3 alkylene or alkylidene, R is C1 - 10 alkyl or C3 - 10 cycloalkyl; S2, the [...] ester in the 1st and 2nd catalyst under the action of a catalyst, with the chlorinating agent to carry out the selective chlorination of, get [...] ester; the Lewis acid catalyst is selected from 1st, 2nd catalyst is C5 - 22 of the thioether compound, thiazole compound, isothiazole compound or thiophene compound; S3, will the [...] ester to acid hydrolysis reaction, as shown in formula I phenoxy carboxylic acid herbicide, R3 Is H, Cl or CH3 . This invention can improve the quality of the products and the operating environment of production, three waste low. (by machine translation)

Preparation method of phenoxycarboxylic acid herbicide

The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out reaction of anhydrous phenol with an active metalto form phenoxide, and carrying out condensation reaction of the phenoxide with chlorocarboxylic ester to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula ofClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 of cycloalkyl; S2, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent in the presence of a first catalyst and a second catalyst to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H,Cl or CH3. The preparation method can improve the product quality and the operation environment of the production site, and has low quantity of three wastes.

Preparation method of phenoxy carboxylic acid herbicide

The invention provides a preparation method of a phenoxy carboxylic acid herbicide, comprising the following steps: S1, carrying out a condensation reaction between a phenolic compound and hydroxycarboxylic ester under the action of a catalyst so as to obtain phenoxycarboxylic ester, wherein the catalyst is one or more of protonic acid, solid acid and a supported catalyst; S2, carrying out 2- and/or 4- selecting chlorination reaction between phenoxycarboxylic ester and a chloridizing agent in the presence of a first catalyst and a second catalyst, so as to obtain chlorinated phenoxycarboxylicester, wherein the first catalyst is selected from Lewis acid, and the second catalyst is selected from a C5-C22 thioether compound, a C5-C22 thiazole compound, a C5-C22 isothiazole compound or a C5-C22 thiophene compound; and S3, carrying out an acidolysis reaction on chlorinated phenoxycarboxylic ester so as to obtain the phenoxy carboxylic acid herbicide. By the method, product quality and thelive environment of production can be improved, and ''three wastes (waste gas, waste water and industrial residue)'' are minimized.

Preparation method of phenoxycarboxylic acid herbicide

The invention provides a preparation method of a phenoxycarboxylic acid herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol withchlorocarboxylic ester under the action of an alkaline substance to obtain phenoxycarboxylic ester, wherein the chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, and R is C1-10 alkyl or C3-10 cycloalkyl; S2, carrying out selective chlorination of phenoxycarboxylic ester with a chlorinating agent under the action of a first catalyst and a second catalyst, to obtain chlorobenzoxycarboxylic ester, wherein the first catalyst is selected from Lewis acid, the second catalyst is C5-22 thioether compounds, thiazole compounds, isothiazole compounds or thiophene compounds; and S3, carrying out acidolysis reaction of chlorobenzoxycarboxylic ester, to obtain the phenoxycarboxylic acid herbicide represented by the formula I, wherein R3 is H, Cl or CH3. The preparation method can improve the product quality and the operation environment of a production site, and has low quantity of three wastes.

Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis

We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.

Synthesis and Herbicidal Activity of α-(Substituted Phenoxybutyryloxy or Valeryloxy)alkylphosphonates and 2-(Substituted Phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

On the basis of our work on the modification of alkylphosphonates 1, a series of α-(substituted phenoxybutyryloxy or valeryloxy)alkylphosphonates (4-5) and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one (6) were designed and synthesized. The bioassay results indicated that 14 of title compounds 4 exhibited significant postemergence herbicidal activity against velvetleaf, common amaranth, and false daisy at 150 g ai/ha. Compounds 5 were inactive against all tested weeds. Compounds 6 exhibited moderate to good inhibitory effect against the tested dicotyledonous weeds. Structure-activity relationship (SAR) analyses showed that the length of the carbon chain as linking bridge had a great effect on the herbicidal activity. Broad-spectrum tests of compounds 4-1, 4-2, 4-9, 4-30, and 4-36 were carried out at 75 g ai/ha. Especially, 4-1 exhibited 100% inhibition activity against the tested dicotyledonous weeds, which was higher than that of glyphosate.

Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2

A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atmospheric pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids.

Active substances for increasing the stress defense in plants to abiotic stress, and methods of finding them

The invention relates to a method of finding compounds which increase the tolerance of plants to abiotic stress factors acting on this plant, such as, for example, temperature (such as chill, frost or heat), water (such as dryness, drought or anoxia), or the chemical load (such as lack of or excess of mineral salts, heavy metals, gaseous noxious substances) by increasing the expression of plant-endogenous proteins, and to the use of these compounds for increasing the tolerance in plants to abiotic stress factors.

Herbicides comprising benzoylcyclohexanediones and safeners

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