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120116-88-3

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120116-88-3 Usage

Uses

Different sources of media describe the Uses of 120116-88-3 differently. You can refer to the following data:
1. Cyazofamid is a imidazole fungicide for use on food crops.
2. Agricultural fungicide.

Definition

ChEBI: A member of the class of imidazoles carrying dimethylsulfamyl, cyano, chloro and 4-tolyl substituents at positions 1, 2, 4 and 5 respectively. A fungicide used mainly for controlling Oomycete and Plasmodiophora diseases on potatoe and tomatoes. It is a skin and eye irritant and is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.

Check Digit Verification of cas no

The CAS Registry Mumber 120116-88-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,1,1 and 6 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 120116-88:
(8*1)+(7*2)+(6*0)+(5*1)+(4*1)+(3*6)+(2*8)+(1*8)=73
73 % 10 = 3
So 120116-88-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H13ClN4O2S/c1-9-4-6-10(7-5-9)12-13(14)16-11(8-15)18(12)21(19,20)17(2)3/h4-7H,1-3H3

120116-88-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name cyazofamid

1.2 Other means of identification

Product number -
Other names Cyazofamid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:120116-88-3 SDS

120116-88-3Synthetic route

5-chloro-4-(4-methylphenyl)-1H-imidazole-2-carbonitrile
120118-14-1

5-chloro-4-(4-methylphenyl)-1H-imidazole-2-carbonitrile

dimethylamino sulfonyl chloride
13360-57-1

dimethylamino sulfonyl chloride

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
With potassium carbonate In ethyl acetate for 3h; Reflux;96.2%
With potassium carbonate In ethyl acetate for 6h; Solvent; Reflux;94%
With potassium carbonate In cyclohexane; ethyl acetate Concentration; Solvent; Reflux;86%
With potassium carbonate In ethyl acetate Reflux;
With potassium carbonate In ethyl acetate at 75℃; for 10.5h;68 g
C13H14N4O2S

C13H14N4O2S

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
With N-chloro-succinimide In acetonitrile at 20℃; for 4h; Time;95%
5-(4'-methylphenyl)imidazole-2-carboxylic acid

5-(4'-methylphenyl)imidazole-2-carboxylic acid

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: thionyl chloride / 5 h / 85 °C / Cooling with ice
2: ammonia / methanol / 36 h / 0 °C
3: thionyl chloride / 12 h / 85 °C
4: N-chloro-succinimide / acetonitrile / 3 h / 25 °C
5: potassium carbonate / ethyl acetate / 6 h / Reflux
View Scheme
5-(4'-methylphenyl)imidazole-2-carboxylic acid ethyl ester

5-(4'-methylphenyl)imidazole-2-carboxylic acid ethyl ester

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ammonia / methanol / 36 h / 0 °C
2: thionyl chloride / 12 h / 85 °C
3: N-chloro-succinimide / acetonitrile / 3 h / 25 °C
4: potassium carbonate / ethyl acetate / 6 h / Reflux
View Scheme
C11H11N3O

C11H11N3O

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 12 h / 85 °C
2: N-chloro-succinimide / acetonitrile / 3 h / 25 °C
3: potassium carbonate / ethyl acetate / 6 h / Reflux
View Scheme
para-methylacetophenone
122-00-9

para-methylacetophenone

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: selenium(IV) oxide / 1,4-dioxane; water / 5 h / 50 - 110 °C
2: hydroxylamine hydrochloride / water; methanol / 2 h / Reflux
3: thionyl chloride / ethyl acetate / 3 h / Reflux
4: potassium carbonate / ethyl acetate / 3 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: acetic acid; bromine / 7 h / 42 °C
2.1: hydroxylamine / methanol / 12 h / 50 °C
3.1: ammonia / methanol / 32 h / 0 °C
3.2: 10 h / 88 °C
3.3: 2.5 h / 28 °C
4.1: potassium carbonate / ethyl acetate / Reflux
View Scheme
4-methylphenylglyoxal
1075-47-4

4-methylphenylglyoxal

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride / water; methanol / 2 h / Reflux
2: thionyl chloride / ethyl acetate / 3 h / Reflux
3: potassium carbonate / ethyl acetate / 3 h / Reflux
View Scheme
2,2-dibromo-1-(4-methylphenyl)ethanone
13664-98-7

2,2-dibromo-1-(4-methylphenyl)ethanone

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydroxylamine / methanol / 12 h / 50 °C
2.1: ammonia / methanol / 32 h / 0 °C
2.2: 10 h / 88 °C
2.3: 2.5 h / 28 °C
3.1: potassium carbonate / ethyl acetate / Reflux
View Scheme
1-hydroxy-4-(4-methylphenyl)-3-oxide-1H-imidazole-2-carboxaldehyde oxime

1-hydroxy-4-(4-methylphenyl)-3-oxide-1H-imidazole-2-carboxaldehyde oxime

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium metabisulfite / N,N-dimethyl acetamide; acetonitrile / 4 h / 80 - 105 °C
2: sulfuryl dichloride / N,N-dimethyl acetamide; acetonitrile / 20 - 25 °C
3: potassium carbonate / ethyl acetate / 10.5 h / 75 °C
View Scheme
4(5)-(4-tolyl)-1H-imidazole
670-91-7

4(5)-(4-tolyl)-1H-imidazole

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide
120116-88-3

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / ethyl acetate / 6 h / 77 °C
2: copper(l) iodide; dipotassium peroxodisulfate / N,N-dimethyl-formamide / 12 h / 110 °C
3: N-chloro-succinimide / acetonitrile / 4 h / 20 °C
View Scheme

120116-88-3Downstream Products

120116-88-3Relevant articles and documents

Preparation method of cyazofamid

-

Paragraph 0019; 0024; 0025; 0026-0032; 0033-0039, (2019/01/06)

The invention discloses a preparation method of cyazofamid, comprising the following steps: carrying out a reaction on 5-(para-toluene)-1H-imidazole, anhydrous potassium carbonate, ethyl acetate and N,N-dimethylamino sulfonyl chloride at 50-77 DEG C for 6-12 h, cooling to room temperature, washing with water, extracting, drying, evaporating to remove ethyl acetate to obtain an intermediate A crudeproduct, and recrystallizing to obtain an intermediate A; (2) carrying out a reaction on the intermediate A, copper salt, a cyanation reagent, an oxidizing agent and N,N-dimethylformamide at 110-130DEG C for 6-12 h, cooling to room temperature, recovering N,N-dimethylformamide, washing with water, extracting, drying, evaporating to remove ethyl acetate to obtain an intermediate B crude product,and recrystallizing to obtain an intermediate B; and (3) stirring and carrying out a reaction on the intermediate B, N-chlorosuccinimide and acetonitrile at room temperature for 2-6 h, recovering thesolvent acetonitrile after the reaction, neutralizing to neutral level by adding a sodium bicarbonate solution, extracting, drying, evaporating to remove ethyl acetate to obtain a cyazofamid crude product, and recrystallizing to obtain cyazofamid. The preparation method of the invention has high reaction yield and good selectivity.

Synthesis method of cyazofamid

-

, (2018/04/01)

The invention discloses a synthesis method of cyazofamid. The synthesis method of cyazofamid comprises the following steps: synthesizing 2,2-halogenated-4'-methyl acetophenone; synthesizing 1-hydroxy-4-(4-methyl phenyl)-2-oxime imidazole-3-oxide; synthesizing 2-cyan-4-chlorine-5-(4'-methyl phenyl)imidazole; adding methanol into 1-hydroxy-4-(4-methyl phenyl)-2-oxime imidazole-3-oxide, performing ice-water bath reaction, adding sulfoxide chloride, performing temperature-rising reaction, adding acetonitrile and N-chlorosuccinimide, and performing reaction; and synthesizing cyazofamid: adding 2-cyan-4-chlorine-5-(4'-methyl phenyl)imidazole, anhydrous potassium carbonate, ethyl acetate and N,N-dimethylsulfamoyl chloride into a reaction kettle, and performing refluxing reaction. The synthesis method of cyazofamid has the advantages of rich raw material source, easily available raw materials, low cost, mild reaction condition, no need of special equipment, high economic property, high total yield and good industrialized prospect.

A 4-chloro-2-cyano-N, N-dimethyl-5 - (4 the [...] -methyl-phenyl) - 1H-imidazole-1-sulfonamide synthesis method

-

, (2017/01/02)

The invention discloses a synthesis method of 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide (cyazofamid). According to the synthesis method, methylacetophenone is taken as a raw material, selenium dioxide is used for oxidation to prepare an intermediate, namely 2-carbonyl-2-p-benzyl aldehyde, then N,N-dimethylformamide and the like are taken as solvents, thionyl chloride is taken as a chlorinating agent and reducing agent for preparing the intermediate, and then intermediate further reacts with N,N-dimethyl sulfonamide chloride to synthesize the cyazofamid. Compared with the prior art, the synthesis method has the advantages that the reaction period is shortened, the post-treatment process is simplified and the synthesis method is suitable for mass industrial production.

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