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119851-28-4

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119851-28-4 Usage

Uses

This compound serves as a reactant in the prepn. of a fungicide that targets plant pathogenic fungi.

Check Digit Verification of cas no

The CAS Registry Mumber 119851-28-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,8,5 and 1 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 119851-28:
(8*1)+(7*1)+(6*9)+(5*8)+(4*5)+(3*1)+(2*2)+(1*8)=144
144 % 10 = 4
So 119851-28-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H10Cl2O2/c1-9(17)13-7-6-12(8-14(13)16)18-11-4-2-10(15)3-5-11/h2-8H,1H3

119851-28-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-[2-Chloro-4-(4-chlorophenoxy)phenyl]ethan-1-one

1.2 Other means of identification

Product number -
Other names 4-Acetyl-3,4'-dichlorodiphenyl Ether

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:119851-28-4 SDS

119851-28-4Synthetic route

2'-chloro-4'-fluoroacetophenone
700-35-6

2'-chloro-4'-fluoroacetophenone

4-chloro-phenol
106-48-9

4-chloro-phenol

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 115℃; for 8h;90%
With potassium carbonate In N,N-dimethyl-formamide for 48h; Reflux;
1-bromo-2-chloro-4-(4-chlorophenoxy)benzene
1419873-85-0

1-bromo-2-chloro-4-(4-chlorophenoxy)benzene

acetyl chloride
75-36-5

acetyl chloride

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride; isopropylmagnesium bromide; copper(l) chloride
3,4'-Dichlorobiphenyl ether
6842-62-2

3,4'-Dichlorobiphenyl ether

acetyl chloride
75-36-5

acetyl chloride

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In 1,2-dichloro-ethane at 10 - 50℃;
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

C22H16Cl2O3

C22H16Cl2O3

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-bromo-1-(2-chloro-4-(4-chlorophenoxy)phenyl)ethanone
906005-51-4

2-bromo-1-(2-chloro-4-(4-chlorophenoxy)phenyl)ethanone

Conditions
ConditionsYield
With bromine In diethyl ether95.8%
With 1-butyl-3-methylimidazolium tribromide In neat (no solvent) for 0.2h;87.8%
With phenyltrimethylammonium tribromide In tetrahydrofuran at 0 - 20℃; for 20h;75%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2,6-dichlorobenzaldehyde
83-38-5

2,6-dichlorobenzaldehyde

C21H12Cl4O2

C21H12Cl4O2

Conditions
ConditionsYield
92.7%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

3,4-dichlorobenzaldehyde
6287-38-3

3,4-dichlorobenzaldehyde

C21H12Cl4O2

C21H12Cl4O2

Conditions
ConditionsYield
91.2%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

benzaldehyde
100-52-7

benzaldehyde

C21H14Cl2O2
338777-09-6

C21H14Cl2O2

Conditions
ConditionsYield
90%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

trimethylsulfonium methylsulfate
2181-44-4

trimethylsulfonium methylsulfate

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methyloxirane

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methyloxirane

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 60℃;86.5%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

C21H12Cl4O2

C21H12Cl4O2

Conditions
ConditionsYield
85.5%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

C21H16Cl2O5S
1034188-96-9

C21H16Cl2O5S

Conditions
ConditionsYield
With Dess-Martin periodane In acetonitrile for 4.5h; Reflux;84%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

C21H13Cl3O2

C21H13Cl3O2

Conditions
ConditionsYield
81.2%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

1-[2-Chloro-4-(4-chloro-phenoxy)-phenyl]-ethylamine

1-[2-Chloro-4-(4-chloro-phenoxy)-phenyl]-ethylamine

Conditions
ConditionsYield
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 15h;79%
methanesulfonic acid
75-75-2

methanesulfonic acid

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[2-chloro-4 (4-chlorophenoxy)phenyl]-2-oxo-ethyl methanesulfonate
1034188-94-7

2-[2-chloro-4 (4-chlorophenoxy)phenyl]-2-oxo-ethyl methanesulfonate

Conditions
ConditionsYield
With Dess-Martin periodane In acetonitrile for 4.5h; Reflux;75%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

C22H16Cl2O2

C22H16Cl2O2

Conditions
ConditionsYield
73.6%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

C21H13Cl2FO2

C21H13Cl2FO2

Conditions
ConditionsYield
58.6%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

3-(4-chlorophenoxy)benzo[4,5]thieno[2,3-b]quinoxaline

3-(4-chlorophenoxy)benzo[4,5]thieno[2,3-b]quinoxaline

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; sulfur In dimethyl sulfoxide at 120℃; for 2h;52%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-chloro-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone

2-chloro-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone

Conditions
ConditionsYield
With sulfuryl dichloride In methanol; dichloromethane at 20℃; for 64h; Reflux;49%
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

C18H19Cl2NO3
1160554-11-9

C18H19Cl2NO3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: copper(ll) bromide / ethanol / 6 h / Reflux
2: 1-methyl-pyrrolidin-2-one / 2 h / 60 °C
3: formic acid / 18 h / 180 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

C18H20BrCl2NO4

C18H20BrCl2NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(ll) bromide / ethanol / 6 h / Reflux
2: 1-methyl-pyrrolidin-2-one / 2 h / 60 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[(2-chloro-4-(4-chlorophenoxy)phenyl)morpholino-4-yl]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-acetate hydrochloride
1243257-37-5

2-[(2-chloro-4-(4-chlorophenoxy)phenyl)morpholino-4-yl]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-acetate hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: copper(ll) bromide / ethanol / 6 h / Reflux
2: 1-methyl-pyrrolidin-2-one / 2 h / 60 °C
3: formic acid / 18 h / 180 °C
4: triethylamine / tetrahydrofuran / 6 h / 20 °C
View Scheme
1,2,4-Triazole
288-88-0

1,2,4-Triazole

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-yl-ethanone
136815-80-0

1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-yl-ethanone

Conditions
ConditionsYield
Stage #1: 1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one With bromine
Stage #2: 1,2,4-Triazole
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

Reaxys ID: 23327348

Reaxys ID: 23327348

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bromine
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-(1-[1,2,4]triazol-1-yl)pentan-2-ol
1419875-35-6

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-(1-[1,2,4]triazol-1-yl)pentan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine
2.1: magnesium bromide diethyl etherate / dichloromethane / 1.5 h / 20 °C
2.2: 2 h / 0 - 20 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-([1,2,4]-triazol-1-yl)pent-3-yn-2-ol
1419875-41-4

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-([1,2,4]-triazol-1-yl)pent-3-yn-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine
2.1: lanthanium (III) chloride bis(lithium chloride) complex / tetrahydrofuran / 1 h / 20 °C
2.2: 1 h / 20 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)hexan-2-ol
1419875-37-8

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)hexan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine; acetic acid / tert-butyl methyl ether / 1 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h
2.2: 2.5 h
3.1: magnesium bromide ethyl etherate / dichloromethane / 1 h / 20 °C
3.2: 2 h / 0 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-hexyl]-1,2,4-triazole
1423010-69-8

1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-hexyl]-1,2,4-triazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: bromine; acetic acid / tert-butyl methyl ether / 1 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h
2.2: 2.5 h
3.1: magnesium bromide ethyl etherate / dichloromethane / 1 h / 20 °C
3.2: 2 h / 0 °C
4.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C
4.2: 3 h / 195 °C / Microwave irradiation
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-yl-ethanone
136815-80-0

1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-yl-ethanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine; acetic acid / tert-butyl methyl ether / 1 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h
2.2: 2.5 h
View Scheme
Multi-step reaction with 2 steps
1.1: bromine; acetic acid / tert-butyl methyl ether / 1 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h
2.2: 2.5 h
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-but-3-enyl]-1,2,4-triazole
1423016-05-0

1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-but-3-enyl]-1,2,4-triazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: bromine; acetic acid / tert-butyl methyl ether / 1 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h
2.2: 2.5 h
3.1: magnesiumbromide etherate / dichloromethane / 1 h / 20 °C
3.2: 2 h / -15 °C
4.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C
4.2: 10 h / Reflux
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)but-3-en-2-ol
1419875-43-6

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)but-3-en-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine; acetic acid / tert-butyl methyl ether / 1 h / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h
2.2: 2.5 h
3.1: magnesiumbromide etherate / dichloromethane / 1 h / 20 °C
3.2: 2 h / -15 °C
View Scheme
1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one
119851-28-4

1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol
1159001-34-9

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / dimethyl sulfoxide; tetrahydrofuran / 1 h / 5 - 20 °C
2: sodium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 110 °C
View Scheme

119851-28-4Relevant articles and documents

Design, synthesis, herbicidal activity, and the molecular docking study of novel diphenyl ether derivatives as protoporphyrinogen IX oxidase inhibitors

Fu, Ying,Gao, Shuang,Hu, Jia-Jun,Peng, Jian-Feng,Wang, Zhi-Xin,Ye, Fei,Yin, Min-Lei,Zhao, Li-Xia,Zou, Yue-Li

, (2022/03/02)

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is an important herbicide target. In this study, a series of novel diphenyl ethers derivatives with 2-pyrrolidone structure were developed as PPO inhibitors. Thereinto, compound H7 (IC50 = 0.0262 mg/L) has better PPO enzyme inhibitory activity than commercial herbicide oxyfluorfen (IC50 = 0.0426 mg/L). Greenhouse herbicidal activity experiments exhibited that even under the condition of 37.5 g ai/ha, H7 still had excellent broad-spectrum herbicidal activity. Moreover, rice, peanut, and cotton had strong tolerance to H7 at 300 g ai/ha. Field trial showed that H7 had comparable herbicidal activity to oxyfluorfen. These experimental results indicated that H7 could be developed as a novel PPO Inhibitor candidate for weed control in the field.

Method for synthesizing high-purity difenoconazole

-

Paragraph 0003; 0004; 0006; 0017-0021, (2021/02/10)

The invention discloses a method for synthesizing high-purity difenoconazole, which comprises the following steps: 1) carrying out acylation reaction on 3,4'-dichlorodiphenyl ether to obtain an intermediate I; 2) performing cyclization reaction on the intermediate I to obtain an intermediate II; 3) brominating 1,2,4-triazole to prepare a 1,2,-4-triazole bromide; 4) carrying out bromination reaction on the intermediate II and 1,2,4-triazole bromide to obtain an intermediate III and triazole, and carrying out condensation reaction on the intermediate III and 1,2,4-triazole under the action of potassium hydroxide to obtain a difenoconazole crude product; and 5) refining the difenoconazole crude product to obtain a difenoconazole refined product. The method is low in cost, high in quality andhigh in yield, dibromo and hydrolysis byproducts are hardly generated, and the product content and appearance quality of the difenoconazole refined product are improved.

FUNGICIDAL SUBSTITUTED 1-{2-CYCLYLOXY-2-[2-HALO-4-(4-HALOGEN-PHENOXY)-PHENYL]-ETHYL}-1H-[1,2,4]TRIAZOLE COMPOUNDS

-

Page/Page column 85, (2013/03/26)

The present invention relates to substituted 1-{2-cyclyloxy-2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-ethyl}-1H-[1,2,4]triazole compounds of formula I as defined in the description, and the N-oxides, and salts thereof, processes and intermediates for preparing these compounds and also to compositions comprising at least one such compound. The invention also relates to the use of such compounds and compositions for combating harmful fungi and seed coated with at least one such compound.

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