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4136-95-2

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4136-95-2 Usage

Chemical Properties

clear yellow liquid

Uses

2,4,6-Trichlorobenzoyl chloride may be used in the preparation of:γ-lactone and δ-lactonealiphatic aromatic anhydrides, required for the synthesis of amphiphilic hyaluronanmixed anhydride, required for the synthesis of angelate esterssynthesis of both spongistatin 1 and spongistatin 2large-ring lactones in high yields.

Check Digit Verification of cas no

The CAS Registry Mumber 4136-95-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,3 and 6 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4136-95:
(6*4)+(5*1)+(4*3)+(3*6)+(2*9)+(1*5)=82
82 % 10 = 2
So 4136-95-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H2Cl4O/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2H

4136-95-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (T1413)  2,4,6-Trichlorobenzoyl Chloride  >98.0%(GC)(T)

  • 4136-95-2

  • 5g

  • 550.00CNY

  • Detail
  • TCI America

  • (T1413)  2,4,6-Trichlorobenzoyl Chloride  >98.0%(GC)(T)

  • 4136-95-2

  • 25g

  • 2,160.00CNY

  • Detail
  • Alfa Aesar

  • (L14159)  2,4,6-Trichlorobenzoyl chloride, 98%   

  • 4136-95-2

  • 5g

  • 643.0CNY

  • Detail
  • Alfa Aesar

  • (L14159)  2,4,6-Trichlorobenzoyl chloride, 98%   

  • 4136-95-2

  • 25g

  • 2571.0CNY

  • Detail
  • Aldrich

  • (345504)  2,4,6-Trichlorobenzoylchloride  97%

  • 4136-95-2

  • 345504-5G

  • 697.32CNY

  • Detail

4136-95-2Synthetic route

2,4,6-trichlorobenzoic acid
50-43-1

2,4,6-trichlorobenzoic acid

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride
With phosphorus pentachloride
With thionyl chloride
2-Bromo-6-chloro-4-methyl-benzoyl chloride
135365-02-5

2-Bromo-6-chloro-4-methyl-benzoyl chloride

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide for 3h; Heating;
2-bromo-6-chloro-4-methylaniline
135340-78-2

2-bromo-6-chloro-4-methylaniline

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) concd. H2SO4, NaNO2 / 1.) HOAc, 15 deg C, 3 h, 2.) H2O, 35-40 deg C, 1 h
2: 40.8 percent / concd. H2SO4 / 3 h / Heating
3: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h
4: SOCl2, DMF / 3 h / Heating
5: SOCl2, DMF / 3 h / Heating
View Scheme
2-bromo-6-chloro-4-methylbenzonitrile
135340-79-3

2-bromo-6-chloro-4-methylbenzonitrile

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 40.8 percent / concd. H2SO4 / 3 h / Heating
2: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h
3: SOCl2, DMF / 3 h / Heating
4: SOCl2, DMF / 3 h / Heating
View Scheme
2-chloro-6-bromo-4-methylbenzoic acid
135340-36-2

2-chloro-6-bromo-4-methylbenzoic acid

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2, DMF / 3 h / Heating
2: SOCl2, DMF / 3 h / Heating
View Scheme
2-bromo-6-chloro-4-methylbenzamide
135340-80-6

2-bromo-6-chloro-4-methylbenzamide

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h
2: SOCl2, DMF / 3 h / Heating
3: SOCl2, DMF / 3 h / Heating
View Scheme
2-chloro-4-methyl-benzenamine
615-65-6

2-chloro-4-methyl-benzenamine

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Br2, HOAc, 2.) 50percent aq. NaOH / 0.5 h / Ambient temperature
2: 1.) concd. H2SO4, NaNO2 / 1.) HOAc, 15 deg C, 3 h, 2.) H2O, 35-40 deg C, 1 h
3: 40.8 percent / concd. H2SO4 / 3 h / Heating
4: 77.4 percent / concd. HCl, NaNO2, HOAc / H2O / 1.) 5 deg C, 30 min, 2.) 85 deg C, 1 h
5: SOCl2, DMF / 3 h / Heating
6: SOCl2, DMF / 3 h / Heating
View Scheme
2,4,6-Trichlorobenzonitrile
6575-05-9

2,4,6-Trichlorobenzonitrile

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; sulfuric acid; water
2: phosphorus (V)-chloride
View Scheme
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

<3-14C>-cinnamic acid
4469-06-1

<3-14C>-cinnamic acid

C15(14)CH9Cl3O3

C15(14)CH9Cl3O3

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 1h; Ambient temperature;100%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

C27H20Cl3NO5
1160053-32-6

C27H20Cl3NO5

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h;100%
With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 0.166667h; Inert atmosphere;
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid

1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid

2,4,6-trichlorobenzoic 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic anhydride

2,4,6-trichlorobenzoic 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic anhydride

Conditions
ConditionsYield
With potassium carbonate In acetone at 25 - 30℃; for 3h; Product distribution / selectivity; Inert atmosphere;100%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid

1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid

C53H81NO14

C53H81NO14

C68H103NO17

C68H103NO17

Conditions
ConditionsYield
Stage #1: 2,4,6-trichlorobenzoyl chloride; 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid With triethylamine In dichloromethane at 0 - 5℃; for 2h; Inert atmosphere;
Stage #2: C53H81NO14 With dmap In toluene at 20℃; Product distribution / selectivity;
100%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid

1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid

C54H87NO13Si

C54H87NO13Si

C69H109NO16Si

C69H109NO16Si

Conditions
ConditionsYield
Stage #1: 2,4,6-trichlorobenzoyl chloride; 1,5',7,7-tetramethylspiro[bicyclo[2.2.1]heptane-2,2'-[1,3]dioxane]-5'-carboxylic acid With triethylamine In dichloromethane at 0 - 5℃; for 2h; Inert atmosphere;
Stage #2: C54H87NO13Si With dmap In toluene at 20℃; Product distribution / selectivity;
100%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

4-iodo-9H-carbazole

4-iodo-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-iodo-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-iodo-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;100%
3-(1,1-dimethylethyl)-9H-carbazole
22401-74-7

3-(1,1-dimethylethyl)-9H-carbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-3-(1,1-dimethylethyl)-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-(1,1-dimethylethyl)-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;100%
4-chloro-9H-carbazole
3652-88-8

4-chloro-9H-carbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-4-chloro-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-chloro-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;100%
4-Nitro-9H-carbazole
57905-76-7

4-Nitro-9H-carbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-4-nitro-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-nitro-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;100%
4-bromo-9H-carbazole
3652-89-9

4-bromo-9H-carbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-4-bromo-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-bromo-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;100%
N-ethyl-N-hydroxy-ethanamine
3710-84-7

N-ethyl-N-hydroxy-ethanamine

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

N,N-diethyl-O-(2,4,6-trichlorobenzoyl)hydroxylamine

N,N-diethyl-O-(2,4,6-trichlorobenzoyl)hydroxylamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.333333h;100%
10-Nitrooleic Acid
875685-46-4

10-Nitrooleic Acid

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

2,4,6-Trichlorobenzoyl 10-nitrooleate

2,4,6-Trichlorobenzoyl 10-nitrooleate

Conditions
ConditionsYield
Stage #1: 10-Nitrooleic Acid With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 23℃; for 0.25h; Inert atmosphere;
Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 23℃; for 3h; Inert atmosphere;
100%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

2,4,6-trichlorobenzoic acid
50-43-1

2,4,6-trichlorobenzoic acid

Conditions
ConditionsYield
With water; triethylamine In acetone at 20℃; for 18h;99%
With water In acetone at 55℃; Kinetics; Mechanism; Concentration;
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

(E)-((hex-3-en-1-yloxy)methyl)benzene
121441-39-2

(E)-((hex-3-en-1-yloxy)methyl)benzene

C13H13Cl3O2

C13H13Cl3O2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;99%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

1-butyn-4-ol
927-74-2

1-butyn-4-ol

C11H7Cl3O2

C11H7Cl3O2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;99%
3-Nitro-carbazol
3077-85-8

3-Nitro-carbazol

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-3-nitro-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-nitro-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 23℃; for 2h; Inert atmosphere;99%
dibenzoazepine
256-96-2

dibenzoazepine

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

Conditions
ConditionsYield
Stage #1: dibenzoazepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;
98%
3-hexen-1-ol
544-12-7

3-hexen-1-ol

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

C13H13Cl3O2

C13H13Cl3O2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;98%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

4-(trimethylsilyl)-9H-carbazole

4-(trimethylsilyl)-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-trimethylsilyl-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-trimethylsilyl-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;98%
3-(trifluoromethyl)-9H-carbazole
2467-83-6

3-(trifluoromethyl)-9H-carbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-3-trifluoromethyl-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-trifluoromethyl-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;98%
2-hexen-1-ol
2305-21-7

2-hexen-1-ol

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

C13H13Cl3O2

C13H13Cl3O2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;97%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol
1280222-59-4

(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octan-1-ol

(R)-4-((tert-butyldimethylsilyl)oxy)hex-5-ynoic acid

(R)-4-((tert-butyldimethylsilyl)oxy)hex-5-ynoic acid

(R)-(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octyl 4-((tert-butyldimethylsilyl)oxy)hex-5-ynoate

(R)-(S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octyl 4-((tert-butyldimethylsilyl)oxy)hex-5-ynoate

Conditions
ConditionsYield
Stage #1: 2,4,6-trichlorobenzoyl chloride; (R)-4-((tert-butyldimethylsilyl)oxy)hex-5-ynoic acid With triethylamine In toluene for 1h; Inert atmosphere;
Stage #2: (S)-1-[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]octan-1-ol With dmap In toluene for 5h; Inert atmosphere;
96%
10-methoxy-5H-dibenzo[b,f]azepine
4698-11-7

10-methoxy-5H-dibenzo[b,f]azepine

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

10-methoxy-5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

10-methoxy-5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

Conditions
ConditionsYield
Stage #1: 10-methoxy-5H-dibenzo[b,f]azepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;
96%
3-iodocarbazole
16807-13-9

3-iodocarbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-3-iodo-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-iodo-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;96%
3-methoxycarbazole
18992-85-3

3-methoxycarbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-3-methoxy-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-methoxy-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;96%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate
7588-36-5

methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate

methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
1267907-58-3

methyl [1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate

Conditions
ConditionsYield
Stage #1: methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate With potassium hexamethylsilazane In tetrahydrofuran; toluene at 20℃; for 0.0833333h;
Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran; toluene at 20℃; for 2h;
95%
(E) and (Z)-4-cyclohexyl-3-buten-1-ol
865444-41-3

(E) and (Z)-4-cyclohexyl-3-buten-1-ol

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

C17H19Cl3O2

C17H19Cl3O2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;95%
4-methyl-9H-carbazole
3770-48-7

4-methyl-9H-carbazole

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

9-(2,4,6-trichlorobenzoyl)-4-methyl-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-4-methyl-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;95%
2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

3-trimethylsilyl-9H-carbazole

3-trimethylsilyl-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-trimethylsilyl-9H-carbazole

9-(2,4,6-trichlorobenzoyl)-3-trimethylsilyl-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 2h; Inert atmosphere;94%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

2,4,6-trichlorobenzoyl chloride
4136-95-2

2,4,6-trichlorobenzoyl chloride

2,4,6-trichloro-benzenecarboperoxoic acid tert-butyl ester

2,4,6-trichloro-benzenecarboperoxoic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at -20 - 20℃; Oxidation;93%

4136-95-2Relevant articles and documents

-

Fuson,Bertetti,Ross

, p. 4380,4382 (1932)

-

SUBSTITUTED 1,2,5-OXADIAZOLE COMPOUNDS AND THEIR USE AS HERBICIDES

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Page/Page column 123, (2013/06/05)

The present invention relates to substituted 1,2,5-oxadiazole compounds of the formula I and the N-oxidesand salts thereof and to compositions comprising the same. The invention also relates to the use of the 1,2,5-oxadiazole compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore,the invention relates to methods of applying such compounds. In formula I, the variables have the following meanigns R is e.g. hydrogen, cyano, nitro, halogen, C1-C6--alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl,C2-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl,C1-C4-haloalkoxy-C1-C4-alkyl,O-Ra, Z-S(O)n-Rb, Z-C(=O)-Rc, Z-C(=O)-ORd, Z-C(=O)-NReRf, Z-NRgRh, Z-phenyl and Z-heterocyclyl etc; R1 ise.g. Z1-cyano, halogen, nitro, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl,C1-C8-haloalkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, Z1-C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkylthio-C1-C4-alkyl, Z1-C1-C4-alkylthio-C1-C4-alkylthio, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4-alkyl, Z1-C1-C4-haloalkoxy-C1-C4-alkoxy, Z1-S(O)k-R1b, Z1-phenoxy and Z1-heterocyclyloxy;R2,R3 are identical or different and e.g. hydrogen, halogen, Z2-OH, Z2-NO2,Z2-cyano,C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Z2-C3-C10-cycloalkyl, Z2-C3-C10-cycloalkoxy, C1-C8-haloalkyl, Z2-C1-C8-alkoxy, Z2-C1-C8-haloalkoxy, Z2-C1-C4-alkoxy-C1-C4-alkoxy, Z2-C1-C4-alkylthio-C1-C4-alkylthio, Z2-C2-C8-alkenyloxy, Z2-C2-C8-alkynyloxy, Z2-C1-C8-haloalkoxy, Z2-C2-C8-haloalkenyloxy, Z2-C2-C8-haloalkynyloxy, Z2-C1-C4- haloalkoxy-C1-C4-alkoxy, Z2-(tri-C1-C4-alkyl)silyl, Z2-S(O)k-R2b, Z2-C(=O)-R2c, Z2-C(=O)-OR2d, Z2-C(=O)-NR2eR2f, Z2-NR2gR2h, Z2a-phenyl and Z2a-heterocyclyl; R4 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C1-C4-alkyl and C1-C4-haloalkyl; R5 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl and C1-C4-haloalkyl; provided that at least one of the radicals R4 and R5 is different from hydrogen; n is 0, 1 or 2; k is 0, 1 or 2.

Solid-phase synthesis of new saphenamycin analogues with antimicrobial activity

Laursen, Jane B.,De Visser, Peter C.,Nielsen, Henrik K.,Jensen, Knud J.,Nielsen, John

, p. 171 - 175 (2007/10/03)

An array of 12 new saphenamycin analogues modified at the benzoate moiety was synthesized on solid support. Synthesis commenced with a chemoselective anchoring of saphenic acid through the carboxyl group to a 2-chlorotrityl functionalized polystyrene resin. The secondary alcohol was acylated in parallel with a series of differently substituted benzoic acid derivatives. Treatment with TFA-CH2Cl2 (5:995) released the expected saphenamycin analogues into solution. These new analogues were purified, characterized and screened for antimicrobial activity against Bacillus subtilis and Proteus mirabilis. Eight analogues exhibited MIC values against B. subtilis ranging from 0.07 to 3.93 μg/mL, comparable to the activities of previously reported saphenamycin analogues.

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