Product Name

  • Name

    METHOPRENE

  • EINECS 254-993-2
  • CAS No. 40596-69-8
  • Article Data15
  • CAS DataBase
  • Density 0.914 g/cm3
  • Solubility Miscible
  • Melting Point 164oC
  • Formula C19H34O3
  • Boiling Point 385.7 °C at 760 mmHg
  • Molecular Weight 310.477
  • Flash Point 162.4 °C
  • Transport Information UN 3082 9/PG 3
  • Appearance
  • Safety 26-36-60-61
  • Risk Codes 36/37/38-51/53
  • Molecular Structure Molecular Structure of 40596-69-8 (METHOPRENE)
  • Hazard Symbols IrritantXi, DangerousN
  • Synonyms 2,4-Dodecadienoicacid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl ester, (E,E)-;(2E,4E)-3,7,11-Trimethyl-11-methoxydodeca-2,4-dienoic acid ethyl ester;Altosid;Altosid Liquid Larvicide;Altosid SR 10;Altosid XR;Apex 600E;Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate;Juvemon;Juvenmon;Manina;Manta;Manta (hormone);Starbar Inhibitor;ZPA 1019;
  • PSA 35.53000
  • LogP 5.06200

Synthetic route

5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid
87416-87-3

5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid

A

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

methoprene
40596-69-8

methoprene

C

isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;A n/a
B n/a
C 20%
5-(6-Methoxy-2,6-dimethyl-heptyl)-3-methyl-2,5-dihydro-thiophene-2-carboxylic acid isopropyl ester
87416-89-5

5-(6-Methoxy-2,6-dimethyl-heptyl)-3-methyl-2,5-dihydro-thiophene-2-carboxylic acid isopropyl ester

A

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

methoprene
40596-69-8

methoprene

C

isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

isopropyl 5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;A n/a
B n/a
C 20%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 12h; Product distribution;A n/a
B n/a
C 90 mg
(E)-4-Bromo-11-methoxy-3,7,11-trimethyl-dodec-2-enoic acid isopropyl ester

(E)-4-Bromo-11-methoxy-3,7,11-trimethyl-dodec-2-enoic acid isopropyl ester

A

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

methoprene
40596-69-8

methoprene

C

isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate
41797-08-4, 55290-71-6, 58222-78-9, 58223-32-8, 68218-72-4

isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate

Conditions
ConditionsYield
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 1h; Heating; Yield given. Title compound not separated from byproducts;A n/a
B 0.18 g
C 10%
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide for 1h; Heating; Yields of byproduct given;A n/a
B 0.18 g
C 10%
Methoprene acid
53092-52-7

Methoprene acid

isopropyl alcohol
67-63-0

isopropyl alcohol

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
(i) SOCl2, (ii) /BRN= 635639/; Multistep reaction;
7-methoxy-3,7-dimethyloctanal
3613-30-7

7-methoxy-3,7-dimethyloctanal

diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid
50798-35-1

diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid

A

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In benzene other reagents; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methyllithium
917-54-4

methyllithium

Isopropyl (2Z,4E)-3-Acetoxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate
80957-93-3

Isopropyl (2Z,4E)-3-Acetoxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
With copper(l) iodide 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h; Yield given. Multistep reaction;
methyllithium
917-54-4

methyllithium

Isopropyl (4E)-3-Diethoxyphosphoryloxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate
80957-87-5, 80957-88-6

Isopropyl (4E)-3-Diethoxyphosphoryloxy-11-methoxy-7,11-dimethyl-2,4-dodecadienoate

A

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate
52341-11-4

Isopropyl (2Z,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoate

B

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
With copper(l) iodide 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h; Yield given. Multistep reaction. Yields of byproduct given;
2-(1-Bromo-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
103768-96-3

2-(1-Bromo-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc dibromide 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h; Multistep reaction;
3-Methylthiophene
616-44-4

3-Methylthiophene

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
2: 77 percent / H2SO4 conc. / 4 h / Heating
3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
5: diethyl ether / 0.5 h / 0 °C
6: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
2: 77 percent / H2SO4 conc. / 4 h / Heating
3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
5: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
2-bromo-6-methylhept-5-ene
4434-77-9

2-bromo-6-methylhept-5-ene

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min
2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C
3: pyridine; diethyl ether / 6 h / Heating
4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
6: 77 percent / H2SO4 conc. / 4 h / Heating
7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
9: diethyl ether / 0.5 h / 0 °C
10: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min
2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C
3: pyridine; diethyl ether / 6 h / Heating
4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
6: 77 percent / H2SO4 conc. / 4 h / Heating
7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
9: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
2,6-dimethyl-5-hepten-1-ol
4234-93-9

2,6-dimethyl-5-hepten-1-ol

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: pyridine; diethyl ether / 6 h / Heating
2: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
3: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
4: 77 percent / H2SO4 conc. / 4 h / Heating
5: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
6: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
7: diethyl ether / 0.5 h / 0 °C
8: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: pyridine; diethyl ether / 6 h / Heating
2: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
3: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
4: 77 percent / H2SO4 conc. / 4 h / Heating
5: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
6: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
7: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
1-bromo-2,6-dimethylhept-5-ene
87416-83-9

1-bromo-2,6-dimethylhept-5-ene

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
2: 77 percent / H2SO4 conc. / 4 h / Heating
3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
5: diethyl ether / 0.5 h / 0 °C
6: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
2: 77 percent / H2SO4 conc. / 4 h / Heating
3: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
4: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
5: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
2,6-dimethyl-5-hepten-1-al
106-72-9

2,6-dimethyl-5-hepten-1-al

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C
2: pyridine; diethyl ether / 6 h / Heating
3: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
4: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
5: 77 percent / H2SO4 conc. / 4 h / Heating
6: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
7: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
8: diethyl ether / 0.5 h / 0 °C
9: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C
2: pyridine; diethyl ether / 6 h / Heating
3: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
4: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
5: 77 percent / H2SO4 conc. / 4 h / Heating
6: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
7: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
8: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
2-(2',6'-dimethylhept-5'-enyl)-4-methylthiophene
87416-84-0

2-(2',6'-dimethylhept-5'-enyl)-4-methylthiophene

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / H2SO4 conc. / 4 h / Heating
2: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
3: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
4: diethyl ether / 0.5 h / 0 °C
5: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: 77 percent / H2SO4 conc. / 4 h / Heating
2: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
3: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
4: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
2-(6'-methoxy-2',6'-dimethylheptyl)-4-methylthiophene
87416-85-1

2-(6'-methoxy-2',6'-dimethylheptyl)-4-methylthiophene

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
2: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
3: diethyl ether / 0.5 h / 0 °C
4: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
2: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
3: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylic acid
87416-86-2

5-(6'-methoxy-2',6'-dimethylheptyl)-3-methylthiophene-2-carboxylic acid

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
2: diethyl ether / 0.5 h / 0 °C
3: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
2: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid
87416-87-3

5-(6'-methoxy-2',6'-dimethylheptyl)-3-methyl-2,5-dihydrothiophene-2-carboxylic acid

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether / 0.5 h / 0 °C
2: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Toluene-4-sulfonic acid 2,6-dimethyl-hept-5-enyl ester

Toluene-4-sulfonic acid 2,6-dimethyl-hept-5-enyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
2: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
3: 77 percent / H2SO4 conc. / 4 h / Heating
4: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
5: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
6: diethyl ether / 0.5 h / 0 °C
7: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C
2: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h
3: 77 percent / H2SO4 conc. / 4 h / Heating
4: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF
5: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction
6: m-CPBA / CH2Cl2 / 12 h / 0 °C
View Scheme
isopropyl acetoacetate
542-08-5

isopropyl acetoacetate

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C
3: 63 percent / p-toluenesulfonic acid / 6 h / Heating
4: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h
View Scheme
Multi-step reaction with 4 steps
2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C
3: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux
4: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h
View Scheme
7-methoxy-3,7-dimethyloctanal
3613-30-7

7-methoxy-3,7-dimethyloctanal

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Et3N / N-(2-hydroxyethyl)-thiazolium bromide / dioxane / 20 h / 95 - 100 °C
2: sodium borohydride / tetrahydrofuran / 1 h / 0 °C
3: pyridine / 24 h / 25 °C
4: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature
5: sodium borohydride / propan-2-ol / 4 h / Heating
6: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
7: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
Multi-step reaction with 4 steps
2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C
3: 63 percent / p-toluenesulfonic acid / 6 h / Heating
4: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h
View Scheme
Multi-step reaction with 4 steps
2: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C
3: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux
4: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h
View Scheme
α-Keto-β-Methyl-buttersaeure-isopropylester
55755-06-1

α-Keto-β-Methyl-buttersaeure-isopropylester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Et3N / N-(2-hydroxyethyl)-thiazolium bromide / dioxane / 20 h / 95 - 100 °C
2: sodium borohydride / tetrahydrofuran / 1 h / 0 °C
3: pyridine / 24 h / 25 °C
4: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature
5: sodium borohydride / propan-2-ol / 4 h / Heating
6: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
7: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
isopropyl 2-hydroxy-3-methylbutyrate
300786-34-9

isopropyl 2-hydroxy-3-methylbutyrate

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: MnO2
2: Et3N / N-(2-hydroxyethyl)-thiazolium bromide / dioxane / 20 h / 95 - 100 °C
3: sodium borohydride / tetrahydrofuran / 1 h / 0 °C
4: pyridine / 24 h / 25 °C
5: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature
6: sodium borohydride / propan-2-ol / 4 h / Heating
7: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
8: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
Isopropyl (4E)-11-Methoxy-7,11-dimethyl-3-oxo-4-dodecenoate

Isopropyl (4E)-11-Methoxy-7,11-dimethyl-3-oxo-4-dodecenoate

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 63 percent / p-toluenesulfonic acid / 6 h / Heating
2: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux
2: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h
View Scheme
Isopropyl 5-Hydroxy-11-methoxy-7,11-dimethyl-3-oxododecanoate

Isopropyl 5-Hydroxy-11-methoxy-7,11-dimethyl-3-oxododecanoate

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C
2: 63 percent / p-toluenesulfonic acid / 6 h / Heating
3: 1.) copper(I) iodide / 1.) ether, -30 degC, 10 min; 2.) ether, -20 degC, 2h
View Scheme
Multi-step reaction with 3 steps
1: 61 percent / 4N HCl / dioxane / 0.25 h / 80 °C
2: 1.) NaH / 1.) ether, 0.5h, room temp.; 2.) ether, 8h, reflux
3: 1.) copper(I) iodide / 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h
View Scheme
2-(1-Hydroxy-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
103768-95-2

2-(1-Hydroxy-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
2: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
2-Hydroxy-11-methoxy-3,7,11-trimethyl-5-oxo-dodecanoic acid isopropyl ester
103768-92-9

2-Hydroxy-11-methoxy-3,7,11-trimethyl-5-oxo-dodecanoic acid isopropyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / 24 h / 25 °C
2: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature
3: sodium borohydride / propan-2-ol / 4 h / Heating
4: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
5: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
11-Methoxy-3,7,11-trimethyl-2,5-dioxo-dodecanoic acid isopropyl ester
103768-91-8

11-Methoxy-3,7,11-trimethyl-2,5-dioxo-dodecanoic acid isopropyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium borohydride / tetrahydrofuran / 1 h / 0 °C
2: pyridine / 24 h / 25 °C
3: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature
4: sodium borohydride / propan-2-ol / 4 h / Heating
5: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
6: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
2-(7-Methoxy-3,7-dimethyl-octanoyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester
103768-94-1

2-(7-Methoxy-3,7-dimethyl-octanoyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium borohydride / propan-2-ol / 4 h / Heating
2: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
3: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme
11-Methoxy-3,7,11-trimethyl-5-oxo-2-(toluene-4-sulfonyloxy)-dodecanoic acid isopropyl ester
103768-93-0

11-Methoxy-3,7,11-trimethyl-5-oxo-2-(toluene-4-sulfonyloxy)-dodecanoic acid isopropyl ester

methoprene
40596-69-8

methoprene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium t-butoxid, 18-Crown-6 / benzene / 0.5 h / Ambient temperature
2: sodium borohydride / propan-2-ol / 4 h / Heating
3: PBr3, LiBr, 2,4,6-collidine / 3 h / -40 - 0 °C
4: 1.) ZnBr, 2.) DBU / 1.) ether, -40 deg C to 0 deg C, 2 h, 2.) 50 deg C, 2 h
View Scheme

Methoprene Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 5gm/kg (5000mg/kg)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
guinea pig LC50 inhalation > 210gm/m3 (210000mg/m3)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
rabbit LD50 oral 3038mg/kg (3038mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A615, Pg. 1986,
rabbit LD50 skin 3gm/kg (3000mg/kg)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
rat LC50 inhalation > 210gm/m3 (210000mg/m3)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
rat LD50 oral 25gm/kg (25000mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 56(10), Pg. 72, 1991.

Methoprene Specification

The Methoprene, with the CAS registry number 40596-69-8, is also known as Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4 dodecadienoate. It belongs to the product categories of Growth regulatorsPesticides&Metabolites;H-MAlphabetic.This chemical's molecular formula is C19H34O3 and molecular weight is 310.47. What's more,Its systematic name is Isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4 dodecadienoate.It is a juvenile hormone analog and insect growth regulator used to control insects by disrupting metamorphosis. Has been effective in controlling mosquito larvae.

Physical properties about Methoprene are:
(1)ACD/LogP:  5.625; (2)# of Rule of 5 Violations:  1; (3)ACD/LogD (pH 5.5):  5.63; (4)ACD/LogD (pH 7.4):  5.63; (5)ACD/BCF (pH 5.5):  11084.06; (6)ACD/BCF (pH 7.4):  11084.06; (7)ACD/KOC (pH 5.5):  27339.10; (8)ACD/KOC (pH 7.4):  27339.10; (9)#H bond acceptors:  3; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  11; (12)Index of Refraction:  1.462; (13)Molar Refractivity:  93.435 cm3; (14)Molar Volume:  339.84 cm3; (15)Surface Tension:  29.636999130249 dyne/cm; (16)Density:  0.914 g/cm3; (17)Flash Point:  162.376 °C; (18)Enthalpy of Vaporization:  63.453 kJ/mol; (19)Boiling Point:  385.697 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(OC(C)C)\C=C(\C=C\CC(CCCC(OC)(C)C)C)C;
(2)Std. InChI:InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+;
(3)Std. InChIKey:NFGXHKASABOEEW-LDRANXPESA-N.

Safety Information of Methoprene chloride:
The Methoprene is irritating to eyes, respiratory system and skin.It is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.Avoid release to the environment. Refer to special instructions safety data sheet. When you use it ,wear suitable protective clothing.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.This material and/or its container must be disposed of as hazardous waste.

The toxicity data of Methoprene as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 5gm/kg (5000mg/kg)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
guinea pig LC50 inhalation > 210gm/m3 (210000mg/m3)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
rabbit LD50 oral 3038mg/kg (3038mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A615, Pg. 1986,
rabbit LD50 skin 3gm/kg (3000mg/kg)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
rat LC50 inhalation > 210gm/m3 (210000mg/m3)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 119, 1976.
rat LD50 oral 25gm/kg (25000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 56(10), Pg. 72, 1991.

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View