Name: METHOPRENE
SKU: 40596-69-8

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Basic Information

Molecular Structure:
CAS No.:	40596-69-8
Name:	METHOPRENE

Formula:	C₁₉H₃₄O₃
Molecular Weight:	310.477
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;
EINECS:	254-993-2
Density:	0.914 g/cm³
Melting Point:	164oC
Boiling Point:	385.7 °C at 760 mmHg
Flash Point:	162.4 °C
Solubility:	Miscible
Hazard Symbols:	Xi, N
Risk Codes:	36/37/38-51/53
Safety:	26-36-60-61
Transport Information:	UN 3082 9/PG 3
PSA:	35.53000
LogP:	5.06200

Synthetic route

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

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

B: 40596-69-8
methoprene

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

Conditions

Conditions	Yield
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%

...Expand

: 87416-89-5
5-(6-Methoxy-2,6-dimethyl-heptyl)-3-methyl-2,5-dihydro-thiophene-2-carboxylic acid isopropyl ester

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

B: 40596-69-8
methoprene

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

Conditions

Conditions	Yield
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

...Expand

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

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

B: 40596-69-8
methoprene

C: 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

Conditions	Yield
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%

...Expand

: 53092-52-7
Methoprene acid

: 67-63-0
isopropyl alcohol

: 40596-69-8
methoprene

Conditions

Conditions	Yield
(i) SOCl2, (ii) /BRN= 635639/; Multistep reaction;

: 3613-30-7
7-methoxy-3,7-dimethyloctanal

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

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

B: 40596-69-8
methoprene

Conditions

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

...Expand

: 917-54-4
methyllithium

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

: 40596-69-8
methoprene

Conditions

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

: 917-54-4
methyllithium

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

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

B: 40596-69-8
methoprene

Conditions

Conditions	Yield
With copper(l) iodide 1.) ether, -30 degC, 30 min; 2.) -78 degC, 1h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 103768-96-3
2-(1-Bromo-7-methoxy-3,7-dimethyl-octyl)-3-methyl-cyclopropanecarboxylic acid isopropyl ester

: 40596-69-8
methoprene

Conditions

Conditions	Yield
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;

: 616-44-4
3-Methylthiophene

: 40596-69-8
methoprene

Conditions

Conditions	Yield
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

: 4434-77-9
2-bromo-6-methylhept-5-ene

: 40596-69-8
methoprene

Conditions

Yield

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

Raw Materials

917-54-4

616-44-4

67-63-0

Total:115 Page 1 of 4 1 2 3 4 Next>>

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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.

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.

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Toxicity Data With Reference

Specification