Isoprothiolane supplier | CasNO.50512-35-1

Name
Isoprothiolane
EINECS
CAS No. 50512-35-1
Article Data4
CAS DataBase
Density 1.228 g/cm³
Solubility 54 mg l-1 (25 °C)
Melting Point 54°C
Formula C₁₂H₁₈O₄S₂
Boiling Point 353 °C at 760 mmHg
Molecular Weight 290.405
Flash Point 159 °C
Transport Information
Appearance
Safety 61
Risk Codes 22-51/53
Molecular Structure
Hazard Symbols Xn,N
Synonyms Isoprothiolane [BSI:ISO];Propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester;1,3-Dithiolan-2-ylidenepropanedioic acid, bis(1-methylethyl) ester;Fujione;Fudiolan;Di-isopropyl 1,3-dithiolane-2-ylidenemalonate;Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate (9CI);
PSA 103.20000
LogP 2.58120

Synthetic route

: 147848-85-9
3-{2-[2-(2,2-Bis-isopropoxycarbonyl-1-methoxy-vinylsulfanyl)-ethyldisulfanyl]-ethylsulfanyl}-2-isopropoxycarbonyl-3-methoxy-acrylic acid isopropyl ester

: 50512-35-1
isoprothiolane

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol 1.) 3 d, room temperature, 2.) 2 h, reflux;	64%

: 147848-87-1
2-[(2-Ethyldisulfanyl-ethylsulfanyl)-ethylsulfanyl-methylene]-malonic acid diisopropyl ester

: 50512-35-1
isoprothiolane

Conditions

Conditions	Yield
With sodium carbonate In methanol; water Ambient temperature;	47%

: 67-56-1
methanol

: 52303-69-2, 108114-60-9, 108114-61-0
Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide

A: 50512-35-1
isoprothiolane

B: 2-[Methoxy-(2-methoxysulfinyl-ethylsulfanyl)-methylene]-malonic acid diisopropyl ester

C: 147848-85-9
3-{2-[2-(2,2-Bis-isopropoxycarbonyl-1-methoxy-vinylsulfanyl)-ethyldisulfanyl]-ethylsulfanyl}-2-isopropoxycarbonyl-3-methoxy-acrylic acid isopropyl ester

Conditions

Conditions	Yield
With sodium carbonate for 0.5h; Ambient temperature;	A 17% B 31% C 40%

...Expand

: 147848-84-8
C26H42O11S4

A: 50512-35-1
isoprothiolane

B: 2-[Methoxy-(2-methoxysulfinyl-ethylsulfanyl)-methylene]-malonic acid diisopropyl ester

C: 147848-85-9
3-{2-[2-(2,2-Bis-isopropoxycarbonyl-1-methoxy-vinylsulfanyl)-ethyldisulfanyl]-ethylsulfanyl}-2-isopropoxycarbonyl-3-methoxy-acrylic acid isopropyl ester

Conditions

Conditions	Yield
With sodium carbonate In methanol; water for 12h; Ambient temperature;	A 5% B 27% C 28%

...Expand

: 18598-63-5
L-cysteine methyl ester hydrochloride

: 52303-69-2, 108114-60-9, 108114-61-0
Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide

A: 50512-35-1
isoprothiolane

B: 2-((R)-4-Methoxycarbonyl-thiazolidin-2-ylidene)-malonic acid diisopropyl ester

Conditions

Conditions	Yield
With pyridine; acetic anhydride; triethylamine 1.) aq. MeOH, 1 h, room temperature, 2.) 23 h, room temperature; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 52303-69-2, 108114-60-9, 108114-61-0
Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide

: 50512-35-1
isoprothiolane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / methanol / 12 h / Ambient temperature 2: 47 percent / Na2CO3 / methanol; H2O / Ambient temperature View Scheme

: 147848-84-8
C26H42O11S4

: 50512-35-1
isoprothiolane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 28 percent / Na2CO3 / methanol; H2O / 12 h / Ambient temperature 2: 64 percent / NaBH4 / methanol; tetrahydrofuran / 1.) 3 d, room temperature, 2.) 2 h, reflux View Scheme

: 50512-35-1
isoprothiolane

: 106262-50-4
2-[1,3]Dithiolan-2-yl-malonic acid diisopropyl ester

Conditions

Conditions	Yield
With magnesium In methanol at 10℃; for 2.5h;	93%

: 50512-35-1
isoprothiolane

: 52322-05-1
1,3-dithiolan-2-ylidenemalonic acid

Conditions

Conditions	Yield
With sodium hydroxide; water In isopropyl alcohol at 30 - 40℃; for 3h;	85%

: 50512-35-1
isoprothiolane

: 133188-15-5, 147848-83-7
anti-Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1,3-dioxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 1h; Ambient temperature;	70%

: 50512-35-1
isoprothiolane

: 52303-69-2, 108114-60-9, 108114-61-0
Diisopropyl 1,3-dithiolan-2-ylidenemalonate 1-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h; Ambient temperature;	65%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 12h; Ambient temperature;	65%

: 50512-35-1
isoprothiolane

: 2-(1,3-dithiolan-2-ylidene)-3-isopropoxy-3-oxopropionic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 25 - 45℃;	55%
With potassium hydroxide
With potassium hydroxide

: 67-56-1
methanol

: 50512-35-1
isoprothiolane

: 3-Methoxy-1,1,4,4-tetraoxo-1λ6,4λ6-[1,4]dithiane-2,2-dicarboxylic acid diisopropyl ester

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid 1.) CH2Cl2, 12 h, room temperature, 2.) 3 d; Yield given. Multistep reaction;

: 50512-35-1
isoprothiolane

A: 72629-81-3
2-(1,3-dithiolan-2-ylidene)acetic acid

B: 144-62-7
oxalic acid

C: 72629-83-5
3,5-bis-1,2,4-trithiolane

D: 52322-05-1
1,3-dithiolan-2-ylidenemalonic acid

E: 2,4-bis-1,3-dithietane

Conditions

Conditions	Yield
With silica gel for 2.5h; Product distribution; Irradiation; effects of surface and air on pesticide photolysis, different time; different λ; furter pesticides;

...Expand

: 50512-35-1
isoprothiolane

: 109480-62-8
2,2-dimethyl-5-5(2,5-dithiacyclopentylidene)-1,3-dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 5-[1,3]Dithiolan-2-ylidene-2-ethyl-2-methyl-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 8-[1,3]Dithiolan-2-ylidene-6,10-dioxa-spiro[4.5]decane-7,9-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 3-[1,3]Dithiolan-2-ylidene-1,5-dioxa-spiro[5.5]undecane-2,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 2-methyl-2-phenyl-5-(1,3-dithiolan-2-ylidene)-1,3-dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 5-[1,3]Dithiolan-2-ylidene-2-furan-2-yl-2-methyl-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 5-[1,3]Dithiolan-2-ylidene-2-ethyl-2-phenyl-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 3-(5-[1,3]Dithiolan-2-ylidene-2-methyl-4,6-dioxo-[1,3]dioxan-2-yl)-propionic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: Diisopropyl 1,3-dioxo-1,3-dithiolan-2-ylidenemalonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 12 h / Ambient temperature 2: m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 12 h / Ambient temperature View Scheme

: 50512-35-1
isoprothiolane

: 2-(2-Chloro-phenyl)-5-[1,3]dithiolan-2-ylidene-2-methyl-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 2,2-Dicyclopentyl-5-[1,3]dithiolan-2-ylidene-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 2-((R)-4-Methoxycarbonyl-thiazolidin-2-ylidene)-malonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 12 h / Ambient temperature 2: 2.) Ac2O, pyridine, NEt3 / 1.) aq. MeOH, 1 h, room temperature, 2.) 23 h, room temperature View Scheme

: 50512-35-1
isoprothiolane

: 5-[1,3]Dithiolan-2-ylidene-2,2-diphenyl-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 3-Ethylsulfanyl-1,4-dioxo-1λ4,4λ4-[1,4]dithiane-2,2-dicarboxylic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 12 h / Ambient temperature 2: 1.) metachloroperbenzoic acid (MCPBA) / 1.) CH2Cl2, 12 h, room temperature, 2.) MeOH, 2 d, room temperature View Scheme

: 50512-35-1
isoprothiolane

: 2-(4-Allyloxy-phenyl)-5-[1,3]dithiolan-2-ylidene-2-ethyl-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 5-[1,3]Dithiolan-2-ylidene-2-methyl-2-(2-prop-2-ynyloxy-phenyl)-[1,3]dioxane-4,6-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / sodium hydroxide, water / propan-2-ol / 3 h / 30 - 40 °C 2: 1.) conc. sulfuric acid, acetic anhydride / 1.) 10 min, 2.) RT, 8 h View Scheme

: 50512-35-1
isoprothiolane

: 2-[(2-Benzyldisulfanyl-ethylsulfanyl)-benzylsulfanyl-methylene]-malonic acid diisopropyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 12 h / Ambient temperature 2: 94 percent / methanol / Ambient temperature View Scheme

Isoprothiolane Chemical Properties

Molecular structure of Isoprothiolane (CAS NO.50512-35-1) is:

Product Name: Isoprothiolane
CAS Registry Number: 50512-35-1
IUPAC Name: dipropan-2-yl 2-(1,3-dithiolan-2-ylidene)propanedioate
Molecular Weight: 290.39892 [g/mol]
Molecular Formula: C₁₂H₁₈O₄S₂
XLogP3: 3.3
H-Bond Donor: 0
H-Bond Acceptor: 4
Surface Tension: 45.2 dyne/cm
Density: 1.228 g/cm³
Flash Point: 159 °C
Enthalpy of Vaporization: 59.78 kJ/mol
Boiling Point: 353 °C at 760 mmHg
Vapour Pressure: 3.7E-05 mmHg at 25°C
Product Categories: Fungicide

Isoprothiolane Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
chicken	LD50	oral	3860mg/kg (3860mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
frog	LD50	oral	75mg/kg (75mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
guinea pig	LD50	oral	1020mg/kg (1020mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
mouse	LD50	intraperitoneal	440mg/kg (440mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
mouse	LD50	oral	1340mg/kg (1340mg/kg)	Pesticide Manual. Vol. 9, Pg. 506, 1991.
mouse	LD50	skin	> 10250mg/kg (10250mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
mouse	LD50	subcutaneous	> 5gm/kg (5000mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
rabbit	LD50	oral	2320mg/kg (2320mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
rat	LD50	intraperitoneal	480mg/kg (480mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.
rat	LD50	oral	1190mg/kg (1190mg/kg)	Farm Chemicals Handbook. Vol. -, Pg. C174, 1991.
rat	LD50	skin	10250mg/kg (10250mg/kg)	Japan Pesticide Information. Vol. (40), Pg. 32, 1982.
rat	LD50	subcutaneous	> 5gm/kg (5000mg/kg)	Japan Pesticide Information. Vol. (27), Pg. 20, 1976.

Isoprothiolane Specification

Isoprothiolane , its cas register number is 50512-35-1. It also can be called Isoprothiolane [BSI:ISO] ; Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate (9CI) ; Di-isopropyl 1,3-dithiolane-2-ylidenemalonate ; Fudiolan ; Fujione ; 1,3-Dithiolan-2-ylidenepropanedioic acid, bis(1-methylethyl) ester ; Propanedioic acid, 1,3-dithiolan-2-ylidene-, bis(1-methylethyl) ester .

Product Name

Isoprothiolane

Synthetic route

Isoprothiolane Chemical Properties

Isoprothiolane Toxicity Data With Reference

Isoprothiolane Specification

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