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56-25-7 Usage

Biological Activity

Natural toxin inhibitor of protein phosphatases 1 and 2A (K i values are 1.1 and 0.19 μ M respectively); similar to okadaic acid (9,10-Deepithio-9,10-didehydroacanthifolicin ). Displays > 500-fold selectivity over PP2B.

Chemical Properties

Cantharidin is a brown to black powder.

Description

Cantharidin is a natural toxicant of blister beetles. Cantharidin has been used as a medicinal agent for over 2000 years and is listed as a drug under the name of Mylabris in the medical monograph Materia Medica published in 77 AD. Some of the most ancient Chinese prescriptions (306–168 BC) refer to the use of Mylabris for the treatment of furuncles and piles. Cantharidin can be used for topically (0.7%) treatment of warts, in which the skin under the wart blisters, thereby, lifting the wart off the skin. It is used to treat molluscum contagiosum. Cantharidin is a strong inhibitor of protein phosphatases types 1 (PP1) and 2A (PP2A), which are potentially novel targets for anticancer therapies. Thus, cantharidin is exploited as anticancer drugs. Cantharidin is shown to be cytotoxic to cancer cells and stimulatory on the bone marrow. The renal toxicity of this drug has prevented its use in mainstream oncology.

Hazard

Extremely toxic; questionable carcinogen; powerful irritant to all cells and tissues; deadly poi- son; respiratory failure; death.

Uses

In veterinary medicine as a vesicant, rubefa- cient, and counterirritant.

Uses

Cantharidin (Cantharone), a mitochondrial poison derived from the blister beetle Cantharis vesicatoria, leads to changes in cell membranes, epidermal cell dyshesion, acantholysis, and blister formation and is also useful. Cantharidin can be compounded with salicylic acid and podophyllin resin; occlusion for only 2 hours is needed with this combination. Thick hyperkeratotic lesions should be pared down before painting. The lesion should then be painted with cantharidin, allowed to dry, and covered with Blenderm or other nonporous occlusive tape; 40% salicylic acid plaster may be used to achieve greater activity. The tape is left on for 24 hours or until the area begins to hurt. A blister, often hemorrhagic, will form, break, crust, and fall off in 7 to 14 days; at this time, the lesion is pared down, and any wart remnants are retreated. Because the effect of cantharidin is entirely intraepidermal, no scarring ensues. Ring-like or 'donut configuration' recurrences may be seen occasionally after treatment with cantharidin or, at times, following liquid nitrogen therapy. Owing to this agent’s toxicity, application by a physician is recommended. Verrusol, which contains 30% salicylic acid, 5% podophyllin, and 1% cantharidin, may be used in the same manner.

Definition

ChEBI: A monoterpenoid with an epoxy-bridged cyclic dicarboxylic anhydride structure secreted by many species of blister beetle, and most notably by the Spanish fly, Lytta vesicatoria. Natural toxin inhibitor of protein phosphatases 1 and 2A.

Indications

Cantharidin, from the beetle Cantharis vesicatoria, causes intraepidermal vesiculation and is used in the treatment of warts and other benign cutaneous lesions. Cantharidin is extremely toxic if taken internally; it should not be prescribed for at-home use.Cantharidin (Cantharone), a mitochondrial poison derived from the blister beetle Cantharis vesicatoria, leads to changes in cell membranes, epidermal cell dyshesion, acantholysis, and blister formation and is also useful. Cantharidin can be compounded with salicylic acid and podophyllin resin; occlusion for only 2 hours is needed with this combination. Thick hyperkeratotic lesions should be pared down before painting. The lesion should then be painted with cantharidin, allowed to dry, and covered with Blenderm or other nonporous occlusive tape; 40% salicylic acid plaster may be used to achieve greater activity. The tape is left on for 24 hours or until the area begins to hurt. A blister, often hemorrhagic, will form, break, crust, and fall off in 7 to 14 days; at this time, the lesion is pared down, and any wart remnants are retreated. Because the effect of cantharidin is entirely intraepidermal, no scarring ensues. Ring-like or "donut configuration" recurrences may be seen occasionally after treatment with cantharidin or, at times, following liquid nitrogen therapy. Owing to this agent’s toxicity, application by a physician is recommended. Verrusol, which contains 30% salicylic acid, 5% podophyllin, and 1% cantharidin, may be used in the same manner.

General Description

Brown to black powder or plates or scales. Formerly used as a counterirritant and vesicant. Used for the removal of warts. Used as an experimental anti tumor agent. Active ingredient in spanish fly, a reputed aphrodisiac.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Shipping

Cantharidin is not specifically listed in the DOT Performance-Oriented Packaging Standards with respect to labeling requirements or restrictions on shipping quantities.

References

[1] Richard E. Honkanen (1993) Cantharidin, another natural toxin that inhibits the activity of serin/threonine protein phosphatases types 1 and 2A, 330, 283-286 [2] Jennette A. Sakoff, Stephen P. Ackland, Monique L. Baldwin, Mirella A. Keane, Adam McCluskey (2002) Anticancer activity and protein phosphatase 1 and 2A inhibition of a new generation of cantharidin analogues, 20, 1-11 [3] Erin F. D. Mathes, Ilona J. Frieden (2010) Treatment of molluscum contagiosum with cantharidin: a practical approach, 39, 124-130

Uses

Cantharidin is a natural toxin produced by blister beetles that moderately inhibits protein phosphatases 1 (PP1) (IC50 = 1.7 μM) and PP2A (IC50 = 0.2 μM) and only weakly inhibits the activity of PP2B (IC50 = 1 mM). It has been shown to stimulate cell cycle progression and induce premature mitosis, used topically (0.7%) as an anti-wart treatment, and has been shown to be active in cervical, tongue, neuroblastoma, bone, leukemia, ovarian, colon, and various other cancer cell lines.

Fire Hazard

When heated to decomposition Cantharidin emits acrid smoke and irritating fumes.

Chemical Properties

white to light yellow crystal powde

Reactivity Profile

Organic anhydrides, such as Cantharidin, are incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.

Health Hazard

Cantharidin is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste of less than 7 drops for a 70 kg (150 lb.) person. It is very toxic by absorption through skin.

Potential Exposure

Formerly used as a counterirritant and vesicant. Also used for the removal of benign epithelial growths, e.g., warts. Used as an experimental antitumor agent. The active ingredient in “Spanish fly,” a reputed aphrodisia
InChI:InChI=1/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5?,6?,9-,10+

56-25-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (C0019)  Cantharidin  >98.0%(GC) 56-25-7 25mg 390.00CNY Detail
TCI America (C0019)  Cantharidin  >98.0%(GC) 56-25-7 100mg 1,190.00CNY Detail
Sigma (C7632)  Cantharidin   56-25-7 C7632-25MG 725.40CNY Detail
Sigma (C7632)  Cantharidin   56-25-7 C7632-100MG 2,135.25CNY Detail
Sigma (C7632)  Cantharidin   56-25-7 C7632-500MG 7,780.50CNY Detail

56-25-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name cantharidin

1.2 Other means of identification

Product number -
Other names 2endo,3endo-dimethyl-7-oxa-norbornane-2exo,3exo-dicarboxylic acid-anhydride

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:56-25-7 SDS

56-25-7Synthetic route

furan
110-00-9

furan

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride
75532-25-1

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Stage #1: furan; 2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride With 1-butyl-3-methylimidazolium Tetrafluoroborate at 50℃; for 19h;
Stage #2: In ethyl acetate for 4h; Reagent/catalyst; Temperature; Reflux;
90%
C10H10O4S
75538-64-6

C10H10O4S

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
With hydrogen In ethyl acetate under 760.051 Torr; Reflux;59%
With hydrogen In ethyl acetate at 50℃; under 1551.49 - 2585.81 Torr; for 20h;17%
With nickel In ethyl acetate Heating;
furan
110-00-9

furan

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride
75532-25-1

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

A

epi-catharidin
80558-50-5

epi-catharidin

B

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
nickel 1.) 7000 bar, 24 h, 2.) ethyl acetate, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
1,2t-dimethyl-3,6-dioxo-cyclohexane-1r,2c-dicarboxylic acid diethyl ester

1,2t-dimethyl-3,6-dioxo-cyclohexane-1r,2c-dicarboxylic acid diethyl ester

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol Behandeln des Reaktionsprodukts mit konz. Schwefelsaeure;
1-<(Ξ)-benzylidene>-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

1-<(Ξ)-benzylidene>-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
With ozone; ethyl acetate at -40℃; Erhitzen des Reaktionsprodukts mit Essigsaeure und wss. Wasserstoffperoxid;
hydrogenchloride
7647-01-0

hydrogenchloride

2-methoxy-3a,7a-dimethyl-hexahydro-4,7-epoxido-isoindole-1,3-dione

2-methoxy-3a,7a-dimethyl-hexahydro-4,7-epoxido-isoindole-1,3-dione

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
at 150℃; im Rohr;
(+/-)-1-((Ξ)-benzylidene)-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

(+/-)-1-((Ξ)-benzylidene)-3a,7a-dimethyl-(3ar,7ac)-3a,4,5,6,7,7a-hexahydro-4t,7t-epoxido-indene

ethyl acetate
141-78-6

ethyl acetate

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
at -40℃; Erhitzen des Reaktionsprodukts mit Essigsaeure und wss. Wasserstoffperoxid;
cantharidene

cantharidene

cantharidin
56-25-7

cantharidin

hydrogenchloride
7647-01-0

hydrogenchloride

2-hydroxy-3a,7a-dimethyl-hexahydro-4,7-epoxido-isoindole-1,3-dione
853200-58-5

2-hydroxy-3a,7a-dimethyl-hexahydro-4,7-epoxido-isoindole-1,3-dione

A

hydroxylamine
7803-49-8

hydroxylamine

B

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
at 150℃; im Rohr;
(-)-2-bromo-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-8-carboxylic acid

(-)-2-bromo-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-8-carboxylic acid

A

cantharidin
56-25-7

cantharidin

B

dextrorotatory cantharic acid

dextrorotatory cantharic acid

C

<3.6-dibromo-1.2-dimethyl-hexahydrophthalic acid >-anhydride

<3.6-dibromo-1.2-dimethyl-hexahydrophthalic acid >-anhydride

Conditions
ConditionsYield
at 215 - 225℃;
hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

acetic acid
64-19-7

acetic acid

(+)-2-bromo-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-8-carboxylic acid

(+)-2-bromo-1,8-dimethyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-8-carboxylic acid

A

cantharidin
56-25-7

cantharidin

B

<3.6-dibromo-1.2-dimethyl-hexahydrophthalic acid >-anhydride

<3.6-dibromo-1.2-dimethyl-hexahydrophthalic acid >-anhydride

C

levorotatory cantharic acid

levorotatory cantharic acid

Conditions
ConditionsYield
at 150 - 155℃;
C10H8O4S
75532-26-2

C10H8O4S

A

cantharidin
56-25-7

cantharidin

B

concentrated aqueous methylamine solution

concentrated aqueous methylamine solution

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd-C
2: Raney Ni / ethyl acetate / Heating
View Scheme
C10H8O4S
75532-26-2

C10H8O4S

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
With hydrogen In water; ethyl acetate for 4h; Reflux;50 mg
Multi-step reaction with 2 steps
1: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
2: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
3-cyano-3-hydroxy-tetrahydrothiophene-4-carboxylic acid methyl ester
155251-30-2

3-cyano-3-hydroxy-tetrahydrothiophene-4-carboxylic acid methyl ester

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine; trichlorophosphate / benzene / 5 h / 20 - 52 °C
2.1: hydrogenchloride; water; acetic acid / Reflux
3.1: thionyl chloride / Reflux
4.1: 1-butyl-3-methylimidazolium Tetrafluoroborate / 19 h / 50 °C
4.2: Raney-Ni / 4 h / Reflux
View Scheme
methyl 4-oxotetrahydrothiophene-3-carboxylate
2689-68-1

methyl 4-oxotetrahydrothiophene-3-carboxylate

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / water; methanol / 16 h / 20 °C / pH 7 - 8
2.1: pyridine; trichlorophosphate / benzene / 5 h / 20 - 52 °C
3.1: hydrogenchloride; water; acetic acid / Reflux
4.1: thionyl chloride / Reflux
5.1: 1-butyl-3-methylimidazolium Tetrafluoroborate / 19 h / 50 °C
5.2: Raney-Ni / 4 h / Reflux
View Scheme
Multi-step reaction with 7 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -30 - -20 °C / Inert atmosphere
2: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 24 h / 50 °C / 2068.65 Torr
3: sodium hydroxide; water / tetrahydrofuran / 2.5 h
4: acetyl chloride / toluene / 4 h / Reflux
5: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
6: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
7: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
3-cyano-2,5-dihydrothiophene-4-carboxylic acid methyl ester
96307-21-0

3-cyano-2,5-dihydrothiophene-4-carboxylic acid methyl ester

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; water; acetic acid / Reflux
2.1: thionyl chloride / Reflux
3.1: 1-butyl-3-methylimidazolium Tetrafluoroborate / 19 h / 50 °C
3.2: Raney-Ni / 4 h / Reflux
View Scheme
dimethyl-3-thiaadipate
7400-45-5

dimethyl-3-thiaadipate

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: methanol; lithium / 7 h / 20 °C / Inert atmosphere; Reflux
2: hydrogenchloride / water / pH Ca. 5
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -30 - -20 °C / Inert atmosphere
4: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 24 h / 50 °C / 2068.65 Torr
5: sodium hydroxide; water / tetrahydrofuran / 2.5 h
6: acetyl chloride / toluene / 4 h / Reflux
7: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
8: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
9: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
C6H7O3S(1-)*Li(1+)

C6H7O3S(1-)*Li(1+)

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogenchloride / water / pH Ca. 5
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -30 - -20 °C / Inert atmosphere
3: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 24 h / 50 °C / 2068.65 Torr
4: sodium hydroxide; water / tetrahydrofuran / 2.5 h
5: acetyl chloride / toluene / 4 h / Reflux
6: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
7: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
8: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydrothiophene-3-carboxylate
170945-21-8

methyl 4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydrothiophene-3-carboxylate

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 24 h / 50 °C / 2068.65 Torr
2: sodium hydroxide; water / tetrahydrofuran / 2.5 h
3: acetyl chloride / toluene / 4 h / Reflux
4: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
5: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
6: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
3,4-dimethyl 2,5-dihydrothiophene-3,4-dicarboxylate
20946-32-1

3,4-dimethyl 2,5-dihydrothiophene-3,4-dicarboxylate

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydroxide; water / tetrahydrofuran / 2.5 h
2: acetyl chloride / toluene / 4 h / Reflux
3: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
4: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
5: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid
20688-07-7

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetyl chloride / toluene / 4 h / Reflux
2: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
3: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
4: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride
75532-25-1

2,2,4,4-tetrahydrothiophene-3,4-dicarboxylic acid anhydride

cantharidin
56-25-7

cantharidin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-methyl-pyrrolidin-2-one / 48 h / 45 °C
2: hydrogen; 20 mol% Pd/C / ethyl acetate / 760.05 Torr
3: hydrogen / ethyl acetate / 760.05 Torr / Reflux
View Scheme
Cyclopropylamine
765-30-0

Cyclopropylamine

cantharidin
56-25-7

cantharidin

(1S,2R,6S,7R)-4-Cyclopropyl-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-4-Cyclopropyl-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;96%
methylamine
74-89-5

methylamine

cantharidin
56-25-7

cantharidin

7-oxabicyclo<2.2.1>heptane-2,3-dimethyl-2,3-dicarboxylic acid methylimide

7-oxabicyclo<2.2.1>heptane-2,3-dimethyl-2,3-dicarboxylic acid methylimide

Conditions
ConditionsYield
In water 1.) reflux, 4 h, 2.) 200 deg C, 1 h;93%
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

cantharidin
56-25-7

cantharidin

(1R,2S,6R,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1R,2S,6R,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;93%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

cantharidin
56-25-7

cantharidin

(1R,2S,6R,7S)-4-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1R,2S,6R,7S)-4-[2-(5-Methoxy-1H-indol-3-yl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;92%
Nδ-(tert-butoxycarbonyl)-L-ornithine
13650-49-2

Nδ-(tert-butoxycarbonyl)-L-ornithine

cantharidin
56-25-7

cantharidin

(S)-5-tert-Butoxycarbonylamino-2-((1S,2R,6S,7R)-2,6-dimethyl-3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-4-yl)-pentanoic acid
849355-19-7

(S)-5-tert-Butoxycarbonylamino-2-((1S,2R,6S,7R)-2,6-dimethyl-3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-4-yl)-pentanoic acid

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 48h;92%
cantharidin
56-25-7

cantharidin

7-oxabicyclo<2.2.1>heptane-2,3-dimethyl-2,3-dicarboxylic acid imide
76970-77-9

7-oxabicyclo<2.2.1>heptane-2,3-dimethyl-2,3-dicarboxylic acid imide

Conditions
ConditionsYield
With ammonium hydroxide at 180℃; for 2h;91%
With ammonium hydroxide 1.) reflux, 2 h, 2.) 200 deg C, 1 h;66%
(i) aq. NH3, (ii) (heating); Multistep reaction;
With ammonia
2-amino-4-phenyl-1,3,5-thiadiazole
17467-15-1

2-amino-4-phenyl-1,3,5-thiadiazole

cantharidin
56-25-7

cantharidin

N-[5-(3-phenyl-1,2,4-thiadiazolyl)]cantharidinimide

N-[5-(3-phenyl-1,2,4-thiadiazolyl)]cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;91%
1-amino-2-propene
107-11-9

1-amino-2-propene

cantharidin
56-25-7

cantharidin

(1R,2S,6R,7S)-4-Allyl-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1R,2S,6R,7S)-4-Allyl-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;90%
5-methyl-2-thiazol-2-amine
7305-71-7

5-methyl-2-thiazol-2-amine

cantharidin
56-25-7

cantharidin

N-[2-(5-methylthiazolyl)]cantharidinimide

N-[2-(5-methylthiazolyl)]cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;89%
1,4-diaminobutane
110-60-1

1,4-diaminobutane

cantharidin
56-25-7

cantharidin

bis[(1S,2R,3S,6R)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboximido]-tetramethylene

bis[(1S,2R,3S,6R)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboximido]-tetramethylene

Conditions
ConditionsYield
With triethylamine In methanol at 180℃; for 24h;89%
4-tert-Butylaniline
769-92-6

4-tert-Butylaniline

cantharidin
56-25-7

cantharidin

C20H25NO3

C20H25NO3

Conditions
ConditionsYield
With acetic acid Sealed tube;89%
tyrosamine
51-67-2

tyrosamine

cantharidin
56-25-7

cantharidin

(1R,2S,6R,7S)-4-[2-(4-Hydroxy-phenyl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1R,2S,6R,7S)-4-[2-(4-Hydroxy-phenyl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;88%
2-thiazolylamine
96-50-4

2-thiazolylamine

cantharidin
56-25-7

cantharidin

N-(2-thiazolyl)cantharidinimide

N-(2-thiazolyl)cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;87%
4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

cantharidin
56-25-7

cantharidin

N-[2-(4-methylthiazolyl)]cantharidinimide

N-[2-(4-methylthiazolyl)]cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;86%
1,5-diaminopentane
462-94-2

1,5-diaminopentane

cantharidin
56-25-7

cantharidin

bis[(1S,2R,3S,6R)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboximido]-pentamethylene

bis[(1S,2R,3S,6R)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboximido]-pentamethylene

Conditions
ConditionsYield
With triethylamine In methanol at 180℃; for 24h;86%
Trimethylenediamine
109-76-2

Trimethylenediamine

cantharidin
56-25-7

cantharidin

bis[(1S,2R,3S,6R)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboximido]-trimethylene

bis[(1S,2R,3S,6R)-1,2-dimethyl-3,6-epoxycyclohexane-1,2-dicarboximido]-trimethylene

Conditions
ConditionsYield
With triethylamine In methanol at 180℃; for 24h;85%
3,4-methylenedioxyphenylethylamine
1484-85-1

3,4-methylenedioxyphenylethylamine

cantharidin
56-25-7

cantharidin

(1R,2S,6R,7S)-4-(2-Benzo[1,3]dioxol-5-yl-ethyl)-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1R,2S,6R,7S)-4-(2-Benzo[1,3]dioxol-5-yl-ethyl)-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;84%
2-(aminoethyl)pyridine
2706-56-1

2-(aminoethyl)pyridine

cantharidin
56-25-7

cantharidin

(1S,2R,6S,7R)-2,6-Dimethyl-4-(2-pyridin-2-yl-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-2,6-Dimethyl-4-(2-pyridin-2-yl-ethyl)-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;83%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

cantharidin
56-25-7

cantharidin

N-(6-methoxypyridyl-3)cantharidinimide

N-(6-methoxypyridyl-3)cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;83%
ethanolamine
141-43-5

ethanolamine

cantharidin
56-25-7

cantharidin

N-hydroxyethyl exo-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide

N-hydroxyethyl exo-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide

Conditions
ConditionsYield
In ethanol at 20℃; for 2.5h; Acylation; Heating;80.1%
2-amino-3-hydroxypyridine
16867-03-1

2-amino-3-hydroxypyridine

cantharidin
56-25-7

cantharidin

N-(3-hydroxypyridyl-2)cantharidinimide

N-(3-hydroxypyridyl-2)cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;79%
With triethylamine In toluene at 200℃; for 2h;52%
4-Isopropylaniline
99-88-7

4-Isopropylaniline

cantharidin
56-25-7

cantharidin

C19H23NO3

C19H23NO3

Conditions
ConditionsYield
With acetic acid at 135℃; for 12h; Sealed tube;79%
tryptamine
61-54-1

tryptamine

cantharidin
56-25-7

cantharidin

(1R,2S,6R,7S)-4-[2-(1H-Indol-3-yl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1R,2S,6R,7S)-4-[2-(1H-Indol-3-yl)-ethyl]-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;77%
6-amino-3,4-benzodioxane
22013-33-8

6-amino-3,4-benzodioxane

cantharidin
56-25-7

cantharidin

3,4-diethyleneoxyphenylcantharidinimide

3,4-diethyleneoxyphenylcantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;76%
1,4-diaminobutane
110-60-1

1,4-diaminobutane

cantharidin
56-25-7

cantharidin

(1S,2R,6S,7R)-4-(4-Amino-butyl)-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

(1S,2R,6S,7R)-4-(4-Amino-butyl)-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;74%
6-methoxybenzothiazol-2-ylamine
1747-60-0

6-methoxybenzothiazol-2-ylamine

cantharidin
56-25-7

cantharidin

4-(6-methoxy-benzothiazol-2-yl)-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

4-(6-methoxy-benzothiazol-2-yl)-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione

Conditions
ConditionsYield
With triethylamine In toluene at 180℃; for 5h;73%
2-Amino-4,6-dimethylpyridine
5407-87-4

2-Amino-4,6-dimethylpyridine

cantharidin
56-25-7

cantharidin

N-(4,6-dimethylpyridyl-2)cantharidinimide

N-(4,6-dimethylpyridyl-2)cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;72%
With triethylamine In toluene at 200℃; for 2h;62%
2-amino-5-nitro-1,3-thiazole
121-66-4

2-amino-5-nitro-1,3-thiazole

cantharidin
56-25-7

cantharidin

N-[2-(5-nitrothiazolyl)]cantharidinimide

N-[2-(5-nitrothiazolyl)]cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;69%
cantharidin
56-25-7

cantharidin

6-methyl-4-phenyl-benzothiazol-2-ylamine

6-methyl-4-phenyl-benzothiazol-2-ylamine

N-[2-(4-phenyl-6-methylbenzothiazolyl)]cantharidinimide

N-[2-(4-phenyl-6-methylbenzothiazolyl)]cantharidinimide

Conditions
ConditionsYield
With triethylamine In toluene at 200℃; for 2h;69%
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