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Norcantharidin

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Name

Norcantharidin

EINECS 637-280-4
CAS No. 5442-12-6 Density 1.468 g/cm3
PSA 52.60000 LogP -0.13660
Solubility N/A Melting Point 110 °C
Formula C8H8O4 Boiling Point 362.464 °C at 760 mmHg
Molecular Weight 168.149 Flash Point 167.017 °C
Transport Information N/A Appearance solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 5442-12-6 (Norcantharidin) Hazard Symbols N/A
Synonyms

7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylicanhydride (8CI);4,10-Dioxatricyclo[5.2.1.02,6]decane-3,5-dione;NSC 14003;4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-;

Article Data 9

Norcantharidin Synthetic route

28871-63-8

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

5442-12-6

endothall anhydride

Conditions
ConditionsYield
In acetyl chloride99%
5426-09-5

7-oxanorborn-5-ene-2,3-dicarboxylic anhydride

5442-12-6

endothall anhydride

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In ethyl acetate for 16h; Heating / reflux;98%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h;97%
With hydrogen In ethyl acetate at 280℃;81%
67-56-1

methanol

5442-12-6

endothall anhydride

57105-58-5

3-(methoxycarbonyl)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

Conditions
ConditionsYield
at 60℃; for 16h;98%
for 3h; Heating / reflux;96%
at 80 - 85℃; for 3.5h;72.2%
at 80 - 85℃; for 15.5h; Cooling;24.2%
5442-12-6

endothall anhydride

64-17-5

ethanol

115122-59-3

7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid monoethyl ester

Conditions
ConditionsYield
at 80℃; for 4.5h;87%
at 80℃; for 4.5h;87%
921607-52-5

2-azido-1-azidomethyl ethylamine

5442-12-6

endothall anhydride

C11H15N7O4

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere;84%
5442-12-6

endothall anhydride

108-00-9

N,N-dimethylethylenediamine

1-N-(3-exocarboxy-7-oxabicyclo[2.2.1]heptane-2-exocarbonyl)amino-2-(N,N-dimethyl)aminoethane

Conditions
ConditionsYield
In toluene for 2h; Heating / reflux;74%
5442-12-6

endothall anhydride

100-51-6

benzyl alcohol

140486-19-7

7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, mono (phenylmethyl)ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 160℃; for 6h;71.2%
5442-12-6

endothall anhydride

57260-71-6

1-t-Butoxycarbonylpiperazine

1047659-23-3

4-(3-carboxy-7-oxa-bicyclo[2.2.1]heptane-2-carbonyl)piperazine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In toluene at 100 - 110℃; for 8h;47%
In toluene at 100℃; for 8h;
5442-12-6

endothall anhydride

A

85-44-9

phthalic anhydride

B

71-43-2

benzene

Conditions
ConditionsYield
With zeolite Y with a silica-alumina at 200℃; Inert atmosphere;A 41%
B 23%
5442-12-6

endothall anhydride

85098-70-0

4-amino-1-(2-(4-methoxyphenyl)ethyl)piperidine

1047659-20-0

3-{1-[2-(4-methoxy-phenyl)-ethyl]piperidin-4-ylcarbamoyl}-7-oxa-bicyclo[2.2.1]-heptane-2-carboxylic acid

Conditions
ConditionsYield
In toluene at 100℃; for 20h;36%

Norcantharidin Specification

The Norcantharidin, with the CAS registry number 5442-12-6, is also known as 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride. It belongs to the product categories of Norbornene Derivatives; Plant extract. This chemical's molecular formula is C8H8O4 and molecular weight is 168.15. What's more, its systematic name is 4,10-Dioxatricyclo[5.2.1.02,6]decane-3,5-dione. It is used as antineoplastic agents.

Physical properties of Norcantharidin are: (1)ACD/LogP: -0.971; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.97; (4)ACD/LogD (pH 7.4): -0.97; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 7.06; (8)ACD/KOC (pH 7.4): 7.06; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 52.6 Å2; (13)Index of Refraction: 1.55; (14)Molar Refractivity: 36.47 cm3; (15)Molar Volume: 114.53 cm3; (16)Polarizability: 14.458×10-24cm3; (17)Surface Tension: 50.12 dyne/cm; (18)Density: 1.468 g/cm3; (19)Flash Point: 167.017 °C; (20)Enthalpy of Vaporization: 60.841 kJ/mol; (21)Boiling Point: 362.464 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CC2C3C(C1O2)C(=O)OC3=O
(2)Std. InChI: InChI=1S/C8H8O4/c9-7-5-3-1-2-4(11-3)6(5)8(10)12-7/h3-6H,1-2H2
(3)Std. InChIKey: JAABVEXCGCXWRR-UHFFFAOYSA-N 

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 10mg/kg (10mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#05066.

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