Product Name

  • Name

    Carbic anhydride

  • EINECS 204-957-7
  • CAS No. 129-64-6
  • Article Data78
  • CAS DataBase
  • Density 1.405 g/cm3
  • Solubility decomposes in water
  • Melting Point 165-167 °C(lit.)
  • Formula C9H8O3
  • Boiling Point 331.1 °C at 760 mmHg
  • Molecular Weight 164.161
  • Flash Point 163.8 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 22-24-26-37/39
  • Risk Codes 41-42/43
  • Molecular Structure Molecular Structure of 129-64-6 (Carbic anhydride)
  • Hazard Symbols HarmfulXn
  • Synonyms 4,7-Methanoisobenzofuran-1,3-dione,3a,4,7,7a-tetrahydro-, (3aa,4a,7a,7aa)-;5-Norbornene-2,3-dicarboxylic anhydride, cis-endo- (8CI);5-Norbornene-endo-2,3-dicarboxylic anhydride;Bicyclo[2.2.1]-2-heptene-endo-5,6-dicarboxylic acid anhydride;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid endo-cis-anhydride;Bicyclo[2.2.1]hept-5-ene-endo,endo-2,3-dicarboxylic anhydride;Bicyclo[2.2.1hept-5-ene-2-endo,3-endo-dicarboxylic anhydride;
  • PSA 43.37000
  • LogP 0.50810

Synthetic route

maleic anhydride
108-31-6

maleic anhydride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide at 20℃; for 0.166667h; Diels-Alder reaction; diastereoselective reaction;100%
With 1-hexyl-3-methylimidazolium tetrafluoroborate; K-10 montmorillonite at 20℃; for 0.0833333h; Diels-Alder reaction;99%
In dichloromethane at 0 - 20℃; for 10h; Diels-Alder Cycloaddition; Inert atmosphere;98%
bicyclo<2.2.1>-5-hepten-2endo,3endo-dicarboxylic anhydride
129-64-6, 826-62-0, 2746-19-2, 85081-15-8, 85081-16-9

bicyclo<2.2.1>-5-hepten-2endo,3endo-dicarboxylic anhydride

A

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

B

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
With sodium hydroxide In water at 70℃; for 0.166667h; Product distribution / selectivity;A n/a
B 87%
With sodium hydroxide In water at 70℃; for 0.166667h; Product distribution / selectivity;A 83%
B 26%
With sodium hydroxide In water at 70℃; for 0.166667h; Product distribution / selectivity;A n/a
B 50%
cis-5-norbornene-endo-2,3-carboxycylic acid disodium salt

cis-5-norbornene-endo-2,3-carboxycylic acid disodium salt

A

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

B

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
Stage #1: cis-5-norbornene-endo-2,3-carboxycylic acid disodium salt With hydrogenchloride In water at 5 - 70℃; for 3.16667h;
Stage #2: With acetic anhydride at 5 - 70℃; for 3.16667h; Product distribution / selectivity;
A n/a
B 85%
maleic anhydride
108-31-6

maleic anhydride

bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

A

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

B

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
at 206℃; for 0.366667h; Diels-Alder reaction; Neat (no solvent);A 35%
B 37%
at 206℃; for 0.166667h; Diels-Alder reaction; Neat (no solvent); optical yield given as %de;
3,4-Bis(trimethylsiloxy)-endo-tricyclo(4.2.1.02,5and)nona-3,7-dien
39762-43-1

3,4-Bis(trimethylsiloxy)-endo-tricyclo(4.2.1.02,5and)nona-3,7-dien

(1α,1'α',2α,2'α',5α,5'α',6α,6'α')-4,4'-Bis(trimethylsilyloxy)-4,4'-bi(tricyclo<4.2.1.02,5>non-7-enyl)-3,3'-dion
94008-60-3

(1α,1'α',2α,2'α',5α,5'α',6α,6'α')-4,4'-Bis(trimethylsilyloxy)-4,4'-bi(tricyclo<4.2.1.02,5>non-7-enyl)-3,3'-dion

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With copper diacetate In acetic acid for 3h; Heating;A 13%
B 23%
2-chloromaleic anhydride
96-02-6

2-chloromaleic anhydride

endo-Dicyclopentadien
1755-01-7

endo-Dicyclopentadien

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

dichloromaleic acid anhydride
1122-17-4

dichloromaleic acid anhydride

endo-Dicyclopentadien
1755-01-7

endo-Dicyclopentadien

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

norbornene-5,6-dicarboxylic acid
1200-88-0

norbornene-5,6-dicarboxylic acid

A

(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
zuletzt Erhitzen unter 15 Torr;
(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
at 190℃; Gleichgewichtsgemisch;
maleic anhydride
108-31-6

maleic anhydride

cyclopentene
142-29-0

cyclopentene

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
In diethyl ether
(1R,2S,3R,4S)-3-Propylcarbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
32392-78-2

(1R,2S,3R,4S)-3-Propylcarbamoyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

A

propylamine
107-10-8

propylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,2S,3R,4S)-3-(2-Fluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
93630-43-4

(1R,2S,3R,4S)-3-(2-Fluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

A

2-fluoroethylamine
406-34-8

2-fluoroethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,2S,3R,4S)-3-(2-Methoxy-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
93630-42-3

(1R,2S,3R,4S)-3-(2-Methoxy-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

A

2-methoxyethylamine
109-85-3

2-methoxyethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,2S,3R,4S)-3-(2,2-Difluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
93630-44-5

(1R,2S,3R,4S)-3-(2,2-Difluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

A

2,2-difluorethylamine
430-67-1

2,2-difluorethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,2S,3R,4S)-3-(2,2,2-Trifluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
93630-45-6

(1R,2S,3R,4S)-3-(2,2,2-Trifluoro-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

A

trifluoroethylamine
753-90-2

trifluoroethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,7S)-5-Hydroxy-5-propylamino-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

(1R,7S)-5-Hydroxy-5-propylamino-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

A

propylamine
107-10-8

propylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,7S)-5-(2-Fluoro-ethylamino)-5-hydroxy-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

(1R,7S)-5-(2-Fluoro-ethylamino)-5-hydroxy-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

A

2-fluoroethylamine
406-34-8

2-fluoroethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,7S)-5-Hydroxy-5-(2-methoxy-ethylamino)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

(1R,7S)-5-Hydroxy-5-(2-methoxy-ethylamino)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

A

2-methoxyethylamine
109-85-3

2-methoxyethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,7S)-5-(2,2-Difluoro-ethylamino)-5-hydroxy-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

(1R,7S)-5-(2,2-Difluoro-ethylamino)-5-hydroxy-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

A

2,2-difluorethylamine
430-67-1

2,2-difluorethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
(1R,7S)-5-Hydroxy-5-(2,2,2-trifluoro-ethylamino)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

(1R,7S)-5-Hydroxy-5-(2,2,2-trifluoro-ethylamino)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one

A

trifluoroethylamine
753-90-2

trifluoroethylamine

B

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With water at 38℃; Rate constant;
cis-5-norbornene-endo-2,3-dicarboxylic acid
3853-88-1

cis-5-norbornene-endo-2,3-dicarboxylic acid

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With 4-methyl-morpholine; methyl chloroformate In tetrahydrofuran at 20℃; for 0.25h;
maleic anhydride
108-31-6

maleic anhydride

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

A

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

B

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
indium(III) chloride In water for 4h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With m-NO2C6H4BF2 In tetrahydrofuran at 0℃; for 1h; Title compound not separated from byproducts;
With m-NO2C6H4BF2 In tetrahydrofuran at 0℃; for 1h; Product distribution; other boron catalysts, other temperature regime;
Stage #1: maleic anhydride With (S)-BINOL-Silica Hybrid (BSH) In dichloromethane at 20℃; for 0.166667h; Diels-Alder Cycloaddition;
Stage #2: cyclopenta-1,3-diene In dichloromethane at 20℃; for 2h; Diels-Alder Cycloaddition; Overall yield = 85 %; Optical yield = 84 %de;
maleic anhydride
108-31-6

maleic anhydride

(1R,6S,7S)-5,5-Dimethyl-2,3-diaza-tricyclo[5.2.1.02,6]deca-3,8-diene
108946-69-6, 119323-10-3

(1R,6S,7S)-5,5-Dimethyl-2,3-diaza-tricyclo[5.2.1.02,6]deca-3,8-diene

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform-d1 for 336h;
acetic acid
64-19-7

acetic acid

(+/-)-2exo-chloro-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride
828-38-6, 6343-12-0, 69743-64-2

(+/-)-2exo-chloro-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

zinc-powder

zinc-powder

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

acetic acid
64-19-7

acetic acid

(+/-)-2exo-bromo-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

(+/-)-2exo-bromo-norborn-5-ene-2endo,3endo-dicarboxylic acid-anhydride

zinc-powder

zinc-powder

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

acetic acid
64-19-7

acetic acid

(1R,2S,3R,4S)-2,3-dibromobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
33140-59-9

(1R,2S,3R,4S)-2,3-dibromobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride

zinc-powder

zinc-powder

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

maleic anhydride
108-31-6

maleic anhydride

endo-Dicyclopentadien
1755-01-7

endo-Dicyclopentadien

mineral oil

mineral oil

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
at 200℃;
maleic anhydride
108-31-6

maleic anhydride

bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
In tetrahydrofuran at 95 - 195℃; Solvent; Temperature;
methanol
67-56-1

methanol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1SR,2RS,3SR,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
96185-91-0

(1SR,2RS,3SR,4RS)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions
ConditionsYield
for 16h; Reflux;100%
With triethylamine at 20℃; for 12h;98%
With triethylamine for 2h; Heating;97%
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
at 180℃; for 24h;100%
With triethylamine In ethanol Mechanism; Irradiation; 2-6 h; other endo-Diels-Alder cycloadducts;94%
With triethylamine In ethanol Irradiation; 2-6 h;94%
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione
6265-30-1

(1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 140℃; for 96h; Inert atmosphere;100%
With ammonium acetate; acetic acid at 140℃; for 16h;100%
With ammonium acetate at 135℃; Industrial scale;98.8%
n-propylmagnesium bromide
927-77-5

n-propylmagnesium bromide

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

dipropyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.02.6>decene-8 one-3
87603-95-0, 94234-39-6

dipropyl-5,5 oxa-4,10 endo-tricyclo<5.2.1.02.6>decene-8 one-3

Conditions
ConditionsYield
100%
In tetrahydrofuran; diethyl ether at 25℃; for 4h;90%
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol
941567-71-1

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0℃; Reflux;100%
With lithium aluminium tetrahydride In diethyl ether at 20℃;97%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;95%
Linoleyl alcohol
506-43-4

Linoleyl alcohol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

C27H42O4

C27H42O4

Conditions
ConditionsYield
With triethylamine at 65℃; for 24h;100%
aniline
62-53-3

aniline

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

3-endo-(N-phenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid
53193-34-3, 66662-10-0

3-endo-(N-phenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

Conditions
ConditionsYield
In benzene at 20℃;99%
1-amino-2-propene
107-11-9

1-amino-2-propene

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(3aRS,4SR,7RS,7aSR)-2-allyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione
6971-11-5

(3aRS,4SR,7RS,7aSR)-2-allyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions
ConditionsYield
In acetic acid for 16h; Inert atmosphere; Reflux;99%
With acetic acid at 20 - 110℃; for 6h; Reflux; Inert atmosphere;89%
With benzene
benzylamine
100-46-9

benzylamine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1α,2α,6α,7α)-4-benzyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
75715-21-8

(1α,2α,6α,7α)-4-benzyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In acetic acid for 5h; Inert atmosphere; Reflux;99%
With triethylamine In toluene for 19h; Heating;93%
In ethanol at 165 - 175℃;85%
With benzene
With triethylamine In toluene for 5h; Reflux;
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

cis-5-norbornene-endo-2,3-dicarboxylic anhydride
17812-27-0, 853658-14-7

cis-5-norbornene-endo-2,3-dicarboxylic anhydride

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In tetrahydrofuran under 75.006 Torr;99%
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 16h; Product distribution / selectivity;99%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; for 16h;99%
methanol
67-56-1

methanol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
96243-73-1

(1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions
ConditionsYield
With (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(dimethylamino)-3-methylbutan-2-yl)thiourea In tert-butyl methyl ether at 20℃; for 32h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
Stage #1: 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride With quinine In tetrachloromethane; toluene Inert atmosphere;
Stage #2: methanol In tetrachloromethane; toluene at -55 - 25℃;
Stage #3: With hydrogenchloride In water; ethyl acetate
98%
With textile immobilized (9S)-9-(3,5-di(trifluoromethyl)phenyl)sulfonamido-9-deoxyquinidine In tert-butyl methyl ether at 20℃; for 14h; enantioselective reaction;94%
methanol
67-56-1

methanol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1S,2R,3S,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
96243-74-2

(1S,2R,3S,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions
ConditionsYield
With quinidine In tetrachloromethane; toluene99%
With 1-((1R,2R)-2-(dimethylamino)cyclohexyl)-3-phenylthiourea In diethyl ether at 20℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With quinidine In tetrachloromethane; toluene at -55℃; for 60h; Ring cleavage; methylation;98%
piperidine
110-89-4

piperidine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

endo-3-(piperidinocarbonyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

endo-3-(piperidinocarbonyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

Conditions
ConditionsYield
In benzene at 20℃; for 24h;99%
N-BOC-1,2-diaminoethane
57260-73-8

N-BOC-1,2-diaminoethane

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1α,2α,6α,7α)-4-[2’-(tertbutoxycarbonylamino)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-en-3,5-dione
872728-22-8

(1α,2α,6α,7α)-4-[2’-(tertbutoxycarbonylamino)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

Conditions
ConditionsYield
In toluene at 100℃; for 0.5h; Microwave irradiation;99%
In toluene at 100℃; for 0.5h; Microwave irradiation;99%
In chloroform at 120℃; for 12h;80.9%
ethylenediamine
107-15-3

ethylenediamine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

[[3,5-dioxo-4-azatricyclo-[5.2.1.02,6]dec-8-en-4-yl]ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
60268-88-4

[[3,5-dioxo-4-azatricyclo-[5.2.1.02,6]dec-8-en-4-yl]ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In toluene for 120h; Reflux; Inert atmosphere;99%
potassium trifluoro(prop-1-en-2-yl)borate

potassium trifluoro(prop-1-en-2-yl)borate

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(3aS(R),4S(R),7R(S),7aR(S))-3,3-diallyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one

(3aS(R),4S(R),7R(S),7aR(S))-3,3-diallyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;99%
3-butene-1-amine
2524-49-4

3-butene-1-amine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(3aRS,4SR,7RS,7aSR)-2-(but-3-en-1-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

(3aRS,4SR,7RS,7aSR)-2-(but-3-en-1-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions
ConditionsYield
In acetic acid for 16h; Inert atmosphere; Reflux;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1α,2α,6α,7α)-4-(pyridin-3-ylmethyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

(1α,2α,6α,7α)-4-(pyridin-3-ylmethyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In toluene at 200℃; for 0.166667h;99%
2-nitro-aniline
88-74-4

2-nitro-aniline

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2S,3R,4S)-3-(2-Nitro-phenylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(1R,2S,3R,4S)-3-(2-Nitro-phenylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 24h;98%
4-bromo-aniline
106-40-1

4-bromo-aniline

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

endo-3-(p-bromophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

endo-3-(p-bromophenylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

Conditions
ConditionsYield
In benzene at 20℃;98%
3-methylantranilic acid
4389-45-1

3-methylantranilic acid

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

C17H15NO4
698393-13-4

C17H15NO4

Conditions
ConditionsYield
at 110℃; for 16h; Inert atmosphere; neat (no solvent);98%
salicylaldehyde
90-02-8

salicylaldehyde

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

C16H14O5

C16H14O5

Conditions
ConditionsYield
With [(1,5-cyclooctadiene)(OH)iridium(I)]2 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; Schlenk technique; Sealed tube; diastereoselective reaction;98%
6-amino-1-hexanol
4048-33-3

6-amino-1-hexanol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(3aR,4S,7R,7aS)-2-(6-hydroxyhexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

(3aR,4S,7R,7aS)-2-(6-hydroxyhexyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions
ConditionsYield
In toluene for 6h; Reflux; Dean-Stark;98%
1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane
2469-55-8

1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyldisiloxane

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

nadic anhydride

nadic anhydride

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 20℃; for 6h; Inert atmosphere;97.2%
allyl alcohol
107-18-6

allyl alcohol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(2R,3S)-3-endo-allyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

(2R,3S)-3-endo-allyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

Conditions
ConditionsYield
With quinidine In tetrachloromethane; toluene at -55℃; for 60h;97%
ethanolamine
141-43-5

ethanolamine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2S,3R,4S)-3-(2-Hydroxy-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(1R,2S,3R,4S)-3-(2-Hydroxy-ethylcarbamoyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 24h;97%
N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1R,2S,6R,7S)-4-[2-(dimethylamino)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
744151-96-0

(1R,2S,6R,7S)-4-[2-(dimethylamino)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In toluene Reflux;97%
In toluene at 80℃;86%
In benzene at 110℃; for 18h;44%
6-aminoquinoxaline
6298-37-9

6-aminoquinoxaline

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

endo-3-(6-quinoxalylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

endo-3-(6-quinoxalylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid

Conditions
ConditionsYield
In benzene at 20℃;97%
S-methylisothiosemicarbazide hydroiodide
35600-34-1

S-methylisothiosemicarbazide hydroiodide

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

C11H13N3O2S
1283093-35-5

C11H13N3O2S

Conditions
ConditionsYield
Stage #1: S-methylisothiosemicarbazide hydroiodide; 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride With acetic acid for 1.5h; Reflux;
Stage #2: With ammonia In water
97%

Carbic anhydride Chemical Properties

The Molecular Structure of Carbic anhydride (CAS NO.129-64-6):

Empirical Formula: C9H8O3
Molecular Weight: 164.158
Nominal Mass: 164 Da
Average Mass: 164.158 Da
Monoisotopic Mass: 164.047344 Da 
Index of Refraction: 1.583
Molar Refractivity: 39.08 cm3
Molar Volume: 116.7 cm3
Surface Tension: 50.9 dyne/cm
Density: 1.405 g/cm3
Flash Point: 163.8 °C
Enthalpy of Vaporization: 57.37 kJ/mol
Boiling Point: 331.1 °C at 760 mmHg
Vapour Pressure: 0.00016 mmHg at 25°C 
Melting Point: 164.5°C 
log P (octanol-water): 1.850at 25°C 
Atmospheric OH Rate Constant: 6.01E-11 cm3/molecule-secat 25°C 
InChI
InChI=1/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2/t4-,5-,6-,7+/m0/s1
Smiles
C1(OC(=O)[C@H]2[C@@H]1[C@H]1C=C[C@@H]2C1)=O 
EINECS: 204-957-7    

Carbic anhydride Specification

 Carbic anhydride (CAS NO.129-64-6) is also called as 3,6-Endomethylene-delta4-tetrahydrophthalic anhydride ; Endic anhydride ; Nadic anhydride ; Endo-5-Norbornene-2,3-dicarboxylic anhydride ; Endo-Himic acid anhydride ; 4,7-Methanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-, (3aalpha,4alpha,7alpha,7aalpha)- (9CI) ; 5-Norbornene-2,3-dicarboxylic anhydride, cis-endo- (8CI) ; 8,9,10-Trinorborn-5-ene-2,3-dicarboxylic anhydride ; Endo-3,6-methylene-1,2,3,6-tetrahydrophthalic anhydride ; cis-5-Norbornene-endo-2,3-dicarboxylic anhydride .

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