115-27-5

Basic information

• Product Name: Chlorendic anhydride
• Synonyms: PERCHLOROBICYCLO (2.2.1)-5-HEPTENE-2,3-DICARBOXYLIC ANHYDRIDE;PERCHLOROBICYCLO[2.2.1]HEPT-5-ENE-2,3-DICARBOXYLIC ANHYDRIDE;,7-methanoisobenzofuran-1,3-dione,4,5,6,7,8,8-hexachloro-3a,4,7,7a-;1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarbosylicanhydride;1,4,5,6,7,7-hexachloro-5-norbornene-3-dicarboxylicanhydride;1,4,5,6,7,7-Hexachlorobicyclo [2.2.1]hept-5-ene-2,3-dicarboxylic anhydride;4,5,6,7,8,8-Hexachloro-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione;1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride,96%
• CAS NO: 115-27-5
• Molecular Formula: C₉H₂Cl₆O₃
• Molecular Weight: 370.83
• EINECS: 204-077-3
• Product Categories: Organics
• Mol File: 115-27-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 235-239 °C(lit.)
• Boiling Point: 486.58°C (rough estimate)
• Flash Point: 200.8 °C
• Appearance: white crystalline powder or chunks
• Density: 1,73 g/cm3
• Vapor Density: 13 (vs air)
• Vapor Pressure: 0-0.003Pa at 20-24.85℃
• Refractive Index: 1.5550 (estimate)
• Water Solubility: insoluble
• Sensitive: Moisture Sensitive
• Merck: 14,2086
• BRN: 92693
• CAS DataBase Reference: Chlorendic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorendic anhydride(115-27-5)
• EPA Substance Registry System: Chlorendic anhydride(115-27-5)

Safety Data

• Hazard Codes: Xi,N,T
• Statements: 36/37/38-51/53-45-52/53-48/20/21/22-40
• Safety Statements: 25-61-36/37/39
• RIDADR: 1759
• WGK Germany: 1
• RTECS: RB9080000
• TSCA: Yes
• Hazardous Substances Data: 115-27-5(Hazardous Substances Data)

Usage

Description

Chlorendic anhydride, also known as Hexahydrophthalic anhydride, is a white crystalline powder or chunks with reactive properties. It is a chemical compound commonly used in the production of various types of polymers and resins due to its flame retardant characteristics and ability to enhance the heat distortion temperature of epoxy products.

Uses

Used in Plastics and Resin Industry:
Chlorendic anhydride is used as a reactive flame retardant for unsaturated polyester, polyurethane, and epoxy resins. It enhances the heat distortion temperature of epoxy products, making them more resistant to high temperatures, with a good resistance of about 180℃.
Used in Polyester Resin Production:
In the preparation of polyester resins, chlorendic anhydride plays a crucial role in improving the properties of the final product, such as heat resistance and flame retardancy.
Used in Chemical Industry Equipment:
Chlorendic anhydride is used in the synthesis of polymers and is particularly useful in the production of fiberglass-reinforced resins for chemical industry equipment. Its flame retardant properties make it an ideal choice for applications where safety and durability are paramount.
Used in Special Inks and Paints:
Chlorendic anhydride is used to make alkyd resins, which are essential components in the formulation of special inks and paints. These inks and paints benefit from the enhanced heat resistance and flame retardancy provided by the anhydride.
Used in Printed Circuit Board Manufacturing:
As a hardening agent in epoxy resins, chlorendic anhydride is used in the manufacture of printed circuit boards. Its ability to improve the heat distortion temperature and provide flame retardancy makes it a valuable component in the production of electronic components that require high-performance characteristics.

Flammability and Explosibility

Nonflammable

Purification Methods

Steam distil the anhydride or recrystallise it from H2O to yield pure diacid. The pure diacid yields the anhydride with Ac2O. [Prill J Am Chem Soc 69 62 1947.]

InChI:InChI=1/C18H6Cl12O7/c19-5-7(21)15(25)3(1(9(31)32)13(5,23)17(15,27)28)11(35)37-12(36)4-2(10(33)34)14(24)6(20)8(22)16(4,26)18(14,29)30/h1-4H,(H,31,32)(H,33,34)

Synthetic route

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + 1,4-phenylenediamine (106-50-3) + cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → 3-{4-[((1R,6S)-6-Carboxy-cyclohex-3-enecarbonyl)-amino]-phenylcarbamoyl}-1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions	Yield
In acetone at 20℃; for 12h;	98%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + m-phenylenediamine (108-45-2) + cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → 3-{3-[((1R,6S)-6-Carboxy-cyclohex-3-enecarbonyl)-amino]-phenylcarbamoyl}-1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions	Yield
In acetone at 20℃; for 12h;	97%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + diethylene glycol (111-46-6) → 5,8,11-trioxa-4,12-dioxo-2,3,13,14-di(1,4,5,6,7,7-hexachlorobicyclo<2.2.1>hept-5-en-2,3-ylene)pentadecanedioic acid (77022-96-9)

Conditions	Yield
In benzene	80%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,2,3,4-tetrachloro-1,3-cyclohexadiene-5,6-dicarboxylic acid anhydride (72524-46-0)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 18 - 35℃;	80%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + 2-amino-5-bromobenzophenone hydrazone (39573-18-7) → N-(2-amino-5-bromobenzhydrylideneamino)-1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboximide

Conditions	Yield
In xylene Heating;	48%

2-amino-5-chlorobenzophenone hydrazone (7039-53-4) + 1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → N-(2-amino-5-chlorobenzhydrylideneamino)-1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboximide

Conditions	Yield
In xylene Heating;	46%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + 2-amino-5-nitrobenzophenone hydrazone (39106-73-5) → N-(2-amino-5-nitrobenzhydrylideneamino)-1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboximide

Conditions	Yield
In xylene for 6h; Heating;	40%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + 2-amino-5-methylbenzophenone hydrazone → N-(2-amino-5-methylbenzhydrylideneamino)-1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboximide

Conditions	Yield
In xylene Heating;	35%

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → maleic anhydride (108-31-6) + hexachlorocyclopentadiene (77-47-4)

Conditions	Yield
Thermodynamic data; gas phase formation;

6-ethyl-o-toluidine (24549-06-2) + 1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → (1R,2S,6R,7S)-1,7,8,9,10,10-Hexachloro-4-(2-ethyl-6-methyl-phenyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions	Yield
at 130 - 140℃; for 3h; Condensation;

2,4-dibromo-6-methylaniline (30273-41-7) + 1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,7,8,9,10,10-hexachloro-4-(2,4-dibromo-6-methyl-phenyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions	Yield
at 130 - 140℃; for 3h; Condensation;

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + 2,6-dimethylaniline (87-62-7) → (1R,2S,6R,7S)-1,7,8,9,10,10-Hexachloro-4-(2,6-dimethyl-phenyl)-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions	Yield
at 130 - 140℃; for 3h; Condensation;

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + o-toluidine (95-53-4) → (1R,2S,6R,7S)-1,7,8,9,10,10-Hexachloro-4-o-tolyl-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions	Yield
at 130 - 140℃; for 3h; Condensation;

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + cis-4-cyclohexene-1,2-dicarboxylic acid N-(p-aminophenyl)amide → 3-{4-[((1R,6S)-6-Carboxy-cyclohex-3-enecarbonyl)-amino]-phenylcarbamoyl}-1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) + cis-4-cyclohexene-1,2-dicarboxylic acid N-(m-aminophenyl)amide → 3-{3-[((1R,6S)-6-Carboxy-cyclohex-3-enecarbonyl)-amino]-phenylcarbamoyl}-1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,4,7,8-tetrachlorobicyclo<2.2.2>oct-7-ene-2,3,5,6-tetracarboxylic acid dianhydride (14427-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / pyridine / dimethylformamide / 18 - 35 °C 2: 90 percent / acetone View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,8,11,12-tetrachlorobicyclo<6.2.2.02,7>dodec-11-ene-4,5,9,10-tetracarboxylic acid dianhydride (33910-30-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / pyridine / dimethylformamide / 18 - 35 °C 2: 80 percent / benzene / 2 h / Heating View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → C22H12Cl14O7

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / benzene 2: SOCl2, pyridine / benzene / 3 h / Ambient temperature View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,4,7,12,15,18-hexaoxacyclodocosane-9,10,20,21-di(1,4,5,6,7,7-hexachlorobicyclo<2,2,1>hept-5-en-2,3-ylene)-8,11,19,22-tetraone (73621-67-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / benzene 2: SOCl2, pyridine / benzene / 3 h / Ambient temperature 3: 10 percent / benzene View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,2,3,4-tetrachloro-1,3-cyclohexadiene-5,6-dicarboxylic acid (49578-22-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / pyridine / dimethylformamide / 18 - 35 °C 2: 10percent aq. KOH View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,4,7,8-tetrachlorobicyclo<2.2.2>oct-7-ene-2,3,5,6-tetracarboxylic acid (140156-07-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / pyridine / dimethylformamide / 18 - 35 °C 2: 90 percent / acetone 3: 10percent aq. KOH View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,7,8,9,10,10-Hexachloro-4-[3-((3aR,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-phenyl]-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 20 °C 2: 96 percent / dimethylformamide / 152 °C View Scheme
Multi-step reaction with 2 steps 1: 97 percent / acetone / 12 h / 20 °C 2: 96 percent / dimethylformamide / 152 °C View Scheme

1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic anhydride (115-27-5) → 1,7,8,9,10,10-Hexachloro-4-[4-((3aR,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-phenyl]-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 20 °C 2: 96 percent / dimethylformamide / 152 °C View Scheme
Multi-step reaction with 2 steps 1: 98 percent / acetone / 12 h / 20 °C 2: 96 percent / dimethylformamide / 152 °C View Scheme

Downstream Products

• 108-31-6 maleic anhydride 
• 77-47-4 hexachlorocyclopentadiene 
• 72524-46-0 1,2,3,4-tetrachloro-1,3-cyclohexadiene-5,6-dicarboxylic acid anhydride 
• 26623-59-6 Chlorendic acid 
• 49578-22-5 1,2,3,4-tetrachloro-1,3-cyclohexadiene-5,6-dicarboxylic acid 

Relevant articles and documents

Flame retardant for polymeric compositions

An additive flame retardant bisimide containing halogen atoms and ammonium acid tetrahalophthalate, e.g. N,N'-bis(2-ethylene tetrabromophthalimide) ammonium acid tetrabromophthalate. These compounds are useful in a variety of polymeric compositions and demonstrate increased thermal stability. They also foam on decomposition with the evolution of gas thus readily lending themselves to the preparation of flame retardant coatings.