115-28-6

Basic information

• Product Name: Chlorendic acid
• Synonyms: CHLORENDIC ACID;LABOTEST-BB LT00159272;HET ACID;HEXACHLORO-ENDO-METHYLENETETRAHYDROPHTHALIC ACID;1,4,5,6,7,7-HEXACHLORO-5-NORBORNENE-2,3-DICARBOXYLIC ACID;1,4,5,6,7,7-HEXACHLOROBICYCLO[2.2.1]-5-HEPTENE-2,3-DICARBOXYLIC ACID;1,4,5,6,7,7-HEXACHLOROBICYCLO[2.2.1]HEPT-5-ENE-2,3-DICARBOXYLIC ACID;1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxy
• CAS NO: 115-28-6
• Molecular Formula: C₉H₄Cl₆O₄
• Molecular Weight: 388.84
• EINECS: 204-078-9
• Product Categories: Organics;Alicyclic/Etch-Resistant Monomers;Lithography Monomers;Self Assembly&Contact Printing
• Mol File: 115-28-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 239-242 °C(lit.)
• Boiling Point: 175°C (rough estimate)
• Flash Point: 239.1 °C
• Appearance: solid
• Density: 1.7157 (estimate)
• Vapor Pressure: 3.37E-10mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.26±0.70(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Chlorendic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorendic acid(115-28-6)
• EPA Substance Registry System: Chlorendic acid(115-28-6)

Safety Data

• Hazard Codes: Xi
• Statements: 40-41
• Safety Statements: 53-22-26-36/37/39-45
• WGK Germany: 3
• RTECS: RB9000000
• Hazardous Substances Data: 115-28-6(Hazardous Substances Data)

Usage

Chemical Properties

Chlorendic acid is a colorless crystalline solid.

Uses

Different sources of media describe the Uses of 115-28-6 differently. You can refer to the following data:
1. Chlorendic acid is used as a flame retardant in polyurethane foams, resins, plasticizers, coatings, epoxy resins, and wool fabrics; in the manufacture of alkyl resins for special paints and inks; in the manufacture of polyester resins with special applications in electrical systems,paneling, engineering plastics, and paint; and in the manufacture of corrosion-resistant tanks, piping, and scrubbers. Chlorendic acid is also used as an extreme-pressure lubricant (NTP 1987, IARC 1990, IPCS 1996, HSDB 2009).
2. Hexachlorobicyclo[2.?2.1]?hept-?5-?ene-?2,?3-?dicarboxylic Acid is a novel flame retardant (NFR) which has also been observed as a toxic and environmental pollutant. Chlorinated Reactive Flame Retardant IntermediateEnvironmental toxin on US EPA Toxic Release Inventory list (TRI) list.

Definition

ChEBI: A bridged organochlorine compound resulting from the Diels-Alder reaction of hexachlorocyclopentadiene with maleic anhydride followed by hydrolysis of the resulting anhydride. A chemical intermediate used in the preparation of fire-retardant polyester resi s and plasticisers.

General Description

Fine white free-flowing crystals or white powder. Odorless.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chlorendic acid readily forms salts with a variety of metals .

Fire Hazard

Chlorendic acid will burn when subject to direct flame, but is self-extinguishing when the flame is removed.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. A severe eye and mild skin irritant. When heated to decomposition it emits toxic fumes of Cl-.

Potential Exposure

Chlorendic acid is used to make other chemicals, polyester resins; in fiberglass reinforced resins; used for anticorrosion equipment and flame retardant applications of fabrics

Carcinogenicity

Chlorendic acid is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN2928 Toxic solids, corrosive, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, 8-Corrosive material, Technical Name Required.

Incompatibilities

Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water, and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur).

Waste Disposal

Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C9H4Cl6O4/c10-3-4(11)8(13)2(6(18)19)1(5(16)17)7(3,12)9(8,14)15/h1-2H,(H,16,17)(H,18,19)/t1-,2+,7+,8-

Synthetic route

cadmium(II) nitrate tetrhydrate + Chlorendic acid (115-28-6) + water (7732-18-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [Cd8(chlorendic acid(-2H))8(N,N-dimethylformamide)4(H2O)12]·8(N,N-dimethylformamide)

Conditions	Yield
In water for 504h;	56%

Chlorendic acid (115-28-6) + propargyl alcohol (107-19-7) → Di-2-propinylchlorendat (114646-85-4)

Conditions	Yield
With toluene-4-sulfonic acid Heating;

Chlorendic acid (115-28-6) → 1,2,3,4,7,7-hexachloro-5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene (2157-19-9)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Heating;

Chlorendic acid (115-28-6) + bis(tri-n-butyltin)oxide (56-35-9) → (C4H9)3SnOOCC7H2Cl6COOH

Conditions	Yield
In benzene byproducts: H2O; mole ratio of (C4H9)3SnOSn(C4H9)3 and carboxylic acid 1:2; at 20°C or at reflux temp. to remove of water formed by azeotropic distn.;

Chlorendic acid (115-28-6) + acetylene (74-86-2) → 1,4,5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid divinyl ester

Conditions	Yield
decacarbonyldirhenium(0) In xylene at 160℃; under 15001.5 Torr; for 6h; Product distribution / selectivity;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-[3-amino-2-(2-nitrophenyl)propionyl]-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-[3-amino-2-(2-nitrophenyl)propionyl]-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-[(2-nitrophenyl)Gly]-(2,3-diaminopropionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-[(2-nitrophenyl)Gly]-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-[3-amino-2-(2-nitrophenyl)propionyl]-(2,3-diaminopropionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-[3-amino-2-(2-nitrophenyl)propionyl]-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-(β-alanyl)-[(2-nitrophenyl)Gly]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-[(2-nitrophenyl)Gly]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-(β-alanyl)-[3-amino-2-(2-nitrophenyl)propionyl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-[3-amino-2-(2-nitrophenyl)propionyl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-(β-alanyl)-[3-amino-2-(2-nitrophenyl)propionyl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-[3-amino-2-(2-nitrophenyl)propionyl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-(β-alanyl)-[4-[4-(1-aminoethyl)-2-methoxy-5-nitrophenoxy]butyryl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-[4-[4-(1-aminoethyl)-2-methoxy-5-nitrophenoxy]butyryl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-(β-alanyl)-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

(4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2,3-diaminopropionyl)-Cys(t-Bu)-[3-amino-2-(2-nitrophenyl)propionyl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-Glu(OtBu)-Glu(OtBu)-Ile-Glu(OtBu)- supported on NovaSyn TGR resin + Chlorendic acid (115-28-6) → (4-methoxy-3-nitrobenzoyl)-Glu(OtBu)-Glu(OtBu)-Glu(OtBu)-Ile-Phe-Gly-Glu(OtBu)-Phe-(2-amino-3-(1,4,5,6,7,7-hexachloro-bicyclo[2.2.1]hept-5-ene-3-(carboxylic acid)-2-carboxamido)propionyl)-(β-alanyl)-[3-amino-2-(2-nitrophenyl)propionyl]-(β-alanyl)-Tyr(PO(benzyloxy)OH)-[3-amino-2-(2-nitrophenyl)propionyl]-Glu(OtBu)-Ile-Glu(OtBu)-cystamine supported on Tentagel S

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate solid phase reaction;

C78H114N13O22PolS2 + Chlorendic acid (115-28-6) → C87H116Cl6N13O25PolS2

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide solid phase reaction;

Downstream Products

• 2157-19-9 1,2,3,4,7,7-hexachloro-5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene 

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Dechlorination of Chlorendic acid (cas 115-28-6) with ozone08/22/2019

An experimental study was conducted to investigate the use of ozone to dechlorinate chlorendic acid [1,4,5,6,7,7-hexachlorobicyclo-(2,2,1)-hept-5-ene-2,3-dicarboxylic acid; CAS Number 115-28-6]. The dechlorination and subsequent degradation of chlorendic acid by ozonation is influenced by the pH...detailed