cis-5-Norbornene-endo-2,3-dicarboxylic anhydride (129-64-6) Physical and Chemical Properties
cis-5-Norbornene-endo-2,3-dicarboxylic anhydride
Bicyclic norbornene dicarboxylic anhydride used as a reactive anhydride monomer and intermediate in polymer synthesis and specialty chemical production.
| CAS Number | 129-64-6 |
| Family | Cyclic anhydrides (norbornene dicarboxylic) |
| Typical Form | Powder or crystalline solid |
| Common Grades | EP |
cis-5-Norbornene-endo-2,3-dicarboxylic anhydride is a bicyclic norbornene-derived cyclic anhydride. The molecule comprises a fused bicyclic hydrocarbon scaffold containing a strained olefinic bond and an anhydride functional group; the empirical composition is \(\ce{C9H8O3}\). The anhydride moiety confers electrophilicity concentrated at the carbonyl carbons and a capacity to undergo nucleophilic acyl substitution, while the norbornene framework increases inherent strain and enhances reactivity as a dienophile in pericyclic reactions.
Electronically the structure combines a relatively nonpolar hydrocarbon framework with a polar, conjugated anhydride functional group. The compound lacks hydrogen-bond donors (HBondDonorCount = 0) but presents multiple acceptor sites (HBondAcceptorCount = 3) and a moderate topological polar surface area (TPSA = 43.4 Å^2), yielding limited aqueous solubility but good compatibility with polar organic solvents. Its modest calculated partition coefficient (XLogP3-AA = 0.7) indicates low-to-moderate lipophilicity compared with small purely hydrocarbon systems. Typical class behaviour includes susceptibility to hydrolysis (producing the corresponding dicarboxylic acid), addition reactions at the anhydride, and use as a reactive dienophile in organic synthesis and polymer chemistry.
Common commercial grades reported for this substance include: EP.
Basic Physical Properties
Density
No experimentally established value for this property is available in the current data context.
Melting Point
No experimentally established value for this property is available in the current data context.
Boiling Point
No experimentally established value for this property is available in the current data context.
Vapor Pressure
No experimentally established value for this property is available in the current data context.
Flash Point
No experimentally established value for this property is available in the current data context.
Chemical Properties
Solubility and Phase Behavior
As a cyclic anhydride, cis-5-norbornene-endo-2,3-dicarboxylic anhydride is generally more soluble in common organic solvents (esters, ketones, chlorinated solvents) than in water. The combination of a constrained bicyclic hydrocarbon skeleton and a relatively small, polar anhydride headgroup produces limited aqueous solubility; the molecule will hydrolyse in the presence of water to yield the corresponding cis-endo dicarboxylic acid. Solubility and phase behaviour in formulation will therefore be strongly dependent on water content and pH: under neutral to basic aqueous conditions hydrolysis is promoted, while nonaqueous organic media preserve the anhydride functionality.
Reactivity and Stability
The anhydride functional group is electrophilic and undergoes standard acyl-transfer chemistry: rapid reaction with alcohols (to give half-esters), with amines (to give amic acids and, upon cyclodehydration, imides), and with water (hydrolysis to the dicarboxylic acid). The strained norbornene double bond increases reactivity as a dienophile in Diels–Alder reactions and can participate in radical or catalytic additions under appropriate conditions. The compound is stable when kept dry and protected from nucleophiles and bases; exposure to moisture, strong nucleophiles, or prolonged heating will lead to hydrolysis or decomposition. Storage under inert, dry conditions reduces the risk of undesired transformation. Avoid strong bases and strong nucleophiles that promote ring opening or rapid hydrolysis.
Thermodynamic Data
Standard Enthalpies and Heat Capacity
No experimentally established value for this property is available in the current data context.
Molecular Parameters
Molecular Weight and Formula
- Molecular formula: \(\ce{C9H8O3}\)
- Molecular weight (computed): 164.16
- Exact / monoisotopic mass: 164.047344113
Additional computed descriptors: HeavyAtomCount = 12; Formal Charge = 0; Complexity = 277.
LogP and Polarity
- XLogP (XLogP3-AA): 0.7
- Topological polar surface area (TPSA): 43.4 Å^2
- Hydrogen-bond donors: 0
- Hydrogen-bond acceptors: 3
- Rotatable bond count: 0
These parameters indicate modest polarity and low capacity for hydrogen-bond donation, consistent with limited water solubility and reasonable solubility in polar organic solvents.
Structural Features
The structure is a cis-endo norbornene bicyclic system bearing a fused anhydride (2,3-dicarboxylic anhydride) in the endo orientation. The combination of ring strain from the bicyclic scaffold, an endo-placed anhydride, and a reactive double bond confers the molecule with pronounced dienophilic and acylating reactivity. Computed stereochemical descriptors indicate Defined Atom Stereocenter Count = 2 and Undefined Atom Stereocenter Count = 2, reflecting the presence of stereogenic centers and certain conformational or stereochemical ambiguities in the computational assignment.
Identifiers and Synonyms
Registry Numbers and Codes
- CAS RN: 129-64-6
- Nikkaji number: J827.810E
- CID: 9964188
- InChIKey: KNDQHSIWLOJIGP-DPTVFECHSA-N
- InChI:
InChI=1S/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? - SMILES:
C1[C@@H]2C=C[C@H]1C3C2C(=O)OC3=O
Synonyms and Structural Names
Depositor-supplied synonyms include:
- cis-5-Norbornene-endo-2,3-dicarboxylic anhydride
- (1S,7R)-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
- cis-endo-5-Norbornene-2,3-dicarboxylic anhydride
- SCHEMBL533614
- KNDQHSIWLOJIGP-DPTVFECHSA-N
- AKOS015901285
- AS-14679
- cis-5-norbomene-endo-2,3-dicarboxylic anhydride
Alternative or historical synonyms (appearance in source annotations) include:
- Carbic anhydride
- Himic anhydride
- Himicanhydride
- Nadic anhydride
- C9H8O3
- 5-Norbornene-2,3-dicarboxylic anhydride
- Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
- (4R,7S)-3a,4,7,7a-Tetrahydro-4,7-methanoisobenzofuran-1,3-dione
Industrial and Commercial Applications
Representative Uses and Industry Sectors
Cyclic norbornene anhydrides such as this compound are primarily used as reactive dienophiles and acylating reagents in organic synthesis and polymer chemistry. Representative class-level applications include use as a monomeric or comonomeric building block in specialty resin and coating formulations, as a curing or crosslinking component in thermoset systems (via anhydride–epoxy chemistry), and as a dienophile in Diels–Alder functionalization strategies for synthesis of complex intermediates. The molecule's reactivity profile also makes it useful in laboratory-scale organic synthesis for preparation of imides and related derivatives.
Role in Synthesis or Formulations
In preparative chemistry the anhydride reacts with nucleophiles (alcohols, amines) to deliver half-esters and amic acids, which can be converted to imides by dehydration. The norbornene double bond allows pericyclic (Diels–Alder) and radical addition reactions, enabling introduction of further functionality or crosslinking. In formulations, the anhydride functionality can act as a latent curing agent (reacting with epoxy resins) or as a site for grafting and polymer modification. No concise application summary is available in the current data context; in practice this substance is selected based on its general properties described above.
Safety and Handling Overview
Acute and Occupational Toxicity
Specific acute toxicity values are not provided in the current data context. As a cyclic anhydride, the substance should be treated as an irritant to skin, eyes and the respiratory tract; anhydrides in general can be respiratory sensitizers or cause bronchial irritation in susceptible individuals. Occupational control measures should minimize inhalation and dermal exposure: use local exhaust ventilation, closed handling systems where feasible, and appropriate personal protective equipment (gloves, eye protection, respiratory protection as required).
Storage and Handling Considerations
Store in a cool, dry, well-ventilated area in tightly closed containers to minimize exposure to moisture and nucleophilic contaminants that will hydrolyse or react with the anhydride. Avoid contact with strong bases, strong nucleophiles, and materials that may catalyse hydrolysis. For long-term stability, inert atmosphere (dry nitrogen or argon) and low-temperature storage are commonly used. For detailed hazard, transport and regulatory information, users should refer to the product-specific Safety Data Sheet (SDS) and local legislation.
