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DESCRIPTION
o-Phthalaldehyde (OPA) is an organic compound with the chemical formula C8H6O2.
o-Phthalaldehyde (OPA) is a colorless crystalline solid that is primarily used in chemical and industrial applications, such as a reagent in the detection of primary amines.
OPA is a reactive compound that forms fluorescent products upon reacting with amino acids and peptides, making it useful in protein quantification.
Cas Number: 643-79-8
SYNONYMS
o-Phthalaldehyde,643-79-8,PHTHALALDEHYDE,o-Phthaldialdehyde,1,2-Benzenedicarboxaldehyde,Benzene-1,2-dicarboxaldehyde,Phthaldialdehyde,Phthalic aldehyde,ortho-Phthalaldehyde,Phthalic dialdehyde,Phthalyldicarboxaldehyde,Phthalic dicarboxaldehyde,benzene-1,2-dicarbaldehyde,o-Phthaldehyde,Phthalaldialdehyde,o-Phthalicdicarboxaldehyde,1,2-Diformylbenzene,2-PHTHALALDEHYDE,ortho Phthalaldehyde,o-Phthalic dicarboxaldehyde,Phtalaldehydes,OPTA,OPA,orthophthalaldehyde,1,2-BENZENEDICARBALDEHYDE,NSC 13394,phtharal,Disopa,CHEBI:70851,EINECS 211-402-2,MFCD00003335,UNII-4P8QP9768A,BRN 0878317,ortho-phthaldialdehyde,DTXSID6032514,4P8QP9768A,NSC-13394,DTXCID4012514,HSDB 8456,4-07-00-02138 (Beilstein Handbook Reference),Phtharal (JAN),NCGC00166206-01,PHTHARAL [JAN],1,2-Phthalic dicarboxaldehyde,Orthophthaldialdehyde,ortho-Phthalic Aldehyde,Phtalaldehydes [French],O-PHTHALDIALDEHYDE (MART.),O-PHTHALDIALDEHYDE [MART.],o Phthalaldehyde,o Phthaldialdehyde,CAS-643-79-8,ortho Phthalic Aldehyde,Aldehyde, ortho-Phthalic,phthalaldehyd,o-Phthalaldehyd,o-phthal aldehyde,Safe OPA,Disopa (TN),Epitope ID:176774,SCHEMBL33393,Benzene-1,2-dicarboxakdehyde,O-PHTHALALDEHYDE [MI],CHEMBL160145,ORTHOPHTHALALDEHYDE [VANDF],BCP29465,NSC13394,STR01056,Tox21_112347,Tox21_300404,1,2-Benzenedialdehyde;Phthalaldehyde,BBL027435,STK802214,AKOS000119186,Tox21_112347_1,CS-W013385,NCGC00166206-02,NCGC00166206-04,NCGC00254339-01,AC-10388,NS00005771,P0280,EN300-21268,D03470,P-6600,SBI-0653909.0001,SR-01000944839,Q5933776,SR-01000944839-1,Phthaldialdehyde, for fluorescence, >=99.0% (HPLC),Z104494958,Phthaldialdehyde, >=97% (HPLC), powder (may contain lumps),InChI=1/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6,25750-62-3
Overview of o-Phthalaldehyde (OPA)
o-Phthalaldehyde (OPA) is a benzene derivative that consists of two aldehyde groups attached to a benzene ring in a 1,2-position (ortho-positions), hence the prefix "o-" in its name.
Its chemical formula is C8H6O2. OPA is an aromatic aldehyde compound that plays a significant role in various industrial and laboratory applications due to its unique chemical properties.
OPA is structurally similar to other aldehydes but its reactivity and ability to form stable complexes with amines and other nucleophiles make it of particular interest in biological and chemical research.
o-Phthalaldehyde (OPA) is commonly used as a reagent in protein labeling and assays, and in sterilization and disinfection, among other applications.
Historical Background
OPA was first synthesized in the mid-19th century and has since gained prominence for its applications in biological and chemical fields.
Early uses focused primarily on its use as a sterilizing agent in medical and laboratory settings.
In the 1980s and 1990s, researchers began exploring its utility in protein research, particularly as a reagent for amino acid analysis and fluorescence labeling.
As understanding of OPA’s biological interactions deepened, its importance in diagnostics and pharmaceuticals grew significantly.
CHEMICAL PROPERTIES OF O-PHTHALALDEHYDE
Molecular Structure and Characteristics
OPA consists of a benzene ring with two aldehyde (-CHO) groups in the ortho positions relative to each other.
This unique structure allows OPA to exhibit specific reactivity toward amino groups. Its molecular characteristics include:
Molecular Formula: C8H6O2
Molecular Weight: 134.13 g/mol
Melting Point: 96-98°C
Boiling Point: 295°C (decomposes)
Solubility: Slightly soluble in water, but more soluble in organic solvents such as ethanol and acetone.
The presence of two aldehyde groups contributes to its reactivity and enables OPA to form Schiff bases with primary amines, a feature that is especially useful in biological assays and protein labeling.
Reactivity and Functional Groups
The two aldehyde groups of OPA are highly reactive and prone to nucleophilic attack, particularly from primary and secondary amines.
This reactivity makes it useful in forming stable covalent bonds with proteins and other biological molecules.
The reaction typically involves the formation of a Schiff base, which is a reversible reaction that can be used to label amine-containing compounds for detection or purification purposes.
OPA also undergoes oxidation under certain conditions, potentially forming quinone derivatives, which can be used for further functionalization in advanced chemical applications.
Synthesis Methods
The synthesis of OPA generally involves the oxidation of ortho-xylene or phthalic acid derivatives under controlled conditions. Some methods include:
From Phthalic Acid: Phthalic acid is reacted with an oxidizing agent (like potassium permanganate or chromic acid) to introduce the aldehyde groups at the ortho positions.
From Ortho-Xylene: Ortho-xylene can be oxidized with reagents such as oxygen or air in the presence of a catalyst, leading to the formation of OPA.
Other synthetic routes involve substitution reactions or Friedel-Crafts alkylation of phthalic derivatives, with various catalysts and reagents.
Analytical Techniques for o-Phthalaldehyde
Spectroscopic Techniques
Several techniques are employed to characterize and analyze OPA:
UV-Vis Spectroscopy: OPA absorbs strongly in the UV region, making it useful for concentration determination. Its characteristic absorption peaks in the range of 270-300 nm are indicative of the presence of the aldehyde functional groups.
Infrared (IR) Spectroscopy: The IR spectrum of OPA typically shows a strong carbonyl stretch (~1725 cm^-1) due to the aldehyde groups and aromatic ring vibrations in the region 1400-1600 cm^-1.
Nuclear Magnetic Resonance (NMR) Spectroscopy: Both ^1H-NMR and ^13C-NMR can be used to elucidate the structure of OPA, with chemical shifts corresponding to the aromatic protons and the protons in the aldehyde groups. ^13C-NMR provides detailed information on the carbon environment in the molecule.
Mass Spectrometry: This technique allows for the determination of the molecular weight and fragmentation pattern of OPA, confirming its structure.
Chromatographic Techniques
High-Performance Liquid Chromatography (HPLC): OPA can be analyzed using HPLC to assess purity or to quantify OPA in mixtures, especially in biological and pharmaceutical contexts.
Gas Chromatography (GC): Although OPA has a relatively high boiling point and is somewhat thermally labile, GC can still be used with proper derivatization techniques to separate and quantify OPA in volatile mixtures.
Other Analytical Methods
Fluorescence Spectroscopy: OPA can form highly fluorescent complexes with certain amines, making it a useful tool in protein and nucleic acid labeling for detection in biological assays.
Electrochemical Analysis: Some electrochemical techniques, such as cyclic voltammetry, are used to study the reduction and oxidation behavior of OPA and its reactivity with other compounds.
Applications of o-Phthalaldehyde
Sterilization and Disinfection
OPA has proven to be a powerful disinfectant and sterilizing agent, particularly for heat-sensitive medical and laboratory equipment.
It is used to sterilize endoscopes, surgical instruments, and other medical devices, due to its ability to kill bacteria, viruses, and fungi effectively.
OPA is considered a safer alternative to glutaraldehyde and formaldehyde, with lower toxicity and less irritating fumes.
Mechanism of Action: OPA reacts with the amine groups on microbial proteins, disrupting the structure and function of the proteins, effectively inactivating the pathogen.
Biological and Pharmaceutical Uses
Protein Labeling: OPA is widely used in biochemical research for labeling proteins and other amine-containing biomolecules.
By reacting with amino acids in proteins, it forms stable Schiff bases, which can then be detected using fluorescence methods.
Assay Development: OPA has been used in assays for amino acid analysis, where it reacts with the amines in amino acids and peptides, producing a highly fluorescent product.
This application has been extended to drug development and diagnostics.
Drug Delivery Systems: OPA’s ability to form stable covalent bonds makes it a candidate for use in drug delivery systems, where it can be attached to therapeutic agents for controlled release.
Industrial Applications
Plastic Production and Dyes: OPA is used in the production of certain types of resins and plasticizers, as well as in the synthesis of dyes and pigments.
Its reactivity allows it to be incorporated into polymer chains, improving the properties of the material.
Cleaning and Degreasing: OPA is also used in industrial cleaning applications, particularly in situations where a highly effective and non-toxic disinfectant is required.
Advances in OPA-Based Research
New Discoveries and Innovations
Recent studies have uncovered new uses for OPA, such as in the development of advanced biosensors and diagnostic devices.
Researchers are exploring its potential in nanomaterial synthesis, where it could be used to functionalize nanoparticles for targeted drug delivery.
Alternative Uses and Future Directions
OPA’s role in green chemistry is an emerging field.
Its reactivity could be harnessed in environmentally friendly processes, such as sustainable polymer production or waste treatment.
Challenges and Limitations
Issues with Handling and Storage
OPA’s stability can be affected by light, temperature, and the presence of certain chemicals, making it necessary to store it in sealed, dark containers at controlled temperatures.
Economic and Production Challenges
The cost of synthesizing OPA can be high due to the need for specialized reagents and solvents.
Scaling production to meet industrial demand can be challenging, and there is ongoing research to improve synthetic methods.
Regulatory and Safety Concerns
OPA's toxicity and environmental impact present challenges for widespread adoption in some sectors.
Regulations surrounding its safe use and disposal are constantly evolving to ensure human and environmental safety.
Summary of Key Findings
OPA is a versatile and valuable compound, with applications spanning from sterilization to advanced biochemical assays.
Its chemical reactivity and relatively safer toxicity profile compared to other aldehydes make it an important reagent in both industrial and biomedical contexts.
Future Prospects
OPA’s future applications in fields such as nanotechnology, environmental chemistry, and drug delivery systems offer promising avenues for continued research and development.
SAFETY INFORMATION ABOUT O-PHTHALALDEHYDE (OPA)
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
