643-79-8 Usage
Chemical Description
o-Phthalaldehyde is a chemical compound used in organic synthesis and as a fluorescent probe for amino acids.
Chemical Properties
o-Phthalaldehyde is a pale yellow crystalline solid.
o-Phthalaldehyde is mainly used as a high-level disinfectant (a low-temperature chemical method) for heat-sensitive medical and dental equipment such as endoscopes and thermometers; in recent years, it has gained popularity as a safe and better alternative to glutaraldehyde.
There are some researches show, pH7.5 contains the sterilizing agent of o-phthalaldehyde 0.5%, and its sterilizing power, sterilization speed, stability and toxicity all are better than glutaraldehyde, can kill mycobacterium in the 5min, the bacterium number reduces by 5 logarithmic value, and o-phthalaldehyde is very stable, tasteless in pH3~9 scopes, non-stimulated to human nose, eye mucosa, and need not activate before using, various materials are had good consistency, have tangible microbiocidal activity.
Uses
Different sources of media describe the Uses of 643-79-8 differently. You can refer to the following data:
1. o-Phthalaldehyde can be widely used for precolumn derivatization of amino acids in HPLC separation or Capillary electrophoresis. For flow cytometric measurements of protein thiol groups.
2. o-Phthalaldehyde can be used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups.
3. Precolumn derivatization reagent for primary amines and amino acids. The fluorescent derivative can be detected by reverse-phase HPLC. The reaction requires OPA, primary amine and a sulfhydryl. In the presence of excess sulfhydryl, amines can be quantitated. In the presence of excess amine, sulfhydryls can be quantitated.
4. Disinfectant. Reagent in fluorometric determination of primary amines and thiols.
Preparation
o-Phthalaldehyde is a high-level chemical disinfectant that is commonly used for disinfection of dental and medical instruments as an alternative to glutaraldehyde, which is a known skin and respiratory sensitizer.
A variety of processes for manufacturing o-phthalaldehyde have been reported in the literature.
o-Phthalaldehyde is produced by heating pure benzaldehyde and chloroform with potassium hydroxide solution. The resulting solution is further acidified with hydrochloric acid and cooled to yield a colorless powder of o-phthalaldehyde.
It is also produced by ozonization of naphthalene in alcohol followed by catalytic hydrogenation.
Catalytic oxidation of various chemicals is also used in manufacturing o-phthalaldehyde. o-Phthalaldehyde can be manufactured by oxidation of phthalan by nitrogen monoxide in acetonitrile with N-hydroxyphthalimide as the catalyst to yield 80% to 90%.
Definition
ChEBI: A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 1668, 1951 DOI: 10.1021/ja01148a076Tetrahedron Letters, 27, p. 1793, 1986 DOI: 10.1016/S0040-4039(00)84377-4
Flammability and Explosibility
Notclassified
Biotechnological Applications
O-phthalaldehyde(OPA) is used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups. Used for fluorometric determination of histamine, histidine and other amino acids. Also used for cholesterol assay in the picomole range.
Phthaldialdehyde has been used:
in the preparation of O-phthaldialdehyde reagent for analysing gentamycin content.
in the preparation of reagent for determining the degree of hydrolysis of milk proteins.
in the measurement of free amino acids of milk samples by O-phthaldialdehyde/N-acetyl-L-cysteine (OPA/NAC) assay.
in the derivatization of putrescine samples.
Potential Exposure
The primary routes of human exposure to o-phthalaldehyde are by inhalation and through the skin, which may occur through accidental or occupational exposures. Along with its increasing popularity as a chemical sterilizer, o-phthalaldehyde has many applications in analytical methods and in diagnostic kits. o-Phthalaldehyde is also used as an intermediate in the synthesis of pharmaceuticals and as a reagent in the tanning industry, hair colorings, wood treatment, and antifouling paints. o-Phthalaldehyde was approved for use as an indoor antimicrobial pesticide in 1997; however, it is no longer registered with the United States Environmental Protection Agency (USEPA) for this use.
Carcinogenicity
No information on the carcinogenicity of o-phthalaldehyde in experimental animals or humans was found in a review of the literature.
Check Digit Verification of cas no
The CAS Registry Mumber 643-79-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 3 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 643-79:
(5*6)+(4*4)+(3*3)+(2*7)+(1*9)=78
78 % 10 = 8
So 643-79-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H
643-79-8Relevant articles and documents
Smart solution chemistry: Prolonging the lifetime of ortho-phthalaldehyde disinfection solutions
Brewer, Bobby N.,Mead, Keith T.,Pittman Jr., Charles U.,Lu, Kaitao,Zhu, Peter C.
, p. 361 - 363 (2006)
The oxidation of ortho-phthalaldehyde to phthalic acid in aqueous solutions can be remedied by the addition of various cyclic acetals, which, when reacted with phthalic acid, yields ortho-phthalaldehyde, thus prolonging the lifetime of the ortho-phthalaldehyde disinfection solution.
A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes
You, Shengyong,Zhang, Rongli,Cai, Mingzhong
supporting information, p. 1962 - 1970 (2021/01/25)
A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.
Oxidaition of cyclic benzylic ethers by an electronically tuned nitroxyl radical
Furuta, Takumi,Hamada, Shohei,Kawabata, Takeo,Kobayashi, Yusuke,Yano, Kyoko
supporting information, (2021/10/04)
The reactivity of an electronically tuned nitroxyl radical catalyst for the oxidation of cyclic benzylic ethers has been investigated. The oxidation of phthalan resulted in oxidative cleavage of the saturated ring to give an aromatic dialdehyde. Additionally, oxidation of isochromans afforded isochromanones, which are often seen in natural products, in a rapid manner.
New methods to synthesize phthalaldehyde and its diacetals
Gazizov,Khairullin,Ivanova, S. Yu.,Kirillina, Yu. S.,Romanenko,Gazizova
, p. 1878 - 1882 (2019/10/21)
A new synthesis of phthalaldehyde that avoided formation of HBr involved treatment of 1,2-bis(dibromomethyl)benzene with trimethyl orthoformate (1: 6, 90 °C, 10 mol.% ZnCl2) to obtain acyclic diacetal without admixture of cyclic one (1,3-dimethoxy-1,3-dihydrobenzo-[c]furan) followed by hydrolysis to give the target dialdehyde. Phthalaldehyde reacted with CH(OMe)3 in the presence of trifluoroacetic acid to yield exclusively cyclic diacetal. Acyclic diacetal was phosphorylated by treatment with secondary chlorophosphines and by the reaction with PCl3 followed by treatment with PIII acid ester.