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o-Phthalaldehyde

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o-Phthalaldehyde Basic information

Product Name:
o-Phthalaldehyde
Synonyms:
  • The developMent of forMaldehyde
  • O-PHTHALDIALDEHYDE REAGENT SOLUTION*
  • PHTHALALDEHYDE
  • TIMTEC-BB SBB008450
  • 2-PHTHALALDEHYDE
  • 2-PHTHALDEHYDE
  • 2-PHTHALDIALDEHYDE
  • o-Phenyldialdehyde
CAS:
643-79-8
MF:
C8H6O2
MW:
134.13
EINECS:
211-402-2
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Mol File:
643-79-8.mol
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o-Phthalaldehyde Chemical Properties

Melting point:
55-58 °C(lit.)
Boiling point:
83-84 °C (0.7501 mmHg)
Density 
1.13
refractive index 
1.4500 (estimate)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
The solubility of o-phthalaldehyde is 3g/100 mL diisopropyl ether, 5g/100mL deionized water, 20g/100mL chloroform, or 20g/100mL acetone at 20°C.
form 
powder
color 
yellow
PH
7 (53g/l, H2O, 20℃)
Water Solubility 
soluble
Sensitive 
Air Sensitive
Merck 
14,7368
BRN 
878317
Stability:
Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.
InChIKey
ZWLUXSQADUDCSB-UHFFFAOYSA-N
CAS DataBase Reference
643-79-8(CAS DataBase Reference)
NIST Chemistry Reference
O-phthalaldehyde(643-79-8)
EPA Substance Registry System
1,2-Benzenedicarboxaldehyde (643-79-8)
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Safety Information

Hazard Codes 
Xi,T,N,C
Risk Statements 
36/37/38-43-34-25-50-52/53
Safety Statements 
26-28-36-45-36/37/39-61-37/39
RIDADR 
UN2923 8/PG 2
WGK Germany 
3
RTECS 
TH6950000
1-8-10
Autoignition Temperature
480 °C
Hazard Note 
Irritant/Air Sensitive
TSCA 
Yes
HazardClass 
8
PackingGroup 
HS Code 
29122900
Toxicity
LD50 orally in Rabbit: 178 mg/kg LD50 dermal Rat > 2000 mg/kg

MSDS

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o-Phthalaldehyde Usage And Synthesis

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

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.

Uses

o-Phthalaldehyde can be used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups.

Uses

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.

Uses

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/ja01148a076
Tetrahedron Letters, 27, p. 1793, 1986 DOI: 10.1016/S0040-4039(00)84377-4

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.

o-Phthalaldehyde Preparation Products And Raw materials

Preparation Products

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