o-Phthalaldehyde

Iupac Name：phthalaldehyde

Molecular Weight：134.13204

Modify Date.: 2022-11-11 20:34

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: o-Phthalaldehyde
1.2 Synonyms: 2-PHTHALALDEHYDE 2-PHTHALDEHYDE 2-PHTHALDIALDEHYDE EINECS 211-402-2 MFCD00003335 o-Phenyldialdehyde O-PHTHALDIALDEHYDE REAGENT SOLUTION* PHTHALALDEHYDE The developMent of forMaldehyde TIMTEC-BB SBB008450

1.3 CAS No.: 643-79-8

1.4 CID: 4807

1.5 EINECS(EC#): 211-402-2

1.6 Molecular Formula: C8H6O2 (isomer)

1.7 Inchi: InChI=1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H

1.8 InChkey: ZWLUXSQADUDCSB-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C(=C1)C=O)C=O

1.10 Isomers Smiles: C1=CC=C(C(=C1)C=O)C=O

2. Properties

2.1 Density: 1.13

2.1 Melting point: 54-57℃

2.1 Boiling point: 83-84℃ (0.7501 mmHg)

2.1 Refractive index: 1.622?

2.1 Flash Point: 132℃

2.2 Precise Quality: 134.03700

2.2 PSA: 34.14000

2.2 logP: 1.31160

2.2 Solubility: 53g/l

2.3 VaporDensity: Relative vapor density (air = 1): 4.6

2.4 Appearance: Light yellow crystalline powder

2.5 Storage: Air Sensitive. Store under Nitrogen. Keep Cold.

2.6 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

2.7 Chemical Properties: o-Phthalaldehyde is a pale yellow crystalline solid.

2.8 Color/Form: yellow

2.9 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.10 PH: 7 (53g/l, H2O, 20℃)

2.11 Water Solubility: soluble

2.12 Stability: Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.

2.13 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.

3.2 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.

3.3 Usage: 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.

4. Safety and Handling

4.1 Symbol: GHS05;GHS06;GHS09;

4.1 Hazard Codes: T

4.1 Signal Word: DANGER

4.1 Risk Statements: R25;R34;R43

4.1 Safety Statements: S26;S36/37/39;S45

4.1 Packing Group: Ⅱ

4.1 Hazard Class: 8

4.1 Hazard Declaration: H301; H314; H317; H400

4.1 RIDADR: 175

4.1 Caution Statement: P273-P280-P301 + P310-P305 + P351 + P338-P310

4.1 WGK Germany: 3

4.1 RTECS: TH6950000

4.1 Report: Reported in EPA TSCA Inventory.

4.2 Safety: Poison by an unspecified route. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Hazard Codes?of Phthalaldehyde (CAS NO.643-79-8): Xi,T,N
Risk Statements: 36/37/38-43-34-25-50
36/37/38:? Irritating to eyes, respiratory system and skin?
43:? May cause sensitization by skin contact?
34:? Causes burns?
25:? Toxic if swallowed?
50:? Very Toxic to aquatic organisms??
Safety Statements: 26-28-36-45-36/37/39-61-37/39
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
45:? In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)?
36/37/39:? Wear suitable protective clothing, gloves and eye/face protection?
61:? Avoid release to the environment. Refer to special instructions safety data sheet?
37/39:? Wear suitable gloves and eye/face protection?
RIDADR: UN2923 8/PG 2
WGK Germany: 3
RTECS: TH6950000
F: 1-8-10: Sensitive to air and humidity. Photosensitive. Keep under argon.
Hazard Note: Irritant/Air Sensitive
HS Code: 29122900

4.3 Sensitive: Air Sensitive

4.4 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	unreported	7mg/kg (7mg/kg)	?	Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 246, Pg. 851, 1958.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable solids, Category 1

Acute toxicity - Oral, Category 3

Skin corrosion, Category 1C

Skin sensitization, Category 1

Serious eye damage, Category 1

Specific target organ toxicity \u2013 repeated exposure, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H228 Flammable solid H301 Toxic if swallowed H314 Causes severe skin burns and eye damage H317 May cause an allergic skin reaction H318 Causes serious eye damage H373 May cause damage to organs through prolonged or repeated exposure H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P273 Avoid release to the environment.
Response	P370+P378 In case of fire: Use ... to extinguish. P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P314 Get medical advice/attention if you feel unwell. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

643-79-8Total: 60 Synthesis Route

88-95-9 50 Suppliers

643-79-8 285 Suppliers

Literatures:
Tetrahedron Letters, , vol. 29, # 11 p. 1271 - 1274
Yield: ~86%

91-13-4 155 Suppliers

643-79-8 285 Suppliers

Literatures:
Chemistry Letters, , p. 891 - 892
Yield: ~84%

91-15-6 118 Suppliers

643-79-8 285 Suppliers

Literatures:
Tetrahedron Letters, , vol. 30, # 28 p. 3677 - 3680
Yield: ~64%

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8. Precursor and Product

precursor:

253-52-1

120-12-7

91-20-3

91-13-4

56-55-3

88-99-3

612-16-8

91-15-6

88-95-9

496-14-0

612-14-6

95-47-6

85-44-9

108-86-1

111-30-8

90-02-8

View all

product :

270-68-8

65869-75-2

89023-96-1

29833-90-7

1090-13-7

46868-19-3

91-15-6

25641-99-0

635-89-2

56306-54-8

6929-65-3

480-91-1

76197-35-8

6940-49-4

88-96-0

612-20-4

88-99-3

70591-70-7

3144-47-6

89023-97-2

89023-98-3

65320-68-5

89023-99-4

21528-31-4

7468-67-9

View all

9. Other Information

9.0 Usage: Phthaldialdehyde is used as a fluorescent reagent for checking the assay of amines present in proteins, peptides by capillary electrophoresis and chromatography. It is also used for cholesterol assay in the picomole range as well as for fluorometric determination of histamine, histidine and other amino acids. Poly(phthalaldehyde) is obtained by the polymerization reaction which is used to make a photoresist. The nitrogen by o-phthaldialdehyde assay (NOPA) is a method used in winemaking process to measure the completion of fermentation.

9.1 Merck: 14,7368

9.2 BRN: 878317

9.3 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.

9.4 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.

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

9.6 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.

9.7 Uses: Disinfectant. Reagent in fluorometric determination of primary amines and thiols.

9.8 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%.

9.9 Definition: ChEBI: A dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.

9.10 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

9.11 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.

9.12 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.

9.13 Carcinogenicity: No information on the carcinogenicity of o-phthalaldehyde in experimental animals or humans was found in a review of the literature.

10. Computational chemical data

Molecular Weight: 134.13204g/mol
Molecular Formula: C₈H₆O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 134.036779430
Monoisotopic Mass: 134.036779430
Complexity: 115
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 34.1
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADACgmAIwAIAAAACIAihSgAACAAAkAAAIiAEAAMgIIDKAFRCAIQAggAAIiYcJiICOgAAAAAAQAAAAAAAAACAAAAAAAAAAAA==

11. Question & Answer

Introduction of Ortho-phthalaldehyde May 14 2021
Abstract In the existence of appropriate amount of disodium ethylenediaminetetraacetate (EDTA), precipitation would not occur in seawater and other natural waters even if the sample solution was adjusted to strong basicity, and the NH3-OPA-sulfite reaction at the optimal pH range could be used to d...

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