Terephthalaldehyd

Terephthalaldehyde

HCID 12173CAS 623-27-8

Grundinformationen

Standard-SMILES
O=Cc1ccc(C=O)cc1
InChIKey
KUCOHFSKRZZVRO-UHFFFAOYSA-N
Summenformel
C8H6O2
Durchschnittliche Molmasse
134,13 g/mol
Monoisotopische Masse
134,03677943

Namen und Bezeichner

Bevorzugter Name
Terephthalaldehyde
IUPAC
terephthalaldehyde
Lokaler Name
Terephthalaldehyd
Englischer Name
Terephthalaldehyde
Summenformel
C8H6O2
Molmasse
134.13

Namen und Synonyme

TEREPHTHALALDEHYDE1,4-BenzenedicarboxaldehydeTerephthaldehydeTerephthaldicarboxaldehyde1,4-PhthalaldehydeUNII-M2Y6E4N2TSEINECS 210-784-8M2Y6E4N2TSP-DIFORMYLBENZENENSC-13395DTXSID6060769HSDB 8458
Weitere Namen anzeigen
P-PHTHALALDEHYDETPALBenzene-1,4-dialdehydeP-benzaldehydeTerephtaldehydeTerephthaladehyde
1,4-TEREPHTHALDICARBALDEHYDE1,4-DICARBOXALDEHYDE-BENZENEpPhthalaldehydepFormylbenzaldehyde4formylbenzaldehyde1,4DiformylbenzenepBenzenedicarboxaldehydeRefChem:187952

Datenbank-Bezeichner

CAS
623-27-8
PubChem CID
12173
DTXSID
DTXSID6060769
UNII
M2Y6E4N2TS
EC Number
210-784-8
Nikkaji
J38.975G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,9
Polarare Oberfläche (TPSA)
34,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

Color/FormNeedles from water
Solubility · 3 Einträge

In water, 200 mg/L at 25 °C

Insoluble in water

Very soluble in ethanol; soluble in ethyl ether, chloroform, alkalies

Flash Point76 °C (169 °F) - closed cup
Boiling Point246 °C
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point117 °C

Physikochemische Eigenschaften

Schmelzpunkt
114 · 114-116 °C (lit.)
Siedepunkt
245 · 245-248 °C (lit.)
Dichte
1 · 1,06 g/cm3
Dampfdruck
0.25 · 0.25-0.46Pa at 20-25℃
Brechungsindex
1.48 · 1.4800 (estimate)
Flammpunkt
76 °C · 76 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 45.7% (21 of 46) of reports.

Danger

H302 (26.1%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (23.9%): Toxic in contact with skin [Danger Acute toxicity, dermal];H315 (19.6%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (23.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H331 (23.9%): Toxic if inhaled [Danger Acute toxicity, inhalation];H335 (19.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 21 of 46 reports by companies.;There are 8 notifications provided by 25 of 46 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 1,4-Benzenedicarboxaldehyde

Status: Active Update: 08-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/27180;Status: Active Update: 26-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20358

1,4-Benzenedicarboxaldehyde: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See o-Phthalaldehyde.
Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides.
Hazard Classes and CategoriesAcute Tox. 4 (26.1%);Acute Tox. 3 (23.9%);Skin Irrit. 2 (19.6%);Eye Irrit. 2A (23.9%);Acute Tox. 3 (23.9%);STOT SE 3 (19.6%)
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents, strong bases.

Sicherheit und Schutzausrüstung

Fire Fighting Procedures · 2 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place.
Cleanup Methods · 1 Eintrag

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

Disposal Methods · 2 Einträge

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

Preventive Measures · 5 Einträge

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Environmental precautions: Do not let product enter drains.

Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: General industrial hygiene practice.

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.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Personal Protective Equipment (PPE) · 4 Einträge

Eye/face protection: 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.

Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place.

Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that terephthalaldehyde is expected to have very high mobility in soil(SRC). Volatilization of terephthalaldehyde from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 3.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Terephthalaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2018).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that terephthalaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Terephthalaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), an estimated BCF of 4(SRC), from an estimated log Kow of 1.43(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in water were not available(SRC, 2018).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terephthalaldehyde, which has an estimated vapor pressure of 4.0X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase terephthalaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Based on structural analogy with o-phthalaldehyde, which has an absorption peak at 297 nm(3), terephthalaldehyde may be susceptible to direct photolysis by sunlight(SRC).

Toxicity Summary · 1 Eintrag

IDENTIFICATION AND USE: p-Phthalaldehyde is a solid. It is used for modification of coal tar pitch to reduce toxic polycyclic aromatic hydrocarbon content. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: There are no data available.

Effluent ConcentrationsFine aerosol emission rates of terephthalaldehyde from heavy-duty diesel trucks, non-catalyst-equipped and catalyst-equipped automobiles were 1.5, 19.2 and 5.2 ug/km, respectively(1).
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of terephthalaldehyde can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that terephthalaldehyde is expected to have very high mobility in soil(SRC).

Artificial Pollution SourcesTerephthalaldehyde's production and use as a laboratory chemical(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 4 was calculated in fish for terephthalaldehyde(SRC), using an estimated log Kow of 1.43(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Regulatorische Informationen

Regulatory Information · 3 Einträge

Chemical: 1,4-Benzenedicarboxaldehyde

Status: Active Update: 08-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/27180;Status: Active Update: 26-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20358

1,4-Benzenedicarboxaldehyde: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29122900
RTECS-Nr.
WZ0430000
risk_code
36/37/38-36/37
hazard_code
Xi

Chemie und Industrie

Verwendung und Herstellung

UsesLaboratory chemicals, manufacture of substances.
General Manufacturing Information · 2 Einträge

1,4-Benzenedicarboxaldehyde: ACTIVE

Coal tar pitch (CTP) was modified with p-phthalaldehyde as a cross-linking agent, p-toluenesulfonic acid as a catalyst, and cyclohexane as solvent, to reduce the toxic polycyclic aromatic hydrocarbon content. The optimum reaction conditions were obtained as follows: 8% of p-phthalaldehyde, 5% of p-toluenesulfonic acid, reaction temperature 60 °C, and reaction time 4 hr. Under the optimum conditions, the reduction rate of the 16 toxic PAHs in CTP achieved 82.75%. The physical properties of modified CTP were improved simultaneously. The detoxification mechanism was investigated via TG-DTG and FT-IR. It was proved that the electrophilic substitution cross-linking reaction took place between PAHs and p-phthalaldehyde, which might significantly contribute to the high reduction rate of the 16 toxic PAHs in CTP.

Anwendungen · 2 Einträge

BeschreibungTerephthalaldehyde is an aromatic dialdehyde. Theoretically, the two aldehydes of terephthalaldehyde (TPA) are equivalent, so the single or double Schiff base from TPA and d-glucosamine (Glc) may be formed at the same time. It is used as an intermediate for the preparation of dyes and fluorescent whitening agents and in the synthesis of polyimines by reacting with aliphatic diamines. It is also used as a precursor for the preparation of paramagnetic microporous polymeric organic frameworks (POFs) through copolymerization with pyrrole, indole, and carbazole. As a good crosslinking agent, it could used in crosslinked chitosan hydrogel for the selective removal of anionic dyes[1].

VerwendenTerephthalaldehyde (cas# 623-27-8) is a compound useful in organic synthesis.

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