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Diphenyl(2,4,6-trimethylbenzoyl)phosphinoxid

2,4,6-Trimethylbenzoyl diphenylphosphine oxide

HCID 166480
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Grundinformationen

CAS
75980-60-8
Standard-SMILES
Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1
InChIKey
VFHVQBAGLAREND-UHFFFAOYSA-N
Summenformel
C22H21O2P
Durchschnittliche Molmasse
348,4 g/mol
Monoisotopische Masse
348,12791654

Namen und Bezeichner

Bevorzugter Name
2,4,6-Trimethylbenzoyl diphenylphosphine oxide
IUPAC
diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone
Lokaler Name
Diphenyl(2,4,6-trimethylbenzoyl)phosphinoxid
Englischer Name
Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide
Summenformel
C22H21O2P
Molmasse
348.37

Namen und Synonyme

75980-60-8Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxidePhosphine oxide, diphenyl(2,4,6-trimethylbenzoyl)-DTXSID4052502EINECS 278-355-8B9EIM2D97X2,4,6-trimethylbenzoyl diphenylphosphine oxidetrimethylbenzoyl diphenylphosphine oxideCHIVACURE TPODOUBLECURE TPOADDITOL TPOGENOCURE TPO
Weitere Namen anzeigen
Photoinitiator TPOTMDPO(Diphenylphosphoryl)(Mesityl)Methanone2,4,6-TRIMETHYLBENZOYLDIPHENYLPHOSPHINE OXIDEbiphenyl(2,4,6-trimethyl-benzoyl)-phosphine oxide2,4,6-TRIMETHYLBENZOYLDIPHENYL PHOSPHINE OXIDE TPODiphenyl(2,4,6-triMethylbenzoyl)phosphine oxide (TPO)HRcure-TPOSPEEDCURE TPOUV photoinitiator TPO
Methanone, (diphenylphosphinyl)(2,4,6-trimethylphenyl)-DTXCID8031075EC 278-355-8(2,4,6-trimethylbenzoyl)diphenylphosphine oxide(DIPHENYLPHOSPHINYL)(2,4,6-TRIMETHYLPHENYL)METHANONERefChem:442966TRIMETHYLBENZOYL DIPHENYLPHOSPHINE OXIDE [INCI]278-355-8

Datenbank-Bezeichner

CAS
75980-60-8
PubChem CID
166480
DTXSID
DTXSID4052502
ChEMBL
CHEMBL3561198
UNII
B9EIM2D97X
EC Number
278-355-8
Nikkaji
J240.339K

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
5
Polarare Oberfläche (TPSA)
34,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
4
Schwere Atome
25
Formalladung
0
Komplexität
468

Experimentelle und physikochemische Eigenschaften

CosmeticsCosmetic ingredients (Trimethylbenzoyl Diphenylphosphine Oxide) -> CIR (Cosmetic Ingredient Review)
pH4 to 5
Density1.218 g/cm³ at 20 degrees C (OECD 109)
SolubilityWater solubility: 3.3 mg/L at 20 °C (OECD Guideline 105, Flask method) and 11.9 mg/L at 20 °C (OECD Guideline 105, Column elution). Readily soluble in dichloromethane, acetone, n-butylacetate; soluble in styrene and in other monomers.
Boiling PointGreater than 300 degrees C
Melting Point93 degrees C (OECD Guideline 102)
Vapor Pressure3.045 x 10-6 Pa at 25 degrees C
Physical Description · 2 Einträge

Large Crystals; Liquid; Liquid; CBI; Dry Powder

Solid (yellow powder)

Stability/Shelf LifeAt least two years (cool and dry; light sensitive, to be stored in the dark)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P203, P261, P272, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.4% (13 of 3088) of reports.

Warning

H317 (12.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Phosphine oxide, diphenyl(2,4,6-trimethylbenzoyl)-

Hazard Traits - Reproductive Toxicity

Methanone, (diphenylphosphinyl)(2,4,6-trimethylphenyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanone, (diphenylphosphinyl)(2,4,6-trimethylphenyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 03-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13110

Substance: diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide

Other Safety InformationIMAP assessments - Phosphine oxide, diphenyl(2,4,6-trimethylbenzoyl)-: Human health tier II assessment
Hazard Classes and Categories · 3 Einträge

Skin Sens. 1 (12.5%)

Reproductive toxicity - category 2

Repr. 1B

Toxikologische Informationen

Toxicity Summary

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

A 2021 review describes in detail the mechanism of actionr of trimethylbenzoyl-diphenylphosphine oxide as a type-1 photoinitiator in dental resin composites. It undergoes rapid cleavage from a triplet excited state to yield two radicals (trimethylbenzoyl radical and diphenylphosphinoyl radical) that initiate polymerization.

Verwendung und Herstellung

UsesCIR ingredient: Trimethylbenzoyl Diphenylphosphine Oxide
U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer Uses · 2 Einträge

Solvent

The European Commission prohibited the use of TPO in cosmetic products beginning on September 1, 2025 (via the adoption of Commission Regulation (EU) 2025/877). This was the result of TPO being classified as a CMR category 1B reproductive toxicant by Commission Delegated Regulation (EU) 2024/197 under the CLP Regulation (Regulation (EC) No 1272/2008), and this classification triggered the mandatory inclusion of TPO in Annex II (prohibited substances) of the Cosmetics Regulation via Regulation (EU) 2025/877.

Industry Uses · 2 Einträge

Not Known or Reasonably Ascertainable

A 2021 review describes use as a photoinitiator in dental resin composites.

Household ProductsCosmetics product ingredient: Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (Trimethylbenzoyl diphenylphosphine oxide)
General Manufacturing Information · 2 Einträge

Printing Ink Manufacturing

Methanone, (diphenylphosphinyl)(2,4,6-trimethylphenyl)-: ACTIVE

Anwendungen

Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide is a photo initiator, used in many kinds of ink industries

Zugehörige Reaktionen

9
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 10932
HRID 10932als Produktuspto-grants-2006_08
Reaktionsgleichung von HRID 112823
HRID 112823als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 330711
HRID 330711als Eduktuspto-grants-2014_11
Reaktionsgleichung von HRID 851516
HRID 851516als Produktuspto-grants-1983_05
Reaktionsgleichung von HRID 1350599
HRID 1350599als Produktuspto-grants-2007_05
Reaktionsgleichung von HRID 1578229
HRID 1578229als Produktuspto-grants-1981_09
Reaktionsgleichung von HRID 1784323
HRID 1784323als Produktuspto-grants-2009_03
Reaktionsgleichung von HRID 2180366
HRID 2180366als Produktuspto-grants-2005_05
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Collision Cross Section191.1 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4052502]

Physikochemische Eigenschaften

Schmelzpunkt
88 · 88-92 °C(lit.)
Siedepunkt
519.6 · 519.6±60.0 °C(Predicted)
Dichte
1.12 g/mL · 1.12 g/mL at 25 °C(lit.)
Dampfdruck
0 Pa · 0Pa at 25℃
Brechungsindex
20 · n20/D 1.475(lit.)
Flammpunkt
230 °F · >230 °F
storage temp.
Sealed in dry,Room Temperature
Löslichkeit
soluble in Methanol
Aggregatzustand
powder to crystal
Farbe
Light yellow to Yellow to Green
Wasserlöslichkeit
3.4 mg/L · 3.4mg/L at 20℃
Stabilität
Stable. Incompatible with strong oxidizing agents.
Kosmetik-Inhaltsstoffe Funktionen
NAIL SCULPTING
InChI
1S/C22H21O2P/c1-16-14-17(2)21(18(3)15-16)22(23)25(24,19-10-6-4-7-11-19)20-12-8-5-9-13-20/h4-15H,1-3H3
InChIKey
VFHVQBAGLAREND-UHFFFAOYSA-N
SMILES
Cc1cc(C)c(c(C)c1)C(=O)P(=O)(c2ccccc2)c3ccccc3
LogP
3.1 at · 3.1 at 23℃
CAS Datenbank
75980 · 75980-60-8(CAS DataBase Reference)
EPA chemische Informationen
Phosphine oxide, diphenyl(2,4,6-trimethylbenzoyl)- (75980-60-8)
· 1 Eintrag

A 2014 Expert Opinion by the European Commission's Scientific Committee on Consumer Safety (SCCS) noted that the acute oral LD50 of Trimethylbenzoyl diphenylphosphine oxide (TPO) in rats was greater than 5000 mg/kg body weight, the dermal LD50 in rats was greater than 2000 mg/kg body weight, and that no data are available for acute inhalation toxicity. Also, the 2014 Expert Opinion described 28-day and 90-day oral studies in rats. The NOAEL in the 28-day study was 50 mg/kg body weight/day and the NOAEL in the 90-day study was 100 mg/kg body weight/day. Further, TPO showed irritation potential to rabbit skin and rabbit eyes, showed moderate sensitization potential in a Local Lymph Node Assay (LLNA) test in mice, and showed no genotoxic/mutagenic potential in bacterial gene mutation and Chinese hamster V79 cell assays. In addition, the 2014 Expert Opinion noted that no carcinogenicity are available while repeated dose toxicity studies in rats found marked testicular atrophy. The 2014 Expert Opinion concluded that Trimethylbenzoyl diphenylphosphine oxide (TPO) is safe when used as a nail modelling product at a concentration of at maximum 5.0%. However, the 2014 SCCS Expert Opinion noted that TPO is considered a moderate skin sensitizer and that other potential uses in cosmetic products cannot be evaluated without further documentation. Further evaluation led to the European Commission prohibitiing the use of TPO in cosmetic products beginning on September 1, 2025 (via the adoption of Commission Regulation (EU) 2025/877). This was the result of TPO being classified as a CMR category 1B reproductive toxicant by Commission Delegated Regulation (EU) 2024/197 under the CLP Regulation (Regulation (EC) No 1272/2008), and this classification triggered the mandatory inclusion of TPO in Annex II (prohibited substances) of the Cosmetics Regulation via Regulation (EU) 2025/877.

Non-Human Toxicity ValuesTrimethylbenzoyl diphenylphosphine oxide caused concentration-dependent cytotoxic effects in human oral keratinocytes (OKF6/Tert2) and Chinese hamster lung fibroblasts (V79), but did not induce genotoxicity in V79 cells.

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 3077 9 / PGIII
hs_code
29319090
RTECS-Nr.
SZ0395000
risk_code
22-62-51/53
hazard_code
Xn,N
safety_code
22-24/25-61-36/37
hazard_class
9
packing_group
III
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Aquatic Chronic 2Repr. 2Skin Sens. 1
Verwenden

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Ethanol2,4,6-Trimethylbenzaldehyd1,3,5-Trimethyl-2-(trichloromethyl)benzeneDiphenylphosphine oxideBenzolChlordiphenylphosphin2,4,6-Trimethylbenzoylchlorid

Nachgelagerte Produkte

Ethyl-2,4,6-trimethylbenzoat