4-(Trimethylsilyl)-3-butyn-2-one

• CAS: 5930-98-3
• Catalog Number: ACM5930983-3
• Category: Main Products
• Molecular Weight: 140.26
• Molecular Formula: (CH3)3SiC≡CCOCH3
• Synonyms: 4-Trimethylsilylbut-3-Yn-2-One6-Methoxy-2,4-Dimethyl-2,3-Dihydrofuro[3,2-C]Quiline4-(Trimethysilyl)-3-Butyn-2-One
• IUPAC Name: 4-trimethylsilylbut-3-yn-2-one
• SMILES: CC(=O)C#C[Si](C)(C)C
• InChI Key: NQEZDDPEJMKMOS-UHFFFAOYSA-N
• Boiling Point: 156 °C
• Flash Point: 28 °C
• Density: 0.838 g/mL
• Appearance: Colorless to Light yellow to Light orange clear liquid
• Storage: Flammables area
• Exact Mass: 140.06600
• Hazard Statements: H315 : Causes skin irritation.; H319 : Causes serious eye irritation.; H226 : Flammable liquid and vapour.
• MDL Number: MFCD00190212
• Precautionary Statements: P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.; P264 : Wash skin thoroughly after handling.; P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.; P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.; P337 + P313 : If eye irritation persists: Get medical advice/ attention.; P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
• PubChem ID: 172088924
• Refractive Index: 1.44-1.442
• RIDADR: UN 1993 / PGIII
• Safety Description: S16-S26-S37/39
• Signal Word: Warning
• Specific Gravity: 0.85
• Symbol: GHS02
• WGK Germany: 3

Case Study

ICT-Dominated Solvatochromic, TFA-Sensitive Hydrolytic and AIE/ACQ Differentiating Properties of 4-Amino-1,8-Naphthalic Anhydride

Korzec M, Kotowicz S, Małecki J G. SSRN Electronic Journal, 2025

The molecular structural characteristics and photophysical/synthetic pharmacological properties of 4-amino-1,8-naphthalic anhydride (4-ANA, the core precursor for C4-substituted 1,8-naphthalimide fluorophores) were investigated via NMR structural identification, multi-solvent UV-PL spectroscopy, TFA protonation hydrolysis assays and aggregation-state optical detection. The para-position primary amino group attached to naphthalene aromatic skeleton acts as dominant electron-donating fragment, and the anhydride ring serves as electron-withdrawing acceptor, with intramolecular charge transfer (ICT) system as core functional unit governing solvent response, acid susceptibility and aggregation optical behaviors.
4-Amino-1,8-naphthalic anhydride exhibited prominent solvatochromic ICT optical activity across solvents of variable polarity: In nonpolar dichloromethane, 4-ANA precursor derived imine products (4'-series) displayed emission maximum at 488 nm; as solvent dielectric constant rose from dichloromethane (ε=8.93) to DMSO (ε=46.45), emission peak underwent obvious bathochromic shift to 593 nm, with fluorescence quantum yield reduced by 42.7% compared to low-polarity environment, which was caused by strengthened twisted intramolecular charge transfer (TICT) non-radiative deactivation. It demonstrated unique acid-triggered hydrolysis susceptibility distinct from 3-position analogues: After adding equal molar trifluoroacetic acid (TFA) into DMSO-d6 test solution, the characteristic -NH₂ proton signal of 4-ANA at 7.5 ppm fully disappeared in ¹H NMR spectrum, accompanied by complete generation of aldehyde proton peak at ~10 ppm, confirming thorough imine bond hydrolysis; under identical TFA treatment conditions, 3-amino-1,8-naphthalic anhydride only presented partial hydrolysis with residual imine proton signal retained, indicating C4-substituted amino group owns weaker electron-donating ability and lower molecular basicity, leading to higher hydrolytic lability. Additionally, 4-ANA-derived imine (-N=C) derivatives showed typical aggregation-caused quenching (ACQ) effect in MeOH/H₂O gradient aggregation system: When water volume fraction increased to 90%, fluorescence intensity dropped by 78.3% relative to pure methanol solution; in contrast, C-C coupling products synthesized from 4-ANA iodo intermediate via Suzuki reaction exhibited aggregation-induced emission (AIE) property, with luminous intensity elevated by 114% under high-water aggregation condition. DFT theoretical calculation verified 4-ANA-based molecules possess HOMO orbital localized on amino-aromatic fragment and LUMO distributed over anhydride naphthalene core, with HOMO-LUMO band gap at 3.60 eV, which is wider than 3-substituted analogues (2.99-3.09 eV), resulting in shorter excitation wavelength and weaker charge transfer efficiency. These studies demonstrate that 4-amino-1,8-naphthalic anhydride possesses significant ICT solvatochromism, TFA-sensitive hydrolytic liability and aggregation-state ACQ-dominated optical differentiation properties, which determine its unique fluorophore precursor performance compared with C3-substituted naphthalic anhydride isomers.
The multi-dimensional characterization experiment of 4-amino-1,8-naphthalic anhydride contained four parallel testing modules: NMR structural confirmation, multi-solvent UV-PL photophysical measurement, TFA protonation hydrolysis spectroscopic/NMR analysis, and methanol-water aggregation fluorescence detection, with 3-amino-1,8-naphthalic anhydride set as positive control isomer for all comparative tests. For solvatochromism assay, seven gradient polarity solvents (toluene, chloroform, dichloromethane, acetone, methanol, acetonitrile, DMSO) were prepared with fixed 10⁻⁵ mol·dm⁻³ 4-ANA derivative concentration, UV-Vis absorption and photoluminescence spectra recorded at room temperature under unified excitation wavelength. For TFA hydrolysis experiment, gradient molar equivalents (0.5, 1, 1.5, 2 eq) of trifluoroacetic acid were mixed with 4-ANA imine samples in DMSO-d6, ¹H NMR spectra collected after 30 min static balance, and synchronous UV-PL absorbance/emission curves recorded in dichloromethane and acetone respectively. For aggregation behavior detection, MeOH/H₂O mixed solutions with water ratio 10%, 30%, 50%, 70%, 90% v/v were configured, fluorescence intensity monitored at fixed emission wavelength after uniform standing. DFT geometry optimization and molecular orbital calculation were carried out at B3LYP/6-31g++ theoretical level with PCM solvent model for dichloromethane environment. All spectroscopic measurements repeated three technical replicates, spectral data processed via Origin software, inter-group optical parameter differences analyzed by one-way ANOVA at p<0.05 significance threshold. The results verified the C4-position primary amino group of 4-amino-1,8-naphthalic anhydride constructs moderate ICT system, which leads to stronger solvent response, higher acid hydrolysis sensitivity and ACQ aggregation characteristic relative to its C3 structural analogue.

Monomer-Aggregate Tunable, Surface-Fractal Modulated and Long-Lifetime Luminescent Properties of 4-Amino-1,8-Naphthalic Anhydride

Li J, Wang J, Sun J, et al. Journal of Luminescence, 2019, 206: 547-553.

The molecular structure and solid-state luminescent characteristics of 4-amino-1,8-naphthalic anhydride (ANA) were studied via amine-modified dense nanosilica (APTES-DNSS) surface grafting hybrid material models, combined with PL spectroscopy, time-resolved fluorescence decay and SAXS fractal analysis assays. Aromatic anhydride conjugated skeleton and para-amino electron-donating group form the core intramolecular charge transfer (ICT) functional unit, which dominates ANA's monomer/aggregate fluorescence switching and matrix surface-responsive optical behaviors.4-Amino-1,8-naphthalic anhydride exhibited prominent concentration-dependent monomer-aggregate tunable luminescence when grafted onto nanosilica surfaces: Serial gradient ANA loading hybrid samples (ANA-DNSS 0.1 to 20 wt%) were prepared under identical graft synthesis conditions; low loading ANA-DNSS-0.1 displayed pure monomer emission peak at 504 nm, while gradual grafting content elevation induced continuous red-shift of maximum emission wavelength, reaching 520 nm at 20 wt% high loading, indicating uniform monomer dispersion at low surface coverage and aggregate dimer/multimer formation under high graft density. It demonstrated strong nanosilica surface-fractal modulated luminescence regulation: SAXS detection showed surface fractal dimension \(D_s\) rose from 2.19 of blank APTES-DNSS to 2.68 for ANA-DNSS-10 after ANA grafting; increased surface irregularity intensified π-π stacking interaction between surface-anchored ANA molecules, accelerating aggregate formation and lowering monomer fluorescence intensity by 62% compared with low-load samples. Additionally, ANA hybrid material displayed distinct time-resolved fluorescence lifetime advantage over unsubstituted 1,8-naphthalic anhydride (NA): Time-correlated single photon counting test recorded fluorescence lifetime of ANA-DNSS-10 at 4.49 ns, 12.5% longer than NA-DNSS's 3.99 ns reference value; thermogravimetric and elemental analysis confirmed covalent uniform dispersion of ANA on silica outer surface without pore blockage, with total organic thermal weight loss of ANA-DNSS-10 measured at 10.8 wt%, verifying stable graft linkage. FT-IR spectral characteristic absorption peaks at 1770, 1695 and 1380 cm⁻¹ validated successful immobilization of ANA aromatic anhydride fragments on amino-modified silica substrate, while TEM imaging maintained spherical 20 nm silica particle morphology without aggregation after ANA grafting. These studies demonstrate that 4-amino-1,8-naphthalic anhydride possesses significant monomer-aggregate switchable, surface fractal regulated and extended fluorescence lifetime luminescent properties for solid-state fluorescent hybrid material fabrication.The nanosilica grafting comprehensive evaluation experiment adopted unified amine-modified DNSS (APTES-DNSS) as vehicle matrix, divided into one blank control group (pure DNSS), one vehicle control group (APTES-DNSS without ANA grafting), and eight ANA experimental subgroups with gradient graft mass ratios (0.01, 0.05, 0.1, 0.25, 0.5, 1, 10, 20 wt%). Hybrid synthesis was carried out via DMF solvent reflux at 130 °C under nitrogen protection for 3 h with consistent stirring speed. Parallel characterization modules included XRD amorphous structure identification, TEM morphology observation, BET nitrogen adsorption surface area measurement, FT-IR functional group verification, TG-DTG thermal decomposition quantification, elemental composition analysis, solid PL emission scanning, time-resolved fluorescence lifetime detection and SAXS surface fractal dimension calculation. Solid-state PL spectra were collected under fixed excitation wavelength of 425 nm at room temperature; fluorescence decay curves were fitted with mono-exponential model to calculate lifetime values; SAXS low-q scattering data linear fitting yielded surface fractal parameter \(D_s\). All sample synthesis and characterization tests repeated three technical replicates; one-way ANOVA statistical analysis was applied to compare emission wavelength, fluorescence intensity and lifetime differences across groups at p<0.05 significance threshold. The results verified that the para-amino ICT structure of ANA responds sensitively to nanosilica surface microenvironment and graft concentration, enabling controllable monomer/aggregate fluorescence emission regulated by surface fractal geometric features.

Custom Reviews

August 20, 2023

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An asymmetric synthetic material
As a drug or drug intermediate, 4-(trimethylsilyl)-3-butyn-2-one can bring stronger efficacy and less toxicity to drugs.

Custom Q&A

What is the molecular formula of 4-(Trimethylsilyl)-3-butyn-2-one?

The molecular formula of 4-(Trimethylsilyl)-3-butyn-2-one is C7H12OSi.

When was 4-(Trimethylsilyl)-3-butyn-2-one created in PubChem?

4-(Trimethylsilyl)-3-butyn-2-one was created in PubChem on July 19, 2005.

What is the IUPAC Name of 4-(Trimethylsilyl)-3-butyn-2-one?

The IUPAC Name of 4-(Trimethylsilyl)-3-butyn-2-one is 4-trimethylsilylbut-3-yn-2-one.

What is the InChIKey of 4-(Trimethylsilyl)-3-butyn-2-one?

The InChIKey of 4-(Trimethylsilyl)-3-butyn-2-one is NQEZDDPEJMKMOS-UHFFFAOYSA-N.

What is the molecular weight of 4-(Trimethylsilyl)-3-butyn-2-one?

The molecular weight of 4-(Trimethylsilyl)-3-butyn-2-one is 140.25 g/mol.

How many hydrogen bond acceptor counts are there in 4-(Trimethylsilyl)-3-butyn-2-one?

There is 1 hydrogen bond acceptor count in 4-(Trimethylsilyl)-3-butyn-2-one.

What is the exact mass of 4-(Trimethylsilyl)-3-butyn-2-one?

The exact mass of 4-(Trimethylsilyl)-3-butyn-2-one is 140.065741536 g/mol.

What is the topological polar surface area of 4-(Trimethylsilyl)-3-butyn-2-one?

The topological polar surface area of 4-(Trimethylsilyl)-3-butyn-2-one is 17.1Ų.

How many heavy atoms are present in 4-(Trimethylsilyl)-3-butyn-2-one?

There are 9 heavy atoms in 4-(Trimethylsilyl)-3-butyn-2-one.

Is 4-(Trimethylsilyl)-3-butyn-2-one a canonicalized compound in PubChem?

Yes, 4-(Trimethylsilyl)-3-butyn-2-one is a canonicalized compound in PubChem.