Cas no 4616-63-1 (N-(Propargyloxy)phthalimide)
N-(Propargyloxy)phthalimide Chemical and Physical Properties
Names and Identifiers
-
- N-(Propargyloxy)phthalimide
- N-Propargyloxyphthalimide
- N-(prop-2-ynyloxy)phthalimide
- 2-prop-2-ynoxyisoindole-1,3-dione
- 2-Prop-2-ynoxyisoindoline-1,3-dione
- <i>N<
- N-(2-Propynyloxy)phthalimide
- NSC 80674
- 6-Hydroxy-2-(pyridin-3-yl)-3,4-dihydronaphthalen-1(2H)-one
- NSC-80674
- N-2-propynoxyphthalimide
- 2-prop-2-ynyloxy-isoindole-1,3-dione
- Z1509506128
- 2-(prop-2-yn-1-yloxy)-2,3-dihydro-1H-isoindole-1,3-dione
- 1H-Isoindole-1,3(2H)-dione, 2-(2-propynyloxy)-
- DTXSID50196745
- InChI=1/C11H7NO3/c1-2-7-15-12-10(13)8-5-3-4-6-9(8)11(12)14/h1,3-6H,7H
- NS00049446
- EINECS 225-024-0
- 2-(Prop-2-yn-1-yloxy)isoindoline-1,3-dione
- 2-(prop-2-ynyloxy)isoindoline-1,3-dione
- SCHEMBL698426
- NSC80674
- SB64194
- Phthalimide, N-(2-propynyloxy)-
- SY049898
- CS-0181792
- AKOS024348844
- AS-75549
- FT-0635374
- P2342
- A12539
- EN300-317032
- 4616-63-1
- MFCD00005890
- 2-prop-2-ynoxyisoindoline-1,3-dione, AldrichCPR
- 2-(2-Propynyloxy)-1H-isoindole-1,3(2H)-dione #
- 2-(prop-2-yn-1-yloxy)isoindole-1,3-dione
- DB-051357
-
- MDL： MFCD00005890
- Inchi： 1S/C11H7NO3/c1-2-7-15-12-10(13)8-5-3-4-6-9(8)11(12)14/h1,3-6H,7H2
- InChI Key： HBGZBVPXPDNXOV-UHFFFAOYSA-N
- SMILES： O(CC#C)N1C(C2C=CC=CC=2C1=O)=O
- BRN： 1530730
Computed Properties
- Exact Mass: 201.04300
- Monoisotopic Mass: 201.043
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 2
- Heavy Atom Count: 15
- Rotatable Bond Count: 2
- Complexity: 317
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Surface Charge: 0
- Tautomer Count: nothing
- XLogP3: nothing
- Topological Polar Surface Area: 46.6A^2
Experimental Properties
- Color/Form: White solid
- Density: 1.3041 (rough estimate)
- Melting Point: 138.0 to 142.0 deg-C
- Boiling Point: 339.09°C (rough estimate)
- Flash Point: 151.2±28.4 °C
- Refractive Index: 1.4900 (estimate)
- PSA: 46.61000
- LogP: 0.78530
- Solubility: Uncertain
- Vapor Pressure: 0.0±0.7 mmHg at 25°C
N-(Propargyloxy)phthalimide Security Information
-
Symbol:
- Prompt：warning
- Signal Word：warning
- Hazard Statement： H315-H319
- Warning Statement： P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- WGK Germany：3
- Hazard Category Code： 22
- Safety Instruction： S24/25
-
Hazardous Material Identification：
- Safety Term：S24/25
- Storage Condition：storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)
N-(Propargyloxy)phthalimide Customs Data
- HS CODE：2925190090
- Customs Data：
China Customs Code:
2925190090Overview:
2925190090 Other imides and their derivative salts. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%
Declaration elements:
Product Name, component content, use to
Summary:
2925190090 other imides and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%
N-(Propargyloxy)phthalimide Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Alichem | A199008104-25g |
2-(Prop-2-yn-1-yloxy)isoindoline-1,3-dione |
4616-63-1 | 95% | 25g |
$331.36 | 2023-09-01 | |
| Fluorochem | 167500-1g |
N-Propargyloxyphthalimide |
4616-63-1 | >98.0%(GC) | 1g |
￡48.00 | 2022-02-28 | |
| Fluorochem | 167500-5g |
N-Propargyloxyphthalimide |
4616-63-1 | >98.0%(GC) | 5g |
￡162.00 | 2022-02-28 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | N159748-200mg |
N-(Propargyloxy)phthalimide |
4616-63-1 | 96% | 200mg |
￥93.90 | 2023-09-01 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | N159748-1g |
N-(Propargyloxy)phthalimide |
4616-63-1 | 96% | 1g |
￥130.90 | 2023-09-01 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | N159748-25g |
N-(Propargyloxy)phthalimide |
4616-63-1 | 96% | 25g |
￥1508.90 | 2023-09-01 | |
| SHANG HAI A LA DING SHENG HUA KE JI GU FEN Co., Ltd. | N159748-5g |
N-(Propargyloxy)phthalimide |
4616-63-1 | 96% | 5g |
￥385.90 | 2023-09-01 | |
| Matrix Scientific | 115738-1g |
2-Prop-2-ynoxyisoindoline-1,3-dione, 95% |
4616-63-1 | 3-dione, 95% | 1g |
$28.00 | 2021-05-17 | |
| Matrix Scientific | 115738-5g |
2-Prop-2-ynoxyisoindoline-1,3-dione, 95% |
4616-63-1 | 95% | 5g |
$365.00 | 2023-09-09 | |
| Matrix Scientific | 115738-25g |
2-Prop-2-ynoxyisoindoline-1,3-dione, 95% |
4616-63-1 | 3-dione, 95% | 25g |
$355.00 | 2021-05-17 |
N-(Propargyloxy)phthalimide Related Literature
-
Tsuyoshi Yamada,Kwihwan Park,Yasunari Monguchi,Yoshinari Sawama,Hironao Sajiki RSC Adv. 2015 5 92954
-
Tsuyoshi Yamada,Kwihwan Park,Yasunari Monguchi,Yoshinari Sawama,Hironao Sajiki RSC Adv. 2015 5 92954
Related Categories
- Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoindoles and derivatives Isoindolones
- Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoindoles and derivatives Isoindolines Isoindolones
- Solvents and Organic Chemicals Organic Compounds Hydrocarbons
Additional information on N-(Propargyloxy)phthalimide
Recent Advances in the Application of N-(Propargyloxy)phthalimide (CAS: 4616-63-1) in Chemical Biology and Pharmaceutical Research
N-(Propargyloxy)phthalimide (CAS: 4616-63-1) has emerged as a versatile building block in chemical biology and pharmaceutical research due to its unique reactivity and functional group compatibility. Recent studies have highlighted its potential in click chemistry, drug discovery, and bioconjugation strategies. This research brief synthesizes the latest findings on this compound, focusing on its synthetic applications, mechanistic insights, and therapeutic implications.
A 2023 study published in Journal of Medicinal Chemistry demonstrated the compound's utility in PROTAC (Proteolysis Targeting Chimera) development. Researchers utilized the alkyne moiety of N-(Propargyloxy)phthalimide for copper-catalyzed azide-alkyne cycloaddition (CuAAC) to create targeted protein degraders. The study reported improved pharmacokinetic properties compared to traditional linker chemistries, with particular success in targeting estrogen receptor-positive breast cancer cells.
In bioconjugation applications, a Nature Communications paper (2024) detailed an innovative photoredox strategy using 4616-63-1 for site-selective protein modification. The phthalimide group's electron-deficient nature enabled unprecedented control over reaction selectivity, achieving >90% conversion rates in antibody-drug conjugate (ADC) synthesis while maintaining protein integrity. This advancement addresses longstanding challenges in ADC manufacturing consistency.
Mechanistic studies published in ACS Chemical Biology (2023) revealed novel insights into the compound's reactivity profile. Through kinetic isotope effect measurements and DFT calculations, researchers established that the propargyloxy group undergoes unexpected [3,3]-sigmatropic rearrangements under physiological conditions, opening new avenues for designing enzyme-activated prodrugs. This finding has already inspired several patent applications for targeted cancer therapies.
The compound's role in nucleic acid modification has also seen progress. A 2024 Chemical Science article described its use in creating stabilized siRNA conjugates, where the phthalimide group served dual purposes as both a protecting group and a solubility enhancer. This approach increased serum stability by 300% compared to conventional modifications while maintaining gene silencing efficiency.
From a safety perspective, recent toxicological assessments (Regulatory Toxicology and Pharmacology, 2023) have established favorable profiles for 4616-63-1 derivatives. Metabolic studies in primates showed rapid clearance of the phthalimide moiety without detectable bioaccumulation, addressing previous concerns about phthalimide-containing compounds. These findings significantly de-risk clinical translation of related drug candidates.
Looking forward, several pharmaceutical companies have disclosed investigational new drug (IND) applications featuring 4616-63-1 derivatives in their pipeline updates. The compound's unique combination of synthetic accessibility, controllable reactivity, and metabolic stability positions it as a key enabler for next-generation biopharmaceuticals. Ongoing research is exploring its potential in targeted radiotherapeutics and microbiome-modulating agents, with preliminary results expected in late 2024.
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