Structure of 1877-71-0
                                
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                            The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
                
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    							Batch number can be found on the product's label following the word 'Batch'.
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    							Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
    							Batch number can be found on the product's label following the word 'Batch'.
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Dzienia, Andrzej ; Taborowska, Patrycja ; Kubica-Cypek, Pawel ; Janas, Dawid ;
Abstract: Semiconducting single-walled carbon nanotubes (SWCNTs) have great potential for optoelectronics and photonics, further enhanced by covalent functionalization. However, scalable and controlled surface modification is challenging due to complex methodologies and unstable reagents. Benzoyl peroxide (BPO) has emerged as a simple alternative for introducing luminescent defects into SWCNTs. Yet, the lack of understanding of its radical chemistry limits precise defect engineering using BPOs. This is a major obstacle to the effective application of BPO in chemistry, despite its widespread use as a radical initiator. We present a thorough investigation into the radical chemistry of self-synthesized BPOs for functionalizing polymer-wrapped (6,5) and (7,5) SWCNTs in non-polar solvents, providing critical insights into the decomposition of BPO and its analogs. By varying the electronic and steric properties of typically unavailable BPO derivatives, we demonstrate tunability over the photoluminescence characteristics of SWCNTs, allowing control over defect density and light emission wavelength. This toolbox of BPO derivatives, created with simple radical chemistry and accessible organic precursors, alongside clarified structure-property relationships, facilitates effective implementation of BPO in chemical transformations and meticulous engineering of luminescent defects in SWCNTs for optoelectronic applications. Notably, this research offers insights into why SWCNTs modified with electron-deficient reactants provide the best optical characteristics.
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Keywords: single-walled carbon nanotubes ; peroxides ; conjugated polymers ; covalent modification ; photoluminescence
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                        | CAS No. : | 1877-71-0 | 
| Formula : | C9H8O4 | 
| M.W : | 180.16 | 
| SMILES Code : | C(C1=CC(=CC=C1)C(=O)O)(=O)OC | 
| MDL No. : | MFCD00029972 | 
| InChI Key : | WMZNGTSLFSJHMZ-UHFFFAOYSA-N | 
| Pubchem ID : | 601880 | 
| GHS Pictogram: | 
                                
                                
                                     
                                
                                
                             | 
| Signal Word: | Warning | 
| Hazard Statements: | H315-H319-H335 | 
| Precautionary Statements: | P261-P305+P351+P338 | 
| Num. heavy atoms | 13 | 
| Num. arom. heavy atoms | 6 | 
| Fraction Csp3 | 0.11 | 
| Num. rotatable bonds | 3 | 
| Num. H-bond acceptors | 4.0 | 
| Num. H-bond donors | 1.0 | 
| Molar Refractivity | 44.68 | 
| TPSA ? Topological Polar Surface Area: Calculated from   | 
                                            63.6 Ų | 
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from   | 
                                            1.53 | 
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by   | 
                                            1.83 | 
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from   | 
                                            1.17 | 
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from   | 
                                            1.51 | 
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by   | 
                                            1.1 | 
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions  | 
                                            1.43 | 
| Log S (ESOL):? ESOL: Topological method implemented from   | 
                                            -2.25 | 
| Solubility | 1.01 mg/ml ; 0.00558 mol/l | 
| Class? Solubility class: Log S scale   | 
                                            Soluble | 
| Log S (Ali)? Ali: Topological method implemented from   | 
                                            -2.79 | 
| Solubility | 0.295 mg/ml ; 0.00164 mol/l | 
| Class? Solubility class: Log S scale   | 
                                            Soluble | 
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by   | 
                                            -1.85 | 
| Solubility | 2.57 mg/ml ; 0.0143 mol/l | 
| Class? Solubility class: Log S scale   | 
                                            Soluble | 
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg  | 
                                            High | 
| BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg  | 
                                            Yes | 
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set)   | 
                                            No | 
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)  | 
                                            No | 
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)  | 
                                            No | 
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)  | 
                                            No | 
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)  | 
                                            No | 
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)  | 
                                            No | 
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from   | 
                                            -6.1 cm/s | 
| Lipinski? Lipinski (Pfizer) filter: implemented from   | 
                                            0.0 | 
| Ghose? Ghose filter: implemented from   | 
                                            None | 
| Veber? Veber (GSK) filter: implemented from   | 
                                            0.0 | 
| Egan? Egan (Pharmacia) filter: implemented from   | 
                                            0.0 | 
| Muegge? Muegge (Bayer) filter: implemented from   | 
                                            1.0 | 
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat   | 
                                            0.56 | 
| PAINS? Pan Assay Interference Structures: implemented from   | 
                                            0.0 alert | 
| Brenk? Structural Alert: implemented from   | 
                                            0.0 alert: heavy_metal | 
| Leadlikeness? Leadlikeness: implemented from   | 
                                            No; 1 violation:MW<1.0 | 
| Synthetic accessibility? Synthetic accessibility score:  from 1 (very easy) to 10 (very difficult)  | 
                                            1.42 | 
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 82% | With methanol; triethylamine;palladium diacetate; 1,3-bis-(diphenylphosphino)propane; at 100℃; under 25858.1 Torr; for 15h; | The following were introduced into a vessel: [10.] Og (40.3 mmol) of <strong>[618-89-3]methyl 3-bromobenzoate</strong>, 2.5g (mmol) of 1, 3-bis (diphenylphosphino) propane ("DPPP"), 14 mL of triethylamine, 0.905 g of palladium acetate, and 140 ml of methanol. The vessel was sealed and pressurized with carbon monoxide to a pressure of 500 psi. The vessel was heated to [100 C] for 15 hours. The mixture was then cooled and concentrated on a rotary evaporator before partitioning between EtOAc and 2M HC1. The layers were separated, and the aqueous layer was extracted with EtOAc [(LX).] The organic extracts were combined and washed with saturated aqueous [NACL] solution and dried [(MGSO4).] Concentration provided a solid, which is slurred in hexane and filtered. The material is dried in a vacuum oven at- 10mmHg at [70 C] ; yield 5.9g [(82%).] NMR: [DMSO'H 8] (ppm) 3.54 (3H, s); 7. [18-7.] 21 [(1H,] m); 7. [34- 7.] 40 [(1H,] m); 7. 46- 7.49 (1H m); 7. [87- 7.] 89 [(1H,] m). | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 60% | Example 169 Amethyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate; To a solution of 3-(methoxycarbonyl)benzoic acid (0.9 g, 5 mmol) in dichloromethane (20 mL), 1-hydroxybenzotriazole (0.75 g, 5.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.06 g, 5.5 mmol) and triethyl amine (2 mL) were added. The mixture was stirred at room temperature for 30 min, and then <strong>[59878-57-8]cyclopropyl(piperazin-1-yl)methanone</strong> (1.0 g, 5 mmol) was added and the mixture was stirred at room temperature for 16 h. The resulting mixture was added water (50 mL) and extracted with dichloromethane (100 mL×3), the organic phase was washed with sodium bicarbonate, brine and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 20:1 to 2:1), 0.95 g of methyl 3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)benzoate as an oil was obtained, Yield 60%. 1H-NMR (400 MHz, CDCl3) 0.80-0.82 (m, 2H), 1.00-1.04 (m, 2H), 1.24-1.27 (m, 1H), 3.25-3.78 (m, 8H), 3.94 (s, 3H), 7.52-7.55 (t, J=7.6 Hz, 1H), 7.63-7.65 (d, J=7.6 Hz, 1H), 8.09-8.14 (m, 2H); LC-MS (ESI) m/z: 317(M+1)+. | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | <strong>[777-12-8]6-(trifluoromethyl)benzo[d]thiazol-2-amine</strong> (commercially available or prepared according to Step 1 and 2 of Example 1) (1 eq), 3-(methoxycarbonyl)benzoic acid (1.05eq) and DIPEA (5 eq) were dissolved in DMF (2 ml). HI3TU(1.2 eq) was added and the reaction were stirred overnightat ambient temperature before extraction with ethylacetate,washed thoroughly 2 times with dilute acid and dried. Thecrude product, methyl 3-((6-(trifluoromethyl)benzo[d]thi-azol-2-yl)carbamoyl)benzoate, was isolated by evaporationof the solvent under reduced pressure. | 
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25.0℃; for 16h; | General procedure: To a solution of 7c (45mg, 0.215mmol) in dry CH2Cl2 (2mL), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDCI) (62mg, 0.322mmol), and 1-hydroxybenzotriazole hydrate (HOBt) (50mg, 0.322mmol) were added followed by amine 10a (27mg, 0.215mmol) and diisopropylethylamine (225μL, 1.290mmol). The reaction mixture was stirred at 25C for 16h then CH2Cl2 was added and the resulting solution was washed with saturated aqueous NH4Cl and water. The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/n-hexane 1:4) | 

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