Structure of 5407-04-5
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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.
Synonyms: 3-Chloro-N,N-dimethylpropan-1-amine hydrochloride
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Molecularly Functionalized Biomass Hydrogels for Sustainable Atmospheric Water Harvesting
Guan, Weixin ; Zhao, Yaxuan ; Lei, Chuxin ; Wang, Yuyang ; Wu, Kai ; Yu, Guihua
Abstract: Atmospheric water harvesting (AWH) offers a promising pathway to alleviate global water scarcity, highlighting the need for environmentally responsible sorbent materials. In this context, this research introduces a universal strategy for transforming natural polysaccharides into effective hydrogel sorbents, demonstrated with cellulose, starch, and chitosan. The methodology unites alkylation to graft thermoresponsive groups, thereby enhancing water processability and enabling energy-efficient water release at lower temperatures, with the integration of zwitterionic groups to ensure stable and effective water sorption. The molecularly functionalized cellulose hydrogel, exemplifying our approach, shows favorable water uptake of 0.86-1.32 g g−1 at 15–30% relative humidity (RH), along with efficient desorption, releasing 95% of captured water at 60 °C. Outdoor tests highlight the water production rate of up to 14.19 kg kg−1 day−1 by electrical heating. The proposed molecular engineering methodology, which expands the range of raw materials by leveraging abundant biomass feedstock, has the potential to advance sorbent production and scalable AWH technologies, contributing to sustainable solutions.
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Keywords: atmospheric water harvesting ; biomass ; cellulose ; chitosan ; hydrogels ; molecular engineering ; starch
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| CAS No. : | 5407-04-5 |
| Formula : | C5H13Cl2N |
| M.W : | 158.07 |
| SMILES Code : | CN(C)CCCCl.[H]Cl |
| Synonyms : |
3-Chloro-N,N-dimethylpropan-1-amine hydrochloride
|
| MDL No. : | MFCD00012521 |
| InChI Key : | LJQNMDZRCXJETK-UHFFFAOYSA-N |
| Pubchem ID : | 94308 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302-H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 8 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 1.0 |
| Num. rotatable bonds | 3 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 40.81 |
| TPSA ? Topological Polar Surface Area: Calculated from |
3.24 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.01 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.98 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.89 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.87 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.35 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-1.89 |
| Solubility | 2.04 mg/ml ; 0.0129 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-1.71 |
| Solubility | 3.12 mg/ml ; 0.0197 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.77 |
| Solubility | 2.66 mg/ml ; 0.0168 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
| 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 |
-5.84 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 |
2.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
1.0 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) |
1.4 |
* 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 |
|---|---|---|
| 86% | With potassium carbonate; sodium iodide; In acetone;Reflux; | The mixture of 6-hydroxy-2-cyanobenzothiozole(0.311 g, 1.77 mmol), 3-chloropropyldimethylamine hydrochloride (0.36 g, 2.27 mmol), potassium carbonate (0.63g, 4.57 mmol) and sodium iodide (0.034 g) in acetone (30 ml) was heated to reflux overnight. Upon cooling to roomtemperature, the insoluble solid was removed by filtration. The compound was purified by flash chromatography usingmethylene chloride/methanol (96:4) as eluent in a yield of 86percent (0.387 g).1H NMR (CD2Cl2): 7.98 (d, J= 9.3 Hz, 1H), 7.32 (d, J= 2.4 Hz, 1H), 7.16 (dd, J = 9.0 Hz, J= 2.1 Hz, 1H), 4.04 (t, J = 6.4Hz, 2H, OCH2), 2.36 (t, J = 7.2 Hz, 2H, NCH2), 2.13 (s, 6H, CH3), 1.90 (m, 2H, CH2). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 60℃; for 28h; | Compound 1 B (2.50 g, 12.3 mm) was dissolved in dry DMF (50 mL) followed by the addition of 3-dimethylaminopropyl chloride hydrochloride (2.34 g, 14.8 mm) and cesium carbonate (10.00 g, 30.7 mm). The mixture was stirred at 60 C for 24 hrs. Additional 3-dimethylaminopropyl chloride hydrochloride (0.5848 g, 3.7 mm) was added and the reaction was stirred at 60 C C for 4 hrs. The mixture was filtered and the filtrate was diluted with ethyl acetate, washed with water (4x) and brine (1X), then dried (NA2SO4) and evaporated in vacuo. The crude product was chromatographed (silica gel 97% DCM/3% MeOH to 95% DCM/5% MeOH) to afford Compound 4c (1.35 G). HNMR (DMSO) 6 1.88- 2.00 (m, 2H, CH2), 2.12 (s, 8H, CH2 and CH3), 3.89 (s, 2H, CH3), 4.34 (t, 2H, CH2), 7.29-7. 38 (m, 2H, H-5 and H-6), 7.67 (d, 1H, H-7), 8.17 (d, 1H, H-4) and 8.49 (s, 1 H, H-2). ES-MS M/Z 289 (MH). Compound 4b (0.060 g, 0.26 mm) and Compound 4c (0.1124 g, 0.39 mm) were dissolved in dry THF (1 mL) followed by the addition of 60% NaH (0.104 g, 2.6 mm). The mixture was stirred at ambient temperature for 3 hrs and then the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with water (1X15 mL) and brine (1x15 mL), then dried (NA2SO4), and evaporated in vacuo. The crude product was chromatographed (silica gel-97% DCM/ 1% MeOH/2% NH40H) to afford Compound 31 (0.0275 g, 23%). HNMR (CD30D) 8 0.3793-0. 4566 (m, 2H, CH2), 0. 6618 (s, 6H, CH3), 0.759 (t, 2H, CH2), 2.71 (t, 2H, CH2), 4.85-4. 99 (m, 2H, aromatics), 5.42-5. 61 (m, 3H, aromatics), 5.80 (d, 2H, aromatics), 6.19 (d, 1H, aromatics), 6.38 (d, 2H, aromatics). ES-MS M/Z 464 (MH+). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With NaH; In N,N-dimethyl-formamide; | EXAMPLE 19 3-[1-[3-(dimethylamino)propyl]-1H-indol-3-yl]-4-[1-(3-pyridinyl)-1H-indazol-3-yl]-1H-pyrrole-2,5-dione (Compound 59) The indol-3-yl-glyoxylic methyl ester (0.50 g, 2.46 mmol) Compound 2b and 3-dimethylamino propyl chloride hydrochloride (0.44 g, 2.78 mmol) were combined in DMF (5 mL) and cooled to 0 C. as 95% NaH (135 mg, 5.34 mmol) was added. The reaction vessel was placed in an oilbath at 55 C. for 20 h and then cooled to ambient temperature. The solution was diluted with DCM (30 mL), washed with water, 3 times with saturated NaHCO3 and once with brine, then dried (K2CO3) and evaporated in vacuo to give an oil (0.44 g, 62%). The oil was purified via flash column (DCM:MeOH; 10:1) to afford Compound 19a. ES-MS m/z 289 (MH+). |
[ 2737-22-6 ]
[ 5407-04-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 25% | With potassium carbonate; In N,N-dimethyl-formamide; at 100 - 110℃; for 24h; | To a solution of <strong>[2737-22-6]2,4,6-tribromo-3-hydroxybenzaldehyde</strong> 15 2a (100 mg, 0.279 mmol) in DMF (1 mL) was added K2CO3 (115 mg, 0.837 mmol) and 2-Chloro-N,N-dimethylpropylamine hydrochloride 3a (62 mg, 0.390 mmol) and the reaction mixture was heated to 100-110 C for 24 h. After completion of the reaction, water (3 mL) was added and the reaction mixture was extracted with EtOAc (8 * 3 mL). Combined organic phases were washed with water (2 mL), brine (2 mL), dried over sodium sulfate, and concentrated in vacuo. The resulting crude was purified over silica gel column chromatography with 15% EtOAc in hexane, which afforded product as colourless solid (24 mg, 25%); mp: 96-98 C; Rf = 0.5 (25% EtOAc in hexane); 1H NMR (400 MHz, CDCl3) δ = 10.14 (s, 1H), 6.84 (s, 1H), 4.26 (t, J = 6.4 Hz, 2H), 3.57 (t, J = 5.4 Hz, 2H), 3.01 (s, 3H), 2.14 (quin, J = 6.3 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ = 190.4, 148.7, 144.5, 121.6, 121.4, 121.3, 119.2, 69.8, 52.2, 41.2, 27.9; IR (neat) = 2928, 2876, 1682, 1565, 1509, 1318, 1274, 1191, 1014, 909; HRMS (ESI+) m/z calculated for C11H12Br2NO2: 347.9235[M+H]+, found: 347.9224. |

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