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Structure of 4-Chloro-1-butanol
CAS No.: 928-51-8
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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.
4.5
*For Research Use Only !
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| CAS No. : | 928-51-8 |
| Formula : | C4H9ClO |
| M.W : | 108.57 |
| SMILES Code : | OCCCCCl |
| MDL No. : | MFCD00002967 |
| InChI Key : | HXHGULXINZUGJX-UHFFFAOYSA-N |
| Pubchem ID : | 13569 |
| GHS Pictogram: |
|
| Signal Word: | Danger |
| Hazard Statements: | H226-H290-H302-H314-H335-H351 |
| Precautionary Statements: | P210-P233-P234-P240-P241-P242-P243-P261-P264-P270-P271-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P370+P378-P390-P403+P233-P403+P235-P405-P406-P501 |
| Class: | 3(8) |
| UN#: | 2924 |
| Packing Group: | Ⅲ |
| Num. heavy atoms | 6 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 1.0 |
| Num. rotatable bonds | 3 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 1.0 |
| Molar Refractivity | 27.3 |
| TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.6 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.85 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.0 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.16 |
| 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 |
1.14 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.85 |
| Solubility | 15.3 mg/ml ; 0.141 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-0.86 |
| Solubility | 15.1 mg/ml ; 0.139 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.48 |
| Solubility | 3.64 mg/ml ; 0.0335 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 |
-6.36 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 |
3.0 |
| 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) |
1.55 |
* 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 |
|---|---|---|
| 35% | EXAMPLE 3; l -(4-Hydroxybutyl)morpholine was prepared as follows. In a 250 mL flask was mixed morpholine (65.5 g, 750 mmol), 4-chlorobutanol (27.2 g, 250 mmol), sodium iodide (3.8 g, 25 mmol) and 75 mL of dioxane. The reaction was heated to reflux. <n="76"/>After 2 days the reaction was allowed to cool to ambient temperature. Solvent was removed by rotary evaporation leaving a brown oil. The oil was dissolved in 100 mL of 2N NaOH, extracted with EtOAc and dried over Na2SO4. After filtration of the drying agent solvent was removed in vacuo leaving an orange oil. The oil was distilled (90 0C, 1 mm Hg), leaving 1 - (4-hydroxylbutyl)morpholine ( 13.9 g, 87 mmol, 35 % yield) as a colorless oil. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride; In tetrahydrofuran; tetrahydrofuran, ethyl bromide; | EXAMPLE 17 1'-[4-[1-(4-Fluorophenyl)-5-trifluoromethylindazol-3-yl]-1-butyl]spiro]isobenzofuran-1(3H),4'-piperidine], 17a. To a suspension of magnesium turnings (135 g) in 300 ml of dry tetrahydrofuran, ethyl bromide (140 g) dissolved in 500 ml of dry tetrahydrofuran was slowly added followed by reflux for 20 min. A solution of 4-chloro-1-butanol (274 g) in 500 ml of tetrahydrofuran was added dropwise at reflux temperature. After stirring for 20 min, the Grignard solution was filtered and added portionwise to a solution of <strong>[1813-33-8]2-chloro-4-trifluoromethyl-benzonitril</strong> (200 g) in 600 ml of dry tetrahydrofuran. The reaction mixture was stirred for 16 h at room temperature followed by addition af 2N hydrochloric acid and ice. Extraction with ether, drying of the ether phase over magnesium sulfate and removal of solvent in vacuo left a viscous oil which was applied to a silica gel column (eluent:dichloromethane/ether=3:1) giving 4-(2-chloro-5-trifluoromethylbenzoyl)-1-butanol (101 g) as an oil. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 65% | at 100℃; for 0.333333h;Sealed tube; Microwave irradiation; | General procedure: The 4-substituted methyl (phenylsulfonyl)carbamate was dissolved in the chosen alcohol (2 mL) in a microwave vial, which was closed using an aluminum open-top seal with PTFE-faced septum. The reaction mixture was heated under microwave irradiation at 100-120 oC for 20-60 min. The crude reaction mixture was concentrated under reduced pressure and the residue was purified using silica gel column chromatography to yield the desired (aryl)carbamate. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 2.84 g | With toluene-4-sulfonic acid; In toluene; at 90℃; for 5.0h;Dean-Stark; | In the reaction (R-3), the compound (A-1) and the compound (B-1) were reacted to obtain a compound (C-1). Hereinafter, the compound (A-1) is sometimes described as the first raw material of the reaction (R-3) and the compound (B-1) is described as the second raw material of the reaction (R-3). 2.24 g (0.01 mol) of the compound (A-1), 3.26 g (0.03 mol) of the compound (B-1) and toluene (100 mL) were added to the flask, The contents of the flask were dissolved. Into the flask, p-toluenesulfonic acid (0.001 mol) was added. The flask was set in a Dean-Stark apparatus. The content of the flask was heated at 90 C. for 5 hours, It was refluxed while dehydrating. The content of the obtained flask was depressurized, Toluene was distilled off. Ion exchanged water was added to the mixture after distillation under reduced pressure, and the mixture was extracted with chloroform. After drying the obtained organic layer, The organic layer was depressurized and chloroform was distilled off. As a result, the compound (C-1) was obtained as a crude product. The yield of the compound (C-1) was 2.84 g, and the yield of the compound (C-1) from the compound (A-1) was 90 mol%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 34 g | With toluene-4-sulfonic acid; In di-isopropyl ether; cyclohexene; for 12h;Dean-Stark; Reflux; | In a reaction vessel equipped with a Dean-Stark apparatus, 20.0 g of a compound represented by the formula (D-6-4)28.4 g of 2-trifluoromethylacrylic acid,1.8 g of p-toluenesulfonic acid monohydrate,300 mL of cyclohexane,150 mL of diisopropyl ether was added.And heated under reflux for 12 hours while removing water.It was diluted with dichloromethane and washed sequentially with a 5% aqueous sodium hydrogen carbonate solution and brine.Purification was carried out by column chromatography (silica gel, dichloromethane)34.0 g of a compound represented by the formula (D-6-5) was obtained. |
| 34 g | With toluene-4-sulfonic acid; In di-isopropyl ether; cyclohexane; for 12h;Dean-Stark; Reflux; | 20.0 g of the compound represented by the formula (I-6-10), 28.4 g of acrylic acid, 1.8 g of p-toluenesulfonic acid monohydrate, 300 mL of cyclohexane and 150 mL of diisopropyl ether were put into a reactor equipped with a Dean-Stark apparatus, and heated under reflux for 12 hours while removing water. This was diluted with dichloromethane, and washed sequentially with an aqueous solution of 5% sodium hydrogencarbonate, and salt water. Purification through column chromatography (silica gel, dichloromethane) gave 34.0 g of the compound of the formula (I-6-12). |