Structure of 3964-54-3
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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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N-(3-Chloro-4-hydroxyphenyl) acetamide
Uppu, Rao M ; Fronczek, Frank R ;
Abstract: In the title compound, C8H8ClNO2, the acetamide substituent is twisted out of the phenyl plane, forming a dihedral angle of 58.61 (7)°. In the extended structure, each molecule donates two hydrogen bonds [N—H···O(carbonyl) and O—H···O(carbonyl)] and thus also accepts two such hydrogen bonds. The chlorine atom is not involved in the hydrogen bonding.
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Keywords: crystal structure ; acetaminophen ; acetaminophen impurity C ; cellular oxidants ; non-enzymatic biotransformation
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| CAS No. : | 3964-54-3 |
| Formula : | C8H8ClNO2 |
| M.W : | 185.61 |
| SMILES Code : | C1=C(C=CC(=C1Cl)O)NC(C)=O |
| English Name : | N-(3-Chloro-4-hydroxyphenyl)acetamide |
| MDL No. : | MFCD01318123 |
| InChI Key : | JULKJDRBSRRBHT-UHFFFAOYSA-N |
| Pubchem ID : | 77579 |
| Num. heavy atoms | 12 |
| Num. arom. heavy atoms | 6 |
| Fraction Csp3 | 0.12 |
| Num. rotatable bonds | 2 |
| Num. H-bond acceptors | 2.0 |
| Num. H-bond donors | 2.0 |
| Molar Refractivity | 47.79 |
| TPSA ? Topological Polar Surface Area: Calculated from |
49.33 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.62 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.02 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.81 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.5 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.53 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.7 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-2.5 |
| Solubility | 0.585 mg/ml ; 0.00315 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-2.68 |
| Solubility | 0.385 mg/ml ; 0.00207 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.83 |
| Solubility | 0.276 mg/ml ; 0.00149 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 |
-6.0 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 |
0.55 |
| 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) |
1.22 |
* 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 |
|---|---|---|
| With acetic anhydride; acetic acid; platinum Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With ethanol Erhitzen des Reaktionsprodukts mit wss. HCl, anschliessend mit 4,7-Dichlor-chinolin; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium ethanolate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| (i) KOtBu, DMSO, (ii) /BRN= 2505480/, DMF; Multistep reaction; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 65% 2: 10% 3: 17% | With potassium chloride; potassium acetate; acetic acid In water at 25℃; other buffers; effect of pH (3.09 - 7.77); | |
| With hydrogenchloride; dipotassium hydrogenphosphate; potassium dihydrogenphosphate In water; acetonitrile at 40℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In water; acetonitrile at 25℃; hydrolysis in HCl solutions with various buffers, KCl or KCl-KClO3, pH range 0.3-10.5; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; potassium chloride In water at 25℃; various buffers; effect of pH (3.09 - 7.82); |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 14 % Chromat. 2: 44 % Chromat. 3: 8 % Chromat. 4: 1.3 % Chromat. | With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; water In acetonitrile at 25℃; also N-acetyl-p-benzoquinone imine, var. buffer, var. pH; mechanism; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 3.7 % Chromat. 2: 4.9 % Chromat. 3: 41 % Chromat. 4: 8.0 % Chromat. | With potassium chloride In water; acetonitrile at 40℃; Further byproducts given; |
[ 91631-54-8 ]
[ 6975-29-7 ]
[ 103-90-2 ]
[ 3964-54-3 ]
[ 16323-09-4 ]
[ CAS Unavailable ]
[ 106-51-4 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride; potassium chloride In water; acetonitrile at 30 - 80℃; activation parameters(ΔH++, ΔS++); further reaction conditions; | ||
| 1: 3.7 % Chromat. 2: 4.9 % Chromat. 3: 41 % Chromat. 4: 20 % Chromat. 5: 8.0 % Chromat. 6: 18 % Chromat. | With hydrogenchloride; potassium chloride In water; acetonitrile at 40℃; further reaction conditions; |
[ 91631-54-8 ]
[ 6975-29-7 ]
[ 103-90-2 ]
[ 3964-54-3 ]
[ 16323-09-4 ]
[ 96648-97-4 ]
[ 106-51-4 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 3.7 % Chromat. 2: 4.9 % Chromat. 3: 41 % Chromat. 4: 20 % Chromat. 5: 8.0 % Chromat. 6: 18 % Chromat. | With potassium chloride In water; acetonitrile at 40℃; various potassium halides; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | With pyridinium p-toluenesulfonate In dichloromethane; ethyl acetate for 48h; Ambient temperature; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With aluminium trichloride; phenylmethanethiol In dichloromethane 1) 0 deg C, 2) r.t., 3 h; Yield given; |

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