Structure of 2420-16-8
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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 !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
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'.
Search for reports by entering the product batch number.
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'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 2420-16-8 |
Formula : | C7H5ClO2 |
M.W : | 156.57 |
SMILES Code : | C1=C(C(=CC=C1C=O)O)Cl |
MDL No. : | MFCD00016981 |
InChI Key : | VGSOCYWCRMXQAB-UHFFFAOYSA-N |
Pubchem ID : | 17022 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 38.86 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.42 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.89 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.86 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.39 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.14 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.74 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.38 |
Solubility | 0.654 mg/ml ; 0.00417 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.3 |
Solubility | 0.792 mg/ml ; 0.00506 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.37 |
Solubility | 0.663 mg/ml ; 0.00424 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) |
Yes |
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 |
-5.91 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) |
1.02 |
* 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 |
---|---|---|
97% | REFERENCE EXAMPLE 4 3-Chloro-4-methoxybenzaldehyde Following a similar procedure to that described in reference example 3, but starting from 3-chloro-4-hydroxybenzaldehyde instead of 4-hydroxybenzaldehyde and using methyl iodide instead of 2-iodopropane, the title compound of the example was obtained as an oil (97% yield). 1H-NMR (300 MHz, CD3OD delta TMS): 3.98 (s, 3H), 7.04 (d, J=8.4 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.89 (s, 1H), 9.84 (s, 1H). | |
96% | With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 80℃; for 1.5h; | Toa mixture of 3-chloro-4-hydroxybenzaldehyde(10.00 g, 63.87 mmol, 1.0 eq) and potassium carbonate (26.48g, 191.61 mmol, 3.0 eq) in DMF (150 mL) was added dropwiseiodomethane (43.23 g, 304.57 mmol,18.96 mL, 4.8 eq) over 30 min at 25 C. The mixture was heated at80 Cfor 1 h. It was cooled to rt, diluted with water (500 mL) and extracted with ethyl acetate (3x500 mL). The combined organic layerswere washedwith saturated brine (3x200 mL), driedover anhydrous sodium sulfate,filtered and concentrated under reduced pressure. The crude product waspurified by flash column chromatography (silica gel, petroleum ether/ethylacetate = 20: 1 to 5: 1) to give the title compound (10.50 g, 61.55 mmol, 96%yield) as a yellow solid.1H NMR: (CDCl3,400 MHz) delta 9.87 (s, 1H), 7.92 (d, J =2.0 Hz, 1H), 7.79 (dd, J =2.0,8.4 Hz, 1H), 7.06 (d, J =8.4 Hz, 1H), 4.00 (s, 3 H). |
93% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 1h;Inert atmosphere; | To a stirred solution of 3-chloro-4-hydroxybenzaldehyde (2.9 g, 18.412 mmol) in DMF (30 mL) was added K2CO3 (7.6 g, 55.238 mmol). CH3I (7.80 g, 55.238 mmol) was then added slowly at RT under an inert atmosphere. After addition was completed, the reaction mixture was brought to 80 0C and stirred for 1 h. The reaction mixture was quenched with water (20 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography to afford 3-chloro-4-methoxybenzaldehyde (2.78 g, 93%) as a yellow solid. |
56% | In diethyl ether; acetone; | 3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), KCO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. The filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1 N NaOH (3*100 mL). The organic layer was dried (Na2SO4) and evaporated under vacuum to yield 24 g, 92% yield of crude product. This material was further purified by chromatography on silica gel (50 mm*30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56% yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf=0.24; GC Rt=4.75 min; MS (EI) m/z 170(M+), 172(M+2). |
With potassium carbonate; In N-methyl-acetamide; | PREPARATION 43 To a solution of 3-chloro-4-hydroxybenzaldehyde (153 g) in dimethylformamide (500 ml) was added potassium carbonate (203 g) under ice-cooling, followed by iodomethane (91.3 ml). After stirring at ambient temperature for 2 hours, the mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer were washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was triturated with n-hexane to obtain 3-chloro-4-methoxybenzaldehyde (156 g) as a white powder. NMR(CDCl3, delta): 4.00 (3H, s), 7.05 (1H, d, J=8 Hz), 7.78 (1H, dd, J=2 Hz, 8 Hz), 7.92 (1H, d, J=2 Hz), 9.86 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In diethyl ether; acetone; | 3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), K2 CO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. the filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1 N NaOH (3*100 mL). The organic layer was dried (Na2 SO4) and evaporated under vacuum to yield 24 g, 92percent yield of crude product. This material was further purified by chromatography on silica gel (50 mm*30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56percent yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf =0.24; GC Rt =4.75 min; MS (EI) m/z 170(M+), 172(M+2). |
56% | In diethyl ether; acetone; | 3-Chloro-4-methoxybenzaldehyde A mixture of 3-chloro-4-hydroxybenzaldehyde (25 g, 160 mmol), iodomethane (27.25 g, 192 mmol), K2 CO3 (granular, anhydrous) (110.6 g, 800 mmol), and acetone (300 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature. Diethyl ether (500 mL) was added and the mixture was filtered through paper to remove the inorganic solids. the filtrate was evaporated under reduced pressure, dissolved in diethyl ether (800 mL), and washed with 0.1N NaOH (3*100 mL). The organic layer was dried (Na2 SO4) and evaporated under vacuum to yield 24 g, 92percent yield of crude product. This material was further purified by chromatography on silica gel (50 mm*30 cm) (elution with hexane-EtOAc, 5:1) to give 15.02 g, 56percent yield of a white solid: TLC (hexane-EtOAc, 5:1) Rf =0.24; GC Rt =4.75 min; MS (EI) m/z 170(M+), 172(M+2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Finely powdered potassium carbonate (18.1 g, 0.131 mol, 2 eq) was added to a well stirred solution of 3-chloro-4-hydroxybenzaldehyde (10 g, 0.064 mol, 1 eq) in acetone (80 mL) under nitrogen. After 10 min., dimethylsulphate (8 g, 0.064 mol, 1 eq) was added slowly at room temperature and stirred for 30 min. The reaction mixture was allowed to reflux for 2h. Reaction progress was monitored by TLC, Reaction mixture cooled to room temperature and K2CO3 was filtered, acetone was distilled out in vacuo to obtain residue and was triturated with hexane (20 mL) at O0C for 30 min. to result pale green colored solid. Yield 9.2 g (85percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.97 g | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; | Diisopropyl azodicarboxylate (1.01 g, 5 mmol) in THF (30 mL) was added dropwise to a cooled (0 C) solution of 4-hydroxy-3-chlorobenzaldehyde (0.782 g, 5 mmol), triphenylphosphine (1.3 g, 4.99 mmol) and intermediate 1A, 2 -methyl- [1,1 '- biphenyl]-3-yl)methanol (0.90 g, 4.54 mmol) in dry THF (30 mL). The resulting yello solution was allowed to slowly warm to room temperature with stirring overnight. Solvent was removed by rotary evaporator. The residue was purified on a 40 g silica gel column with 10: 1 Hexane:Ethyl acetate. Isolated 0.97 g of the desired product as white solid. 1H NMR (400MHz, CHLOROFORM-d) delta 9.90 (s, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.81 (dd, J=8.6, 2.0 Hz, 1H), 7.53 - 7.49 (m, 1H), 7.49 - 7.43 (m, 2H), 7.39 (d, J=7.1 Hz, 1H), 7.36 - 7.29 (m, 4H), 7.20 (d, J=8.3 Hz, 1H), 5.30 (s, 2H), 2.30 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | General procedure: To a solution of 1-tritylimidazole (8.12 g, 26.160 mmol) in anhydrous THF (165 mL) was added n-BuLi (1.28 M in THF, 20.0 mL, 1.67 g, 13.08 mmol) at -20°C over a period of 20 min under nitrogen atmosphere. The red solution was allowed to attain room temperature and stirred for 1 h, then cooled to -78°C. In a separate flask the appropriate aldehyde 1a?c (10.47 mmol) was dissolved in anhydrous THF (4 mL) and added to the red solution dropwise at -78 °C. The reaction mixture was stirred at -78°C for 1 h and slowly brought to room temperature during which red color tuned to yellow and then to colorless. After complete reaction, saturated NH4Cl (250 mL) was added to the reaction mixture at -78°C. The resulting mixture was extracted with EtOAc (3 x 100 mL); the organic layer was separated, washed with water, saturated NaCl, and dried over anhydrous Na2SO4. The organic layer was evaporated in vacuo and the residue washed with cold CH2Cl2. |
A116134 [56962-12-0]
4-Chloro-3-hydroxybenzaldehyde
Similarity: 0.96
A107494 [1927-94-2]
3-Chloro-2-hydroxybenzaldehyde
Similarity: 0.94
A238886 [56962-10-8]
2-Chloro-3-hydroxybenzaldehyde
Similarity: 0.94
A161922 [1829-33-0]
3-Chloro-5-hydroxybenzaldehyde
Similarity: 0.94
A204560 [2314-36-5]
3,5-Dichloro-4-hydroxybenzaldehyde
Similarity: 0.92
A116134 [56962-12-0]
4-Chloro-3-hydroxybenzaldehyde
Similarity: 0.96
A107494 [1927-94-2]
3-Chloro-2-hydroxybenzaldehyde
Similarity: 0.94
A238886 [56962-10-8]
2-Chloro-3-hydroxybenzaldehyde
Similarity: 0.94
A161922 [1829-33-0]
3-Chloro-5-hydroxybenzaldehyde
Similarity: 0.94
A204560 [2314-36-5]
3,5-Dichloro-4-hydroxybenzaldehyde
Similarity: 0.92
A116134 [56962-12-0]
4-Chloro-3-hydroxybenzaldehyde
Similarity: 0.96
A107494 [1927-94-2]
3-Chloro-2-hydroxybenzaldehyde
Similarity: 0.94
A238886 [56962-10-8]
2-Chloro-3-hydroxybenzaldehyde
Similarity: 0.94
A161922 [1829-33-0]
3-Chloro-5-hydroxybenzaldehyde
Similarity: 0.94
A204560 [2314-36-5]
3,5-Dichloro-4-hydroxybenzaldehyde
Similarity: 0.92