*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'.
Developing Allosteric Inhibitors of SARS-CoV-2 RNA-dependent RNA polymerase
Chayka, Artem ; Danda, Matěj ; Dostálková, Alžběta ; Spiwok, Vojtěch ; Klimešová, Anna ; Kapisheva, Marina , et al.
Abstract: The use of Fpocket and virtual screening techniques enabled us to identify potential allosteric druggable pockets within the SARS-CoV-2 RNA-dependent RNA polymerase (RdRp). Of the compounds screened, compound 1 was identified as a promising inhibitor, lowering a SARS-CoV-2 RdRp activity to 57% in an enzymatic assay at 10 µM concentration. The structure of compound 1 was subsequently optimized in order to preserve or enhance inhibitory activity. This involved the substitution of problematic ester and aromatic nitro groups with more inert functionalities. The N,N’-diphenylurea scaffold with two NH groups was identified as essential for the compound's activity but also exhibited high toxicity in Calu-3 cells. To address this issue, a scaffold hopping approach was employed to replace the urea core with potentially less toxic urea isosteres. This approach yielded several structural analogues with notable activity, specifically 2,2’-bisimidazol (in compound 55 with residual activity RA = 42%) and (1H-imidazol-2-yl)urea (in compounds 59 and 60, with RA = 50 and 28%, respectively). Despite these advances, toxicity remained a major concern. These compounds represent a promising starting point for further structure-activity relationship studies of allosteric inhibitors of SARS-CoV-2 RdRp, with the goal of reducing their cytotoxicity and improving aqueous solubility.
Show More >
Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;
Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
Show More >
Purchased from AmBeed: 607-35-2 ; 578-66-5 ; 613-50-3 ; 100-19-6 ; 579-71-5 ; 3034-94-4 ; 5683-43-2 ; 99-92-3 ; 13534-97-9 ; 5676-60-8 ; 5470-18-8 ; 619-45-4 ; 553-26-4 ; 580-15-4 ; 611-34-7 ; 619-72-7 ; 100-13-0 ; 540-37-4 ; 1849-25-8 ; 4487-59-6 ; 555-16-8 ; 6298-19-7 ; 556-08-1 ; 953-26-4 ; 54060-30-9 ; 62-23-7 ; 607-34-1 ; 3867-18-3 ; 873-74-5 ; 3544-24-9 ; 94-52-0 ; 1520-21-4 ; 5470-34-8 ; 619-50-1 ; 586-39-0 ; 934-22-5 ; 402-54-0 ; 15411-43-5 ; 455-14-1 ; 17763-80-3 ; 3085-54-9 ; 1942-30-9 ; 1694-20-8 ; 6305-66-4 ; 41656-75-1 ; 6393-17-5 ; 4309-66-4
Show More >
CAS No. : | 873-74-5 |
Formula : | C7H6N2 |
M.W : | 118.14 |
SMILES Code : | N#CC1=CC=C(N)C=C1 |
MDL No. : | MFCD00007821 |
InChI Key : | YBAZINRZQSAIAY-UHFFFAOYSA-N |
Pubchem ID : | 13396 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
87% | With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane; hydrogen bromide In water; acetonitrile at 20℃; for 2.5 h; | General procedure: To a solution of aniline/phenol (1 mmol) in CH3CN (4 mL), HBr and THPDPE (depending on the substrate as shown in Table 7) were added and the solution was stirred at room temperature. After the reaction was completed, Na2SO3 (3M, 1mL) was added to the stirring mixture followed by the addition of H2O (10 mL). The solution was stirred until the desired precipitates appeared. The products were filtered and more purification was carried out using silica- packed column chromatography (Hexane–EtOAc). All of the products were characterized on the basis of their melting points, IR, 1H NMR, and 13C NMR spectral analysis and compared with those reported |
74% | With bromine In 1,4-dioxane; sodium hydroxide | EXAMPLE 25 PREPARATION OF 4-AMINO-3,5-DIBROMOBENZONITRILE STR37 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 μL (1.78 moles) of 5N sodium hydroxide solution and mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 μL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as the eluant provided 175 mg (74percent) of the entitled product. NMR(CDCl3) δ5.1 (bs, 2H), 7.66 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With bromine In 1,4-dioxane; sodium hydroxide | EXAMPLE 1 Preparation of 4-Amino-3,5-dibromobenzonitrile STR15 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 μL (1.78 mmoles) of 5 N sodium hydroxide solution and 284 mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 μL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as eluant provided 175 mg (74percent) of the entitled product. NMR(CDCl3) δ: 5.1 (bs, 2H), 7.66 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; dichloromethane; | (c) 4-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine A solution of <strong>[15513-48-1]4-chloro-2,6-dimethyl-3-nitropyridine</strong> (9.80 g, 52.5 mmol) and 4-aminobenzonitrile (6.20 g, 52.5 mmol) in ethanol (160 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (200 ml), and washed with saturated aqueous sodium bicarbonate (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give a gum which was crystallized by adding ether (100 ml) and sonicating for 5 minutes. | |
In ethanol; dichloromethane; | (c) 4-[N-(4-Cyanophenyl)amino]-2,6-dimethyl-3-nitropyridine A solution of <strong>[15513-48-1]4-chloro-2,6-dimethyl-3-nitropyridine</strong> (see part (b)) (9.80 g, 52.5 mmol) and 4-aminobenzonitrile (6.20 g, 52.5 mmol) in ethanol (160 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (200 ml) and washed with saturated aqueous sodium bicarbonate (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give a gum which was crystallized by adding ether (100 ml) and sonicating for 5 minutes. The title compound was obtained as a yellow solid which was filtered off and dried in vacuo, (9.80 g, 70percent) m.p. 171°-172° C. 1 H-NMR (300 MHz, CDCl3): delta=2.49 (3H, s), 2.76 (3H, s), 6.96 (1H, s), 7.35 (2H, d, J 8 Hz), 7.74 (2H, d, J 8 Hz), 8.69 (1H, br s) p.p.m. | |
In ethanol; dichloromethane; | (c) 4-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine A solution of <strong>[15513-48-1]4-chloro-2,6-dimethyl-3-nitropyridine</strong> (9.80 g, 52.5 mmol) and 4-aminobenzonitrile (6.20 g, 52.5 mmol) in ethanol (160 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (200 ml), and washed with saturated aqueous sodium bicarbonate (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give a gum which was crystallized by adding either (100 ml) and sonicating for 5 minutes. The yellow solid (9.80 g, 70percent) was filtered off and dried in vacuo , mp 171-172°C. 1H NMR (300 MHz, CDCl3) 2.49 (3H, s), 2.76 (3H, s), 6.96 (1H, s), 7.35 (2H, d, J 8Hz), 7.74 (2H, d, J 8Hz), (1H, br s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sulfuryl dichloride; In chloroform; | EXAMPLE 15 (+-)-(2E,4E) N-(1,2-Dimethylpropyl)-5-[trans-2-(3,5-dichloro-4-bromophenyl)cyclopropyl]penta-2,4-dienamide (compound 61) P-Aminobenzonitrile (11.8 g) (ex Aldrich) in dry chloroform (250 ml) under nitrogen was treated with sulphuryl chloride (4.05 g) (ex BDH) maintaining reaction temperature below 35. After 2 hours at reflux the mixture was poured onto ice and made alkaline with 2M sodium hydroxide solution. Work up in the usual manner gave 3,5-dichloro-4-aminobenzonitrile (18.2 g) NMR 1 H 7.35(2H,s), 4.70(2H,bs). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; | 1. Preparation of 4-cyano-2,6-dichlorobenzamine. Reaction of 4-cyanobenzamine (10 g., 0.085 m, Aldrich Chem. Co.) with 292 ml of 6N HCl and 30% H2 O2 (17.2 mL, 0.17 m) led to the formation of a white crystalline compound with a melting point of 113-115 C. The yield of this compound was 12.3 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | Example 111 N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-cyanoaniline 4-Cyanoaniline (0.189 g, 1.60 mmol), triethylamine (0.162 g, 1.60 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.271 g, 1.60 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexane: ethyl acetate = 1:2) to obtain the titled compound (0.141 g, 0.297 mmol, 56percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of P-aminobenzonitrile (100 gm), ethanol (500 ml), concentrated nitric acid (36 ml) and aqueous cyanamide (50%, 54 ml) was heated at reflux. The solution was maintained for 16 hours at reflux. The reaction mass was further cooled to 0C and then added methyl tert-butyl ether (500 ml) at 0 to 5C. The reaction mass was maintained for 5 hours at 0 to 5C and separated solid obtained was collected by filtration to obtain 59 gm of guanidine nitrate.Guanidine nitrate (59 gm) was dissolved in water (590 ml) and then added sodium hydroxide solution (1M, 325 ml). The separated solid obtained was filtered and dried to obtain 33 gm of l-(4-cyanophenyl)guanidine. | ||
33 g | A solution of P-aminobenzonitrile (100 gm), ethanol (500 ml), concentrated nitric acid (36 ml) and aqueous cyanamide (50%, 54 ml) was heated at reflux. The solution was maintained for 16 hours at reflux. The reaction mass was further cooled to 0 C. and then added methyl tert-butyl ether (500 ml) at 0 to 5 C. The reaction mass was maintained for 5 hours at 0 to 5 C. and separated solid obtained was collected by filtration to obtain 59 gm of guanidine nitrate. Guanidine nitrate (59 gm) was dissolved in water (590 ml) and then added sodium hydroxide solution (1M, 325 ml). The separated solid obtained was filtered and dried to obtain 33 gm of 1-(4-cyanophenyl)guanidine. | |
30 g | With nitric acid; In methanol; water; at 10 - 65℃; for 8h; | 100 g of 4-aminobenzonitrile was dissolved in 500 mL of methanol and cooled the reaction mixture to 10-15 C. 161 mL of con. Nitric acid was added to the reaction mixture followed by 65.6 ml of 50% aqueous solution cynamide to the reaction mixture and maintained the reaction at 65 C. for 8 hrs. Cooled the reaction mass to 0 C. and charged 500 ml of methyl-t-butyl ether at 0 C. The solids were filtered, washed with water and acetone and dried to give 30 g of the product as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In iso-butanol; at 20 - 102℃; for 21h; | Example 7: Preparation of 4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile ("Compound la")To a solution of 4-aminobenzonitrile (ABN; 7 g; 59.3 mmol) in 2-butanol (190 ml), 2,6- dichloropyrimidin-4-amine ("DCAP"; 10.2 g; 62.2 mmol) was added at room temperature. The resulting suspension was heated to reflux (102 C) and stirred for 20 hours. The suspension was then cooled to 20-25 C and stirred for lhour at 20-25 C. A solid was separated from the suspension by filtration and washed with 2-butanol (20 ml) and dried (2h/ 50 C/ 10 mbar). Yield: 12.20 g (73.0 %) of 4-(4-amino-6-chloropyrimidin-2-ylamino)benzonitrile hydrochloride.Purity (HPLC/ MS): 99.0 Area % |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40 g | With toluene-4-sulfonic acid; In isopropyl alcohol; at 20 - 85℃; for 4h; | Example 5:Preparation of rilpivirineTo a mixture of (E)-3-( 4-(2-chloropyrimidin-4-ylamino )-3,5-dimethylphenyl)acrylonitrile ( 40 gm), 4-aminobenzonitrile (17 gm), isopropanol ( 400 ml)5 and p-toluenesulfonic acid (20 ml) were added at room temperature. The reaction mixturewas then heated to 80 to 85C and stirred for 4 hours. The reaction mass was then cooledto 0C and pH was adjusted to 10 to 11 with aqueous ammonia solution. The separatedsolid was filtered and then dried to provide 40 gm of rilpivirine.Chromatographic purity: 96.0%;10 Content of Z-isomer: 3.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | To a stirred solution of 2-mcthoxyi enzonitrile (10 g, 0075 mol) in tolucne (200ml) at 0 C was added trimcthylaiuminum (90 mL. 0.09 mol) drop-wise over a period of 10 mi The reaction mixture was then stirred at room temperature for 3 h followed byaddition of 4-aminobcnzonitrilc (8.6g. 0,074mo1) in tohienc 100 mL. The reaction mixturewas heated to 70 C for 1 6 h. After confirming the completion by LCMS the reactionmixture was quenched with ice-cold water; the aqueous layer was filtered through a pad of diatomaccous earth, and the resultant filtrate was washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2504, filtered, and concentrated under reducedpressure to provide a residue. Purification by column chromatography on silica gel (100-200 mesh) using ethyl acetate in hcxane afforded the title compound as a white solid. (12.8 g, 68%). | |
68% | Example 1 Preparation of intermediate A1; N-(4-cyanophenyl)-2-methoxybenzimidamide To a stirred solution of 2-methoxybenzonitrile (10 g, 0.075 mol) in toluene (200 ml) at 0 C. was added trimethylaluminum (90 mL, 0.09 mol) drop-wise over a period of 10 min. The reaction mixture was then stirred at room temperature for 3 h followed by addition of 4-aminobenzonitrile (8.6 g, 0.074 mol) in toluene 100 mL. The reaction mixture was heated to 70 C. for 16 h. After confirming the completion by LCMS the reaction mixture was quenched with ice-cold water; the aqueous layer was filtered through a pad of diatomaceous earth, and the resultant filtrate was washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide a residue. Purification by column chromatography on silica gel (100-200 mesh) using ethyl acetate in hexane afforded the title compound as a white solid. (12.8 g, 68%). By using analogous protocols as described in the foregoing example the intermediates described in Table 1 have been prepared using appropriate starting materials |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1-methyl-pyrrolidin-2-one; at 200℃; for 5.0h;Microwave irradiation; | Step 1: Synthesis of 4-((8-bromo-6-fluoroquinazolin-2-yl)amino)benzonitrile (Compound 4a) Compound 4a [0257] A mixture of <strong>[953039-63-9]8-bromo-2-chloro-6-fluoroquinazoline</strong> (500 mg, 1.91 mmol, Ark Pharm Inc, AK-93358) and 4-aminobenzonitrile (250 mg, 2.12 mmol, Sigma-Aldrich) in dry N-methylpyrrolidone was heated in microwave at 200 C for 5 hours. The reaction mixture was cooled down to room temperature and subjected to silica gel chromatography (gradient from 5-50% ethyl acetate in wo-hexanes).to afford the title compound 4a. NMR (400 MHz, DMSO-i ) delta 10.69 (s, 1H), 9.37 (s, 1H), 8.32 (d, J= 8.7 Hz, 2H), 8.26 (dd, J= 8.5, 2.7 Hz, 1 H), 7.86 (dd, J= 8.5, 2.7 Hz, 1 H), 7.78 (d, J = 8.7 Hz, 2H). LCMS (m/z) 343.0 [M+H], Tr = 4.72 min (LCMS method 1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.6% | In methanol; at 20℃; for 2h; | General procedure: The equimolar aldehyde 3a-3d (1 mmol) and substituted phenylhydrazine 5a-5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a-6ai (in 45-80% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 120℃; for 1h;Inert atmosphere; Microwave irradiation; | General procedure: A G10 microwave vial equipped with a stir-bar was charged with compound 5-bromo-2-substituted pyrimidine (0.3 mmol), amino compound (0.33 mmol), Pd2dba3 (2 mol%), XPhos (8 mol%), NaOtBu (0.42 mmol) and anhydrous 1,4-dioxane (2 ml). The reaction vial was purged with argon, and heated by microwave irradiation until its temperature was 120 C. Then, the irradiation was automatically controlled to keep the mixture at this temperature for 1h. The reaction mixture was concentrated under reduced pressure and the crude residue was purified by flash chromatography on silica gel. The purified material was dried in vacuo to afford the corresponding products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With acetic acid; at 120℃; for 4h; | General procedure: To a 10 mL round-bottomed flask equipped with a stirring bar and refluxcondenser was charged the appropriate mono-, di-, or tetrafluorophthalicanhydride 1 (0.5-4 mmol, 1 equiv). Glacial AcOH (0.5-4mL) was then added, and to the stirred solution was added the appropriateamine 2 (0.55-4.4 mmol, 1.1 equiv). The solution was heated at120 C and allowed to stir at this temperature for 4-12 h, then theflask was allowed to cool to rt. The reaction mixture was taken in aseparatory funnel, treated with sat. aq Na2CO3 (4-30 mL), and extractedwith EtOAc (2 × 2.5-15 mL). The combined organic phases weredried (anhyd MgSO4) and concentrated. The crude product was purifiedby recrystallization or flash chromatography using silica gel withhexanes/EtOAc as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27.4 mg | General procedure: To a solution of the corresponding aniline (1.0 equiv) in anhydrousTHF was added BF3·Et2O (1.4 equiv) at 0 C. The mixture was stirredfor 30 min, then tert-butyl nitrite (1.2 equiv) was added dropwise andthe resulting suspension was allowed to warm to room temperatureover 1 h. The solvent was removed under reduced pressure and theobtained solid was washed with cold methanol and diethyl ether. Allthe aryldiazonium salts were dried using a high vacuum pump andwere stored in the dark at -20 C.Biaryl Compounds 2; General Procedure BA Schlenk tube was charged with Ph3PAuCl, (8 mg, 0.016 mmol, 0.1equiv), the corresponding aryldiazonium salt (1.5 equiv) and the corresponding arylboronic acid (1.0 equiv). The tube was evacuated andbackfilled with nitrogen (×3). Acetonitrile (1.5 mL previously degassed by the freeze-pump-thaw method, three cycles) was added.Next, a freshly prepared solution of ascorbic acid [0.05 M in dryDMSO (0.01 equiv), 32 L] was added followed by KF (9.4 mg, 1.6mmol, 1.0 equiv). The reaction mixture was stirred at room temperature for 16 h under irradiation with blue LEDs or without irradiation.The solvent was then removed under reduced pressure and the cruderesidue was purified by column chromatography on silica gel usinghexanes or hexanes/EtOAc as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.5% | With tri-tert-butyl phosphine; Palladium(0) bis(dibenzylideneacetone); sodium tertiary butoxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 17h;Reflux; | In a 1-neck 250 mL flask, 1.5 g (12.7 mmol) of 4-aminobenzonitrile, <strong>[57774-35-3]4'-bromo-[1,1'-biphenyl]-4-carbonitrile</strong> (4'-bromo-[ 1,1'-biphenyl]-4-carbonitrile) 13.1 g (50.8 mmol), Pd (dba) 21.5 g (2.5 mmol),P(tBu) 32.4 mL (5.1 mmol), NaOtBu 4.9 g (50.8 mmol) and xylene 63 mL were mixed, followed by refluxing and stirring for 17 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through Celite. After purification by silica gel column chromatography (HEX:DCM), it was recrystallized from a mixed solution (Acetone/MeOH) to obtain 1.7 g (yield: 29.5%) of compound 2-29 (LT20-30-182) as a beige solid. |
Tags: 4-Aminobenzonitrile | Nitriles | Amines | Aryls | Fluorinated Building Blocks | Organic Building Blocks | 873-74-5
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL