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CAS No. : | 871-84-1 | MDL No. : | MFCD00008580 |
Formula : | C8H10 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DSOJWVLXZNRKCS-UHFFFAOYSA-N |
M.W : | 106.17 | Pubchem ID : | 70099 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 36.89 |
TPSA : | 0.0 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.2 cm/s |
Log Po/w (iLOGP) : | 2.5 |
Log Po/w (XLOGP3) : | 2.46 |
Log Po/w (WLOGP) : | 1.97 |
Log Po/w (MLOGP) : | 3.95 |
Log Po/w (SILICOS-IT) : | 2.32 |
Consensus Log Po/w : | 2.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.85 |
Solubility : | 1.5 mg/ml ; 0.0141 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.1 |
Solubility : | 0.836 mg/ml ; 0.00787 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.6 |
Solubility : | 2.69 mg/ml ; 0.0254 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.2 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | 3295 |
Hazard Statements: | H225-H315-H319-H335 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
83% | With N-Bromosuccinimide; silver nitrate; In dichloromethane; at 20℃; for 4h;Inert atmosphere; | General Procedure: Silver nitrate (16.2 mmol) and N-iodo- or N-bromosuccinimide (15 mmol) were added to a solution of the diyne or the triyne (6.8 mmol) in CH2Cl2 (60 mL). The mixture was stirred at room temperature for 4 h, filtered through a pad of celite, and the solvent was removed in vacuo. The residue was purified by flash column chromatography using a gradient mixture of pentane and Et2O as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 20℃; for 16h; Inert atmosphere; | |
34% | With dicarbonylcyclopentadienylcobalt In octane; toluene at 125℃; for 24h; Inert atmosphere; | |
49 % Chromat. | Stage #1: 1,7-Octadiyne With molybdenum(V) chloride; aluminium In 1,2-dimethoxyethane at 50℃; for 1h; Stage #2: dimethyl acetylenedicarboxylate With molybdenum(V) chloride; aluminium In 1,2-dimethoxyethane at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | A solution of LiHMDS was prepared by dropwise addition of nBuLi (1.6 M in hexanes, 94.2 mL, 150.7 mmol) to a stirred solution of hexamethyldisilazane (31.42 mL, 150.7 mmol) in THF (78 mL) at -78 oC. Once the addition was complete, the mixture was allowed to reach 0 C and stirred for 30 min before use. The LiHMDS solution was cooled to -78 oC before and then added to a solution of 1,7-octadiyne (20 mL, 150.7 mmol) in THF (210 mL)kept at -78 oC. After stirring the resulting mixture for 0.5 hours at -78 C, chlorotrimethylsilane (19.1 mL, 150.7mmol) was added dropwise. The mixture was stirred for 10 min at -78 C and then it was allowed to reach room temperature. After stirring for 2 h, the reaction was quenched with water (400 mL). The mixture was extracted with hexane (3 ×400 mL) and the combined organic extracts were then washed with 1 M aq. HCl (400 mL), water (400 mL) and brine (400 mL), before being dried over Na2SO4 and concentrated. Distillation of the crude product (Vigreux column, b.p. = 50-55 oC at 1 mbar) gave the title compound as a colorless oil. Yield: 14.23 g (53%). Spectroscopic data are in agreement with those reported in the literature [5]. 1H NMR (400 MHz, CDCl3):2.20-2.17 (m, 4H), 1.90 (t, J = 2.68 Hz, 1H), 1.61-1.57 (m, 4H), 0.10 (s, 9H); 13C NMR (100 MHz, CDCl3):106.92, 84.80, 84.07, 68.62, 27.61, 27.57, 19.44, 18.02, 0.23; FT-IR: ν = 3308.3, 2950.6, 2865.7, 2360.4, 2175.3,2118.42, 1457.9, 1431.9, 1326.8, 1249.7, 1046.2, 992.2, 936.3, 902.5, 842.7, 759.8, 699.1, 638.3 cm-1 elementalanalysis (%): C 70.44, H 9.90, (calcd. for C11H18Si: C 74.08, H 10.17). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 24h; | |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With formic acid at 100℃; for 13.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With triethylamine; zinc(II) chloride In acetonitrile for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere; | General procedure: A solution of compound 5 (0.1 g, 0.26 mmol) in dry DMF (5 mL), was treated with CuI (0.01 g, 0.05 mmol), Pd(PPh3)4 (0.031 g, 0.03 mmol), dry Et3N (0.053 g, 73 μL, 0.52 mmol) and 6 equiv of tri(prop-2-ynyl)amine (0.35 g, 480 μL, 2.6 mmol). The reaction mixture, which slowly turns to black was stirred under inert atmosphere for 12 h. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated and the oily residue was adsorbed on silica gel and subjected to FC (silica gel, column 15×3 cm, eluted with 98:2→94:6) affording one main zone. Evaporation of the solvent gave 12 (0.065 g, 67%) as a colorless foam. TLC (silica gel, CH2Cl2/MeOH 9:1). Rf 0.5. UV λmax (MeOH)/nm 248 (/dm3 mol-1 cm-1 10,600), 286 (10,000). 1H NMR [DMSO-d6, 300 MHz]: δ 2.20-2.28 (1H, m, C2'-Hα), 2.74-2.82 (1H, m, C2'-Hβ), 3.27 (2H, s, CH2), 3.48-3.53 (4H, m, CH2), 3.75 (2H, s, CCH), 3.78-3.83 (1H, m, C4'-H), 4.40-4.43 (1H, m, C3'-H), 4.78-4.82 (1H, t, J=5.7 Hz, C5'-OH), 5.29-5.30 (1H, d, J=4.5 Hz, C3'-OH), 6.52-6.56 (1H, t, J=6.3 Hz, C1'-H), 8.24 (1H, s, C2-H). Anal. Calcd for C19H20N6O3 (380.4): C, 59.99; H, 5.30; N, 22.09. Found: C, 59.94; H, 5.24; N, 21.96. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Table 5. Copper catalyzed carboxylation of terminal alkynes with CCv Reaction conditions: for LI, CuCl (2.0 mol %), TMEDA, 1.5 mol %; for L12, P(NHC)(NHC-Cu), 5 mol%; alkynes (2.0 mmol), base (2.4 mmol), C02 (1 atm), DMF (4 mL), r.t.. M monocarboxylic acid was obtained. General Procedure for Carboxylation of the Terminal Alkynes (lb as Example); CuCl (4.0 mg, 0.04 mmol, 2.0 mol %), TMEDA (3.5 mg, 0.03 mmol, 1.5 mol %), and K2C03 or Cs2C03 (2.4 mmol) were added to the DMF (4 mL) in the reaction tube (10 mL). C02 and 2 mmol of terminal alkynes (la, 204 mg) were introduced into the reaction mixture under stirring. The reaction mixture was stirred at room temperature (about 24 C) for 16 hours. After completion of the reaction, the reaction mixture was transferred to the potassium carbonate solution (2 N, 5 mL) and the mixture was stirred for 30 mins. The mixture was extracted with dichloromethane (3 >< 5 mL) and the aqueous layer was acidified with concentrated HC1 to PH = 1 , then extracted with diethyl ether (3 χ 5 mL) again. The combined organic layers were dried with anhydrous Na2S04, filtered and the solution was concentrated in vacuum affording pure product. Element analysis calcd (%) for lb [C9H602 (146.0)]: C 73.97, H 4.14; found: C 73.82, H 4.07. Data for 1H and 13C NMR of acids were all conducted in d - DMSO or CDC13 and consistent with the data in reported literatures. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.6% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃; | Add 5-iodo-2'-deoxyuridine (0.531g, 1.50mmol), tetratriphenylphosphine palladium (0.173g, 0.15mmol), cuprous iodide (0.058g, 0.30mmol) to 15mL of anhydrous N, Dissolve in N-dimethylformamide, then add 0.5mL of anhydrous triethylamine and 1,7-octadiyne (0.800g, 7.5mmol), stir overnight at room temperature, concentrate the reaction product after column chromatography (dichloromethane Methane→dichloromethane:methanol 92:8, volume ratio) After separation and purification, a pale yellow powder was obtained with a yield (0.391 mg, 78.6%). |
78.6% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | 5-Iodo-2'-deoxyuridine (0.531g, 1.50mmol), Pd (PPh3)4 (0.173g, 0.15mmol), CuI (0.058g, 0.30mmol), DMF (15mL) was added to dissolve the mixture, Et3N (0.41mL, 3mmol), and 1, 7-octadiyne (0.800g, 7.5mmol) were added. The mixture was stirred overnight at room temperature under N2. The reaction mixture was extracted with CH2Cl2 and ddH2O. The organic layer was collected, dried with Na2SO4, evaporated, and then purified through silica gel column chromatography (CH2Cl2→CH2Cl2/MeOH, 92:8). The yield is (0.391mg, 78.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [(1,3,4-triphenyl-4,5-dihydro-1H-triazol-5-ylidene)RuCl2(CHPh)(tricyclohexylphosphine)]; In toluene; at 110℃; for 2.5h; | General procedure: To a solution of 0.032 mmol of catalyst 4 in toluene (3 ml), is added 3.2 mmol of 1-alkyne. The reaction is stirred at 110 C and followed in situ by 1H-NMR. Yield and selectivity is determined by 1H-NMR and GC/MS [8]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 52.8 % Spectr. 2: 20.4 % Spectr. | With [CpRu(6-Ph2P-Py-2-yl)(MeCN)][PF6(1-)]; water In acetone at 70℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,7-Octadiyne With 2,6-dimethylaniline In toluene at 100℃; for 24h; Stage #2: With hydrogenchloride Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dichloro bis(acetonitrile) palladium(II); diisopropylamine; triphenylphosphine In tetrahydrofuran at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 87% 2: 5% | With water; hafnium tetrachloride; butan-1-ol at 70℃; for 15h; | |
1: 47% 2: 34% | With gadolinium(III) chloride; water; butan-1-ol at 70℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol; at 20℃; | General procedure: To a 50 mL round bottom flask 100 mg of azide (100 mg, 0.26 mmol) and 10-undecynoic acid (62 mg, 0.34 mmol) were dissolved in tBuOH:THF:Water: 1:1:1 (6 mL). To this solution copper (II) sulfate (8 mg, 0.052 mmol) and L-ascorbic sodium salt (21 mg, 0.104 mmol) were added. Reaction was stirring at room temperature for typically 14h. Reaction was monitored using TLC and LC-MS. The solvents were evaporated under reduced pressure. The resulting residue was dissolved in chloroform (10 mL), washed with water (2 mL) and the crude product was purified using flash chromatography on silica gel by EtOAc:Hexane (95:5) or DCM:MeOH (97:3). The desired product 11 was obtained as a white solid (0.114 g, 81%). The other compounds were synthesized and purified similarly. The characterization data are given below for these compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With silver tetrafluoroborate;[RhCl(η2:η2-COD)]2; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In dichloromethane; at 20℃; for 16h; | (b) 3, 3 '-bis(diphenylphosphinoyl)-5, 6, 7, 8,5',6', 7',8 '-octahydro[2, 2 ']binaphthalene (3a) ; A flame-dried Schlenk flask was charged with [RhCI(COD)]2 (0.037 g, 0.075 mmol), AgBF4 (0.029 g, 0.15 mmol), rac-BINAP (0.093 g, 0.15 mmol) and CH2CI2 (25 mL). 1 ,4-Bis(diphenylphosphinoyl)buta-1 ,3-diyne (2) (0.675 g, 1.5 mmol) and 1 ,7-octadiyne (0.48 mL, 3.6 mmol) were added and the resulting solution stirred at room temperature for 16 hours. After this time, diethyl ether (40 mL) was added followed by water (40 mL). The organic layer was removed and the aqueous phase extracted with diethyl ether (2 x 30 mL). The organic phases were combined, dried over MgSO4, filtered and the solvent removed in vacuo to leave a crude brown solid which was purified by column chromatography eluting with ethyl acetate/acetone (2:1) to yield the product as an off-white solid (0.944 g, 95%). 31P(1HJ NMR (202.5 MHz, CDCI3, δ): 28.4; 1H NMR (500.0 MHz, CDCI3, δ): 7.73 (dd, J = 11.4, 7.5 Hz, 4H, C6H5 o-H), 7.64 (dd, J = <n="24"/>11.6, 7.4 Hz, 4H, C6H5 o-H) 7.48 (m, 2H, C6H5 p-H), 7.43 (m, 4H, C6H5 m-H), 7.29-7.23 (m, 6H, C6H5 m/p-H), 6.83 (d, J = 14.4 Hz, 2H, C6H2 H3), 6.66 (d, J = 4.4 Hz, 2H, C6H2 H6), 2.54-2.42 (m, 4H, C4H8), 2.39-2.34 (m, 4H, C4H8), 1.66 (br s, 8H1 C4H8); 13C{1H} NMR (75.5 MHz, CDCI3, δ): 140.6 (m, Q), 139.0 (Q), 135.6 (Q), 134.7 (d, J = 12.6 Hz, Q), 134.2 (d, J = 7.8 Hz, Q), 133.7 (d, J = 12.2 Hz, C6H2 C3), 132.9 (d, J = 10.3 Hz, C6H2 C6), 131.3 (d, J = 9.6 Hz, C6H5 o-C), 131.0 (d, J = 9.3 Hz, C6H5 o-C), 130.0 (C6H5 p-C), 129.4 (C6H5 p-C), 127.9 (Q), 127.2 (d, J = 11.9 Hz, C6H5 /77-C), 126.7 (d, J = 12.1 Hz, C6H5 m-C), 28.2 (C4H8), 28.1 (C4H8), 22.9 (C4H8), 21.8 (C4H8); LRMS (ES+) m/z 663 [M+H]+; HRMS (ESI+) exact mass calcd for (C44H41P2O2) [M+H]+ requires m/z 663.2582, found m/z 663.2560. Anal. Calcd for C44H40O2P2: C1 79.74; H, 6.08. Found: C, 79.91 ; H, 6.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium; ammonium sulfate; liquid ammonia / Reagens 4: Aether 2: chloroform; peroxybenzoic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) EtMgBr, (ii) Br2 2: H2 / Pd-C / petroleum ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of iodochromone A (0.5 mmol), acetylene B (0.2 mmol), Cupper (I) iodide (0.01 mmol), and dichloribis(triphenylphosphine)palladium (0.005 mmol) in CH3CN (6 ml) was added with DIEPA (2 mmol) and then stirred for 5 h at room temperature. The reaction mixture was treated with methyl hydrazine (1 mmol) and stirred at RT overnight. After evaporation, the crude product was directly purified by a flash column chromatography to give the pure product. Purification by a flash chromatography (Hexanes/EtOAc=2/1) gave VQ25048. 1H NMR: δ 10.73 (s, 2H), 8.54 (d, J=7.5 Hz, 2H), 7.46 (s, 2H), 7.21 (m, 2H), 7.02 (d, J=8.0 Hz, 2H), 6.92 (m, 2H), 3.87 (s, 6H), 2.56 (m, 4H), 1.86 (m, 4H); LC-MS: m/z, 451 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In methyl ethyl ketone=butan-2-one 20 min of vigorous stirring; pptn. upon addn. of pentane to nitromethane/2-butanone soln., washing with nitromethane, drying in vacuo; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | cyclopentadienyl-cobalt(I)-dicarbonyl; In 1,4-dioxane; at 20℃; for 18h;Heating / reflux; | Example 7; (lR)-l-({4-[(5,6,7,8-Tetrahydro-3-isoquinolinylmethyl)amino]-l- piperidinyl} methyl)- 1 ,2-dihydro-4H,9H-imidazo [1,2,3-//] - 1 ,8-naphthyridine-4,9- dione hydrochloride; (a) Ethyl 5,6,7,8-tetrahydro-3-isoquinolinecarboxylate; A solution of 1 ,7-octadiyne (4.00 ml, 30.1 mmol) and ethyl cyanoformate (2.95 ml, 30.1 mmol) in dry degassed 1,4-dioxane (500 ml) under argon at rt was treated with cyclopentadienyl-Cobalt(I)-dicarbonyl (0.814 g, 4.52 mmol) and then heated at reflux for 18h. Reaction was then evaporated, treated with toluene (100ml), re-evaporated, dissolved in DCM (100ml), filtered through a short pad of Kieselguhr, eluting with DCM, organic extracts evaporated, chromato graphed (0-100% DCM:40-60 Petroleum ether then 0-10% methanol/DCM) to give product as an impure brown oil (1.27 g, 21%). MS (ES+) m/z 206 (MH+). |
11% | With C12H13CoO5; In toluene; for 16h;Reflux; Irradiation; | A mixture of 1 ,7-octadiyne (20 g, 0.19 mol), ethyl carbonocyanidate (23 g, 0.23 mol) and B-174 (5.6 g, 19 mmol, 0.1 eq) in anhydrous toluene (600 mL) were heated at reflux under visible light irradiation for 16 hours. On completion, the reaction mixture was concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 10: 1] to give compound B-175 (4.2 g, 1 1% yield) as a yellow solid. |
3% | With dicarbonylcyclopentadienylcobalt; In 1,4-dioxane; at 20℃; for 18h;Inert atmosphere; Reflux; | A solution of 1 ,7-octadiyne (4.00 ml, 30.1 mmol) and ethyl cyanoformate (2.95 ml, 30.1 mmol) in dry degassed 1,4-dioxane (500 ml) under nitrogen at rt was treated with cyclopentadienyl-cobalt(I)-dicarbonyl (0.814 g, 4.52 mmol) and heated at reflux for 18 h. The mixture was thenconcentrated in vacuo, treated with PhCH3(100ml), concentrated in vacuo, dissolved in CH2Cl2(100ml), filtered through a short pad of Celite, eluted with CH2Cl2, concentrated in vacuo to afford a residue which was purified by silica gel column chromatography (Petroleumether/EtOAc = 4:1) to give the product as a brown oil (90 mg, yield: 3%). ESI-MS (M+H+): 206.1.1H NMR (400 MHz, CDCl3) : 8.42 (s, 1H), 7.84 (s, 1H), 4.60 (q, J = 7.2 Hz, 2H), 2.81- 2.74 (m, 4H), 1.85-1.84 (m, 4H), 1.44 (t, J = 7.2 Hz, 3H). |
With dicarbonylcyclopentadienylcobalt; In 1,4-dioxane; for 18h;Inert atmosphere; Reflux; | A solution of 1,7-octadiyne (4.00 ml, 30.1 mmol) and ethyl cyanoformate (2.95 ml, 30.1 mmol) in dry degassed 1,4-dioxane (500 ml) under argon at rt was treated with cyclopentadienyl-Cobalt(I)-dicarbonyl (0.814 g, 4.52 mmol) and then heated at reflux for 18 h. Reaction was then evaporated, treated with toluene (100 ml), re-evaporated, dissolved in DCM (100 ml), filtered through a short pad of Kieselguhr, eluting with DCM, organic extracts evaporated, chromatographed (0-100% DCM:40-60 Petroleum ether then 0-10% methanol/DCM) to give product as an impure brown oil (1.27 g, 21%). MS (ES+) m/z 206 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: 1,7-Octadiyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 2-(2-iodoethyl)-1,3-dioxolane With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78 - 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With (cyclohexylisocyanide)gold(I) chloride; water; potassium tetrakis(pentafluorophenyl)borate In methanol at 20℃; for 48h; | |
90% | With hexafluoroantimonic acid; AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); water at 120℃; for 24h; | |
82% | With mercury(II) bis(p-toluenesulfonamidate); water In methanol for 39h; Reflux; Inert atmosphere; chemoselective reaction; |
76 %Spectr. | With silver hexafluoroantimonate; chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In tetrahydrofuran; 1,4-dioxane at 120℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Example 20 Synthesis of [((3,5-Me2C6H4[i-Pr]N)3Mo)2(1,7-octadiyne)]2+[I2]2- To 2.56 g (4.40 mmol) of the molybdaziridine hydride dissolved in 20 mL of THF was added 558 mg (2.20 mmol) of 12 dissolved in 10 mL of THF. After 1 h, 1,7-octadiyne (223 mg, 2.1 mmol) dissolved in 5 mL of THF was added to the dark green solution. After 2 h, the solution was concentrated in vacuo providing dark brown solid. This solid was washed thoroughly with hexane and then dried in vacuo affording 3.32 g of a golden-brown solid (95% based on 1,7-octadiyne). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; triethylamine;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 60℃; | To a solution of compound 5 (440 mg, 0.73 mmol) in anhydrous DMF (12 mL), Pd(PPh3)4 (92 mg, 0.08 mmol), Cul (30.5 mg, 0.16 mmol), 1 ,7-octadiyne (1.0 mL, 8.01 mmol) and then triethylamine (0.22 mL, 1.6 mmol) was added. The reaction mixture was heated at 60 C for overnight. Solvent was evaporated under vacuum and the residue was purified on flash silica gel column chromatography (CH2Cl2:MeOH = 70: 1) to give the compound 7 (352 mg, 83%) as a foamy syrup. NMR (CD3OD, 300 MHz) 6 8.1 1 (s, 1H), 7.43 (s, 1H), 7.26-7.33 (m, 3H), 5.74 (d, J = 7.2 Hz, 1H), 5.01 (s, 1H), 4.83 (m, 1H), 2.87 (s, 3H), 2.53 (t, J= 6.9 Hz, 2H), 2.34-2.31 (m, 3H), 2.10-2.15 (m, 1H), 1.71-1.84 (m, 4H), 1.54- 1.57 (m, 4H), 1.40 (t, J= 5.4 Hz, 1H), 1.29 (s, 3H). HRMS calculated for C3,H34C1N603 (M + H)+: 573.2381 ; found 573.2397. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dicarbonylcyclopentadienylcobalt In toluene at 150℃; for 0.666667h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With C16H20Cl2N2O2Pd; potassium hydroxide; In water; acetonitrile; at 60℃; for 6h; | General procedure: In a 10 mL round bottom flask, the palladium complex (0.010 mmol) was dissolved in acetonitrile (2 mL). Aryl halide (1.0 mmol), alkyne (1.2 mmol), KOH (2.00 mmol) and distilled water (2 mL) were added. The mixture was stirred at room temperature (or 60 C) for the required time. After reaction completion, the product was extracted with ethyl acetate (3x5 mL). The combined organic layers were dried with anhydrous sodium sulfate. The product was analyzed with GC and GC-MS. The product was purified using column chromatography with hexane-ethyl acetate as eluent. The characterization data were in entire agreement with the previously reported literature.32-39 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | In pentane at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | PdCl2(PPh3)2 (5.7 mg, 0.008 mmol), Cul (1.0 mg, 0.005 mmol), and 1 ,7-octadiyne (27 ih, 0.2 mmol) followed by triethylamine (57 μ,, 0.4 mmol) were added to a solution of compound (IR, 2R, 3S, 4R, 55)-4-(2-chloro-6-(3- iodobenzylamino)-9H-purin-9-yl) 2,3-O-isopropylidine-bicyclo[3.1.0]hexane (20.4 mg, 0.04 mmol) in anhydrous DMF (1.2 mL) and the reaction mixture was stirred overnight at room temperature. Solvent was evaporated under vacuum, and the residue was roughly purified on flash silica gel column chromatography and the obtained product was dissolved in CH2CI2 (3 mL) and 2 mL of trifluoromethane sulfonic acid- water (2: 1) were added into it and stirred at room temperature overnight. Solvent was evaporated, and the residue was purified on flash silica gel chromatography (CH2Cl2:MeOH = 60:1) to give compound 212 (12.6 mg, 70%) as a syrup. NMR (CDCI3, 400 MHz) d 7.80 (s, 1H), 7.42 (s, 1H), 7.35-7.29 (m, 3H), 6.43 (br s, 1H), 4.88 (s, 1H), 4.80 (br s, 2H), 4.03 (d, J= 7.2 Hz, 1H), 3.97 (s, 1H), 2.64 (m, 1H), 2.45 (t, J = 6.4 Hz, 2H), 2.29-2.26 (m, 3H), 2.08-2.06 (m, 1H), 1.98 (t, J= 2.4 Hz, 1H), 1.71-1.66 (m, 3H), 1.28-1.31 (m, 1H), 0.86-0.82 (m, 1H). HRMS calculated for C26H27C1N502 (M + H) +: 476.1853; found 476.1869. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In toluene; at 20℃; for 18h;Inert atmosphere; | General procedure: To a solution of 5''-azide-neomycin B (62 mg, 0.05 mmol) in dry toluene (5 mL), diyne (0.025 mmol, 0.50 equiv) was added followed by the addition of CuI (4.76 mg, 0.025 mmol) and DIPEA (6.46 mg, 0.05 mmol). The reaction mixture stirred at rt for 18 h in the atmosphere of argon. The volatiles were removed under vacuum. Purification by flash column chromatography (0-10% ethanol in CH2Cl2) afforded the desired product as a white solid (80-89%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(II) sulfate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 - 50℃; for 10h; | General procedure: CuSO4 solution (5 μL of 0.5 M solution, 2.5 μmol) and sodium ascorbate solution (18 μL of a 1.0 M solution, 18 μmol) were added to a solution of azide 8 (20 mg, 0.023 mmol) and diyne 14a-e or 16a-c (0.011 mmol) or alkyne 9a-e or 11 (0.023 mmol) in tBuOH/H2O (1 mL, 1:1) at rt. The reaction mixture was heated for 10 h at 50 C and then diluted with CHCl3 (10 mL), and washed with brine (3 mL). The phases were separated and the aqueous layer was extracted with CHCl3 (2 × 5 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by flash column chromatography afforded dimers 13a-e and 14a-c and monomers 10a-e and 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium azide; copper(II) ferrite; In water; at 70℃; for 9h; | General procedure: Benzyl bromide (1 mmol), phenyl acetylene (1 mmol) and NaN3 (72 mg, 1.1 mmol) were placed in a 10 ml round-bottomed flask in H2O (2 mL). Sequentially CuFe2O4 (5 mol %, 12 mg) was added. The reaction mixture was warmed to 70 C and monitored by TLC until conversion of the starting materials is satisfactory. After completion of the reaction, the reaction mixture was magnetically concentrated with the aid of a magnet to separate the catalyst. Catalyst was separated and washed several times with ether followed by water, dried under vacuum. Water (30 mL) was added to the resulting reaction mixture followed by extraction with EtOAc (4 × 10 mL). The collected organic phases were dried with Na2SO4 and the solvent was removed under vacuum to give the corresponding triazole, which did not require any further purification (except compounds 3ga, 3ha and 3ii). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In ethanol; water; at 20℃; for 24h; | General procedure: The azide 23 (53.7 mg, 0.16 mmol) and 1-dodecyne (35 μL, 0.16 mmol) were suspended in a 1:1 mixture of water and ethanol (0.1 M). Sodium ascorbate (9.6 mg, 0.05 mmol) and copper(II) sulfate pentahydrate (4 mg, 0.02 mmol) were added. The resulting mixture was stirred at room temperature for 24 h. Then, the reaction was diluted with water, extracted with ethyl acetate (10 mL * 3), dried over MgSO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using a mixture of n-hexane-ethyl acetate as eluent, to obtain the pure product 27 (38.6 mg, yield 48%) as a clear oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7%; 29%; 40% | With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; water; In ethyl acetate; at 80℃; for 24h;Sealed tube; Green chemistry; | General procedure: Calculated amount of AgBArF (97.1 mg, 0.1 mmol) was weighed into a long necked glass vessel, followed by addition of alkyne (1 mmol). 10 μL of EtOAc was added and stirred for 5 minutes. Internal standard n-dodecane (1 mmol) and 3 mL water was then added and the vessel was sealed under vacuum. The whole set-up was placed in an oil bath at 80 C, stirred and heated for 12/24 hours. After the completion of reaction, the seal was broken and 3 mL EtOAc was added to it, stirred for 5 minutes and the organic layer was collected. The organic layer was passed through a very short column of silica to remove any impurities and subjected to GC-MS analysis. Products were purified by chromatography on a silica gel column using hexane/EtOAc as eluent. The isolated products were characterized by 1H and ESI-MSspectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 10h;Inert atmosphere; | General procedure: To a mixture of 5-bromotetrandrine2 (700 mg, 1 mmol), Pd(PPh3)2Cl2(0.03 mmol), and cesium carbonate(1.2 mmol), a solution of terminal alkyne (1.2 mmol) in degassed DMSO (20 ml)was added under an argon atmosphere.The reaction mixture was heated at 1008Cfor 10 h and then cooled down to roomtemperature prior to being quenched by theaddition of ammonia solution. The mixturewas filtered through silica gel, the filterpad was washed with ethyl acetate(100 ml), and the combined solvent waswashed with saturated aqueous sodiumchloride solution, dried over anhydroussodium sulfate, and concentrated in vacuoto yield a residue. The residue wascollected on preparative thin layer plateseluting with chloroform:methanol (10:1)to obtain the coupling products (1a-1l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 70℃;Sealed tube; | General procedure: 1,6-Heptadiyne (173 μl, 1.51 mmol, 1 equiv.) was added to a mixtureof azidomonosaccharide 2 (0.90 g, 3.17 mmol, 2.1 equiv.), CuI (57 mg, 0.30 mmol, 0.2 equiv.)and DIPEA (105 μl, 0.60 mmol, 0.4 equiv.) in THF (10 mL). The resulting reaction mixture wasstirred in a resealable pressure tube at 70 C for 14 h (TLC control). The solvent wasevaporated under reduced pressure and the residue was dissolved in CH2Cl2 (DCM) (15 mL).The DCM solution was washed with EDTA solution (5 × 3 mL), brine (2 × 5 mL), dried over Na2SO4 and evaporated under reduced pressure. The solid residue was dissolved in THF (5 mL)and a solution of Na2S (25 mg) in water (1 mL) was added. The resulting suspension was filteredthrough a silica gel pad that was suspended in THF. The filtrate was evaporated under reducedpressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; 5,5′-bis(trifluoromethyl)-2,2′-bipyridine In 1-methyl-pyrrolidin-2-one; water at 25℃; for 24h; Inert atmosphere; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trimethylsilylazide; water; silver carbonate; In dimethyl sulfoxide; at 80℃; | General procedure: To a solution of substrate (5 mmol), TMSN3 (0.98 ml, 7.5 mmol) and H2O (0.18 mL, 10 mmol) inDMSO (5 mL) at 80 oC was added Ag2CO3 (138 mg, 0.5 mmol). Then the mixture was stirred until (1-2 h)the complete consumption of substrate as indicated by TLC. The resulting mixture was concentrated andtaken up by dichloromethane (3 × 30 mL). The organic layer was washed with brine (3 × 40 mL), driedover MgSO4 and concentrated. The resulting crude materials were purified by flash columnchromatography (silica gel; hexane) to afford vinyl azides. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With copper(II) sulfate; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol; at 20℃; for 14h; | General procedure: To a 50 mL ofround bottom flask 100 mg of azide 3(100 mg, 0.26 mmol) and 4-pentynoic acid (55 mg, 0.33 mmol)were dissolved in tBuOH:THF:Water/1:1:1 (6 mL).To this solution copper (II) sulfate (8 mg, 0.052 mmol) and L-ascorbic sodium salt (21 mg, 0.104 mmol) were added. Reactionwas kept at room temperature for 14h. Reactionwas monitored using TLC and LC-MS, shows the conversion by this time. Thesolvents were evaporated under reduced pressure. The resulting residue wasdissolved in chloroform (10 mL), washed with water (2 mL) and the extractedcrude product was purified using flash chromatography DCM:MeOH ( 95:5) toafford the desired product compound 5 as asolid of 0.120 g (82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In triethylamine; at 45℃; for 72h;Inert atmosphere; | Method A1: A mixture of <strong>[2005-43-8]2-bromoquinoline</strong> (577 mg, 2.77 mmol), [Pd(PPh3)2Cl2] (48.6 mg; 0.069 mmol), CuI (13.2 mg, 0.069 mmol), octa-1,7-diyne (0.18 mL, 1.39 mmol) and Et3N (30 mL) was stirred under nitrogen at room temperature for 5 days. Et3N was removed under reduced pressure, and the resulting solids were extracted with Et2O. The solvent was stripped, and the crude brown oil was subjected to chromatography (SiO2, hexane : CH2Cl2, 1 : 9 v/v) to give1,8-di(quinol-2-yl)octa-1,7-diyne as a beige solid, yield 10%. Method A2: Procedure as described for method A1 except for temperature (45 C) and reaction time (3 days), yield 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In triethylamine; at 45℃; for 72h;Inert atmosphere; | Method A1: A mixture of 9-bromophenanthrene (560 mg, 2.18 mmol), [Pd(PPh3)2Cl2] (35.5 mg, 0.051 mmol, CuI (10.5 mg, 0.060 mmol), octa-1,7-diyne (0.15 mL, 1.09 mmol) and Et3N (30 mL) was stirred under nitrogen at room temperature for 5 d. Et3N was removed under reduced pressure, and the resulting solids were extracted with Et2O. The solvent was stripped, and the crude brown oil was subjected to chromatography (SiO2, hexane : CH2Cl2, 8 : 2 v/v) to give 1,8-di(phenanthren-9-yl)octa-1,7-diyne as a beige solid, yield 3%. Method A2: Procedure as described for method A1 except for temperature (45 C) and reaction time (3 days), yield 79%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With copper(II) acetate monohydrate; In methanol; at 50℃; for 4h; | Triazole prepared from 1,7-octadiyne and 2.2 equivalents of benzyl azide:8Benzyl azide (0.15 g 1.1 mmol) and 1,7-octadiyne (0.053 g 0.5 mmol) wereadded to a 3 mL vial fitted with magnetic stirrer bar. Copper(II) acetate monohydrate(1.0 mg, 0.005 mmol - from a stock solution in methanol 0.1 mL from a10 mg/mL solution) was added and the mixture suspended in methanol (2 mL).The reaction was then heated to 50C on a stirrer hotplate with a aluminium vial holder adapter. The reactionwas stirred for 4 h and then allowed to cool to room temperature. The colourless precipitate was filtered,washed with cold methanol, (2 x 5 mL), diethyl ether (5 mL) and allowed to dry in air. Colourless crystals(0.13 g, 72%); m.p.. 156-158 C; 1H (400 MHz, CDCl3) δ = 7.35-7.34 (6 H, m), 7.26-7.22 (4 H, m), 7.17 (2 H,s), 5.47 (4 H, s), 2.72-2.68 (4 H, m), 1.72-1.69 (4 H); 13C NMR (400 MHz, CDCl3, 25C, TMS) δ = 148.7,135.2, 129.3, 128.8, 128.2, 120.9, 54.2, 29.1, 25.7; HR-MS C22H24N6Na (M+Na) calcd. 395.1960, obs.395.1959. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41%; 27% | With palladium diacetate; trimethylphosphane; In acetone; at 60℃; for 7h;Inert atmosphere; | General procedure: A mixture of 0.05 mmol Pd(OAc)2 (11.2 mg, 10 mol %) and 0.15 mL of PMe3 solution (0.15 mmol, 1.0 M PMe3 dissolved in toluene, 30 mol %) was stirred at 110 C under argon for 10 min until all palladium acetate was dissolved. Then 0.5 mL of water or 1 mL acetone was added, followed by a mixture of terminal alkyne 1 (0.5 mmol) and acrolein (2) (2.5 mmol). The reaction mixture was then stirred at 60 C in an oil bath. After full conversion of the alkyne starting material, as shown by TLC, the reaction mixture was extracted with ethyl ether (3*10 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=95:5 or 50:50) to give the pure product 3Tetradeca-4,10-diynedial (3m) Colorless liquid; 1H NMR (500 MHz, CDCl3) δ 9.78 (t, J=1.4 Hz, 2H), 2.66-2.55 (m, 4H), 2.52-2.41 (m, 4H), 2.20-2.04 (m, 4H), 1.61-1.43 (m, 4H); 13C NMR (125 MHz, CDCl3) δ 201.2, 81.2, 78.3, 43.1, 28.1, 18.3, 12.3; HRMS (ESI) calcd for C14H18O2Na (M++Na): 241.1199; Found: 241.1197. Undeca-4,10-diynal (3m') Colorless liquid; 1H NMR (500 MHz, CDCl3) δ 9.79 (s, 1H), 2.61 (t, J=7.9 Hz, 2H), 2.47 (tt, J=7.0, 2.4 Hz, 2H), 2.25-2.12 (m, 4H), 1.94 (t, J=2.7 Hz, 1H), 1.70-1.51 (m, 4H); 13C NMR (125 MHz, CDCl3) δ 201.1, 84.3, 81.0, 78.4, 68.6, 43.1, 27.9, 27.6, 18.3, 18.1, 12.3; HRMS (ESI) calcd for C11H14ONa (M++Na): 185.0937; Found: 185.0937. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 70℃; | General procedure: 1,6-Heptadiyne (122 μl, 98 mg, 1.06 mmol, 1.0 equiv) was added to a mixture of azidomonosaccharide 5 (670 mg, 2.35 mmol, 2.2 equiv),CuI (89 mg, 0.47 mmol, 0.2 equiv), and DIPEA (164 μl,121 mg, 0.94 mmol, 0.4 equiv) in THF (8 ml). The resulting reaction mixture was stirred in a resealable pressure tube at 70C for 1-4 h (TLC control). The solvent was evaporated under reduced pressure, the residue was dissolved in CH2Cl2 (10 ml), washed with EDTA solution (5×2 ml), brine (2×4 ml), dried over Na2SO4, and evaporated under reduced pressure. The solid residue was dissolved in THF (5 ml) and a solution of Na2S (25 mg) in water (1 ml) was added. The resulting suspension was filtered through silica gel pad which was suspended in THF. The filtrate was evaporated under reduced pressure and the resulting solid was chromatographically purified by flash chromatography (eluent CH2Cl2-MeOH, 93:7), followed by recrystallization from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 70℃; | General procedure: 1,6-Heptadiyne (122 μl, 98 mg, 1.06 mmol, 1.0 equiv) was added to a mixture of azidomonosaccharide 5 (670 mg, 2.35 mmol, 2.2 equiv),CuI (89 mg, 0.47 mmol, 0.2 equiv), and DIPEA (164 μl,121 mg, 0.94 mmol, 0.4 equiv) in THF (8 ml). The resulting reaction mixture was stirred in a resealable pressure tube at 70C for 1-4 h (TLC control). The solvent was evaporated under reduced pressure, the residue was dissolved in CH2Cl2 (10 ml), washed with EDTA solution (5×2 ml), brine (2×4 ml), dried over Na2SO4, and evaporated under reduced pressure. The solid residue was dissolved in THF (5 ml) and a solution of Na2S (25 mg) in water (1 ml) was added. The resulting suspension was filtered through silica gel pad which was suspended in THF. The filtrate was evaporated under reduced pressure and the resulting solid was chromatographically purified by flash chromatography (eluent CH2Cl2-MeOH, 93:7), followed by recrystallization from EtOH. |
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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.
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