Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 3589-41-1 | MDL No. : | MFCD00033175 |
Formula : | C10H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DVUXKEFDAGQPQU-UHFFFAOYSA-N |
M.W : | 190.20 | Pubchem ID : | 244143 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 50.05 |
TPSA : | 62.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.42 cm/s |
Log Po/w (iLOGP) : | 1.83 |
Log Po/w (XLOGP3) : | 1.47 |
Log Po/w (WLOGP) : | 1.28 |
Log Po/w (MLOGP) : | 0.87 |
Log Po/w (SILICOS-IT) : | 1.14 |
Consensus Log Po/w : | 1.32 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 2.22 mg/ml ; 0.0117 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.38 |
Solubility : | 0.791 mg/ml ; 0.00416 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.04 |
Solubility : | 0.175 mg/ml ; 0.00092 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.07 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302+H312+H332 | Packing Group: | N/A |
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 |
---|---|---|
54% | at -10 - 20℃; for 3.5 h; | (a) 2-benzyloxy-carbonyl-amino-acetimido-ethylester 47.6 g (250 mmol) 2-benzyloxy-carbonyl-amino-acetonitrile in 450 ml of ethanol are combined with 150 ml 5m ethanolic hydrochloric acid at -8° C. with cooling, while keeping the temperature below -5° C. The mixture is stirred for 1.5 h at -10° C. and for 2 h at ambient temperature. After evaporation i. vac. the residue is triturated with diethyl ether, filtered off and dried i. vac. Yield: 36.60 g (134.2 mmol, 54percent) C12H16N2O3*HCl (236.29/272.73) Mass spectrum: (M+H)+=237 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With Dowex 1X8 SH(1-); hydrogen sulfide In methanol at 20℃; for 3h; | |
87% | With sodium sulfide; hydrogen sulfide; Aliquat 336 In water; benzene at 70℃; for 6h; | |
85% | With hydrogen sulfide; triethylamine In chloroform for 20h; Ambient temperature; |
84% | With hydrogen sulfide; triethylamine In pyridine | |
With hydrogen sulfide; ammonia anschliessendes Erhitzen auf 100grad; | ||
Multi-step reaction with 2 steps 1: 81 percent / HCl / diethyl ether / 1.) -5 deg C, 25 min, 2.) 20 deg C, 1 h 2: 1.) 4M K2CO3, 2.) H2S / 1.) Et2O, 0.5 h, 2.) Et2O, 0 deg C, 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.3% | With sodium hydrogencarbonate In 1,4-dioxane; water; toluene at 0 - 20℃; for 16h; | 62a To a vigorously stirred solution of aminoacetonitrile (20g; 0.216 mole), NaHCO3 (50g ; 0.595 mole) in water (450 ml) and dioxane (250 ml), 50% benzyl chloroformate in toluene (67.88 ml; 0.475 mole) was added at 0°C. After stirring at room temperature for 16h, the reaction mixture was extracted with EtOAc. The EtOAc layer was washed with water and dried over anhydrous Na2S04. Solvent was removed and the dark brown oil was purified by flash chromatography over silica gel with 30-50% EtOAc-PE 60-80°C. Yield, 33g (80. 3%); mp, 42- 43°C ; MS (EI) : 190 (M+), 145,130, 117,108, 91; analysis: CloHloN2o2 requires C, 63.15 ; H, 5. 30 ; N, 14.73 ; found: C, 62.95 ; H, 5.05 ; N, 14. 50%. |
80.3% | With sodium hydrogencarbonate In 1,4-dioxane; water; toluene at 0 - 20℃; | 62.a Example 62a Cyanomethyl-carbamic acid benzyl ester To a vigorously stirred solution of aminoacetonitrile (20 g; 0.216 mole), NaHCO3 (50 g; 0.595 mole) in water (450 ml) and dioxane (250 ml), 50% benzyl chloroformate in toluene (67.88 ml; 0.475 mole) was added at 0° C. After stirring at room temperature for 16 h, the reaction mixture was extracted with EtOAc. The EtOAc layer was washed with water and dried over anhydrous Na2SO4. Solvent was removed and the dark brown oil was purified by flash chromatography over silica gel with 30-50% EtOAc-PE 60-80° C. Yield, 33 g (80.3%); mp, 42-43° C.; MS (EI): 190 (M+), 145, 130, 117, 108, 91; analysis: C10H10N2O2 requires C, 63.15; H, 5.30; N, 14.73; found: C, 62.95; H, 5.05; N, 14.50%. |
With sodium hydroxide; ethyl acetate unter Kuehlung; |
With potassium hydroxide; ethyl acetate unter Kuehlung; | ||
With potassium hydroxide; diethyl ether unter Kuehlung; | ||
With sodium hydroxide; diethyl ether unter Kuehlung; | ||
With sodium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia In ethanol | ||
Multi-step reaction with 2 steps 1: ethanol; diethyl ether; HBr 2: ethanolic NH3 | ||
Multi-step reaction with 2 steps 1: HCl; diethyl ether 2: ethanolic NH3 |
With N-Acetylcysteine; ammonium acetate In methanol at 50℃; for 48h; | 2 Example 2: 5-methyl-2- (N-benzyloxycarbonylamino) pyrimidine (4b) .5.01 g N- (benzyloxycarbonyl) -2-aminoacetonitrile (26.3 mmol) and 0.49 g of N-acetylcystein (3 mmol) are dissolved in 30 mL methanol. 2.39 g ammonium acetate (31 mmol) are added and left under agitation 48 h at 500C. The methanol is evaporated under reduced pressure and the residue collected in a water/dichloromethane mixture, decanted and the aqueous phase is evaporated under reduced pressure. The white solid obtained is vacuum dried (5.45g of benzyloxycarbonyl- aminomethylamidine) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium hydrogencarbonate In 1,4-dioxane; water at 0℃; | |
50% | With sodium hydroxide; sodium hydrogencarbonate In water for 3h; | |
(i) aq. Na2CO3, (ii) /BRN= 509751/; Multistep reaction; |
With sodium hydroxide | ||
With sodium hydroxide In water | ||
With triethylamine In dichloromethane at 60℃; Sealed tube; | General Method B. General procedure: A 2-acylamidoacetonitrile was prepared similarly at room temperature, using an acid chloride as a starting compound. To a solution of the compound thus obtained (3 mmol) in dry methanol (50 mL) at room temperature under N2 atmosphere was added L-cysteine methyl ester hydrochloride (770 mg, 4.5 mmol) and triethylamine (0.63 mL, 4.5 mmol). The resulting mixture was stirred for 3 h and evaporated to dryness. The residue was taken up in CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic extract was dried over sodium sulfate, filtered, evaporated, and purified by column chromatography (silica gel, hexane/ethyl acetate, 5:1) to give a methyl ester of compounds 14 - 17. Precooled LiOH (0.9 mL, 1 N, 0.9 mmol) was added to the methyl ester (1.0 mmol) in methanol (5 mL) at 0 oC. The suspension was stirred for 1 h at room temperature, diluted with acetone (20 mL) to precipitate the product. The white powder was filtered and dried to give compounds 14 - 17. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether at 4℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In tetrahydrofuran at 4℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogenchloride In diethyl ether at -5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With hydrogenchloride; at -10 - 20℃; for 3.5h; | (a) 2-benzyloxy-carbonyl-amino-acetimido-ethylester 47.6 g (250 mmol) 2-benzyloxy-carbonyl-amino-acetonitrile in 450 ml of ethanol are combined with 150 ml 5m ethanolic hydrochloric acid at -8 C. with cooling, while keeping the temperature below -5 C. The mixture is stirred for 1.5 h at -10 C. and for 2 h at ambient temperature. After evaporation i. vac. the residue is triturated with diethyl ether, filtered off and dried i. vac. Yield: 36.60 g (134.2 mmol, 54%) C12H16N2O3*HCl (236.29/272.73) Mass spectrum: (M+H)+=237 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium cyanide; tetra(n-butyl)ammonium hydroxide In tetrahydrofuran at 20℃; for 336h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In tetrahydrofuran; water; at 5 - 20℃; for 15h;Inert atmosphere; | To a solution of aminoacetonitrile hydrochloride (25.27 g) and K2C03 (109.80 g) in THF/H20 (200 mL/400 mL) at 5-10C was added benzyl chloroformate (45.22 g) under an atmosphere of nitrogen. The mixture was stirred at room temperature for 15 h and then quenched with NH4C1(aq) (100 mL, 2 M). The resulting mixture was extracted with ethyl acetate (3x200 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to get the crude product S-VI-II (46.88 g, y: 90%). | |
1.7 g | With sodium hydrogencarbonate; In 1,4-dioxane; water; toluene; at 0 - 20℃; for 12h; | A mixture of <strong>[6011-14-9]2-aminoacetonitrile hydrochloride</strong> (5 g, 54.0 mmol), NaHC03(18.16 g, 216 mmol) and dioxane (50 mL) in H20 (100 mL) was stirred at 0C. Then a solution of benzyl carbonochloridate (1 1.06 g, 64.8 mmol, 9.22 mL) in toluene (10 mL) was added at 0C and stirred at 20C for 12 hours. The mixture was poured into water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mLchi3).The combined organic phases were washed with brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give benzyl(cyanomethyl)carbamate (1 .70 g).1H NMR (chloroform-c/400 MHz): 7.40-7.31 (m, 5H), 5.35- 5.13 (m, 3H), 4.16-4.12 (m, 2H). |
1.7 g | With sodium hydrogencarbonate; In 1,4-dioxane; water; toluene; at 0 - 20℃; for 12h; | A mixture of <strong>[6011-14-9]2-aminoacetonitrile hydrochloride</strong> (5 g, 54.0 mmol), NaHCC>3 (18.16 g, 216 mmol) and dioxane (50 mL) in H2O (100 mL) was stirred at 0C. Then a solution of benzyl carbonochloridate (11.06 g, 64.8 mmol, 9.22 mL) in toluene (10 mL) was added at 0C and stirred at 20C for 12 hours. The mixture was poured into water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mL c 3).The combined organic phases were washed with brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give benzyl (cyanomethyl)carbamate (1.70 g). 1H NMR (chloroform-d 400 MHz): 7.40-7.31 (m, 5H), 5.35-5.13 (m, 3H), 4.16-4.12 (m, 2H). |
1.7 g | mixture of 214 <strong>[6011-14-9]2-aminoacetonitrile hydrochloride</strong> (5 g, 54.0 mmol), 37 NaHCO3 (18.16 g, 216 mmol) and 136 dioxane (50 mL) in 99 H2O (100 mL) was stirred at 0 C. Then a solution of 215 benzyl carbonochloridate (11.06 g, 64.8 mmol, 9.22 mL) in 119 toluene (10 mL) was added at 0 C. and stirred at 20 C. for 12 hours. The mixture was poured into water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mL×3). The combined organic phases were washed with brine (100 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give 216 benzyl (cyanomethyl)carbamate (1.70 g). 1H NMR (chloroform-d 400 MHz): 7.40-7.31 (m, 5H), 5.35-5.13 (m, 3H), 4.16-4.12 (m, 2H). | |
1.7 g | With sodium hydrogencarbonate; In 1,4-dioxane; water; toluene; at 0 - 20℃; for 12h; | A mixture of <strong>[6011-14-9]2-aminoacetonitrile hydrochloride</strong> (5 g, 54.0 mmol), NaHCC>3 (18.16 g, 216 mmol) and dioxane (50 mL) in H2O (100 mL) was stirred at 0C. Then a solution of benzyl carbonochloridate (11.06 g, 64.8 mmol, 9.22 mL) in toluene (10 mL) was added at 0C and stirred at 20C for 12 hours. The mixture was poured into water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mL c 3).The combined organic phases were washed with brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give benzyl (cyanomethyl)carbamate (1.70 g). 1H NMR (chloroform-d 400 MHz): 7.40-7.31 (m, 5H), 5.35-5.13 (m, 3H), 4.16-4.12 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride In diethyl ether at -5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With hydrogenchloride In diethyl ether 1.) -5 deg C, 25 min, 2.) 20 deg C, 1 h; | |
With hydrogenchloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In tetrahydrofuran at 4℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With ammonia; sodium methylate In methanol at 180℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; trifluoroacetic anhydride; In tetrahydrofuran; at 0℃; for 3h; | General procedure: To a solution of Nalpha-protected amino acid (10 mmol) in THF (10 mL), NMM(11 mmol) and ethyl chloroformate (11 mmol) were added at -15 C followed by stirring for 20 min NH3 solution (0.4 mL) was added and stirring was continued for another 4 h. After completion of the reaction (TLC), the solvent was removed in vacuo andthe residue was dissolved in EtOAc (30 mL), washed twice with 10% HCl (10 mL)(in case of Fmoc, Z-amino acids), or 10% citric acid (10 mL) (in case of Boc-amino acids), brine solution (10 mL) and dried over anhydrous Na2SO4. After evaporation of the solvent, the crude product was purified by recryastallization from EtOAc:hexane (3:8). The solution of amino acid amide (10mmol) in dry THF (10 mL) was treated with pyridine (20 mmol) and TFAA (12 mmol)and the reaction mixture was stirred at 0 C for 3 h. After completion of the reaction (TLC), the solvent was evaporated and residue wasdissolved in EtOAc (30 mL), washed twice with 10% HCl (10 mL) (in case of Fmoc,Z-amino acids), or 10% citric acid (10 mL) (in case of Boc-amino acids), saturatedNaHCO3 (10 mL), brine solution (10 mL) and dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography (hexane:EtOAc 9:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether at -20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In diethyl ether at -20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium azide; zinc dibromide In water; isopropyl alcohol for 16h; Heating; | |
95% | With sodium azide; zinc dibromide In Isopropyl acetate; water at 75℃; for 15h; Inert atmosphere; | A solution of S-VI-II (37.10 g), sodium azide (31.73 g), and zinc bromide (30.75 g) in IPA/H20 (300 mL/600 mL) under an atmosphere of nitrogen was stirred at 75 °C for 15 h. To the mixture at room temperature was added HC1(aq) (4 M) slowly until all solid has dissolved. The resulting mixture was extracted with ethyl acetate (3x200 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to get the crude product S-XI-I (43.22 g, y: 95%). |
61% | With sodium azide; zinc dibromide In water; isopropyl alcohol at 25℃; for 15h; | 5.22.22 A mixture of benzyl cyanomethylcarbamate (FFA, 2.0Og, 10.5mmol, Sigma-Aldrich), sodium azide (1.37g, 21.0mmol), zinc bromide (1.18g, 5.26mmol, Sigma-Aldrich), 2-propanol (15mL), and water (3OmL) at a temperature of about 25°C was stirred for 15h. To the reaction mixture was added 2N aqueous HCl (7mL). The mixture was partitioned between EtOAc and water, the organic portion was separated, washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to provide 1.51 g of the compound of formula FFB as a white solid (yield 61%).The identity of the compound of formula FFB. benzyl (2H-tetrazol- 5-yl)methylcarbamate, was confirmed using LC/MS.Compound FFB: LC/MS: m/z=234 [M+H]+ (CaIc: 233). |
6 g | With sodium azide; zinc dibromide In water; isopropyl alcohol at 100℃; for 12h; | Intermediate: benzyl ((2H-tetrazol-5-yl)methyl)carbamate Intermediate: benzyl ((2H-tetrazol-5-yl)methyl)carbamate A mixture of benzyl (cyanomethyl)carbamate (5.0 g, 26 mmol), NaN3 (3.4 g, 53 mmol), ZnBr2 (3.3 g, 15 mmol) and isopropyl alcohol (30 mL) in water (60 mL) was stirred at 100° C. for 12 hours. The mixture was poured into water (250 mL), and aqueous KHSO4 was added until pH=2. The aqueous phase was extracted with ethyl acetate (100 mL*3). The combined organic phase were washed with brine (80 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuum to afford benzyl ((2H-tetrazol-5-yl)methyl)carbamate (6.0 g). |
200 mg | With sodium azide; zinc dibromide In water; isopropyl alcohol at 100℃; for 24h; | Preparation of benzyl ((2/- -tetrazol-5-yl)methyl)carbamate. A mixture of benzyl (cyanomethyl)carbamate (200 mg, 1 .05 mmol), sodium azide (250 mg, 3.85 mmol) zinc dibromide (1 18 mg, 525 μηιοΙ) and isopropyl alcohol (2 mL) in H20 (4 mL) was stirred at 100°C for 24 hours. The mixture was poured into water (50 mL), and added KHSO4 (aq.) until pH=2. The aqueous phase was extracted with ethyl acetate (20 mLχ3). The combined organic phases were washed with brine (10 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=10/1 to 3/1 ) to give benzyl ((2H-tetrazol-5- yl)methyl)carbamate (200 mg). |
200 mg | With sodium azide; zinc dibromide In water; isopropyl alcohol at 100℃; for 24h; | Preparation of benzyl ((2/-/-tetrazol-5-yl)methyl)carbamate A mixture of benzyl (cyanomethyl)carbamate (200 mg 1.05 mmol) sodir- azide (250 mg, 3.85 mmol) zinc dibromide (118 mg, 525 pmol) and isopropyl alcohol (2 mL) in H2O (4 mL) was stirred at 100°C for 24 hours. The mixture was poured into water (50 mL), and added KHS04 (aq.) until pH=2. The aqueous phase was extracted with ethyl acetate (20 mL c 3). The combined organic phases were washed with brine (10 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=10/l to 3/1) to give benzyl ((2/-/-tetrazol-5-yl)methyl)carbamate (200 mg). |
200 mg | With sodium azide; zinc dibromide In water; isopropyl alcohol at 100℃; for 24h; | |
200 mg | With sodium azide; zinc dibromide In water; isopropyl alcohol at 100℃; for 24h; | Preparation of benzyl ((2H-tetrazol-5-yl)methyl)carbamate A mixture of 216 benzyl (cyanomethyl)carbamate (200 mg, 1.05 mmol), 218 sodium azide (250 mg, 3.85 mmol) 219 zinc dibromide (118 mg, 525 umol) and isopropyl alcohol (2 mL) in 99 H2O (4 mL) was stirred at 100° C. for 24 hours. The mixture was poured into water (50 mL), and added 220 KHSO4 (aq.) until pH=2. The aqueous phase was extracted with ethyl acetate (20 mL×3). The combined organic phases were washed with brine (10 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=10/1 to 3/1) to give 221 benzyl ((2H-tetrazol-5-yl)methyl)carbamate (200 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine In methanol at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | Stage #1: phenylmethyl cyanomethylcarbamate With sodium methylate In methanol at 20℃; Stage #2: With ammonium bromide at 20℃; for 1h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | Stage #1: phenylmethyl cyanomethylcarbamate With sodium methylate In methanol at 20℃; Stage #2: With ammonium chloride In methanol at 20℃; for 48h; Further stages.; | |
97% | Stage #1: phenylmethyl cyanomethylcarbamate With sodium methylate In methanol at 20℃; Stage #2: With ammonium chloride In methanol at 20℃; for 48h; Stage #3: With hydrogenchloride In methanol; ethyl acetate for 2h; Further stages.; | |
91% | Stage #1: phenylmethyl cyanomethylcarbamate With sodium methylate In methanol at 25℃; for 8h; Stage #2: With ammonium chloride at 25℃; for 72h; |
Multi-step reaction with 2 steps 1: sodium methylate / 24 h / 20 °C 2: sodium methylate; ammonium chloride / methanol / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NH2OH / methanol / 60 °C 2: CHCl3 / 3 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NH2OH / methanol / 60 °C 2: CHCl3 / 3 h / 60 °C 3: xylene / Heating | ||
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; potassium hydroxide / methanol / 60 °C 2: chloroform / 60 °C 3: o-xylene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: NH2OH / methanol / 60 °C 2: CHCl3 / 3 h / 60 °C 3: xylene / Heating 4: methanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: di-tert-butyl dicarbonate; NH4HCO3; pyridine / dioxane / 20 h / 20 °C 2: Et3N; trifluoroacetic anhydride / CH2Cl2 / 3.5 h / 20 °C | ||
Multi-step reaction with 2 steps 1: pyridine; di-tert-butyl dicarbonate; NH4HCO3 / dioxane / 20 h / 20 °C 2: Et3N; trifluoroacetic anhydride / CH2Cl2 / 3.5 h / 20 °C | ||
Multi-step reaction with 3 steps 1: 4-methyl-morpholine / tetrahydrofuran / 0.33 h / -15 °C 2: ammonia / water / 4 h 3: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 88 percent / HCl / 0 - 20 °C 2: 18 percent / NaOH / H2O; methanol / 1 h / 20 °C / pH 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl / diethyl ether / -20 °C 2: 70 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: HCl / diethyl ether / -20 °C 2: 62 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling 3: 80 percent / Et3N; aq. H2NOH*HCl / diethyl ether / 18 h / 20 °C 4: 71 percent / H2 / 10 percent Pd/C / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl / diethyl ether / -20 °C 2: 60 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl / diethyl ether / -20 °C 2: 60 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling 3: 55 percent / Et3N; aq. H2NOH*HCl / diethyl ether / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl / diethyl ether / -20 °C 2: 70 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling 3: 66 percent / Et3N; aq. H2NOH*HCl / diethyl ether / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl / diethyl ether / -20 °C 2: 62 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl / diethyl ether / -20 °C 2: 62 percent / pyridine; H2S / tetrahydrofuran / 1 h / cooling 3: 80 percent / Et3N; aq. H2NOH*HCl / diethyl ether / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 20 percent / sodium methoxide, ammonia / methanol / 6 h / 180 °C 2: 40 percent / isoamyl nitrite / acetic acid; H2O / 72 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl / CH2Cl2 2: H2S / pyridine / 0.33 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / gaseous H2S, Na2S*10H2O, tricaprylmethylammonium chloride / H2O; benzene / 6 h / 70 °C 2: 93 percent / CH2Cl2 / 2.5 h / Ambient temperature 3: 99 percent / gas. H2S, pyridine / tetrahydrofuran / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / gaseous HCl / diethyl ether / -5 °C 2: 94 percent / gaseous H2S, pyridine / tetrahydrofuran / 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 92 percent / gaseous HCl / diethyl ether / -5 °C 2: 97 percent / gaseous H2S, pyridine / tetrahydrofuran / 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / gaseous H2S, Na2S*10H2O, tricaprylmethylammonium chloride / H2O; benzene / 6 h / 70 °C 2: 93 percent / CH2Cl2 / 2.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / triethylamine, H2S / CHCl3 / 20 h / Ambient temperature 2: 76 percent / molecular sieve / ethanol / 5 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 22 h, 2.) benzene, reflux, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 22 h, 2.) benzene, reflux, 3 h 3: 77 percent / NH2NH2*H2O, AcOH / ethanol / 2 h / Heating 4: 81.7 percent / dimethylformamide / Ambient temperature 5: 78 percent / AcOH / 2.5 h / Heating | ||
Multi-step reaction with 3 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 14 h, 2.) C6H6, reflux, 4 h 3: 78 percent / AcOH / 2.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 22 h, 2.) benzene, reflux, 3 h 3: 77 percent / NH2NH2*H2O, AcOH / ethanol / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 22 h, 2.) benzene, reflux, 3 h 3: 77 percent / NH2NH2*H2O, AcOH / ethanol / 2 h / Heating 4: HMPA / acetonitrile / 4 h / 0 °C 5: 25 percent / AcOH / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 22 h, 2.) benzene, reflux, 3 h 3: 77 percent / NH2NH2*H2O, AcOH / ethanol / 2 h / Heating 4: 81.7 percent / dimethylformamide / Ambient temperature | ||
Multi-step reaction with 2 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 14 h, 2.) C6H6, reflux, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: HCl gas / diethyl ether / 0 °C 2: 2.) AcOH / 1.) EtOH, Rt, 22 h, 2.) benzene, reflux, 3 h 3: 77 percent / NH2NH2*H2O, AcOH / ethanol / 2 h / Heating 4: HMPA / acetonitrile / 4 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / hydrogen chloride / diethyl ether / 2 h / 0 °C 2: 67 percent / acetonitrile / 72 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl (g) / diethyl ether / 2 h / 4 °C 2: 92 percent / H2S, pyridine / methanol / 0.25 h / 0 - 20 °C 3: 76 percent / Na2CO3 / tetrahydrofuran; H2O / 24 h / Ambient temperature; pH 9-9.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl (g) / diethyl ether / 2 h / 4 °C 2: 92 percent / H2S, pyridine / methanol / 0.25 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl (g) / tetrahydrofuran / 2 h / 4 °C 2: 90 percent / H2S, pyridine / phenylmethanol / 0.25 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HCl (g) / tetrahydrofuran / 2 h / 4 °C 2: 47 percent / H2S, pyridine / tetrahydrofuran / 0.25 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl (g) / diethyl ether / 2 h / 4 °C 2: 92 percent / H2S, pyridine / methanol / 0.25 h / 0 - 20 °C 3: 73 percent / Na2CO3 / tetrahydrofuran; H2O / 24 h / Ambient temperature; pH 9-9.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: HCl (g) / diethyl ether / 2 h / 4 °C 2: 92 percent / H2S, pyridine / methanol / 0.25 h / 0 - 20 °C 3: 82 percent / Na2CO3 / tetrahydrofuran; H2O / 20 h / Ambient temperature; pH 9-9.2 | ||
Multi-step reaction with 3 steps 1: HCl (g) / tetrahydrofuran / 2 h / 4 °C 2: 47 percent / H2S, pyridine / tetrahydrofuran / 0.25 h / 0 - 20 °C 3: 72 percent / Na2CO3 / tetrahydrofuran; H2O / 8 h / Ambient temperature; pH 9-9.2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) sodium hydride / 1) THF, 0 deg C, 2) 18 h 2: 63 percent / hydrogen sulfide, triethylamine / pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) sodium hydride / 1) THF, 0 deg C, 2) 18 h 2: 70 percent / hydrogen sulfide, triethylamine / pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84 percent / hydrogen sulfide, triethylamine / pyridine 2: 2) triethylamine / 1) overnight, room temp., 2) 1h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) sodium hydride / 1) THF, 0 deg C, 2) 18 h 2: 63 percent / hydrogen sulfide, triethylamine / pyridine 3: 2) triethylamine / 1) overnight, room temp., 2) 1h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) sodium hydride / 1) THF, 0 deg C, 2) 18 h 2: 70 percent / hydrogen sulfide, triethylamine / pyridine 3: 2) triethylamine / 1) overnight, room temp., 2) 1h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 84 percent / hydrogen sulfide, triethylamine / pyridine 2: dimethylformamide; ethanol / 24 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; zinc(II) chloride In diethyl ether at 0℃; for 17h; | 62b Dry HCl gas was passed through a suspension of 5-methoxy-benzene-1, 3-diol (llg ; 78.49 mmol), 62a (16.42g ; 86.36 mmol) and fused ZnCl2 (1.96g) in dry ether (40 ml), for lh at 0°C. The reaction mixture was kept at 0°C overnight (-16h). The ether was decanted and the yellow residue was hydrolyzed with water as reported in literature (J. S. H. Davies, JCS, 1950,3206-13). The title compound obtained was purified using flash chromatography (silica gel, 5% CH3CN-CHC13.) Yield, lOg (28%); mp, 147-48°C ; MS (EI) : 331 (M), 167 (100%); analysis: C17Hl7NO6 requires: C, 61.63 ; H, 5.17 ; N, 4.23 ; found: C, 61.20 ; H, 4.85 ; N, 4.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In chloroform; water | 28 2-[(2,3-Dichlorothiophene)-5-sulfonyl]-1,2,3,5,6,7-hexahydro-N,N-dipropylcyclopent[f]isoindol-6-amine. 46 EXAMPLE 28 2-[(2,3-Dichlorothiophene)-5-sulfonyl]-1,2,3,5,6,7-hexahydro-N,N-dipropylcyclopent[f]isoindol-6-amine. 46 Using procedure 9, 1,2,3,5,6,7-hexahydro-N,N-dipropylcyclopent[f]isoindol-6-amine (38) was treated with 2,3-dichlorothiophene-5-sulfonyl chloride. Crystallization from methanol gave 46 as tan crystals (m.p. 150-151° C.). Procedure 30: t-Butyl [6,7-dihydro-3-[[benzyloxycarbonyl]aminomethyl]-5H-cyclopenta[c]pyridin-6-yl]carbamate. 55 A solution of benzyl chloroformate (17.1 g, 0.100 mol) in chloroform (50 ml) was added dropwise at room temperature over a period of 10 minutes to a mixture of aminoacetonitrile hydrochloride (13.89 g, 0.150 mol) and sodium carbonate (21.2 g, 0.200 mol) in water (50 ml) and chloroform (20 ml) in a flask equipped with a mechanical stirrer. The mixture was stirred for 2 hours, diluted with water, and extracted twice with diethylether. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an oil. Crystallization from ethyl acetate/hexane gave N-benzyloxycarbonyl-2-aminoacetonitrile as colorless crystals (m.p. 61-62). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triethylamine In ethyl acetate; N,N-dimethyl-formamide | 1 Synthesis of N-{D,L-2-(hydroxyaminocarbonyl)methyl-4-methylpentanoyl}-L-3-(2'-naphthyl)alanyl-L-alanine, 2-aminoethyl Amide (Compound 1) STR5 To a solution of 24.9 g (0.10 mol) of benzyl succinimidylcarbonate and 10.2 g (0.11 mol) of aminoacetonitrile hydrochloride dissolved in anhydrous N,N-dimethylformamide (100 ml) was added 15.4 ml (0.11 mol) of triethylamine over a period of 30 minutes at room temperature. The mixture was stirred at room temperature for 12 hours. Removal of the N,N-dimethylformamide in vacuo produced a residue which was dissolved in 350 ml of ethyl acetate. The solution was washed with water (350 ml), 2M HCl (3*50 ml) and brine (50 ml). After drying over anhydrous magnesium sulfate, the solution was filtered and concentrated in vacuo to give 17.3 g (91% yield) of N-CBZ-aminoacetonitrile (1e) as an amber solid. TLC: Rf 0.65 (ethyl acetate-hexane 1:1); 1 H NMR (CDCl3) δ 4.05(d, 2H), 5.13(s, 2H), 5.46(bt, 1H), 7.35(bs, 5H); 13 C NMR (CDCl3) δ 29.5, 67.9, 116.2, 128.3, 128.5, 128.7, 135.5, 155.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: phenylmethyl cyanomethylcarbamate With tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane In tetrahydrofuran; toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: 6-(tetrahydro-2H-pyran-2-yloxy)hex-2-ynyl methanesulfonate In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: phenylmethyl cyanomethylcarbamate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4-[(tert-butyldimethylsilyl)oxy]but-2-yn-1-yl 4-methylbenzene-1-sulfonate In N,N-dimethyl-formamide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: phenylmethyl cyanomethylcarbamate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 5-tetrahydropyran-2-yloxypent-2-ynyl 4-methylbenzenesulfonate In N,N-dimethyl-formamide at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine In dichloromethane at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With hydrogenchloride; zinc(II) chloride In diethyl ether at 0℃; for 17h; | 62.b Example 62b (2-{2,4-Dihydroxy-6-methoxy-phenyl}-2-oxo-ethyl)-carbamic acid benzyl ester Dry HCl gas was passed through a suspension of 5-methoxy-benzene-1,3-diol (11 g; 78.49 mmol), 62a (16.42 g; 86.36 mmol) and fused ZnCl2 (1.96 g) in dry ether (40 ml), for 1 h at 0° C. The reaction mixture was kept at 0° C. overnight (~16 h). The ether was decanted and the yellow residue was hydrolyzed with water as reported in literature (J. S. H. Davies, JCS, 1950, 3206-13). The title compound obtained was purified using flash chromatography (silica gel, 5% CH3CN-CHCl3.) Yield, 10 g (28%); mp, 147-48° C.; MS (EI): 331 (M+), 167 (100%); analysis: C17H17NO6 requires: C, 61.63; H, 5.17; N, 4.23; found: C, 61.20; H, 4.85; N, 4.0%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydride In N,N-dimethyl-formamide at -60 - 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With silver carbonate In nitromethane at 20℃; for 144h; Darkness; | 3.5. N-[(1R)-2,3,4,6-Tetra-O-acetyl-1,5-anhydro-d-galactitol-spiro[1.4]-2-benzyloxycarbonylaminomethyl-2-oxazolin-5-ylidene]glycine methylester (22) Compound 19 (0.17 g, 0.33 mmol) was dissolved in dry CH3NO2 (3 mL), NCCH2NHCOOCH2Ph (10 equiv) and Ag2CO3 (1.1 equiv) were added. The mixture was stirred in the dark at rt for 6 d. After completion of the reaction (TLC, 3:1 EtOAc-hexane) the mixture was filtered on a Celite pad and the solvent was removed. The crude oil was purified by column chromatography (3:1 EtOAc-hexane) to give 0.04 g (29%) of 22 (1:1 mixture of two isomers) as a colourless oil. Rf = 0.29 (EtOAc); 1H NMR (CDCl3, 360 MHz): δ (ppm): 7.44-7.32 (m, 5H, Ph), 7.01 (s, 1H, NH), 5.71 (d, 1H, J2,310.6 Hz, H-2), 5.58-5.52 (m, 2H, H-4, H-4'), 5.48-5.30 (m, 3H, H-2', H-3, H-3'), 5.20-5.14 (m, 2H, CH2), 4.60-4.62 (m, 2H, H-5, H-5'), 4.32-4.04 (m, 10H, H-6a, H-6a', H-6b, H-6b', CH2a, CH2b, CH2Ph), 3.79 (s, 3H, OCH3), 2.19, 2.17, 2.13, 2.11, 2.03, 2.01, 1.99, 1.97 (8s, 24H, OCOCH3); 13C NMR (CDCl3, 125 MHz): δ (ppm): 170.5, 170.3, 170.1 (2), 169.9, 169.4, 168.8 (2) (CO), 168.2 (CO2CH3), 165.1 (CN), 157.1, 157.0 (CO2CH2Ph), 135.9-128.2 (aromatics), 95.3 (C-1), 94.1 (C-1'), 73.6, 71.0, 69.8, 69.5, 68.3, 67.9, 67.5, 66.6 (C-2-C-5 and C-2'-C-5'), 71.0 (CH2), 60.7 (C-6), 60.4 (C-6'), 52.6 (OCH3), 52.2 (OCH3'), 41.2 (2) (CH2, CH2'), 20.9 (6), 20.5 (CH3) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Stage #1: N-(3,4,5,7-tetra-O-acetyl-2-bromo-2-deoxy-α-D-galacto-hept-2-ulopyranosonoyl)glycine methyl ester; phenylmethyl cyanomethylcarbamate With silver trifluoromethanesulfonate In nitromethane at 20℃; Darkness; Stage #2: In dichloromethane; water at 20℃; Acidic conditions; | |
Multi-step reaction with 2 steps 1: silver carbonate / nitromethane / 144 h / 20 °C / Darkness 2: dichloromethane; water / 20 °C / Acidic conditions |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In methanol at 20℃; for 3h; Inert atmosphere; | General Method B. General procedure: A 2-acylamidoacetonitrile was prepared similarly at room temperature, using an acid chloride as a starting compound. To a solution of the compound thus obtained (3 mmol) in dry methanol (50 mL) at room temperature under N2 atmosphere was added L-cysteine methyl ester hydrochloride (770 mg, 4.5 mmol) and triethylamine (0.63 mL, 4.5 mmol). The resulting mixture was stirred for 3 h and evaporated to dryness. The residue was taken up in CH2Cl2 and washed with saturated NaHCO3 solution and brine. The organic extract was dried over sodium sulfate, filtered, evaporated, and purified by column chromatography (silica gel, hexane/ethyl acetate, 5:1) to give a methyl ester of compounds 14 - 17. Precooled LiOH (0.9 mL, 1 N, 0.9 mmol) was added to the methyl ester (1.0 mmol) in methanol (5 mL) at 0 oC. The suspension was stirred for 1 h at room temperature, diluted with acetone (20 mL) to precipitate the product. The white powder was filtered and dried to give compounds 14 - 17. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate at 20℃; for 24h; | 2 Intermediate 2: Benzyl 2-amino-2-iminoethylcarbamate hydrochloride To a solution of benzyl cyanomethylcarbamate (65.4 g, 344 mmol) in methanol was added sodium methoxide (7.86 mL, 34.4 mmol, 25% in methanol). The mixture was stirred at ambient temperature for 24 h | |
8.02 g | With hydrogenchloride at 25℃; for 2h; | To a solution of S-VI-II (7.01 g) in methanol (3 mL) was added HC1 (50 ml, 2N in ether) dropwise. The mixture was stirred at 25 °C for 2 h and then filtered. The filtrated cake was dried to give the S-VI-III (8.02 g, y: 98%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: phenylmethyl cyanomethylcarbamate With methanol; sodium methylate at 20℃; for 24h; Stage #2: With ammonium chloride at 20℃; for 24h; | Intermediate 2: Benzyl 2-amino-2-iminoethylcarbamate hydrochloride Intermediate 2: Benzyl 2-amino-2-iminoethylcarbamate hydrochloride To a solution of benzyl cyanomethylcarbamate (65.4 g, 344 mmol) in methanol was added sodium methoxide (7.86 mL, 34.4 mmol, 25% in methanol). The mixture was stirred at ambient temperature for 24 h. Ammonium chloride (18.4 g, 344 mmol) was then added. The mixture was stirred at ambient temperature for another 24 h, and concentrated under reduced pressure. The resulting material was added into hexane/ethyl acetate (1 :1 ) (240mL) and ether (50 mL), stirred at ambient temperature for 1.5 h, then filtered to provide the title compound as a pale colored solid (78.8 g, 94% yield). 1 H NMR (400 MHz, DMSO-d6) δ 8.79 (br. s., 4 H), 7.78 (t, J=5.5 Hz, 1 H), 7.24 - 7.47 (m, 5 H), 5.07 (s, 2 H), 3.98 (d, J=5.5 Hz, 2 H). MS m/z 208.2 (M+1 ), retention time = 0.64 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 2,3,5,6,7-pentaselena-1,4-dophosphabicyclo{2.2.1}heptane In ethanol; water Reflux; | General procedure for the synthesis of Nα-protected amino selenocarboxamides 2a-j. General procedure: To a solution of Nα-protected amino nitrile (10 mmol) in EtOH (10 mL), freshly prepared glassy black powdered P2Se5 (20 mmol) was added. The reaction mixture was refluxed followed by the addition of a few drops ofwater. After complete consumption of the starting material (TLC analysis; 3-4 h), the reaction mixture was filtered. The solvent was removed in vacuo and the crude residue was purified by column chromatography (hexane/EtOAc8:2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
700 mg | With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 35℃; for 15h; | 111.1 Synthesis of Benzyl (cyanomethyl)carbamate NaHCO3 (1.09 g, 12.97 mmol) in water (5 mL) was added to a stirred solution of 2-aminoacetonitrile sulfate (1.0 g, 6.48 mmol) in 1,4-Dioxane (10 mL) at 0-5° C. followed by addition of Benzylchloroformate (1.3 g, 1.11 mL, 7.78 mmol) and stirring was continued at 20-35° C. for 15 h. Reaction mixture was diluted with DCM and washed it with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude, which was purified by Column chromatography (using Silica gel 60-120 and 10% MeOH in DCM as eluent) to afford 700 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.5-7.3 (5H, m), 5.25 (2H, s), 4.2 (2H, d, J=6.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.92% | With hydroxyamino hydrochloride; triethylamine In ethanol at 85℃; for 2h; | 4-5 Example 5 Add compound B3 (40.0g, 0.21mol) prepared in Example 3, ethanol (300mL), and stir into the reaction flask, add hydroxylamine hydrochloride (21.9g, 0.32mol, 1.5eq), and add triethylamine (63.84g, 0.63mol, 3eq), after the addition, the temperature was increased at 85 and the reaction was stirred for 2h, then concentrated, added water (400mL), extracted with dichloromethane (400mL), separated, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to obtain compound C3 (45.5g, 96.92%) |
90.4% | With hydroxyamino hydrochloride; triethylamine In ethanol at 80℃; for 2h; | 77 Preparation of benzyl (2-amino-2-(hydroxyimino)ethyl)carbamate: To a solution of benzyl (cyanomethyl)carbamate (33 g, 173.5 mmol, 1 eq) in ethanol (250 mL) were added hydroxylamine hydrochloride (18.09 g, 260.3 mmol, 1.5 eq) and TEA (347 mmol, 48.3 mL, 2 eq). The mixture was stirred at 80 °C for 2 hr. The mixture was extracted with DCM (1000 mL x 2), and the organic phase was washed with water (1000 mL) and brine (1000 mL), dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to afford benzyl (2-amino-2- (hydroxyimino)ethyl)carbamate (35 g, 156.8 mmol, 90.4% yield) as a white solid |
90.4% | With hydroxyamino hydrochloride; triethylamine In ethanol at 80℃; for 2h; | 77 Preparation of benzyl (2-amino-2-(hydroxyimino)ethyl)carbamate: To a solution of benzyl (cyanomethyl)carbamate (33 g, 173.5 mmol, 1 eq) in ethanol (250 mL) were added hydroxylamine hydrochloride (18.09 g, 260.3 mmol, 1.5 eq) and TEA (347 mmol, 48.3 mL, 2 eq). The mixture was stirred at 80 °C for 2 hr. The mixture was extracted with DCM (1000 mL x 2), and the organic phase was washed with water (1000 mL) and brine (1000 mL), dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to afford benzyl (2-amino-2- (hydroxyimino)ethyl)carbamate (35 g, 156.8 mmol, 90.4% yield) as a white solid |
With hydroxyamino hydrochloride; potassium hydroxide In methanol at 60℃; | 5.11. Methyl 2-(aminomethyl)-5,6-dihydroxypyrimidine-4-carboxylate (38b) General procedure: A 1.0 M solution of hydroxylamine hydrochloride in MeOH (2.0eq) and a 1.0 M solution of KOH in MeOH (2.0 eq) were combined at 0°C and stirred for ~30 min (slowly warming from 0°C to rt). The potassium chloride salt formed was removed by filtration. The filtrate was added to the nitrile 21 [1.0 eq; the corresponding nitrile was either purchased from commercial source (analogs 21a-l and 21o), or synthesized starting from a commercial nitrile, which was further modified via a Suzuki coupling reaction using established methods (21m-n)] and the mixture was heated at 60°C for 17-24h. MeOH was removed under vacuum and the residue was diluted with EtOAc, washed with brine, and the organic layer was concentrated. The product 22 was typically obtained in quantitative yield and >90% purity, and was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: phenylmethyl cyanomethylcarbamate; acetyl chloride In ethanol at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: L-Cysteine methyl ester With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19 g | Stage #1: 2-aminoacetonitrile hydrochloride With sodium hydroxide In water for 1h; Stage #2: benzyl chloroformate In 1,4-dioxane; water at 0 - 20℃; for 13h; | Intermediate: benzyl (cyanomethyl)carbamate To a solution of NaOH (11 g, 0.26 mol) in water (170 mL) was added 2-aminoacetonitrile hydrochloride (24 g, 0.26 mol) in portions over 30 min. The mixture was stirred for 30 minutes at which time dioxane (20 mL) was added and the mixture cooled to 0° C. Benzyl carbonochloridate (23 g, 132 mmol) was added dropwise via an additional funnel over 1 hour. The cooling bath was removed and the mixture stirred for 12 hours at room temperature. To the mixture was added aqueous HCl (6N) until pH=3, the aqueous layer extracted with dichloromethane (100 mL*3). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to afford (19 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium azide; zinc dibromide / water; isopropyl alcohol / 24 h / 100 °C 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 30 °C | ||
Multi-step reaction with 2 steps 1: sodium azide; zinc dibromide / isopropyl alcohol; water / 24 h / 100 °C 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 30 °C | ||
Multi-step reaction with 2 steps 1: sodium azide; zinc dibromide / water; isopropyl alcohol / 24 h / 100 °C 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 30 °C |
Multi-step reaction with 2 steps 1: sodium azide; zinc dibromide / water; isopropyl alcohol / 24 h / 100 °C 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 - 30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; hydroxylamine hydrochloride / ethanol / 2 h / 85 °C 2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 1 h / 20 °C 2.2: 6 h / 20 - 80 °C | ||
Multi-step reaction with 3 steps 1: triethylamine; hydroxylamine hydrochloride / ethanol / 2 h / 85 °C 2: 1,4-dioxane / 5 h / 100 °C / Cooling with ice 3: dichloromethane; water / 2 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With Caswell No. 744A; anhydrous zinc bromide In lithium hydroxide monohydrate; isopropanol Reflux; |
Tags: 3589-41-1 synthesis path| 3589-41-1 SDS| 3589-41-1 COA| 3589-41-1 purity| 3589-41-1 application| 3589-41-1 NMR| 3589-41-1 COA| 3589-41-1 structure
[ 17343-54-3 ]
(S)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 176894-58-9 ]
(R)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 72080-83-2 ]
Benzyl (2-aminoethyl)carbamate
Similarity: 0.87
[ 18807-67-5 ]
Dibenzyl ethane-1,2-diyldicarbamate
Similarity: 0.87
[ 17343-54-3 ]
(S)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 176894-58-9 ]
(R)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 72080-83-2 ]
Benzyl (2-aminoethyl)carbamate
Similarity: 0.87
[ 18807-67-5 ]
Dibenzyl ethane-1,2-diyldicarbamate
Similarity: 0.87
[ 17343-54-3 ]
(S)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 176894-58-9 ]
(R)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 72080-83-2 ]
Benzyl (2-aminoethyl)carbamate
Similarity: 0.87
[ 18807-67-5 ]
Dibenzyl ethane-1,2-diyldicarbamate
Similarity: 0.87
[ 17343-54-3 ]
(S)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
[ 176894-58-9 ]
(R)-Benzyl (1-cyanoethyl)carbamate
Similarity: 0.91
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 :