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CAS No. : | 816-27-3 | MDL No. : | MFCD06797654 |
Formula : | C6H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DSHWMBCJDOGPTB-UHFFFAOYSA-N |
M.W : | 145.16 | Pubchem ID : | 10920638 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.92 |
TPSA : | 59.38 Ų |
GI absorption : | High |
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) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.97 |
Log Po/w (XLOGP3) : | 1.22 |
Log Po/w (WLOGP) : | 0.56 |
Log Po/w (MLOGP) : | 0.25 |
Log Po/w (SILICOS-IT) : | 0.51 |
Consensus Log Po/w : | 0.9 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.18 |
Solubility : | 9.62 mg/ml ; 0.0663 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.06 |
Solubility : | 1.25 mg/ml ; 0.00863 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.96 |
Solubility : | 15.8 mg/ml ; 0.109 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.5 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
30% | With potassium hydroxide In ethanol at 20℃; for 16 h; | Step 1Ethyl F 1 ,2,4ltriazo loll ,5-alpyridine-2-carboxylate To solution of ethyl 2-ethoxy-2-iminoacete (1.91 g, 13.2 mmol) in ethanol (66.1 mL) was added1,2-diaminopyridinium iodide (2.35 g, 9.91 mmol) followed by potassium hydroxide (556 mg,9.91 mmol) and stirred at r.t. for 16 h. Water was then added, the mixture extracted with EtOAc, the organic layer was separated, and concentrated in vacuo. Purification by chromatography (silica, 60 100 percent ethyl acetate in hexanes) gave ethyl [1,2,4]triazolo[1,5-a]pyridine-2- carboxylate (570 mg, 30 percent). 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.67 (dt, J=6.9, 1.2Hz, 1 H), 7.86 (dt,J=9.1, 1.2 Hz, 1 H), 7.62 (m, 1 H), 7.17 (td,J=7.0, 1.3 Hz, 1 H), 4.56 (q, J=7.2 Hz, 2 H), 1.48 (t, J=7.1 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.9% | Stage #1: With hydrogenchloride In dichloromethane; water at -5 - 0℃; Inert atmosphere Stage #2: With triethylamine In dichloromethane; water at 0℃; for 1 h; Inert atmosphere |
To a solution of ethyl carbonocyanidate (40 g, 404 mmol) in DCM (200 mL) stirred under nitrogen at 0 °C was added a solution of HCI (45 wt. percent, 27.3 mL, 404 mmol) in EtOH dropwise over 15 min. The reaction mixture was stirred at 0 °C for 3 hr and allowed to stand overnight at -5 °C to -3 °C. To the resulting mixture was added DCM (250 mL) at 0 °C. TEA (113 mL, 807 mmol) in DCM (50 mL) was added dropwise over 30 min at 0 °C. The mixture was stirred for 30 min at 0 °C, and water (100 mL) was added at 0 °C. The resulting mixture was stirred for 5 min. The organic layer was separated, dried over sodium sulfate, and evaporated. Diethyl ether (50 mL) was added to the residue and the solid was filtered. The filtrate was dried to afford ethyl 2-ethoxy-2-iminoacetate as a pale yellow liquid (31.0 g, 214 mmol, 52.9 percent yield). NMR (400 MHz, CDC) δ 8.78 (s, 1H), 4.36-4.28 (m, 4H), 1.40-1.35 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With ammonium chloride; In ethanol; at 20℃; | A mixture of <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (2.5 g, 17.22 mmol, 1.0 eq) and H4C1 (738 mg, 13.78 mmol, 0.8 eq) in EtOH (60 mL) was stirred at rt overnight. The reaction solution was filtered. The filtrate was concentrated and the residue was washed with acetone. The resulting residue was dried in vacuo to afford ethyl 2-amino-2- iminoacetate (1.8 g, 69%) as a white solid. IH NMR (DMSO-d6, 300 MHz): delta 9.76 (br, 4 H), 4.35 (q, 2 H), 1.31 (t, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.9% | To a solution of ethyl carbonocyanidate (40 g, 404 mmol) in DCM (200 mL) stirred under nitrogen at 0 C was added a solution of HCI (45 wt. %, 27.3 mL, 404 mmol) in EtOH dropwise over 15 min. The reaction mixture was stirred at 0 C for 3 hr and allowed to stand overnight at -5 C to -3 C. To the resulting mixture was added DCM (250 mL) at 0 C. TEA (113 mL, 807 mmol) in DCM (50 mL) was added dropwise over 30 min at 0 C. The mixture was stirred for 30 min at 0 C, and water (100 mL) was added at 0 C. The resulting mixture was stirred for 5 min. The organic layer was separated, dried over sodium sulfate, and evaporated. Diethyl ether (50 mL) was added to the residue and the solid was filtered. The filtrate was dried to afford ethyl 2-ethoxy-2-iminoacetate as a pale yellow liquid (31.0 g, 214 mmol, 52.9 % yield). NMR (400 MHz, CDC) delta 8.78 (s, 1H), 4.36-4.28 (m, 4H), 1.40-1.35 (m, 6H). | |
EXAMPLE 43; N-(5-(2-amino-3-oxo-3,4-dihydro-6-quinoxalinyl)-2-chloro-3-pyridinyl)-4- fluorobenzenesulfonamide; (1) Ethyl 2-ethoxy-2-iminoacetate.; (Some starting materials may be obtained from Aldrich, St. Louis, MO) To a 100 mL round-bottomed flask was added ethyl cyanoformate (8 ml, 83 mmol), EtOH (10 ml, 171 mmol), pentane (30 mL). Anhydous HCl gas was bubbled to the solution at -15 0C for three hours. The solid was filtered out and washed with EtOH, ether. After the drying, the solid was suspended in Et2theta (60 mL), Et3N (12 ml) was then added. The mixture was stirred at room temperature for 2 hours. The solid was filtered out and washed with Et2O. The solvent was removed in vacuo to give ethyl 2-ethoxy-2-iminoacetate (7.2 g, 60% yield) as a crude product which was used for the next step reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol; at 20℃; | Step 1 : Ethyl-2-Amino[(phenylacetyl)hydrazono]acetate (i-2); Adapting a route similar to that described in Catarzi, D.; et al J. Med. Chem.; 1995; 38; 2196- 2201; 2-phenyl-acetohydrazide (M1 6.92 g, 46.1 mmol, Prata, J. V; J. Chem. Soc. Perkin trans.1; 2002; 513-528) and ethyl ethoxy(imino)acetate ( 6.69 g, 46.1 mmol, McKillop, A.; Synthesis; 1997; 3; 301 - 304) in EtOH (60 mL) was stirred under nitrogen at ambient temperature for overnight, the resultant suspension was filtered. The white solid was washed with EtOH and dried under vacuum to give the title compound i-2 {9.0 g, yield 78%) which was used without further purification. 1H NMR {300 MHz, DMSO- d6) mixture of isomers 3.51 (s, 0.56 H, major isomer) 3.87 (s, 0.44 H, minor isomer) 6.44 (s, 0.88 H, minor isomer) 6.53 (s, 1.12 H1 major isomer) 9.93 (s, 1.12 H, major isomer) 9.98 {s, 0.88 H, minor isomer) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In ethanol; water; at 20℃; for 16h; | To a suspension of 3-methoxy-benzene-1,2-diamine sulfate, Example 25(b), (2.36 g, 10 mmol) in EtOH (15 mL) and H2O (1 mL) was added NaHCO3 (1.68 g, 20 mmol, J T Baker). When gas evolution was complete, <strong>[816-27-3]ethoxy-imino-acetic acid ethyl ester</strong> (1.6 g, 11 mmol, prepared according to J. Chem. Soc. Perkin. Trans. 1, 1999, 1789) was added and the mixture was stirred at room temperature for 16 h. The reaction was diluted with sat. aq. NaHCO3 and extracted with 25% i-PrOH(CHCl3 (5×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (gradient: 0-5% MeOH/CH2Cl2) afforded 3-amino-8-methoxy-1H-quinoxalin-2-one as a light-brown powder [MS (ESI, pos. ion) m/z: 192 (M+1)] and 3-amino-5-methoxy-1H-quinoxalin-2-one as a light-brown powder [MS (ESI, pos. ion) m/z: 192 (M+1)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 20℃; for 18h; | A mixture of N1-(2,4-dimethoxybenzyl)-5-fluoro-3-methoxybenzene-1,2-diamine from step (d) above (4.92 g, 16.1 mmol) and <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (5.54 g, 38.14 mmol, prepared according to J. Chem. Soc. Perkin. Trans. 1, 1999, 1789) in EtOH (100 mL) was stirred at room temperature for 18 h. The reaction mixture was filtered and the filter cake was washed with EtOH, and dried in vacuo to give the title compound as a fine white powder. MS (ESI, pos. ion.) m/z: 360 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.9% | To a solution of ethyl carbonocyanidate (40 g, 404 mmol) in DCM (200 mL) stirred under nitrogen at 0 C was added a solution of HC1 (45 wt. %, 27.3 mL, 404 mmol) in EtOH dropwise over 15 min. The reaction mixture was stirred at 0 C for 3 hr and allowed to stand overnight at -5 C to -3 C. To the resulting mixture was added DCM (250 mL) at 0 C. TEA (113 mL, 807 mmol) in DCM (50 mL) was added dropwise over 30 min at 0 C. The mixture was stirred for 30 min at 0 C, and water (100 mL) was added at 0 C. The resulting mixture was stirred for 5 min. The organic layer was separated, dried over sodium sulfate, and evaporated. Diethyl ether (50 mL) was added to the residue and the solid was filtered. The filtrate was dried to afford ethyl 2-ethoxy-2-iminoacetate as a pale yellow liquid (31.0 g, 214 mmol, 52.9 % yield). 'HNMR (400 MHz, CDCb) d 8.78 (s, 1H), 4.36-4.28 (m, 4H), 1.40-1.35 (m, 6H). | |
With hydrogenchloride; triethylamine; In dichloromethane; di-isopropyl ether; water; | (4) To a solution of ethyl cyanoformate (25.0 g) in methylene chloride (55 ml) was added 43.5% ethanolic solution of hydrogen chloride (16.8 g) with stirring at 3 C. The mixture was stirred for 5 hours at 3 to 5 C. and allowed to stand over night at -5 to -3 C. To the resulting mixture were added methylene chloride (120 ml) at below 6 C. and a solution of triethylamine (20.2 g) in methylene chloride (20 ml) over a period of 30 minutes at below 6 C. The mixture was stirred for 40 minutes and thereto was added water (40 ml) at below 6 C. The resulting mixture was stirred for 3 minutes and the methylene chloride layer was separated, dried over magnesium sulfate and then evaporated. After the addition of diisopropyl ether (40 ml) to the residue, insoluble material was separated by filtration and washed with diisopropyl ether (10 ml). The filtrate and washing were combined and then evaporated to give a pale yellow oil of ethyl 2-imino-2-ethoxyacetate (26.2 g). | |
With hydrogenchloride; triethylamine; In dichloromethane; di-isopropyl ether; water; | (4) To a solution of ethyl cyanoformate (25.0 g) in methylene chloride (55 ml) was added 43.5% ethanolic solution of hydrogen chloride (16.8 g) with stirring at 3 C. The mixture was stirred for 5 hours at 3 to 5 C. and allowed to stand over night at -5 to -3 C. To the resulting mixture were added methylene chloride (120 ml) at below 6 C. and a solution of triethylamine (20.2 g) in methylene chloride (20 ml) over a period of 30 minutes at below 6 C. The mixture was stirred for 40 minutes and thereto was added water (40 ml) at below 6 C. The resulting mixture was stirred for 3 minutes and the methylene chloride layer was separated, dried over magnesium sulfate and then evaporated. After the addition of diisopropyl ether (40 ml) to the residue, insoluble material was separated by filtration and washed with diisopropyl ether (10 ml). The filtrate and washing were combined and then evaporated to give a pale yellow oil of ethyl 2-imino-2-ethoxyacetate (26.2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; bromine; triethylamine; In methanol; water; | (3) A mixture of <strong>[816-27-3]ethyl 2-imino-2-ethoxyacetate</strong> (60 g) (purity 78.8%) and ammonium chloride (17.4 g) in methanol (180 ml) was stirred for 3 hours at room temperature and cooled to -15 to -10 C. To the resulting mixture containing 1-methoxycarbonyl formamidine hydrochloride were dropwise added bromine (51.2 g) over a period of 10 minutes, triethylamine (71.1 g) over a period of 30 minutes and a solution of potassium thiocyanate (31.0 g) in methanol (150 ml) over a period of 30 minutes. The resulting mixture was stirred at -10 to -5 C. for 15 minutes and at 0 to 5 C. for an additional 1.5 hours. Precipitates were collected by filtration, washed with methanol and thereto was added cold water (200 ml). The mixture was stirred and the precipitates were collected by filtration, washed with cold water and dried to give methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (32.5 g). | |
With ammonium chloride; bromine; triethylamine; In methanol; water; | (3) A mixture of <strong>[816-27-3]ethyl 2-imino-2-ethoxyacetate</strong> (60 g) (purity 78.8%) and ammonium chloride (17.4 g) in methanol (180 ml) was stirred for 3 hours at room temperature and cooled to -15 to -10 C. To the resulting mixture containing 1-methoxycarbonylformamidine hydrochloride were dropwise added bromine (51.2 g) over a period of 10 minutes, triethylamine (71.1 g) over a period of 30 minutes and a solution of potassium thiocyanate (31.0 g) in methanol (150 ml) over a period of 30 minutes. The resulting mixture was stirred at -10 to -5 C. for 15 minutes and at 0 to 5 C. for an additional 1.5 hours. Precipitates were collected by filtration, washed with methanol and thereto was added cold water (200 ml). The mixture was stirred and the precipitates were collected by filtration, washed with cold water and dried to give methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (32.5 g). | |
With ammonium chloride; bromine; triethylamine; In methanol; water; | (3) A mixture of <strong>[816-27-3]ethyl 2-imino-2-ethoxyacetate</strong> (60 g) (purity 78.8%) and ammonium chloride (17.4 g) in methanol (180ml) was stirred for 3 hours at room temperature and cooled to -15 to -10 C. To the resulting mixture containing 1-methoxycarbonyl formamidine hydrochloride were dropwise added bromine (51.2 g) over a period of 10 minutes, triethylamine (71.1 g) over a period of 30 minutes and a solution of potassium thiocyanate (31.0 g) in methanol (150 ml) over a period of 30 minutes. The resulting mixture was stirred at -10 to -5 C. for 15 minutes and at 0 to 5 C. for an additional 1.5 hours. Precipitates were collected by filtration, washed with methanol and thereto was added cold water (200 ml). The mixture was stirred and the precipitates were collected by filtration, washed with cold water and dried to give methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (32.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium chloride; In ethanol; acetone; | (7) A mixture of <strong>[816-27-3]ethyl 2-imino-2-ethoxyacetate</strong> (18.1 g), ammonium chloride (5.8 g) in ethanol (90 ml) was stirred for 6 hours at room temperature. Insoluble materials were separated by filtration and washed with ethanol. The filtrate and washing were combined and evaporated. To the residual oil was added acetone (50 ml). The precipitates were collected by filtration and washed with acetone (10 ml*2) to give a white powder of 1-ethoxycarbonylformamidine hydrochloride (1.2 g). The filtrate and washing were combined and evaporated. The residue was pulverized with acetone (30 ml), collected by filtration, washed successively with acetone, methylene chloride and diisopropyl ether to give a white powder of the same (7.3 g). Total yield: 8.5 g. I.R. (Nujol): 3400-3100, 1770, 1730-1680, 1650, 1300-1260, 1120, 1010, 860, 760 cm-1. | |
With ammonium chloride; In ethanol; acetone; | (7) A mixture of <strong>[816-27-3]ethyl 2-imino-2-ethoxyacetate</strong> (18.1 g), ammonium chloride (5.8 g) in ethanol (90 ml) was stirred for 6 hours at room temperature. Insoluble materials were separated by filtration and washed with ethanol. The filtrate and washing were combined and evaporated. To the residual oil was added acetone (50 ml). The precipitates were collected by filtration and washed with acetone (10 ml*2) to give a white powder of 1-ethoxycarbonylformamidine hydrochloride (1.2 g). The filtrate and washing were combined and evaporated. The residue was pulverized with acetone (30 ml), collected by filtration, washed successively with acetone, methylene chloride and diisopropyl ether to give a white powder of the same (7.3 g). Total yield: 8.5 g. I.R. (Nujol): 3400-3100, 1770, 1730-1680, 1650, 1300-1260, 1120, 1010, 860, 760 cm-1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | EXAMPLE 5 To 20 ml of water containing 10.0 m mol (millimole) of ethyl ethoxyiminoacetate were added 10 ml of water containing 10.0 m mol of n-butylamine and then the reaction was carried out at room temperature for 4 hours. The reaction mixture thus obtained was filtered to give 0.17 g (yield:12%) of N-n-butylmidinecarboxylic acid as crystal. The filtrate was concentrated under reduced pressure to additionally afford 1.25 g (yield:87%) of crystalline N-n-butylamidinecarboxylic acid. Both the crystals were combined and recrystallized from ethanol to give colorless block crystals with m.p. 179~180 C. (with decomposition). Its elementary analysis is as shown below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
[2-AMINO-5-HYDROXY-BENZOIC] acid [(15MMOL)] are suspended in ethanol (water free, [600ML)] and heated up to 60 [C] and stirred. Then triethylamine [(30MMOL)] is added and a clear solution is formed. Ethoxy-imino-acetic acid ethyl ester (16. 5mmol) is added at [60 C] and after 15 minutes another portion [OF TRIETHYLAMINE ( 5MMOL)] is added and the mixture stirred for another 30 minutes. The mixture is cooled down to RT and left at RT without stirring over night. The solid material formed was filtered off, washed with [ETHANOL/ETHER] and dried (vacuum). A pale brown powder with mp. [258-260C] (decomposition) is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59.6% | In ethanol; at 100℃; for 2h; | (2) 3-amino-7-bromoquinoxalin-2(lH)-one.; To a 100 mL round-bottomed flask was added 4-bromobenzene-l,2-diamine (1.87 g, 10.00 mmol),<strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (1.60 g, 11.0 mmol), EtOH (20 mL). The reaction mixture was stirred at 100 0C for 2 h. The mixture was cooled down to room temperature. The solid was filtered out and washed with EtOH to give 3-amino-7-bromoquinoxalin-2(lH)-one (1.43 g, 59.6% yield). MS (ESI pos. ion) m/z calc'd for C8H6BrN3O: 239, 241 found: 240, 242. 1H NMR (300 MHz, DMSO-^6) delta ppm 7.07 (d, J=8.48 Hz, 1 H) 7.12 - 7.33 (m, 3 H) 7.40 (d, J=2.05 Hz, 1 H) 12.16 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
a) 5-Benzyl-1H-[1,2,4]triazole-3-carboxylic acid butyl ester Ethyl-2-ethoxy-2-iminoacetate (1.318 g, 9.08 mmol) and phenyl acetic acid hydrazide (1.364 g, 9.08 mmol) were mixed together in ethanol (20 ml) and stirred at 80 C. for 1 h. Ethanol was evaporated. The residue was dissolved in n-butanol (20 ml). The reaction mixture was stirred at 150 C. for 20 h, then solvents were evaporated. The residue was suspended in acetonitrile and the precipitate was filtered off. The filtrate was purified by prep. HPLC (column: Interchrom C18 ODB, 10 um, 250*28 mm, 23 C.; A: water+0.1% HCOOH, B: ORG+0.1% HCOOH [ORG=methanol/acetonitrile 4:1]; gradient 20% B 2.5 min, 20-100% B in 35 min, 100% B for 2.5 min) to give the title compound. UPLC-MS (method F) Rt=0.85 min, [M+H]+=260.3; HPLC (method G) Rt=1.861 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With potassium hydroxide; In ethanol; at 20℃; for 16h; | Step 1Ethyl F 1 ,2,4ltriazo loll ,5-alpyridine-2-carboxylate To solution of ethyl 2-ethoxy-2-iminoacete (1.91 g, 13.2 mmol) in ethanol (66.1 mL) was added1,2-diaminopyridinium iodide (2.35 g, 9.91 mmol) followed by potassium hydroxide (556 mg,9.91 mmol) and stirred at r.t. for 16 h. Water was then added, the mixture extracted with EtOAc, the organic layer was separated, and concentrated in vacuo. Purification by chromatography (silica, 60 100 % ethyl acetate in hexanes) gave ethyl [1,2,4]triazolo[1,5-a]pyridine-2- carboxylate (570 mg, 30 %). 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.67 (dt, J=6.9, 1.2Hz, 1 H), 7.86 (dt,J=9.1, 1.2 Hz, 1 H), 7.62 (m, 1 H), 7.17 (td,J=7.0, 1.3 Hz, 1 H), 4.56 (q, J=7.2 Hz, 2 H), 1.48 (t, J=7.1 Hz, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.2% | In ethanol; at 20℃;Inert atmosphere; | 2-(3-Fluorophenyl)acetohydrazide (2.90 g, 17.22 mmol) and ethyl 2-ethoxy-2- iminoacetate (2.5 g, 17.22 mmol) in ethanol (30 mL) was stirred under nitrogen at rt for overnight, the resultant suspension was filtered. The white solid was washed with EtOH and dried under vacuum to give the title compound ethyl 2-amino-2-(2-(2-(3- fluorophenyl)acetyl)hydrazono)acetate (3 g, 11.23 mmol, 65.2 % yield) which was used without further purification. MS (m/z) 268 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In diethyl ether; ethanol; for 22h; | To 2-phenylacetohydrazide (39.5 g, 263 mmol) in ethanol (150 mL) was added ethyl 2- ethoxy-2-iminoacetate (39.5 g, 272 mmol) and diethyl ether (200 mL). The reaction mixture was stirred for 10 min and solid formed. The reaction mixture was stirred for 5 hours and diethyl ether (50 mL) was added. The resulting mixture was stirred for 17 hours The solid was filtered, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2- phenylacetyl)hydrazono)acetate as a white solid (59 g, 85 % yield). The filtrate sat for 5 days and additional white solid precipitated out. The solid was filtered and dried to give 2-amino-2-(2-(2-phenylacetyl)hydrazono)acetate as a white solid (4.8 g) (92% total yield). MS ES+ m/z 250.1 [M+H]+; NMR (400 MHz, DMSO-d6) delta 9.95 (d, J=17.18 Hz, 1H), 7.13-7.37 (m, 5H), 6.50 (d, 2H), 4.24 (dq, J=7.07, 10.86 Hz, 2H), 3.86 (s, 1H), 3.50 (s, 1H), 1.27 (dt, J=7.07, 17.43 Hz, 3H). |
92% | In diethyl ether; ethanol; for 22.16h; | To 2-phenylacetohydrazide (39.5 g, 263 mmol) in ethanol (150 mL) was added ethyl 2- ethoxy-2-iminoacetate (39.5 g, 272 mmol) and diethyl ether (200 mL). The reaction mixture was stirred for 10 min and solid formed. The reaction mixture was stirred for 5 hours and diethyl ether (50 mL) was added. The resulting mixture was stirred for 17 hours. The solid was filtered, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2- phenylacetyl)hydrazono)acetate as a white solid (59 g, 85 % yield). The filtrate sat for 5 days and additional white solid precipitated out. The solid was filtered and dried to give 2- amino-2-(2-(2-phenylacetyl)hydrazono)acetate as a white solid (4.8 g) (92% total yield). MS ES+ m/z 250.1 [M+H]+; 'H NMR (400 MHz, DMSO-d6) d 9.95 (d, J=l7. l8 Hz, 1H), 7.13-7.37 (m, 5H), 6.50 (d, 2H), 4.24 (dq, J=7.07, 10.86 Hz, 2H), 3.86 (s, 1H), 3.50 (s, 1H), 1.27 (dt, J=7.07, 17.43 Hz, 3H). |
82% | In diethyl ether; ethanol; at 20℃; for 4h; | To a solution of 2-phenylacetohydrazide (20 g, 133 mmol) in ethanol (75 mL) and diethyl ether (250 mL) was added <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (20 g, 138 mmol). Stirred at room temperature for 4 hours. A precipitate started to form after 10 minutes. The resulting solid was filtered off, rinsed with diethyl ether and dried to give ethyl 2-amino-2- (2-(2-phenylacetyl)hydrazono)acetate (27.85 g, yield 82%) as a white solid, which was used without further purification. MS (m/z) 250 (M+H+). |
82% | In diethyl ether; ethanol; at 20℃; for 4h; | To a solution of 2-phenylacetohydrazide (20 g, 133 mmol) in ethanol (75 inL) and Et20 (250 mL) was added <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (20 g, 138 mmol). The resulting reaction mixture was stirred at room temperature for 4 hours. A precipitate started to form after 10 minutes. The resulting solid was filtered off, rinsed with Et20 and dried to give ethyl 2-amino-2-(2-(2-phenylacetyl)hydrazono)acetate (27.85 g, yield 82%) as a white solid, which was used without further purification. MS (m/z) 250 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Compound 1a (2100 g, 8.59 mol) was mixed with methanol (8400 mL)The compound 1b (1245 g, 8.59 mol) was added dropwise under ice-cooling to control the reaction temperature not to exceed 20 C.After the drop, keep the temperature reaction for 30 minutes.Quickly drip to the systemAmmonia solution (6300 mL, 7 mol / L) was added dropwise and the reaction was continued at room temperature for 1.5 hours.The reaction solution was distilled under reduced pressure to remove the methanol solvent, stirred with ice water (20 L) for 30 minutes, filtered, and the filter cake was washed with water (600 mL x 2), dried and dried to give a white solid compound 2a (1440 g, 65% ), Directly for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.2% | In ethanol; at 0℃; for 1.5h; | Compound la (358.6 g, 2.47 mol) was diluted with ethanol (1200 mL) and added dropwise to the reaction solution, and the temperature was maintained at 0 C. The compound 1a (550 g, 2.32 mol) was mixed with ethanol (4300 mL) and cooled to 0 C. or so. And the reaction was carried out at 0 C for 1.5 hours. The reaction was concentrated and the reaction was concentrated to dryness and dissolved in dichloromethane (1.5 L). Water (1 L) and triethylamine (114 g, 1.13 mol) were added, stirred and homogenized. The aqueous phase was washed with dichloromethane × 1), the organic phases were combined, washed with saturated sodium chloride (600 mL x 2), dried over anhydrous sodium sulfate, concentrated by filtration,Add petroleum ether (1200mL) beating, filter, filter cake with petroleum ether leaching,And dried to give the white solid compound 1c (580 g, yield 91.2%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 100% | In ethanol; at 30℃; for 72h; | 2-(3-Chloroquinolin-6-yl)acetohydrazide (170.0 mg, 0.723 mmol, 1.0 eq) and <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (231.0 mg, 1.591 mmol, 2.0 eq) in ethanol (20.0 mL) were stirred at 30 C for 72.0 h. The solvent was removed in vacuo, to provide (Z)-ethyl 2-amino- 2-(2-(2-(3-chloroquinolin-6-yl)acetyl)hydrazono)acetate (242.0 mg, ca. 100%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
105 mg | With sodium acetate; acetic acid; at 110℃; for 6h;Sealed tube; | A) ethyl 4-benzyl-1H-imidazole-2-carboxylate To a solution of 1-amino-3-phenylpropan-2-one hydrochloride (0.93 g) and <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (0.727 g) in acetic acid (10 mL) was added sodium acetate (0.74 g), and the mixture was stirred in a sealed tube at 110C for 6 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (105 mg). MS: [M+H]+ 231.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In dichloromethane; for 12h;Reflux; | A solution of 461 <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (19 g, 123.26 mmol) and 462 2-fluorobenzoic hydrazide (19.68 g, 135.59 mmol) in 16 DCM (350 mL) was stirred at reflux for 12 h. The resulting solid was collected by filtration and washed with DCM (200 mL) to afford the 387 title compound as an off-white solid (24.5 g, 80%). 1HNMR (400 MHz, DMSO-d6) 1.28 (t, 3H), 4.25 (q, 2H), 6.66 (s, 2H), 7.29 (m, 2H), 7.57 (m, 2H), 10.18 (s, 1H). LCMS m/z=254 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 40℃; for 12h; | To a solution of 1-amino-3-phenyl-pyrrolidin-2-one (590 mg, 3.35 mmol) in ethanol (10 mL) was added ethyl 2-ethoxy-2-imino-acetate (1458 mg, 10.04 mmol). The mixture was stirred at 40 C. for 12 h and concentrated under reduced pressure to obtain crude ethyl (2Z)-2-amino-2-(2-oxo-3-phenyl-pyrrolidin-1-yl)imino-acetate (1370 mg. 100%), used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 16h; | To a solution of 1-amino-5-(1,1-difluoroethyl)pyrrolidin-2-one (30 mg, 0.18 mmol) in ethanol (3 mL) was added ethyl 2-ethoxy-2-imino-acetate (80 mg, 0.55 mmol). he reaction mixture was stirred at 60 C. for 16 h and concentrated under reduced pressure to afford the crude ethyl 2-[[2-(1,1-difluoroethyl)-5-oxo-pyrrolidin-1-yl]amino]-2-imino-acetate (40 mg, 83%) as a yellow oil, used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 15h; | To a solution of (5S)-1-amino-5-(trifluoromethyl)pyrrolidin-2-one (30.0 g, 178.4 mmol) in ethanol (280 mL) was added ethyl 2-ethoxy-2-imino-acetate (38.9 g. 267.7 mmol). The reaction mixture was stirred at 60 C. for 15 h and concentrated under reduced pressure to afford crude ethyl 2-imino-2-[[(5S)-2-oxo-5-(trifluoromethyl)pyrrolidin-1-yl]amino]acetate as a yellow oil (38.0 g, 80%) which was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 16h; | To a solution of 1-amino-5-(1,1-difluoropropyl)pyrrolidin-2-one (120 mg, 0.67 mmol) in ethanol (5 mL) was added ethyl 2-ethoxy-2-imino-acetate (489 mg, 3.37 mmol). The reaction mixture was stirred at 60 C. for 16 h and subsequently concentrated under reduced pressure to afford ethyl 2-[[2-(1,1-difluoropropyl)-5-oxo-pyrrolidin-1-yl]amino]-2-imino-acetate (600 mg, 80%, 40% purity) as a yellow oil, used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 40℃; for 12h; | To a solution of 1-amino-5-(2-fluorophenyl)pyrrolidin-2-one hydrochloride (400 mg, 2.06 mmol) in ethanol (10 mL) was added ethyl 2-ethoxy-2-imino-acetate (1.8 g, 12.36 mmol). The mixture was stirred at 40 C. for 12 h and concentrated under reduced pressure to afford crude ethyl (2Z)-2-amino-2-[2-(2-fluorophenyl)-5-oxo-pyrrolidin-1-yl]imino-acetate (500 mg, 82%) as a yellow oil, used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 90℃; for 16h; | To a solution of 1-amino-5-(2-fluorophenyl) pyffolidin-2-one (6.6 g, 33.98 mmol) in ethanol (50 mL) was added ethyl 2-ethoxy-2-imino-acetate (24.7 g, 169.92 mmol). The mixture was stirred at 90 C for 16 h and concentrated under reduce pressure to afford crude ethyl (2Z)-2-amino-2- [2-(2-fluorophenyl)-5-oxo-pyrrolidin- 1 -yl] imino acetate (9.0 g, 90%)as brown oil, used in the next step without further purification. LCMS RT = 1.498 mi mlz = 294.2 [M + H]. LCMS (0 to 60% acetonitrile in water + 0.03% trifluoroacetic acid over 3.0 mins) retention time 1.498 mi ESI+found [M+H] = 294.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 25℃; for 2h; | To a solution of 4-chloro-2-(2-fluorophenyl)butanehydrazide (746 mg, 3.23 mmol) in ethanol (10 mL) was added ethyl 2-ethoxy-2-imino-acetate (469 mg, 3.23 mmol). The mixture was stirred at 25 C. for 2 h and then filtered. The solid was dried in vacuo to afford crude (Z)-ethyl 2-amino-2-(2-(4-chloro-2-(2-fluorophenyl)butanoyl)hydrazono)acetate (650 mg, 61%) as a white solid, used in the next step without any further purification. LCMS RT=0.786 min, m/z=329.9 [M+H]+. LCMS (5 to 95% acetonitrile in water+0.03% trifluoroacetic acid over 1 .5 mins) retention time 0.786 mm, ESI+ found [M+H]=329.9. | |
In ethanol; at 25℃; for 2h; | To a solution of 4-chloro-2-(2-fluorophenyl)butanehydrazide (746 mg, 3.23 mmol) in ethanol (10 mL) was added ethyl 2-ethoxy-2-imino-acetate (469 mg, 3.23 mmol). The mixture was stirred at 25 C. for 2 h and then filtered. The solid was dried in vacuo to afford crude (Z)-ethyl 2-amino-2-(2-(4-chloro-2-(2-fluorophenyl)butanoyl)hydrazono)acetate (650 mg, 61%) as a white solid, used in the next step without any further purification. LCMS RT=0.786 min, m/z=329.9 [M+H]+. LCMS (5 to 95% acetonitrile in water+0.03% trifluoroacetic acid over 1.5 mins) retention time 0.786 min, ESI+ found [M+H]=329.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 40℃; for 12h; | To a solution of 1-amino-3-phenyl-pyrrolidin-2-one (590 mg, 3.35 mmol) in ethanol (10 mL) was added ethyl 2-ethoxy-2-imino-acetate (1458 mg, 10.04 mmol). The mixture was stirred at 40 C. for 12 h and concentrated under reduced pressure to obtain crude ethyl (2Z)-2-amino-2-(2-oxo-3-phenyl-pyrrolidin-1-yl)imino-acetate (1370 mg, 100%), used as is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 6h; | To a solution of cis-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C. for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cis-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-1-yl]amino]-2-imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT=2.106 min, m/z=406.2 [M+H]-. LCMS (10 to 80% acetonitrile in water+0.1% ammonia water over 3.0 mins) retention time 2.106 mm, ESI+ found [M+H]=406.2. | |
In ethanol; at 60℃; for 6h; | To a solution of cis-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C. for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cis-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-1-yl]amino]-2-imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT=2.106 min, m/z=406.2 [M+H]+. | |
In ethanol; at 60℃; for 6h; | To a solution of c-l-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cw-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-l -yl]amino]-2- imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT = 2.106 min, m/z =406.2 [M + H]+. LCMS (10 to 80% acetonitrile in water + 0.1% ammonia water over 3.0 mins) retention time 2.106 min, ESI+ found [M+H] =406.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 16h; | To a solution of trans-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (7.0 g, 22.8 mmol) in ethanol (150 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.63 g, 45.7 mmol). The reaction mixture was stirred at 60 C. for 16 h and subsequently concentrated under reduced pressure to afford crude trans-ethyl 2-(3-((tert-butyldimethylsilyl)oxy)-2-oxo-5-phenylpyrrolidin-1-yl)amino)-2-iminoacetate (8.50 g, 92%) as a yellow oil, used in the next step without further purification. LCMS RT=2.154 min, m/n=406.3 [M+H]+. LCMS (0 to 60% acetonitrile in water+0.03% trifluoacetic acid over 3.0 mins) retention time 2.143 min, ESI+ found [M+H]=406.3. | |
In ethanol; at 60℃; for 16h; | To a solution of ?ran5-l-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (7.0 g, 22.8 mmol) in ethanol (150 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.63 g, 45.7 mmol). The reaction mixture was stirred at 60 C for 16 h and subsequently concentrated under reduced pressure to afford crude trans-ethyl 2-(3-((tert-butyldimethylsilyl)oxy)-2-oxo-5-phenylpyrrolidin-l-yl)amino)- 2-iminoacetate (8.50 g, 92%) as a yellow oil, used in the next step without further purification. LCMS RT= 2.154 min, m/z = 406.3 [M + H]+. LCMS (0 to 60% acetonitrile in water + 0.03% trifluoacetic acid over 3.0 mins) retention time 2.143 min, ESI+ found [M+H] = 406.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In diethyl ether; ethanol; for 18.5h; | 2-(2-fluorophenyl)acetohydrazide (7.05 g, 41.9 mmol) was partially dissolved in ethanol (30 mL), and then <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (6.39 g, 44.0 mmol) and diethyl ether (35 mL) were added. The reaction mixture was stirred for 0.5 hours, and diethyl ether (100 mL) was added. The resulting mixture was stirred for 18 hours. The solid was filtered off, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2-(2- fluorophenyl)acetyl)hydrazono)acetate as an off-white solid (10 g, 89% yield). MS ES+ m/z 26% [M+H]+; NMR (400 MHz, DMSO-de) delta 9.80-10.25 (m, 1H), 7.25-7.43 (m, 2H), 7.09-7.21 (m, 2H), 6.42-6.60 (m, 2H), 4.23 (dq, J=1.52, 7.07 Hz, 2H), 3.92 (s, 1H), 3.58 (s, 1H), 1.26 (dt, J=5.05, 7.07 Hz, 3H). |
89% | In diethyl ether; ethanol; at 20℃; for 18.5h; | 2-(2-fluorophenyl)acetohydrazide (7.05 g, 41.9 mmol) was partially dissolved in ethanol (30 mL), and then <strong>[816-27-3]ethyl 2-ethoxy-2-iminoacetate</strong> (6.39 g, 44.0 mmol) and diethyl ether (35 mL) were added. The reaction mixture was stirred for 0.5 hours, and diethyl ether (100 mL) was added. The resulting mixture was stirred for 18 hours. The solid was filtered off, rinsed with diethyl ether, and dried to give ethyl 2-amino-2-(2-(2-(2- fluorophenyl)acetyl)hydrazono)acetate as an off-white solid (10 g, 89% yield). MS ES+ m/z 268 [M+H]+; NMR (400 MHz, DMSO-de) d 9.80-10.25 (m, 1H), 7.25-7.43 (m, 2H), 7.09-7.21 (m, 2H), 6.42-6.60 (m, 2H), 4.23 (dq, .7=1.52, 7.07 Hz, 2H), 3.92 (s, 1H), 3.58 (s, 1H), 1.26 (dt, 7=5.05, 7.07 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 150℃; for 0.5h;Sealed tube; | A mixture of <strong>[33263-43-3]4-chloropyridine-3-sulfonamide</strong> (500 mg, 2.6 mmol), ethyl 2-ethoxy-2- iminoacetate (565 mg, 3.9 mmol) and DBU (790 mg, 5.2 mmol) in ethanol (10 mL) was heated in a sealed tube at 150 °C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and exacted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20, v/v) to give the product as a yellow solid (100 mg, 15percent yield). LCMS (ES-API) Rt 0.47 min; m/z 256 [M+H]+. 1H NMR (400 MHz, d6-DMSO), 9.05 (s, 1H), 8.76 (d, J = 5.6 Hz, 1H), 7.64 (d, J = 5.6 Hz, 1H), 4.40 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H). |
Tags: 816-27-3 synthesis path| 816-27-3 SDS| 816-27-3 COA| 816-27-3 purity| 816-27-3 application| 816-27-3 NMR| 816-27-3 COA| 816-27-3 structure
[ 17229-14-0 ]
Ethyl 2-(2-chloroethoxy)acetate
Similarity: 0.54
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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 |
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