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CAS No. : | 26054-60-4 | MDL No. : | MFCD01318309 |
Formula : | C11H11NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CWFZPRQDHIUBDO-VIFPVBQESA-N |
M.W : | 221.21 | Pubchem ID : | 489182 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.28 |
TPSA : | 64.63 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) : | -6.82 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 1.17 |
Log Po/w (WLOGP) : | 0.69 |
Log Po/w (MLOGP) : | 0.76 |
Log Po/w (SILICOS-IT) : | 1.16 |
Consensus Log Po/w : | 1.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.9 |
Solubility : | 2.81 mg/ml ; 0.0127 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.12 |
Solubility : | 1.67 mg/ml ; 0.00754 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.78 |
Solubility : | 0.368 mg/ml ; 0.00166 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | 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 |
---|---|---|
72% | With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; acetonitrile at -55℃; for 2 h; Inert atmosphere | Example 4; Standard Procedure for the Synthesis of Ddz-Dap(Boc-Me)-OH (Ddz-AA4, FIG. 2); Step 4-1. Z-Serine-β-lactone (AA4-2).; This intermediate was prepared in an analogous fashion to that described previously for the Boc derivative AA3-1. In a dry 250 mL 3-neck flask equipped with a mechanical stirrer under nitrogen atmosphere was added triphenylphosphine (4.5 g, 17.1 mmol, 1.1 eq.), followed by 100 mL of an anhydrous THF:CH3CN (1:9) solvent mixture. The mixture was stirred until a solution was obtained and then cooled to -55° C. (bath temperature) and dimethylazodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq) was added dropwise over 10 min. After completion of the addition, the mixture was stirred for 20 min, then a solution of Z-Ser-OH (AA4-1, 3.7 g, 15.5 mmol, 1.0 eq) in 50 mL of anhydrous THF:CH3CN (1:9) was added dropwise over 30 min. The reaction mixture was stirred at -55° C. for 1.5 h, then the cooling bath removed and the solution allowed to warm slowly to room temperature. Once the mixture reached room temperature, the solvent was evaporated under reduced pressure. The resulting yellow oil was purified by flash chromatography [gradient, hexanes/EtOAc, (80:20) to (60:40)] to give 2.5 g of AA4-2 as a white solid in 72percent yield. Purification of the crude oil is preferentially performed the same day to avoid decomposition. DCM can be added to help solubilize the residue.TLC (hexanes/EtOAc (60/40): Rf=0.55 (UV, CMA) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With triphenylphosphine In acetonitrile | a L-2-Amino-3-phenylaminoethylpropionic Acid 54.8 g (0.209 mol) of triphenylphosphine were suspended in 600 ml of acetonitrile and, with exclusion of moisture, cooled to -35° C. to -45° C. At this temperature, 36.4 g (0.209 mol) of diethyl azodicarboxylate were then added dropwise over a period of 50 min. The mixture was stirred at -35° C. for another 15 min. A solution of 50 g (0.209 mol) of N-benzyloxycarbonyl-L-serine in 500 ml of acetonitrile was added dropwise to this mixture, the temperature being kept below -35° C. The mixture was then allowed to react at 5° C. for another 12 h and warmed to RT. The reaction solution was freed from solvent under reduced pressure and the crude product was purified by medium pressure chromatography over silica gel (DCM/AcCN: 25/1). Removal of the solvent gave 20.8 g (yield 45percent) of pure N-benzyloxy-carbonyl-L-serine-β-lactone (see also Org. Synth. 1991 (70) 1ff.) in fine needles. Empirical formula C11H11NO4; M.W.=221.2; MS (M+H) 222.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With dimethyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; acetonitrile; at -55℃; for 2h;Inert atmosphere; | Example 4; Standard Procedure for the Synthesis of Ddz-Dap(Boc-Me)-OH (Ddz-AA4, FIG. 2); Step 4-1. Z-Serine-beta-lactone (AA4-2).; This intermediate was prepared in an analogous fashion to that described previously for the Boc derivative AA3-1. In a dry 250 mL 3-neck flask equipped with a mechanical stirrer under nitrogen atmosphere was added triphenylphosphine (4.5 g, 17.1 mmol, 1.1 eq.), followed by 100 mL of an anhydrous THF:CH3CN (1:9) solvent mixture. The mixture was stirred until a solution was obtained and then cooled to -55 C. (bath temperature) and dimethylazodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq) was added dropwise over 10 min. After completion of the addition, the mixture was stirred for 20 min, then a solution of Z-Ser-OH (AA4-1, 3.7 g, 15.5 mmol, 1.0 eq) in 50 mL of anhydrous THF:CH3CN (1:9) was added dropwise over 30 min. The reaction mixture was stirred at -55 C. for 1.5 h, then the cooling bath removed and the solution allowed to warm slowly to room temperature. Once the mixture reached room temperature, the solvent was evaporated under reduced pressure. The resulting yellow oil was purified by flash chromatography [gradient, hexanes/EtOAc, (80:20) to (60:40)] to give 2.5 g of AA4-2 as a white solid in 72% yield. Purification of the crude oil is preferentially performed the same day to avoid decomposition. DCM can be added to help solubilize the residue.TLC (hexanes/EtOAc (60/40): Rf=0.55 (UV, CMA) |
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -78 - 20℃; | Step 1: (Steps 1 and 2 are done similar to that described in Organic Syntheses, Coll. Vol. 9, p. 58-63) To a solution of triphenylphosphine (27.7 g, 106 mmol) in THF (500 mL) at -78 C., DIAD (20.8 mL, 106 mmol) was added dropwise. The mixture is stirred at -78 C. for 20 min. A solution of N-(benzyloxycarbonyl)-L-serine (25.3 g, 106 mmol) in THF (150 mL) is added to the reaction mixture. The reaction mixture is stirred for an additional 30 min at -78 C., warmed to rt, and stirred for an additional 3 h. The reaction mixture is concentrated in vacuo, dissolved in ether, and filtered. The filtrate was concentrated in vacuo, and the residue is purified by column chromatography (SiO2, gradient 10%-40% ethyl acetate in hexanes). This gave 8.0 g of N-(benzyloxycarbonyl)-L-serine p-lactone. 1H NMR (300 MHz, DMSO-d6) delta 7.73-7.43 (m, 5H), 5.80-5.66 (m, 1H), 5.48-5.28 (m, 3H), 4.77-4.89 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With acetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; | A. 2R-2-N(Benzyloxycarbonyl)amino-3-phenylthio propanoic acid The desired subtitled intermediate was prepared substantially in accordance with the procedure detailed in Procedure 2A, using 13.1 mL (127 mmol) of thiophenol, 4.6 g (117 mmol) of a 60% sodium hydride solution and 25.6 g (116 mmol) of L-N(benzyloxycarbonyl)-serine beta-lactone in 450 mL of tetrahydrofuran to provide a residue. This residue was purified using flash chromatography (gradient eluent of 0-2% acetic acid in a 4:1 methylene chloride/ethyl acetate mixture) to provide 27.9 g of a white solid. Yield: 72%. 1 H NMR (CDCl3): delta 7.55-7.18 (m, 10H), 5.55 (d, J=7 Hz, 1H), 5.08 (s, 2H), 4.73-4.60 (m, 1H), 3.55-3.30 (m, 2H). IR (KBr): 3304, 3035, 1687, 1532, 736 cm-1. MS(FD): m/e 332, 288, 271, 181. |
72% | With acetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; | A. 2R-2-N(Benzyloxycarbonyl)amino-3-phenylthio propanoic acid The desired subtitled intermediate was prepared substantially in accordance with the procedure detailed in Procedure 2A, using 13.1 mL (127 mmol) of thiophenol, 4.6 g (117 mmol) of a 60% sodium hydride solution and 25.6 g (116 mmol) of L-N(benzyloxycarbonyl)serine beta-lactone in 450 mL of tetrahydrofuran to provide a residue. This residue was purified using flash chromatography (gradient eluent of 0-2% acetic acid in a 4:1 methylene chloride/ethyl acetate mixture) to provide 27.9 g of a white solid. Yield: 72%. 1 H NMR (CDCl3): delta7.55-7.18 (m, 10H), 5.55 (d, J=7 Hz, 1H), 5.08 (s, 2H), 4.73-4.60 (m, 1H), 3.55-3.30 (m, 2H). IR (KBr): 3304, 3035, 1687, 1532, 736 cm-1. MS(FD): m/e 332, 288, 271, 181. Analysis for C17 H17 NO4 S: Calcd: C, 61.61; H, 5.17; N, 4.23; Found: C, 61.69; H, 5.22; N, 4.47. |
72% | With acetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; | A. 2R-2-N(Benzyloxycarbonyl)amino-3-phenylthio propanoic acid The desired subtitled intermediate was prepared substantially in accordance with the procedure detailed in Procedure 2A, using 13.1 mL (127 mmol) of thiophenol, 4.6 g (117 mmol) of a 60% sodium hydride solution and 25.6 g (116 mmol) of L-N(benzyloxycarbonyl)-serine beta-lactone in 450 mL of tetrahydrofuran to provide a residue. This residue was purified using flash chromatography (gradient eluent of 0-2% acetic acid in a 4:1 methylene chloride/ethyl acetate mixture) to provide 27.9 g of a white solid. Yield: 72%. 1 H NMR (CDCl3): delta7.55-7.18 (m, 10H), 5.55 (d, J=7 Hz, 1H), 5.08 (s, 2H), 4.73-4.60 (m, 1H), 3.55-3.30 (m, 2H). IR (KBr): 3304, 3035, 1687, 1532, 736 cm-1. MS(FD): m/e 332, 288, 271, 181. Analysis for C17 H17 NO4 S: Calcd: C, 61.61; H, 5.17; N, 4.23; Found: C, 61.69; H, 5.22; N, 4.47. |
72% | With acetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; | A. (2R)-2-N(benzyloxycarbonyl)amino-3 -phenylthio propanoic acid The desired subtitled intermediate was prepared substantially in accordance with the procedure detailed in Procedure 3A, using 13.1 mL (127 mmol) of thiophenol, 4.6 g (117 mmol) of a 60% sodium hydride solution and 25.6 g (116 mmol) of (L)-N(benzyloxycarbonyl)serine beta-lactone in 450 mL of tetrahydrofuran to provide a residue. This residue was purified using flash chromatography (gradient eluent of 0-2% acetic acid in a 4:1 methylene chloride/ethyl acetate mixture to provide 27.9 g of a white solid. Yield: 72%. 1 H NMR CDCl3): delta7.55-7.18 (m, 10H), 5.55 (d, J=7 Hz, 1H), 5.08 (s, 2H), 4.73-4.60 (m, 1H), 3.55-3.30 (m, 2H). IR (KBr): 3304, 3035, 1687, 1532, 736 cm1. MS (FD): m/e 332, 288, 271, 181. Analysis for C17 H17 NO4 S: Calcd: C, 61.61; H, 5.17; N, 4.23; Found: C, 61.69; H, 5.22; N, 4.47. |
72% | With acetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; | A. 2R-2-N(Benzyloxycarbonyl)amino-3-phenylthio propanoic acid The desired subtitled intermediate was prepared substantially in accordance with the procedure detailed in Procedure 2A, using 13.1 mL (127 mmol) of thiophenol, 4.6 g (117 mmol) of a 60% sodium hydride solution and 25.6 g (116 mmol) of L-N(benzyloxycarbonyl)serine beta-lactone in 450 mL of tetrahydrofuran to provide a residue. This residue was purified using flash chromatography (gradient eluent of 0-2% acetic acid in a 4:1 methylene chloride/ethyl acetate mixture) to provide 27.9 g of a white solid. Yield: 72%. 1 H NMR (CDCl3): delta7.55-7.18 (m, 10H), 5.55 (d, J=7 Hz, 1H), 5.08 (s, 2H), 4.73-4.60 (m, 1H), 3.55-3.30 (m, 2H). IR (KBr): 3304, 3035, 1687, 1532, 736 cm-1. MS(FD): m/e 332, 288, 271, 181. Analysis for C17 H17 NO4 S: Calcd: C, 61.61; H, 5.17; N, 4.23; Found: C, 61.69; H, 5.22; N, 4.47. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 4-2. Z-Dap(Me)-OH hydrochloride salt (AA4-3).; A dry 500 mL round bottom flask under nitrogen atmosphere was charged with 60 ml of anhydrous CH3CN followed by N-methyl trimethylsilylamine (AA4-0, synthesized as described in Step 4-6, 1.9 mL, 13.3 mmol, 1.5 eq.). A solution of AA4-2 (2.0 g, 8.9 mmol, 1.0 eq) in 40 mL of anhydrous MeCN was added to the flask and the mixture was stirred under nitrogen at room temperature until TLC indicates no trace of starting material [hexanes:EtOAc (60:40), UV, CMA]. The mixture was then cooled to 0 C. and 180 mL of cold 0.1 M HCl added. The mixture was allowed to warm to room temperature and stirred for 30 min. The solvent was evaporated under reduced pressure, the resulting residue azeotroped twice with toluene then dried under vacuum to give 3.1 g of crude AA4-3 as a light yellow foam. The crude material was used without any purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In acetonitrile; at 50℃; for 24h; | A suspension of (S) -benzyl 2 -oxooxetan-3 -ylcarbamate (0.67 g, 3.03 mmol} , and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 ?iL) was heated at 500C for 24h. The mixture was cooled' to rt overnight and the solid filtered to afford (S) -2- (benzyloxycarbonylamino) -3- (lH-pyrazol-1- yl) propanoic acid (330.1 mg) . The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg) . Total yield 370.4 mg (44%) . m.p. 165.5 - 168C. lit m.p. 168.5 - 169.5 [Vederas et al . J. Am. Chem, Soc. 1985, 107, 7105] . 1HNMR (400 MHz, CD3OD) 5 7.51 {d, .J = 2.0, IH), 7.48 (s, J = 1.5 Hz, IH), 7.24 - 7.34 (m,5H), 6.23 m, IH), 5.05 (d, 12.7 H, IH), 5.03 (d, J = 12.7 Hz, IH), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, IH) . LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H) + . |
44% | In acetonitrile; at 50℃; for 24h; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 500C for 24h.The mixture was cooled to rt overnight and the solid filtered to afford (S)~2- (benzyloxycarbonyIamino)-3-(lH-pyrazol-l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 1680C. lit m.p. 168.5 - 169.5 [Vederas et al., J. Am. Chem. Soc, 107:7105 (1985)]. 1H NMR (400 MHz, CD3OD) delta 7.51 (d, J - 2.0, IH), 7.48 (s, J = 1.5 Hz,IH), 7.24 - 7.34 (m, 5H)3 6.23 m, IH), 5.05 (d, 12.7 H, IH), 5.03 (d, J = 12.7 Hz, IH), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, IH). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+ |
44% | In acetonitrile; at 20 - 50℃; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 500C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2-(benzyloxycarbonylamino)-3-(lH-pyrazol-l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN(ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168C. Ht m.p. 168.5 ~ 169.5 [Vederas et al, J. Am. Chem. Soc, 107:7105 (1985)]. 1H NMR (400 MHz, CD3OD) 5 7.51 (d, J = 2.0, IH), 7.48 (s, J = 1.5 Hz9 IH), 7.24 - 7.34 (m, 5H), 6.23 m, IH), 5.05 (d, 12.7 H, IH)5 5.03 (d, J = 12.7 Hz, IH), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, IH). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+. |
44% | In acetonitrile; at 20 - 50℃; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2- (benzyloxycarbonylamino)-3-(lH-pyrazol-l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168C. lit m.p. 168.5 - 169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105]. ¾ NMR (400 MHz, CD3OD) delta 7.51 (d, J = 2.0, 1H), 7.48 (s, J = 1.5 Hz, 1H), 7.24 - 7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d, J = 12.7 Hz, 1H), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, 1H). LCMS: Anal. Calcd. forCi4H15 304: 289; found: 290 (M+H)+. |
44% | In acetonitrile; at 50℃; for 24h; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2- (benzyloxycarbonylamino)-3-(l H-pyrazol- l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168 C. lit m.p. 168.5 - 169.5 [Vederas et al, J. Am. Chem. Soc, 107:7105 (1985)]. 1H NMR (400 MHz, CD3OD) delta 7.51 (d, J = 2.0, 1H), 7.48 (s, J = 1.5 Hz, 1H), 7.24 - 7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d, J = 12.7 Hz, 1H), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4:289; found: 290 (M+H)+. |
44% | In acetonitrile; at 20 - 50℃; | Step 1. Preparation of (S)-2-(benzyloxycarbonylamino)-3 -( 1 H-pyrazol- 1 -yl)propanoic acid (cj-31).CbzHN C02Hcj-31[00229] A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2- (benzyloxycarbonylamino)-3-(l H-pyrazol- l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168 C. lit m.p. 168.5 - 169.5 [Vederas et al, J. Am. Chem. Soc, 107:7105 (1985)]. 'H NMR (400 MHz, CD3OD) delta 7.51 (d, J = 2.0, 1H), 7.48 (s, J = 1.5 Hz, 1H), 7.24 - 7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d, J = 12 Hz, 1H), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, 1H). LC-MS: Anal. Calcd. for C^H^CY 289; found: 290 (M+H)+. Step 2. Preparation of (S)-2-(methoxycarbonylamino)-3-(lH-pyrazol-l-yl)propanoic acid (Cap- 129). |
44% | In acetonitrile; at 20℃; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2- (benzyloxycarbonylamino)-3-(lH-pyrazol-l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168C. lit m.p. 168.5 - 169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 707, 7105]. 1HNMR (400 MHz, CD3OD) delta 7.51 (d, J = 2.0, 1H), 7.48 (s, J = 1.5 Hz, 1H), 7.24 - 7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d, J = 12.7 Hz, 1H), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, 1H). LCMS: Anal. Calcd. forC14H15N3O4: 289; found: 290 (M+H)+. |
44% | In acetonitrile; at 50℃; for 24h; | Step 1. Preparation of (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (cj-31) A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C. for 24 h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5-168 C. lit m.p. 168.5-169.5 Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105. 1H-NMR (400 MHz, CD3OD) delta 7.51 (d, J=2.0, 1H), 7.48 (s, J=1.5 Hz, 1H), 7.24-7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d, J=12.7 Hz, 1H), 4.59-4.66 (m, 2H), 4.42-4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+. |
44% | In acetonitrile; at 20 - 50℃; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C. for 24 h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%).m.p. 165.5-168 C. lit m.p. 168.5-169.5 Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105.1HNMR (400 MHz, CH3OD) delta 7.51 (d, J=2.0, 1H), 7.48 (s, J=1.5 Hz, 1H), 7.24-7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d, J=12.7 Hz, 1H), 4.59-4.66 (m, 2H), 4.42-4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+. |
44% | In acetonitrile; at 50℃; for 24h; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 500C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2- (benzyloxycarbonylamino)-3-(lH-pyrazol-l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168C. lit m.p. 168.5 - 169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 707, 7105]. 1HNMR (400 MHz, CD3OD) delta 7.51 (d, J = 2.0, IH), 7.48 (s, J = 1.5 Hz, IH), 7.24 - 7.34 (m, 5H), 6.23 m, IH), 5.05 (d, 12.7 H, IH), 5.03 (d, J = 12.7 Hz, IH), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, IH). LCMS: Anal. Calcd. for Ci4H15N3O4: 289; found: 290 (M+H)+. |
44% | In acetonitrile; at 50℃; for 24h; | Step 1. Preparation of (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (cj-31). A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C. for 24 h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5-168 C. lit m.p. 168.5-169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105]. 1HNMR (400 MHz, CD3OD) delta 7.51 (d, J=2.0, 1H), 7.48 (s, J=1.5 Hz, 1H), 7.24-7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7H, 1H), 5.03 (d, J=12.7 Hz, 1H), 4.59-4.66 (m, 2H), 4.42-4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+. |
In acetonitrile; for 16h; | Example D; Synthesis of2(S)-benzyloxycarbonylamino-3-pyrazol-l-ylpropionic acid; The title compound was prepared by treating jS-benzyloxycarbonylserine-beta-lactone with pyrazole in acetonitrile at 60 0C for 16 h {see J. Am. Chem. Soc, 1985, 107, 7105-7109).Following the procedure described above, but substituting pyrazole with [1.2.4]-triazole and [1.2.3]-triazole provided 2()S)-benzyloxycarbonylamino-3-[1.2.4]-triazol-l-ylpropionic acid and 2(5)-benzyloxycarbonylamino-3-[l .2.3]-triazol-l-ylpropionic acid respectively. | |
In acetonitrile; at 20 - 50℃; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 50 C. for 24 h. The mixture was cooled to rt overnight and the solid filtered to afford (S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5-168 C. lit m.p. 168.5-169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105]. 1H NMR (400 MHz, CD3OD) delta7.51 (d, J=2.0, 1H), 7.48 (s, J=1.5 Hz, 1H), 7.24-7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7H, 1H), 5.03 (d, J=12.7 Hz, 1H), 4.59-4.66 (m, 2H), 4.42-4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+. | |
In acetonitrile; at 60℃; for 16h; | The title compound was prepared by treating S-benzyloxycarbonylserine-beta-lactone with pyrazole in acetonitrile at 60 C for 16 h (see J. Am. Chem. Soc., 1985, 107, 7105- 7109). | |
In acetonitrile; at 60℃; for 16h; | Example G; Synthesis of 2(S)-benzyloxycarbonylamino-3-pyrazol-1-yl propionic acid; The title compound was prepared by treating S-benzyloxycarbonylserine-p-lactone with pyrazole in acetonitrile at 60 C for 16 h (see J. Am. Chem. Soc., 1985,107, 7105-7109). Following the procedure described above, but substituting pyrazole with 1,2,4-triazole and 1,2,3-triazole provided 2(5)-benzyloxycarbonylamino-3-[l,2,4]-triazol-l-ylpropionic acid and 2(S)-benzyloxycarbonylamino-3-[l,2,3]-triazol-l-ylpropionic acid respectively. | |
In acetonitrile; at 60℃; for 16h; | Example F Synthesis of 2 (S)-BENZYLOXYCARBONYLAMINO-3-PYRAZOL-1-YLPROPIONIC acid The title compound was prepared by treating S-BENZYLOXYCARBONYLSERINE-ss-LACTONE with pyrazole in acetonitrile at 60 C for 16 h (see J. Am. Chem. Soc., 1985, 107, 7105-7109). Following the procedure described above, but substituting pyrazole with 1,2, 4-triazole and 1,2, 3-triazole provided 2 (S)-BENZYLOXYCARBONYLAMINO-3- [1, 2, 4]-TRIAZOL-1-YLPROPIONIC acid and 2 (S)-BENZYLOXYCARBONYLAMINO-3- [1, 2, 3]-TRIAZOL-1-YLPROPIONIC acid respectively. | |
In acetonitrile; at 55℃; for 24h; | Step 2: N-(Benzyloxycarbonyl)-L-serine p-lactone (1.5 g, 6.8 mmol), pyrazole (0.49 g, 7.2 mmol), and acetonitrile (25 mL) are combined and stirred for 12 h at 55 C. An additional charge of pyrazole (0.25 g, 3.6 mmol) is added to the reaction and stirred for an additional 12 h. The reaction mixture is concentrated in vacuo. The residue is dissolved in sodium hydroxide solution (1 M), and washed with DCM. The aqueous solution was neutralized with HCl solution (1 M) to precipitate N-(benzyloxycarbonyl)-p-(pyrazol-1-yl)-L-alanine (1.1 g). The compound is used in the next reaction without further purification. | |
In acetonitrile; at 60℃; for 16h; | Example D; Synthesis of 2(S)-benzyloxycarbonylamino-3-pyrazol-l-ylpropionic acid The title compound was prepared by treating S-benzyloxycarbonylserine-beta-lactone with pyrazole in acetonitrile at 60 0C for 16 h (see J. Am. Chem. Soc, 1985, 107, 7105-7109). | |
In acetonitrile; at 60℃; for 16h; | Reference G Synthesis [OF 2 (S)-BENZYLOXYCARBONYLAMINO-3-PYRAZOL-1-YLPROPIONIC] acid The title compound was prepared by [KEATING (USD-BENZYLOXYCARBONYLSERINE-ss-LACTONE] with pyrazole in acetonitrile at [60 C] for 16 h (see J. [AM.] Chem. [SOC.,] 1985, [107,] 7105-7109). Following the procedure described above, but substituting pyrazole with 1,2, 4-triazole and [1,] 2, 3-triazole provided 2 [(S)-BENZYLOXYCARBONYLAMINO-3- [1,] 2, [4]-TRIAZOL-1-YLPROPIONIC] acid and 2 [(S)-BENZYLOXYCARBONYLAMINO-3- [1,] 2, [3]-TRIAZOL-1-YLPROPIONIC] acid respectively. | |
43.5 mg | In acetonitrile; at 50℃; for 24h; | A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol)in CH3CN (12 mL) was heated at 50 C for 24h. The mixture was cooled to rt overnight and the solid filtered to afford(S)-2-(benzyloxycarbonylamino)-3-(1H-pyrazol-1-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuoand then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg(44%). m.p. 165.5 - 168C. lit m.p. 168.5-169.5 [Vederas et al. J. Am. Chem. Soc. 1985, 107, 7105]. 1HNMR (400 MHz,CD3OD) delta 7.51 (d, J = 2.0, 1H), 7.48 (s, J = 1.5 Hz, 1H), 7.24 - 7.34 (m, 5H), 6.23 m, 1H), 5.05 (d, 12.7 H, 1H), 5.03 (d,J = 12.7 Hz, 1H), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, 1H). LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H)+. |
In acetonitrile; at 50℃; for 24h; | Step 1. Preparation of (S)-2-(benzyloxycarbonylamino)-3 -(I H-pyrazol- 1- yl)propanoic acid (cj-31).A suspension of (S)-benzyl 2-oxooxetan-3-ylcarbamate (0.67 g, 3.03 mmol), and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 mL) was heated at 500C for 24h. The <n="105"/>mixture was cooled to rt overnight and the solid filtered to afford (S)-2- (benzyloxycarbonylamino)-3-(lH-pyrazol-l-yl)propanoic acid (330.1 mg). The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg). Total yield 370.4 mg (44%). m.p. 165.5 - 168C. lit m.p. 168.5 - 169.5 Vederas et al. J. Am. Chem. Soc. 1985, 707, 7105.1HNMR (400 MHz, CD3OD) 8 7.51 (d, J = 2.0, IH), 7.48 (s, J = 1.5 Hz, IH), 7.24 - 7.34 (m, 5H), 6.23 m, IH), 5.05 (d, 12.7 H, IH), 5.03 (d, J = 12.7 Hz, IH), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, IH). LCMS: Anal. Calcd. for Ci4H15N3O4: 289; found: 290 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With triphenylphosphine; In acetonitrile; | a L-2-Amino-3-phenylaminoethylpropionic Acid 54.8 g (0.209 mol) of triphenylphosphine were suspended in 600 ml of acetonitrile and, with exclusion of moisture, cooled to -35 C. to -45 C. At this temperature, 36.4 g (0.209 mol) of diethyl azodicarboxylate were then added dropwise over a period of 50 min. The mixture was stirred at -35 C. for another 15 min. A solution of 50 g (0.209 mol) of N-benzyloxycarbonyl-L-serine in 500 ml of acetonitrile was added dropwise to this mixture, the temperature being kept below -35 C. The mixture was then allowed to react at 5 C. for another 12 h and warmed to RT. The reaction solution was freed from solvent under reduced pressure and the crude product was purified by medium pressure chromatography over silica gel (DCM/AcCN: 25/1). Removal of the solvent gave 20.8 g (yield 45%) of pure N-benzyloxy-carbonyl-L-serine-beta-lactone (see also Org. Synth. 1991 (70) 1ff.) in fine needles. Empirical formula C11H11NO4; M.W.=221.2; MS (M+H) 222.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.475 g (55%) | In chloroform; acetonitrile; | EXAMPLE 156 Benzyloxycarbonyl-(1-Imidazolyl)Alanine Methyl Ester N-Benzyloxycarbonyl-L-serine lactone (1.972 g, 8.91 mmol, Arnold et al., J. Am. Chem. Soc., 1987, 109, 4649) and imidazole (1.25 g, 18.4 mmol) were stirred in acetonitrile (40 mL) for 24 h at room temperature. The mixture was then cooled (0 C., bath temperature), treated with a solution of diazomethane in ether until the persistence of yellow color, and then purged with a steady stream of nitrogen while allowing the mixture to reach room temperature. The mixture was evaporated to a viscous oil and chromatographed on silica gel eluding with 1.8%-2.0% methanol in chloroform to give 1.475 g (55%) of an orange oil: TLC (15% methanol/85% chloroform) Rf =0.49; 1 H NMR (CDCl3) 7.03 (s, 1H), 6.78 (s, 1H), 5.44 (d, 1H), 5.14 (s, 2H), 4.70-4.59 (m, 1H), 4.49-4.38 (m, 2H), 3.79 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | Step 1. Sodium hydride (60% in mineral oil, 85mg, 2.08mmol) was added to a mixture of thymine (265mg, 2.28mmol) and dry DMF (19ml). Reaction mixture was stirred at room temperature for 2h and cooled to -78C. A solution of (S)-(2-oxooxetan-3-yl)carbamate (460mg, 2.08mmol) in DMF (5ml) was added dropwise within 1h. The cooling bath was removed and the reaction mixture was stirred at room temperature for 18h. Volatiles were distilled off under reduced pressure. The residue (1.255g) was dissolved in water and acidified with 2M HCl to pH 2 and extracted with ethyl acetate (3×80ml). The extracts were combined and dried (MgSO4). Volatiles were distilled off under reduced pressure and the residue (0.74g) was subjected to column chromatography (DCM:MeOH:AcOH, 97:3:0.1, v/v/v then 90:10:0.1, v/v/v) to give (S)-2-(((benzyloxy)carbonyl)amino)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acid 2c as a white solid 0.265g (36%). [alpha] -85.1 (c 0.20 in MeOH). 1H NMR (500MHz, DMSO-d6): delta 1.68 (s, 3H); 3.58 and 4.24 (AB part of ABX system, 2JAB 13.6 3JAX 10.1Hz 3JBX 4.7Hz, 2H), 4.30-4.35 (X part of ABX system, 1H); 4.97 and 5.02 (AB quartet, 2JAB 10.0, 2H); 7.27-7.35 (m, 6H); 7.48 (br s, 1H); 11.25 (s, NH, 1H). 13C NMR (125MHz, DMSO-d6): delta 12.0; 48.7; 52.7; 65.4; 107.8; 127.4; 127.8; 128.4; 137.0; 142.0; 150.9; 156.0; 164.3; 171.3. Step 2. Thionyl chloride (0.1ml, 1.37mmol) was added drop by drop to a mixture of (S)-2-(((benzyloxy)carbonyl)amino)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acid 2c (85mg, 0.24mmol) and ethanol (8ml) cooled in ice-water bath (-5÷0C). The mixture was stirred at the cooling bath for 30min. The bath was removed and the mixture was left at room temperature overnight. Volatiles were distilled off under reduced pressure. The residue was dissolved in AcOEt (30ml) and washed with aqueous saturated solution of NaHCO3 (15ml) and water (15ml), brine (15ml) and dried (MgSO4). Volatiles were distilled off under reduced pressure to give (S)-ethyl 2-(((benzyloxy)carbonyl)amino)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate 2a as a white solid (75mg, 83%). [alpha] -85.6 (c 0.11 in MeOH). 1H NMR (500MHz, DMSO-d6): delta 1.16 (t, 3JHH 7.1Hz, 3H); 1.70 (d, 4JHH 1.5Hz, 3H), 3.68 and 4.16 (part AB of ABX system, 2JAB 13.8Hz, 3JAX 9.0Hz, 3JBX 5.5Hz, 2H), 4.10 (q, 3JHH 7.1Hz, 2H); 4.38-4.43 (partXof ABX system, 1H); 5.01 and 5.04 (AB quartet, 2JAB 12.5Hz, 2H); 7.30-7.38 (m, 6H); 7.84 (d, 4JHH 8.5Hz, 1H, NH); 11.31 (br s, 1H, NH). 13C NMR (125MHz, DMSO-d6): delta 11.9, 13.9, 47.9, 52.2, 61.10, 65.6, 108.2, 127.5, 127.8, 128.4, 136.8, 141.7, 150.9, 156.0, 164.2, 169.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Under N2, in a RB flask was added <strong>[657-36-3]4-(trifluoromethyl)piperidine</strong> (2.97 g, 19.39 mmol) and (Z)-trimethylsilyl N-(trimethylsilyl)acetimidate (2.371 mL, 9.70 mmol) in acetonitrile (80 mL). The mixture was stirred at rt for 5 hours, followed by addition of (S)benzyl (2-oxooxetan-3-yl)carbamate (3.3 g, 14.92 mmol) and continued to stir overnight. The mixture was concentrated and the residue was dissolved in ether, extracted w/ aq. 1 N HCI. The aqueous layer was adjusted to PH6.6 w/ 6N NaOH in an ice-bath and extracted w/ EtOAc. The organic layer was dried over Na2SO4, concentrated to give (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(trifluoromethyl)piperidin-1 -yl)propanoic acid (4.62 g, 12.34 mmol, 83 percent yield). LCMS: M+1 = 375.2, 0.68mm |
Tags: 26054-60-4 synthesis path| 26054-60-4 SDS| 26054-60-4 COA| 26054-60-4 purity| 26054-60-4 application| 26054-60-4 NMR| 26054-60-4 COA| 26054-60-4 structure
[ 1676-81-9 ]
Methyl ((benzyloxy)carbonyl)-L-serinate
Similarity: 0.97
[ 14464-15-4 ]
Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate
Similarity: 0.97
[ 28819-05-8 ]
(S)-Methyl 2-(((benzyloxy)carbonyl)amino)propanoate
Similarity: 0.97
[ 21209-51-8 ]
Benzyl ((benzyloxy)carbonyl)-L-serinate
Similarity: 0.95
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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.
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