Structure of 124-42-5
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CAS No. : | 124-42-5 |
Formula : | C2H7ClN2 |
M.W : | 94.54 |
SMILES Code : | CC(N)=N.[H]Cl |
MDL No. : | MFCD00013016 |
InChI Key : | WCQOBLXWLRDEQA-UHFFFAOYSA-N |
Pubchem ID : | 67170 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 5 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.5 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 24.99 |
TPSA ? Topological Polar Surface Area: Calculated from |
49.87 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.03 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.74 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.03 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.59 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.04 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.45 |
Solubility | 33.9 mg/ml ; 0.359 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.63 |
Solubility | 22.2 mg/ml ; 0.235 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
0.18 |
Solubility | 143.0 mg/ml ; 1.51 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.86 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.55 |
* 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 |
---|---|---|
81% | With copper(l) iodide; TPGS-450-M; caesium carbonate In water at 20℃; for 12 h; Inert atmosphere; Green chemistry | General procedure: A two-neck round bottom flask was charged with a magnetic stirrer, evacuated and backfilled with nitrogen. Substituted 2-halobenzoic acid (1, 0.5 mmol) and amidine hydrochloride (2, 0.75 mmol) or bis(guanidine) sulphate (2, 0.38 mmol) in 2 wt percent TPGS-750-M (3 mL) were added under nitrogen atmosphere. After a 10-min stirring, Cs2CO3 (1 mmol, 326 mg) was added to the flask. 15 min later, CuI (0.1 mmol, 19 mg) was added to the flask. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for 12 h (see Table 3 in text). After completion of the reaction, the mixture was extracted with EtOAc (1 mL), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1 to 1:1) as eluent to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of sodium ethoxide (1.15g, 50mmol), and acetamidine hydrochloride (4.7g, 50mmol) in ethanol solution (60mL) was stirred at room temperature for 1h. After this, the reaction mixture was filtered out affording filtrate. Then 2-(ethoxymethylene)malononitrile (6.1g, 50mmol) was added to the filtrate, and the mixture was stirred at room temperature for 3h. After this, the reaction mixture was filtered and washed with 10mL ethanol and dried to give the desired compound 4-amino-2-methylpyrimidine-5-carbonitrile 1a, which was used directly for the next step. Under the same condition, the intermediate compounds 1b and 1c were also prepared. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol; for 6h;Heating / reflux; Argon atmosphere; | 745mg, 5.17mmol) was dissolved in ethanol (15ml). Acetamidine hydrochloride (489mg, 5.17mmol) and sodium ethoxide in ethanol (0.41ml, 5.17mmol) were added and the mixture heated under argon at reflux for 6 hours and then overnight. The solvent was evaporated and the residue was treated with water (50ml) and extracted with diethyl EPO <DP n="34"/>ether (4 x 30ml). The diethyl ether layers were combined, dried over magnesium sulphate, filtered and evaporated. The crude product was purified using silica gel chromatography, eluting with a mixture of ethyl acetate and pentane (20-50percent) to afford the product (D33); MS (ES+) m/e 167 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium hydroxide; In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; | EXAMPLE 2 Acetamidine hydrochloride (9.5 g) was added to a predissolved solution of methanol (50 mL) and KOH pellets (6.8 g) at 10° C. It was then dropped into a solution of 11.4 g of dimethyl N-cyanoimidocarbonate and 40 mL of methanol at 10° C. After the addition, the reaction mixture was stirred at 25° C. for 2 hours onto 40 mL of ice water. The solid crystals were collected by filtering and washing with water and methanol. After drying at 70° C. overnight, 11.8 g (84percent yield) of 2-methyl-4-amino-6-methoxy-1,3,5-triazine was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.7% | As shown in Scheme 1, to a 250 mL round-bottomflask, trifluoroacetoacetate (0.05 mol), acetamidine hydrochloride (0.05 mol), sodium methoxide (0.075 mol),and ethanol (100 mL) were added and refluxed for 10 h. After that, the mixture was acidified with 1 mol/L HCl to pH 7. The crude products were extracted using ethylacetate to produce intermediate 1. Then, intermediate 1(0.05 mol), POCl3(0.1 mol), and CH3CN(120 mL) wereadded to a 250 mL round-bottom flask to react for 0.5 hat a reflux temperature, and then, diisopropylethylamine(0.06 mol) was added dropwise. After continuously refluxingfor 8 h, excess POCl3and CH3CNwere distilled, andthen, ice water mixture (60 mL) was added. Finally, themixture was alkalify with 5 mol/L to pH 9 and extractedusing CH2Cl2to give intermediate 2 (Xie et al. 2013).2-Methyl-6-(trifluoromethyl)pyrimidin-4-ol (1) White crystals;yield 85.7%; m.p. 140-142 C; 1H NMR (DMSO-d6,500 MHz, ppm) delta: 13.03 (s, 1H, pyrimidine-OH), 6.68 (s,1H, pyrimidine-H), 2.36 (s, 3H); 13C NMR (DMSO-d6,125 MHz, ppm) delta: 162.78, 162.16, 152.03 (q, J = 35.5 Hz),122.33, 120.15, 111.12, 21.74. | |
With sodium methylate; In ethanol; water; | (1) To a suspension of ethyl trifluoroacetoacetate (18.4g, 0.1mol) and acetamidine hydrochloride (9.5g, 0.1mol) in ethanol (100ml) was dropwise added 28% sodium methylate (19.3g, 0.1mol) under cooling with ice. The resulting mixture was stirred at room temperature for 1 hour, and further refluxed for 12 hours. After cooling, the reaction mixture was evaporated, water (150ml) was added to the residue, then the mixture was neutralized with concentrated hydrochloric acid. The crystal separated was collected by filtration, washed with water, and dried to give 4-hydroxy-2-methyl-6-trifluoromethylpyrimidine (9.8g). m.p.:141-143 ØC 1H-NMR(CDCl3) delta 2.57(3H, s), 6.72(1H, s), 13.4(1H, br s). 1H-NMR(DMSO-d6) delta 2.36(3H, s), 6.67(1H, s). 19F-NMR(DMSO-d6) delta -72.13. | |
To 12.6 g of sodium methoxide (28% methanol solution), 3.1 g of acetoamidine hydrochloride and 3 g of 4,4,4- trifluoro-3-oxo-butanoic acid ethyl ester were added. This mixture was stirred at 800C for 20 hours. The reaction mixture was left standing to cool and then concentrated. To the residue, 10% hydrochloric acid was added, followed by extraction three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was washed with hexane to obtain 2.4 g of 2-methyl-6-trifluoromethylpyrimidin-4-ol . 2-methyl-6-trifluoromethylpyrimidin-4-ol1H-NMR (DMSO-d6): 2.35(s,3H), 6.68(s,lH), 13.02(bs,lH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Acetamidine hydrochloride (413 mg, 4.4 mmol) was added to a solution of sodium ethoxide (594 mg, 2.0 equiv.) in ethanol (8 mL). After stirring for half an hour at room temperature, the resultant sodium chloride was removed by filtration. The filtrate was added to ethyl 2-cyano- 4,4-diethoxybutanoate (1.0 g, 4.4 mmol) and the mixture was refluxed for 5 hours. Most of the solvent was removed and the remaining slurry was <n="73"/>dissolved in ice water, and extracted with ethyl acetate. The extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (100percent methanol). The desired product was obtained as a red solid (421 mg, 40percent). MS: (M + H)/z = 242. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-Methyl-4-hydroxypyrrolo[2,3-d]pyrimidine (3).; Acetamidine hydrochloride (2, 0.05 mol, 4.7 g) was added to the 0.1 M sodium ethoxide solution (75 ml) and kept stirring under room temperature for 0.5 h. After removing the formed sodium chloride by filtration, the filtrate was added the ethyl alpha-cyano-gamma,gamma-diethoxybutyrate (1, 0.05 mol, 11.5 g) and the solution was heated under reflux for 5 h. After the removal of most solvent under vacuum, acetic acid was added to adjust the pH to 7.0 and 10.8 g precipitation as white powder. Ethanol (110 ml) with concentrated sulfuric acid (2 ml) was added to the collected powder and was refluxed for 2 h. By the end of the reaction an equal volume of water was added and kept at 4° C. overnight. The pyrrolopyrimidine 3 precipitated as white powder (2.1 g) was used for next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium ethanolate; In ethanol; for 3h;Reflux; | The synthesis of target compound 3 (Scheme 1C), started with the synthesis of a reported method for compound i.?3 2-Bromo-i,i-diethoxyethane (compound 10) was reacted with ethyl2-cyanoacetate to obtain compound 1 lwhich was cyclized to compound 12 using acetamidine hydrochloride under basic conditions. Chlorination of compound 12 using POC13 provided compound 13 in 80% yield. Displacement of the chloride of compound 13 with 4-methoxy-N- methyl aniline (compound 14) and catalytic amounts of HC1 in isopropanol, provided compound1. Methylation of compound 1 with Mel under basic conditions afforded compound 3 in 85% yield. The synthesis of target compound 5 (Scheme 1C), involved N-formylation of 4-methoxy- 2-methylanline (compound 15) to afford compound 16 in 70% yield. LAH reduction of compound 16 provided substituted aniline compound 17. Displacement of the chloride of compound 13 with anilines (compounds 15 and 17) and catalytic amounts of HC1 in isopropanol provided compounds 4 and 5 (75% and 70% respectively). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride; In 1,4-dioxane; for 14h;Reflux; | Example 2; 4- Amino-5-cyano-2-methylpyrimidine (I, R = methyl); To a solution of sodium 2,2-dicyanoethenolate (2.0 g, 16.9 mmol, prepared according to Example 1) in 1,4-dioxane (8 mL) was added acetamidine hydrochloride (1.98 g, 20.3 mmol) and acetic anhydride (1.91 mL). The reaction mixture was heated under reflux for 14 hours. Afterwards the solvent was completely evaporated and the resulting solid was taken up in hot water (80 C). The suspension was cooled to room temperature under stirring, then filtered and washed with water. Drying of the residue under reduced pressure at 60 C gave 4-amino-5- cyano-2-methylpyrimidine as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 3; 4-Amino-5-cyano-2-methylpyrimidine (I, R = methyl); Reagent 1 :To a solution of sodium 2,2-dicyanoethenolate (7.6 g, 70 mmol, prepared according to Example 1) in dichloromethane (45.6 mL) was added acetyl chloride (5.3 g, 70 mmol) within 30 min. After complete addition the mixture was heated under reflux (about 43 C) for 1.5 h, then cooled to about 0 C and afterwards stirred for additional 1.5 h. The mixture was used as reagent 1.Reagent 2:Acetamidine hydrochloride (18.42 g, 0.19 mol) was dissolved in ethanol (37.5 mL). Sodium methoxide (10.94 g, 0.2 mol) was added within 5 min and the reaction mixture was stirred for about 30 min. The resulting white suspension was filtered and the filter cake washed with ethanol. The filtrate comprising the acetamidine was used as reagent 2.Within 45 min Reagent 2 was added dropwise to Reagent 1 at 0 C and stirred for additional 2.5 h. The resulting orange suspension (104 g) was concentrated by evaporating the solvent under reduced pressure (50 C/65 kPa (650 mbar)) to about ½ volume (28.8 g). Water (35 mL) was added to the residue to obtain an orange suspension which was filtrated with a P3 frit. The filter cake was washed four times with water (10, 20, 25, and 30 mL, wherein the first 10 mL where prior used to wash the vessel). Finally the filter cake was dried at 1.7 kPa (17 mbar) and 45 C to obtain a yellow solid.Yield: 3.65 g (42.2%, based on sodium 2,2-dicyanoethenolate) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium methylate; In methanol; at 0℃; for 0.333333h;Product distribution / selectivity; | Sodium methoxide solution (26.5 g, 0.49 mol) in methanol (400 mL) was cooled down to 0C. After acetamidine hydrochloride (46.3 g, 0.49 mol) was added in portions, the mixture was stirred at 0C for 20mins and then filtrated. The filtrate was poured into the above oily product and stirred at 25C for 12 hours. The produced mixture was filtrated, washed with methanol (3x20 mL) and dried under vacuum (50C, 2 hours, -O.lMPa) to obtain 51.8 g white solid with 65% yield (based on cyanoacetamide) and 99% purity (GC).1H-NMR (DMSO, 400MHz): 8.59 (s, 1H), 1.78 (br s, 2H), 2.37 (s, 1H), 13C-NMR (DMSO, 400MHz): 170.5, 162.8, 151.5, 116.1, 87.1.m/z (GC-MS), 134 (M+), 94, 66 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium methylate; In methanol; at 0℃; for 0.333333h; | Sodium methoxide solution (25.4 g, 0.47 mol) in methanol (400 mL) was cooled down to 0C. After acetamidine hydrochloride (44.4g, 0.47mol) was added in portions, the mixture was stirred at 0"C for 20mins and then filtrated. The filtrate was poured into the above oily product and stirred at 25 C for 12 hours. The produced mixture was filtrated, washed with methanol (3x20mL) and dried under vacuum (50C, 2 hours, -O.lMPa) to obtain 50.2 g white solid with 63% yield (based on cyanoacetamide) and 98% purity (GC).1H-NMR and MS are identical with Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With caesium carbonate; copper(I) bromide; In dimethyl sulfoxide; at 120℃; for 3h; | A solution of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> (1 g), acetamidine hydrochloride (714 mg), cesium carbonate (5 g) and copper (I) bromide (36 mg) in dry dimethyl sulfoxide (25 mL) was stirred at 120 C. for 3 h. The mixture was chilled, diluted with EtOAc (200 mL) and washed with water. The organic layer was dried and the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiO2, 150 g, DCM/MeOH) to yield the desired product (36% yield). LC-MS (Method 1): m/z [M+H]+=252.1 (MW calc.=252.11); Rt=3.5 min. |
36% | With caesium carbonate; copper(I) bromide; In dimethyl sulfoxide; at 120℃; for 3h; | Intermediate 28a) A solution of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> (1 g), acetamidine hydrochloride (714 mg), cesium carbonate (5 g) and copper (I) bromide (36 mg) in dry dimethyl sulfoxide (25 mL) was stirred at 120 C for 3 h. The mixture was chilled, diluted with EtOAc (200 mL) and washed with water. The organic layer was dried and the volatiles were removed under reduced pressure. The residue was purified by chromatography (Si02, 150 g, DCM/ MeOH) to yield the desired product (36% yield). LC-MS (Method 1): m/z [M+H]+ = 252.1 (MW calc. = 252.11 ); R, = 3.5 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(l) iodide; TPGS-450-M; caesium carbonate; In water; at 20℃; for 12h;Inert atmosphere; Green chemistry; | General procedure: A two-neck round bottom flask was charged with a magnetic stirrer, evacuated and backfilled with nitrogen. Substituted 2-halobenzoic acid (1, 0.5 mmol) and amidine hydrochloride (2, 0.75 mmol) or bis(guanidine) sulphate (2, 0.38 mmol) in 2 wt % TPGS-750-M (3 mL) were added under nitrogen atmosphere. After a 10-min stirring, Cs2CO3 (1 mmol, 326 mg) was added to the flask. 15 min later, CuI (0.1 mmol, 19 mg) was added to the flask. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for 12 h (see Table 3 in text). After completion of the reaction, the mixture was extracted with EtOAc (1 mL), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (3:1 to 1:1) as eluent to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium acetate; In 2-methoxy-ethanol; at 120℃; for 6h; | The compound <strong>[58483-95-7]5-amino-2-chloropyridine-4-carboxylic acid</strong> (1000 g, 5.8 mol) was dissolved in 5000 ml of ethylene glycol monomethyl ether and acetamidine hydrochloride (2193 g, 23.2 mol) Sodium (2360 g, 17.4 mol). The reaction was heated to 120 ° C for 6 hours. After the reaction was complete, the reaction was cooled to room temperature, poured into 4000 ml of water and extracted twice with ethyl acetate. The organic phase was combined, dried and concentrated to afford the crude product which was filtered to give 6-chloro- Pyridine [3,4-d] pyrimidin-4 (3 H) -one (976 g, 5.01 mol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | To a 50 ml three-necked flask equipped with a magnetic stirrer, a thermometer and a reflux condenser were added 10 g of t-butanol,1.13 g (12 mmol) of acetamidine hydrochloride, 0.66 g (0.1 mol) of malononitrile and 1.2 g (12 mmol) of 30% aqueous formaldehyde were added, and the mixture was reacted at 65-70 C for 4 hours.Cooled to 20 ~ 25 C, 1.4 g of 70wt% t-butylperoxy peroxide was added and the reaction was carried out at 30-35 C for 1 hour. Samples were taken and detected by external standard method. The product 2-methyl-4-amino-5-cyanopyrimidine The yield was 92.6% and the HPLC purity was 99.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tert-butyl alcohol; at 80℃; for 24h;Inert atmosphere; | Acetamidine hydrochloride (16.94 g, 179 mmol) was added to a solution of 1-benzyl 3- ethyl 4-oxopyrrolidine-l,3-dicarboxylate (CAS 51814-19-8) (29 g, 100 mmol) and triethylamine (25 mL, 179 mmol) in tert-BuOH (250 mL). The mixture was heated at 80 C for 24 hours under nitrogen. The mixture was concentrated in vacuo and partitioned between water and EtOAc. THF was added and the mixture filtered to give benzyl 4- hyckoxy-2-memyl-5H,6H,7H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (11.18 g). The organic phase from the filtrate was passed through a pad of silica, eluting with EtOAc, and the resulting solution concentrated in vacuo. The residue was suspended in ether and THF (4:1, 200 mL) and filtered to afford the title compound. 1H NMR (400 MHz, DMSO-i): delta ppm 2.32 (s, 3H), 4.33 - 4.54 (m, 4H), 5.14 (s, 2H), 7.29 - 7.45 (m, 5H), 12.57 (br s, 1H). MS ES+ 286 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tert-butyl alcohol;Reflux; | A mixture of 1-tert-butyl 3-ethyl 4-oxopyrrolidine-l,3-dicarboxylate (CAS 146256-98-6) (20 g, 78 mmol), acetamidine hydrochloride (7.35 g, 78 mmol), and triethylamine (28.2 mL, 202 mmol) in tert-butanol (100 mL) was heated under reflux overnight. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was partitioned between EtOAc and water. The organic layer was dried (phase separator) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluting with 0-15 percent MeOH in EtOAc to afford the title compound. H NMR (400 MHz, DMSO- 6): delta ppm 1.42 - 1.47 (m, 9H), 2.31 (s, 3H), 4.25 - 4.39 (m, 4H), 12.52 (br s, 1H). MS ES+ 252 |
Tags: 124-42-5 synthesis path| 124-42-5 SDS| 124-42-5 COA| 124-42-5 purity| 124-42-5 application| 124-42-5 NMR| 124-42-5 COA| 124-42-5 structure
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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 |
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