There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 15430-52-1 | MDL No. : | MFCD00012907 |
Formula : | C3H6ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IKXNIQJDNKPPCH-UHFFFAOYSA-N |
M.W : | 91.54 | Pubchem ID : | 11205720 |
Synonyms : |
|
Num. heavy atoms : | 5 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 24.37 |
TPSA : | 26.02 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) : | -6.6 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.37 |
Log Po/w (WLOGP) : | 0.46 |
Log Po/w (MLOGP) : | 0.6 |
Log Po/w (SILICOS-IT) : | -0.37 |
Consensus Log Po/w : | 0.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.64 |
Solubility : | 20.9 mg/ml ; 0.229 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.48 |
Solubility : | 30.2 mg/ml ; 0.33 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.18 |
Solubility : | 140.0 mg/ml ; 1.52 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.17 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P301+P310-P305+P351+P338 | UN#: | 2811 |
Hazard Statements: | H301-H315-H319-H335 | Packing Group: | Ⅱ |
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 |
---|---|---|
96% | With triethylamine In dichloromethane for 2 h; Cooling with ice | Propargylamine hydrochloride (3.6 g, 39 mmol) and triethylamine (11.5 mL, 83 mmol, 2.13 equiv) were dissolved in CH2Cl2 (100 mL) and this solution was cooled on ice. Then, a solution of Boc2O (8.5 g, 40 mmol), (1.03 equiv) in CH2Cl2 (50 mL) was added dropwise and the obtained reaction mixture was stirred for 2 h. After removing the solvent under reduced pressure, the residue was redissolved in EtOAc (150 mL) and this solution was washed with 1 N KHSO4 (3 x 75 mL) and brine (150 mL). The EtOAc solution was dried (Na2SO4) and concentrated in vacuo to give 8 as pink crystals in 96percent yield (5.8 g). Rf 0.70 (CH2Cl2/MeOH 95:5); 1H NMR (300 MHz, CDCl3, 25 °C): d 4.71 (broad s, 1H; urethane NH), 3.93(m, 2H; CH2), 2.22 (s, 1H; ^CH), 1.46 (s, 9H; C(CH3)3); 13C NMR(75.5 MHz, CDCl3, 25 °C): d 155.3, 80.0, 69.3, 30.4, 28.3, 27.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of potassium thiocyanate (31.1 g), dihydroxyacetone dimer (19.2 g) and (2-propyn-1-yl)amine hydrochloride (25.0 g) was added by portionsportions to a mixed solution of acetic acid (23 ml) and 1-butanol (155 ml). The mixture was stirred for 10 days at room temperature, water (30 ml) was added to the mixture, and the mixture was stirred for 30 minutes. The precipitated solid was collected by filtration, and further washed with water (45 ml) twice and diisopropyl ether once. The obtained solid was dried under reduced pressure, to give 5-hydroxymethyl-2-mercapto-1-(2-propyn-1-yl)imidazole (28.9 g) as colorless crystals. 1H-NMR (200 MHz, DMSO-d6) delta 3.31 (1H, t, J = 2.6 Hz), 4.42 (2H, d, J = 5.2 Hz), 4.90 (2H, d, J = 2.6 Hz), 5.37 (1H, t, J = 5.2 Hz), 6.85 (1H, s), 12.18 (1H, br) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With sodium acetate; In ethanol; at 110℃; for 16h; | Step 2; A mixture of the product of Step 1 (38 mg, 0.13 mmol), sodium acetate (11 mg, 0.14 mmol), and <strong>[15430-52-1]propargylamine hydrochloride</strong> (13 mg, 0.14 mmol) in ethanol (1 mL) in a sealed reaction vessel was heated with stirring at 110 C for 16 h. The reaction mixture was filtered through a 0. 45 mum syringe-tip filter (PTFE) and purified by reverse phase preparative HPLC to give the product as an oil (12 mg, 31%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; water; ethyl acetate; | EXAMPLE 9 1-(5-Chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedione 5-Chloro-2-methylphenyl isothiocyanate (18.3 g; 0.1 mol) was added dropwise to the mixture of 2-propynylamine hydrochloride (9.2 g, 0.1 mol) and triethyl amine (20 mL) in methylene chloride (200 mL). The mixture was stirred for 18 hours at ambient temperature. The mixture was evaporated to dryness. The residue was stirred in water (200 mL) for 1 hour then filtered. The solid was dissolved in ethyl acetate (300 mL) and washed with 1 N hydrochloric acid (2*200 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness to give 16.8 g of N-(5-chloro-2-methylphenyl)-N'-(2-propynyl)thiourea. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
And 36% hydrochloric acid (20.7 g, 0.2 mol) was added dropwise at 60 C. over one hour, followed by stirring at 60 C. for 1.5 hours. Then, 3.5 g of water was added and the mixed solution was separated to obtain the aqueous phase and organic phase. The organic phase was extracted once with 5 g of water and the resulting aqueous phase was combined with the above aqueous phase. To the mixture, 64 g of 2-propanol was added at 60 C. and after cooling to 5 C., the deposited crystal was obtained by filtration. This crystal was washed with 20 g of 2-propanol three times and dried to obtain propargylamine hydrochloride (10.1 g, purity: 100%, yield: 65%). | ||
Example 2 Propargyl methanesulfonate (31.6 g, 0.236 mol) and benzaldehyde (31.9 g, 0.3 mol) were dissolved in 103 g of toluene and an aqueous 28% ammonia solution (122 g, 2 mol) was added dropwise at 21 C. over 8 hours to the solution, followed by stirring at the same temperature for 15 hours. After separating, the resultant organic phase was washed with water and concentrated until the weight became 57.3 g to obtain a toluene solution containing 28.6 g (yield: 85%) of N-benzylidene-2-propynylamine. To the resulting solution, 36% hydrochloric acid (30.4 g, 0.3 mol) was added dropwise at 20 C. over one hour, followed by stirring at 20 C. for 2 hours. Then, 2.5 g of water was added and the mixed solution was separated at 60 C. to obtain the aqueous phase and organic phase. The organic phase was extracted once with 5 g of water and the resulting aqueous phase was combined with the above aqueous phase. After 42.4 g of toluene was added, the mixture was heated to 62 C. and dehydrated by azeotropic distillation under 120 mmHg. Thus 10.6 g of water was distilled off. After returning to an atmospheric pressure, 18.8 g of 2-propanol was added to the mixture at 60 C. After cooling, the deposited crystal was obtained by filtration. This crystal was washed twice with 15 g of 2-propanol and dried to obtain propargylamine hydrochloride (18.1 g, purity: 86%, yield: 85%). | ||
Example 3 An aqueous 28% ammonia solution (166.4 g, 2.74 mol) and benzaldehyde (30.6 g, 0.288 mol) were mixed and a solution prepared by dissolving propargyl methanesulfonate (36.7 g, 0.274 mol) in 147 g of toluene was added dropwise at 20-25 C. over 3 hours to the solution, followed by stirring at the same temperature for 3 hours. After separating, the organic phase and aqueous phase were obtained. The organic phase obtained by washing the aqueous phase twice with 25 g of toluene was combined with the above organic phase and concentrated until the weight became 78 g to obtain a toluene solution of N-benzylidene-2-propynylamine. To this solution, 36% hydrochloric acid (41.7 g, 0.411 mol) was added dropwise at 20-25 C. over 10 minutes, followed by stirring at 20-25 C. for 2.5 hours. Fifty grams of ethanol was added and, after cooling to 5 C., the deposited crystal was obtained by filtration and the filtrate was simultaneously obtained. This crystal was washed once with 25 g of ethanol and dried to obtain 13.7 g of propargylamine hydrochloride. The filtrate and wash ethanol after the crystal was obtained by filtration were combined and, after separating, the resulting lower layer was concentrated until the weight became 82 g. After cooling to 5 C., the deposited crystal was obtained by filtration. This crystal was washed once with 6.2 g of ethanol and dried to obtain 3.2 g of propargylamine hydrochloride. |
To this crude product, 5 ml of ethanol and 36% hydrochloric acid (3.0 g, 30 mmol) were added, followed by stirring at 20 C. for 5 hours. After cooling to 5 C., the deposited crystal was obtained by filtration and the filtrate was simultaneously obtained. The obtained crystal was washed with ethanol and dried to obtain 878 mg of propargylamine hydrochloride. The filtrate was concentrated and recrystallized from ethanol to obtain 546 mg of propargylamine hydrochloride. | ||
Example 5 According to the same manner as that described in Example 4 except for using p-methoxybenzaldehyde (3.54 g, 26 mmol) in place of o-chlorobenzaldehyde, the operation was conducted to obtain propargylamine hydrochloride (1.32 g, purity: 87%, yield: 63%). | ||
Example 6 According to the same manner as that described in Example 4 except for using benzaldehyde (2.76 g, 26 mmol) in place of o-chlorobenzaldehyde, propargyl benzenesulfonate (3.92 g, 20 mmol) in place of propargyl methanesulfonate and 19.6 g of toluene in place of 10.7 g of toluene, the operation was conducted to obtain propargylamine hydrochloride (1.40 g, purity: 99%, yield: 77%). | ||
Then, 2.5 g of water was added and the mixed solution was separated at 60 C. to obtain the aqueous phase and organic phase. The aqueous phase obtained by extracting organic phase (24.9 g) once with 4 g of water was combined with the above aqueous phase. To this aqueous phase (18.2 g) was added 18.2 g of toluene and, after the mixture was heated to 62 C. and dehydrated by azeotropic distillation under 90 mmHg, 10 g of water was distilled off. After returning to an atmospheric pressure, 10 g of 2-propanol was added to the mixture at 60 C. After cooling to 5 C., the deposited crystal was obtained by filtration. This crystal was washed twice with 5 g of 2-propanol and dried to obtain propargylamine hydrochloride (5.93 g, purity: 100%, yield: 94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; ammonia; benzaldehyde; In toluene; | Example 7 An aqueous 28% ammonia solution (12.1 g, 200 mmol) and benzaldehyde (2.23 g, 21 mmol) were mixed and a solution prepared by dissolving propargyl bromide (2.38 g, 20 mmol) in 9.5 g of toluene was added dropwise at 20 C. over 0.7 hour to the solution, followed by stirring at the same temperature for 10 hours. After separating, the resulting organic phase was concentrated until the weight became to 10 g to obtain a toluene solution containing N-benzylidene-2-propynylamine. To this solution, 36% hydrochloric acid (3.0 g, 30 mmol) was added, followed by stirring at 20 C. for 5 hours. Then, the toluene phase was removed by decantation. After cooling to 5 C., the deposited crystal was obtained by filtration and the filtrate was simultaneously obtained. The resulting crystal was washed with ethanol and dried to obtain 889 mg of propargylamine hydrochloride. The filtrate was concentrated and recrystallized from ethanol to obtain 271 mg of propargylamine hydrochloride. The resulting propargylamine hydrochlorides were combined (weight: 1.16 g). As a result, the purity was 99% and the yield to the raw material (propargyl methanesulfonate) was 63%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; | Example 8 According to the same manner as that described in Example 7 except for using propargyl chloride (1.49 g, 20 mmol) in place of propargyl bromide and 6.0 g of toluene in place of 9.5 g of toluene, the operation was conducted to obtain propargylamine hydrochloride (790 mg, purity: 96%, yield: 42%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With sodium carbonate; In water; | EXAMPLE 29 (E)-2-[(2-propynyl)amino]phenylmethylene}-benzo[b]thiophen-3-(2H)-one Prepared as in Example 1 from 2-benzoyl-benzo[b]thiophen-3-ol, phosphorus(V) chloride and an aqueous propargylamine solution obtained by reacting a solution of 10 gm of <strong>[15430-52-1]propargylamine hydrochloride</strong> in 10 cc of water with a solution of 10.6 gm of anhydrous sodium carbonate in 20 cc of water, with a yield of 46% of theory. M.p. 126-128 C. (ethyl acetate/petroleum ether 1:1). C18 H13 NOS (291.37): Calc.: C-74.20%; H-4.50%; N-4.81%; S-11.00%; Found: C-74.04%; H-4.47%; N-4.70%; S-11.05%. p IR(CH2 Cl2): --C=C--H 3300, C=O approx. 1600 cm-1; also associated H; UV (ethanol): lambda max (neutral) 266-276 (E=0.45); 286 (E=0.48); 319 (E=0.56); 434 (E=0.54); lambda max (alkaline) 255 (E=0.70); 313 (E=0.34); 434 (E=0.22). (Concentration: 50 mug/ml: layer thickness 0.2 cm). 1 H-NMR(CDCl3, 80 MHz): delta 11.75 (1H, broad, internal H bridge); 7.95 (1H-dd, J=7 Hz and 2 Hz; ar. H); 7.7-7.1 (8H-m; ar. H); 3.94 (2H-dd, J=6 Hz and 2.5 Hz; --CH2 --); 2.32 (1H-t; J=2.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In methanol; | EXAMPLE 33 A mixture of 2-guanidino-4-[3-(3-cyano2-methylisothioureido)phenyl]thiazole (0.5 g.), <strong>[15430-52-1]propargylamine hydrochloride</strong> (1.45 g.) and triethylamine (3 ml.) was stirred overnight in methanol (5 ml.). The mixture was then evaporated to dryness and the residue triturated successively with water, ethyl acetate and acetonitrile to give a solid. This was filtered off and air-dried to give 0.075 g. of 2-guanidino-4-[3-(2-cyano3-propargylguanidino)phenyl]thiazole, m.p.>300 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With triethylamine; In methanol; chloroform; | Example 69 N-{4-[(6,7-Dimethoxy-4-quinazolinyl)-oxy]phenyl}-N'-(2-propynyl)urea 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.2 ml), and a solution of triphosgene (50 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, <strong>[15430-52-1]propargylamine hydrochloride</strong> (31 mg) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol to give 26 mg (yield 41%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): delta 3.11 - 3.12 (m, 1H), 3.89 - 3.90 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 6.49 (t, J = 5.9 Hz, 1H), 7.17 (d, J = 9.0 Hz, 2H), 7.38 (s, 1H), 7.48 (d, J = 8.8 Hz, 2H), 7.55 (s, 1H), 8.53 (s, 1H), 8.68 (s, 1H) Mass analysis, found (ESI-MS, m/z): 379 (M++1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With triethylamine; In chloroform; | Example 81 N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(2-propynyl)urea 2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (50 mg) was dissolved in chloroform (5 ml) and triethylamine (1 ml), and a solution of triphosgene (45 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, <strong>[15430-52-1]propargylamine hydrochloride</strong> (21 mg) was added to the reaction solution, and the mixture was stirred at room temperature for additional 30 min. The precipitated crystal was collected by filtration and was washed togive 38 mg (yield 61%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): delta 3.16 - 3.17 (m, 1H), 3.93 - 3.95 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 7.25 (dd, J = 2.7 Hz, 9.0 Hz, 1H), 7.30 (t, J = 5.6 Hz, 1H), 7.39 (s, 1H), 7.50 (d, J = 2.7 Hz, 1H), 7.55 (s, 1H), 8.16 (d, J = 9.3 Hz, 1H), 8.18 (s, 1H), 8.56 (s, 1H) Mass analysis, found (ESI-MS, m/z): 413 (M++1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With triethylamine; In chloroform; | Example 92 N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}-N'-(2-propynyl)urea 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene(47 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, <strong>[15430-52-1]propargylamine hydrochloride</strong> (29 mg) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was washed with chloroform to give 21 mg (yield 33%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): delta 3.15 (t, J = 2.4 Hz, 1H), 3.91 - 3.94 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 7.07 - 7.11 (m, 1H), 7.33 (dd, J = 2.4 Hz, 11.7 Hz, 1H), 7.39 (s, 1H), 7.54 (s, 1H), 8.09 - 8.15 (m, 1H), 8.47-8.48 (m, 1H), 8.56 (s, 1H) Mass analysis, found (ESI-MS, m/z): 397 (M++1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.2% | With triethylamine; In tetrahydrofuran; water; at 20℃; for 0.75h; | Example 1 Synthesis of mesylate salt of 5-(2-dimethylaminoethoxy)-1H-indole-2-carboxylic acid [3-(4-hydroxycarbamoylphenyl)prop-2-ynyl]amide Step 1 To a suspension of <strong>[15430-52-1]propargylamine hydrochloride</strong> (25 g, 273.1 mmol) in anhydrous THF (250 mL) were added in sequence Et3N (38.06 mL, 273.1 mmol), di-tert-butyl dicarbonate (59.6 g, 273.1 mmol), and Et3N (38.06 mL, 273.1 mmol). After stirring at room temperature for 15 min, additional Et3N (19.03 mL, 136.6 mmol) and water (~20 mL) were added and gas evolution was monitored. After stirring for 30 min, no further gas evolution was observed and TLC [EtOAc/hexane, (1:2)] showed complete consumption of <strong>[15430-52-1]propargylamine hydrochloride</strong>. The reaction was quenched with 0.25M aqueous HCl (~300 mL) until the solution became clear and diluted with EtOAc (250 mL). The organic phase was separated and washed with 0.5M aqueous HCl, brine, then dried over sodium sulfate. Concentration in vacuo provided crude 1-N-(tert-butyloxycarbonylamino)-2-propyne (40.35 g, 95.2%) which became a white solid after drying under high vacuum overnight. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.4% | With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; | Example 10. Synthesis of [*r°ns-4-({2-[3-(3-amino-prop-l-ynyl)-2-methyl- benzylamino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cycIohexyl] -methanol; To a solution of (^ralphar°-4-[2-(3-bromo-2-methyl-benzylamino)-5-nitro-pyrimidin-4- ylamino] -methyl} -cyclohexyO-methanol (100 mg, 0.215 mmol) and prop-2-ynylamine hydrochloride (39.4 mg, 0.431 mmol) in triethylamine (300 muL, 2.15 mmol) and N, N- dimethylformamide (1.0 mL) was added copper (I) iodide (6.8 mg, 0.022 mmol) and bis(triphenylphosphine)palladium(II) chloride (9.7 mg, 0.013 mmol), and the solution was heated at 80 0C overnight. The solution was diluted with saturated NaHCO3 and extracted with dichloromethane. The combined organics were dried over Na2SO4 and concentrated. The material was purified via silica gel chromatography using from 0-10% methanol in dichloromethane to afford 2.3 mg (2.4%) of [4-({2-[3-(3-amino-prop-l-ynyl)-2-methyl- benzylarnino]-5-nitro-pyrimidin-4-ylarnino}-methyl)-cyclohexyl]-inethanol, m/z 439.5 (M + H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine; In dichloromethane; at -40 - 20℃; for 24h;Inert atmosphere; | The reaction was run under an inert gas atmosphere (Ar). In a dried round-bottomed flask equipped with a septum <strong>[15430-52-1]propargylamine hydrochloride</strong> (740 mg, 8.08 mmol, 1.5 equiv) and triethylamine (12.4 mL) in 22 mL of dry dichloromethane were placed. Then the mixture was cooled to -40 C and a solution of 4-nitrobenzoyl chloride (1 g, 5.39 mmol, 1 equiv) in dry CH2Cl2 (22 mL) was added dropwise. The reaction was stirred for 24 h at room temperature. Afterwards the reaction was quenched by the addition of water (7.4 mL). After 10 minutes, additional 22 mL of water were added and the mixture extracted with CHCl3 (3 × 80 mL). The combined extracts were dried (MgSO4) and concentrated to give the crude product, which was purified by column chromatography (DCM/acetone 0-30%). Yield 1.080 g (98%) from 1 g(5.39 mmol) of 4-nitrobenzoyl chloride. |
77% | With pyridine; In tetrahydrofuran; for 16h;Reflux; | To a stirred solution of <strong>[15430-52-1]propargylamine hydrochloride</strong> (5.0 g, 54.6mmol) and pyridine (7.8 g, 99.1 mmol) in tetrahydrofuran (3OmL) was added 4-nitro- benzoylchloride (9.2 g, 49.6 mmol) in tetrahydrofuran (20 mL) and the mixture was heated at reflux for 16 h. The mixture was allowed to cool to ambient temperature and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford 4-nitro-N-prop-2-ynyl- benzamide (7.74 g, 77%) as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In ethyl acetate; isopropyl alcohol; at 0 - 5℃;pH 2 - 5; | Propargylamine (200 g) is charged into a round bottom flask containing ethyl acetate (1500 mL) and stirred for about 10 minutes. The solution is cooled to 0-50C, pH is adjusted to 2-5 by addition of hydrogen chloride in isopropanol (18%, 1405 mL), and the mixture is stirred for solid formation. The solid is filtered and washed with ethyl acetate (400 mL), and then suction dried for about 30 minutes. The obtained solid is dried at 700C for 6-7 hours to afford 300 g of the title compound. | |
With hydrogenchloride; In ethyl acetate; isopropyl alcohol; at 0 - 5℃;pH 2 - 5; | Propargylamine (200 g) is charged into a round bottom flask containing ethyl acetate (1500 mL) and stirred for about 10 minutes. The solution is cooled to 0-5 C., pH is adjusted to 2-5 by addition of hydrogen chloride in isopropanol (18%, 1405 mL), and the mixture is stirred for solid formation. The solid is filtered and washed with ethyl acetate (400 mL), and then suction dried for about 30 minutes. The obtained solid is dried at 70 C. for 6-7 hours to afford 300 g of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.6% | 1 -lndanone (5 g), progargylamine hydrochloride (6.9 g), and methanol (50 mL) are charged into a round bottom flask and stirred for about 30 minutes at room temperature. To the solution, sodium acetate (3.1 g) and sodium cyanoborohydhde (2.37 g) are added, and then the mixture is heated to reflux and maintained for completion of the reaction. The mass is distilled completely under vacuum to produce a residue. Water (500 mL) is added to the residue, the pH is adjusted to 1-2 by addition of aqueous HCI (5 mL), the mixture is washed with toluene (2chi25 mL), and the aqueous layer is separated. The obtained aqueous layer pH is adjusted to 11 -13 by addition of caustic lye (5 mL) and extracted with ethyl acetate (2chi30 mL). The organic layer is separated, washed with water (2chi30 mL), and is distilled completely under vaccum to afford 5.8 g of the title compound as a residue (89.6% yield). | |
89.6% | 1-Indanone (5 g), progargylamine hydrochloride (6.9 g), and methanol (50 mL) are charged into a round bottom flask and stirred for about 30 minutes at room temperature. To the solution, sodium acetate (3.1 g) and sodium cyanoborohydride (2.37 g) are added, and then the mixture is heated to reflux and maintained for completion of the reaction. The mass is distilled completely under vacuum to produce a residue. Water (500 mL) is added to the residue, the pH is adjusted to 1-2 by addition of aqueous HCl (5 mL), the mixture is washed with toluene (2×25 mL), and the aqueous layer is separated. The obtained aqueous layer pH is adjusted to 11-13 by addition of caustic lye (5 mL) and extracted with ethyl acetate (2×30 mL). The organic layer is separated, washed with water (2×30 mL), and is distilled completely under vacuum to afford 5.8 g of the title compound as a residue (89.6% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; sodium hydrogencarbonate; In acetone; for 1h; | A solution of 9-fluorenylmethoxycarbonyl chloride (2.6 g) in 20 mL of acetone was added slowly to a stirred mixture of <strong>[15430-52-1]propargylamine hydrochloride</strong> (0.91 g) and NaHC03 (2.5 g) in 20 mL of water. After 1 hour, the solid precipitate was collected by vacuum filtration, washed with water, and air dried. Crystallization from ethyl acetate/hexane provided the product. | |
With sodium hydrogencarbonate; In water; acetone; for 1h; | A solution of 9-fluorenylmethoxycarbonyl chloride (2.6 g) in 20 mL of acetone was added slowly to a stirred mixture of <strong>[15430-52-1]propargylamine hydrochloride</strong> (0.91 g) and NaHC03 (2.5 g) in 20 mL of water. After 1 hour, the solid precipitate was collected by vacuum filtration, washed with water, and air dried. Crystallization from ethyl acetate/hexane provided the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; toluene; at 20℃; for 168h; | General procedure: To a solution of (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one (2) (175 mg, 1 mmol) in EtOH (2 mL) was added a solution of DEAD (3) in toluene (512 muL, w=39%, 1.1 mmol). The reaction mixture was stirred for 4 h at room temperature. Then, amine (5a-n) (1 mmol) with 4 drops of concd HClaq or amine hydrochloride (1 mmol) was added and the reaction mixture was stirred for t1. NaOH (100 mg, 2.5 mmol) was then added and the reaction mixture was stirred for t2. Volatile components were evaporated in vacuo and products were purified by column chromatography and crystallised from appropriate solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With triethylamine; In dichloromethane; at 0℃;Inert atmosphere; | The proparagylamine hydrochloride (0.5 g, 5.46 mmol ) was dissolved in 10 mL of MC and subsequently TEA (1.53 mL, 10.92 mmol ) and acetyl chloride (0.505 mL, 7.10 mmol) were added at 0C under N2 gas. The reaction mixture was stirred for additional 1h and purification by silica gel column chromatography with EtOAc as an eluent gave the desired amide as a colorless liquid in 34 % yield (0.1775g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 1h; | General procedure: 1.1 mmol of appropriate primary amine was added to the solution of 586 mg (1 mmol) of enol acetate 219 in 50 mL of CHCl3 at room temperature. In 1 h the solution was washed with water, 5% aqueous acetic acid and aqueous sodium bicarbonate, dried (Na2SO4), and then evaporated to dryness. The residue and 10 mg (0.05 mmol) of sodium acetate were refluxed for 1 h in 50 mL of i-PrOH. After cooling to room temperature a mixture was diluted with water, extracted with CH2Cl2, dried (Na2SO4), and evaporated to dryness. The crude product was purified by silica gel column chromatography (25% EtOAc/hexane) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.24 g | With sodium hydrogencarbonate; at 20℃;Cooling with ice; | A solution of 1.08 grams of propargylamine hydrochloride in 50 ml of saturated sodium bicarbonate was cooled with an ice water bath, and 2.0 grams of <strong>[55750-49-7]N-carboethoxymaleimide</strong> were added portionwise over a few minutes. The reaction was stirred in the cold for 30 min., then while warming to room temperature over 25 min. The reaction was then extracted with 3*25 ml of dichloromethane, which was dried over sodium sulfate, filtered and concentrated. The residue was taken up in 10 ml of ethyl acetate and heated at 50 C. for two hours to complete the cyclization. The reaction was concentrated and the residue was which was subjected to flash column chromatography on silica gel with 30% ethyl acetate in hexane. A second chromatography as before gave 1.24 g of the product as a very light yellow oil. NMR (CDCl3): delta 6.77 (s, 2H, CHC=O), 4.30 (d, 2H, NCH2, J=2.4 Hz), 2.22 (t, 1H, CCH, J=2.5 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h; | N-Boc-Lys (Fmoc)-OH (504 mg, 1.08 mmol) in dry DMF (4.5 mL)was added with propargylamineHCl (98.4 mg, 1.08 mmol), HBTU(495.3 mg, 1.02 mmol) and DIPEA (370 lL, 2.14 mmol) at 0 C thenwas warmed to room temperature. After stirring for 1 h, the reaction mixture was diluted with EtOAc, washed with water andbrine, and then dried over Na2SO4. The crude product concentratedin vacuo was purified by flash column chromatography(CH2Cl2/EtOAc = 9:1 to 7:3) to give compound 7 as white solid(534 mg, 1.06 mmol, 94%). 1H NMR (300 MHz, CDCl3): d 7.74 (d,J = 7.6 Hz, 2H), 7.57 (d, J = 7.2 Hz, 2H), 7.38 (dd, J = 7.2, 7.6 Hz,2H), 7.29 (dd, J = 8.3, 7.2 Hz, 2H), 6.96 (br, 1H), 5.37 (br, 1H), 5.07(br, 1H), 4.38 (m, 2H), 4.18 (t, J = 6.9 Hz, 1H), 4.06 (m, 3H), 3.16(dd, J = 6.5, 5.9 Hz, 2H), 2.17 (s, 1H), 1.80 (m, 2H), 1.64 (m, 2H),1.51 (m, 2H), 1.42 (s, 9H); 13C NMR (75 MHz, CDCl3): d 171.9,156.6, 155.8, 143.9, 141.2, 127.6, 127.0, 125.0, 119.9, 80.1, 79.3,71.5, 66.5, 54.0, 47.1, 40.3, 31.8, 29.4, 29.0, 28.3, 22.4; HRMS(ESI-TOF) calcd for C29H35N3NaO5 (M+Na+): 528.2474; found:528.2474. |
Tags: 15430-52-1 synthesis path| 15430-52-1 SDS| 15430-52-1 COA| 15430-52-1 purity| 15430-52-1 application| 15430-52-1 NMR| 15430-52-1 COA| 15430-52-1 structure
[ 88211-50-1 ]
But-3-yn-1-amine hydrochloride
Similarity: 0.62
[ 173987-24-1 ]
Pent-4-yn-1-amine hydrochloride
Similarity: 0.53
[ 88211-50-1 ]
But-3-yn-1-amine hydrochloride
Similarity: 0.62
[ 624-60-2 ]
N-Methylethanamine hydrochloride
Similarity: 0.55
[ 173987-24-1 ]
Pent-4-yn-1-amine hydrochloride
Similarity: 0.53
[ 870-24-6 ]
2-Chloroethanamine hydrochloride
Similarity: 0.50
[ 88211-50-1 ]
But-3-yn-1-amine hydrochloride
Similarity: 0.62
[ 624-60-2 ]
N-Methylethanamine hydrochloride
Similarity: 0.55
[ 173987-24-1 ]
Pent-4-yn-1-amine hydrochloride
Similarity: 0.53
[ 870-24-6 ]
2-Chloroethanamine hydrochloride
Similarity: 0.50
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :