Home Cart Sign in  
HazMat Fee +

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+
Chemical Structure| 1008130-15-1 Chemical Structure| 1008130-15-1

Structure of 1008130-15-1

Chemical Structure| 1008130-15-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1008130-15-1 ]

CAS No. :1008130-15-1
Formula : C6H9N3O2
M.W : 155.15
SMILES Code : O=C(C1=NC=CN1N)OCC
MDL No. :MFCD21336206
InChI Key :VUEWVPSSFIXDKG-UHFFFAOYSA-N
Pubchem ID :58332105

Safety of [ 1008130-15-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:3259
Packing Group:

Application In Synthesis of [ 1008130-15-1 ]

* 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.

  • Downstream synthetic route of [ 1008130-15-1 ]

[ 1008130-15-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 33543-78-1 ]
  • [ 1008130-15-1 ]
YieldReaction ConditionsOperation in experiment
94% Preparation of intermediate compound (33)a. To a solution of ethyl lH-imidazole-2-carboxylate (Aldrich, 3.0 g, 21.40 mmol) in anhydrous DMF (10 mL) at -10 0C was added dropwise Lithium hexamethyldisilazane (1.10 mL, 1 M solution in THF, 1.1 mmol). After the mixture was stirred for 10 min, diphenylphosphinyl)hydroxylamine (6.49 g, 27.83 mmol) was added at 0 0C, followed by stirring at room temperature overnight. The reaction was quenched with water until a clear solution was formed and concentrated in vacuum to dryness. The residue obtained was extracted with ethyl acetate (5 x 100). The organic extracts were combined and concentrated in vacuo to furnish ethyl 1- amino-lH-imidazole-2-carboxylate (31) (3.1 g, 94%) as a brown oil. This was pure enough to be used in next step.
85% Ethyl 1H-imidazole-2-carboxylate at 0 C(40.01 g, 285.5 mmol) in a dry THF (600 mL) suspension Sodium hydride (13.82 g, 345.5 mmol, mass fraction 60%) was added.The reaction mixture was stirred at room temperature for 1 hour and then cooled to 0 C.O-(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) was added portionwise.The reaction system was stirred at room temperature overnight and then diluted in water (600 mL).The resulting mixture was extracted with EA (600 mL×10).The separated organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The residue obtained is purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1).The title compound is a brown solid(37.6 g, yield 85%).
85% To a suspension of ethyl lH-imidazole-2-carboxylate (40.01 g, 285.5 mmol) in dried THF (600 mL) was added sodium hydride (13.82 g, 345.5 mmol, 60 mass%) at 0 C. The mixture was stirred at room temperature for 1 h, and then cooled down to 0 C. To the mixture was added ( -(2,4-dinitrophenyl)hydroxylamine (80.00 g, 401.8 mmol) in portions, and then the resulted mixture was stirred at room temperature overnight. The mixture was diluted with water (600 mL), and the resulted mixture was extracted with EA (600 mLchi10). The combined organic layers were dried over anhydrous Na2SC>4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EA/PE (v/v) = 1/2 to 1/1 to 2/1) to afford the title compound as a brown solid (37.6 g, yield 85%).MS (ESI, pos. ion) m/z: 156.1 [M + H]+;NMR (400 MHz, CDCb) delta (ppm): 7.19 (s, IH), 7.07 (s, IH), 5.82 (s, 2H), 4.43 (q, J = 7.1 Hz, 2H), 1.44 (t, J = 7.1 Hz, 3H).
6.5% To a stirred solution of hydroxylamine-o-sulfonic acid (26.64 g, 235.8 mmol, 3.0 eq) in H20 (17 mL) at 0 C, ethyl lH-imidazole-2-carboxylate (11.0 g, 78.6 mmol, 1.0 eq) was added and the resulting mixture was stirred at 90 C for 30 min. The mixture was cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) was added in portions. The resulting mixture was stirred at RT overnight, filtered and rinsed with H20 (10 mL x 3). The filtrate was extracted with ethyl acetate (50 mL x 5). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (1% MeOH in DCM) to afford ethyl 1 -amino- lH-imidazole-2-carboxylate (800 mg, 6.5 % yield). ESI-MS m/z: 156.1 [M+H]+.
To a stirred solution of hydro xylamine-o-sulfonic acid (26.64 g, 235.8 mmol, 3.0 eq) in H20 (17 mL) at 0 C, ethyl lH-imidazole-2-carboxylate (C-3) (11.0 g, 78.6 mmol, 1.0 eq) is added and the resulting mixture is stirred at 90 C for 30 min. The mixture is cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) is added in portions. The resulting mixture is stirred at RT overnight, filtered and rinsed with H20 (10 mLx 3). The filtrate is extracted with ethyl acetate (50 mL x 5). The combined organic layer is washed with brine, dried over Na2S04 and filtered. The filtrate is evaporated in vacuo and the residue is purified by flash column chromatography on silica gel (1 % MeOH-DCM) to afford the product, ethyl l-amino-lH-imidazole-2-carboxylate (C-4) as a colorless oil.
With sodium chlorite; chloroamine; tert-butyl methyl ether; sodium hydride; ammonium chloride; In N,N-dimethyl-formamide; at -20 - 20℃; for 3h; Ethyl 1-amino-1H-imidazole-2-carboxylate To a stirred suspension of ammonium chloride (228 g, 4.28 mol) in MTBE (2.4 L), aq. NH3 (1.2 L) was added at -20 C., prior to the addition of 11-14% sodium hypochlorite (3.5 L, 4.79 mol) at the same temperature over a period of 30 min. The reaction mixture was stirred at the same temperature for 1 h, after which the MTBE layer was separated and washed with brine solution. MTBE layer was dried over Na2SO4 and kept in the refrigerator and used immediately. In an another flask NaH (20 g, 513.9 mmol) was suspended in DMF (600 mL) at -10 C., to which a solution of <strong>[33543-78-1]ethyl 1H-imidazole-2-carboxylate</strong> (60 g, 428.2 mmol) in DMF (150 mL) was added slowly. The reaction mixture was stirred at room temperature for 1.5 h and cooled to -20 C., prior to the drop-wise addition of the chloramine solution in MTBE. The reaction was stirred at -10 C. for 1 h and at room temperature for 2 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to 0 C. and quenched with 1 L of 10% Na2S2O3 solution. Organic layer was separated; and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine (500 mL), dried over Na2SO4, filtered and evaporated to get crude ethyl 1-amino-1H-imidazole-2-carboxylate as a solution in DMF, which was used in the next step as such. A small portion of the solution was dried in vacuo to remove DMF and the product was characterized by 1H-NMR and LC-MS. ES+, m/z 156.3 [M+1].
A solution of <strong>[33543-78-1]ethyl 1H-imidazole-2-carboxylate</strong> (10.0 g, 71.4 mmol) [Combi-Blocks, SS-7811] in DMF (357 mL) was treated with potassium tert-butoxide (74.9 mL, 74.9 mmol) dropwise and stirred at 20 C. for 1 h. The reaction mixture was then treated with a solution of O-(4-nitrobenzoyl)hydroxylamine (13.7 g, 74.9 mmol) in N,N-dimethylformamide (120 mL) dropwise via an addition funnel and stirred at 20 C. for 3 h. The reaction mixture was filtered and the solid was washed with acetonitrile. The filtrate was evaporated to give the crude product as a slightly oily red solid that was used without further purification.
To a solution of ethyl lH-imidazole-2-carboxylate (1 g, 7.14 mmol, 1 eq) in DMF (80 mL) cooledo -10 C was added LiHMDS (1 M, 7.85 mL, 1.1 eq). The mixture was stirred at -10 C for 0.5 h. To the mixture was added N-diphenylphosphorylhydroxylamine (1.83 g, 7.85 mmol, 1.1 eq). The mixture was stirred at 15 C for 11.5 h. The mixture was quenched with saturated aqueous H4CI solution (50 mL) at -10 C. The mixture was concentrated and to the residue was added EtOAc (100 mL). After filtration, washed with EtOAc (50 mL x 3), the filtrate was concentrated to yield ethyl l-aminoimidazole-2-carboxylate (3 g, crude) as a yellow solid which was used in the next step without further purification. NMR (400 MHz, CDCb) S ppm 7.10 (s, 1H), 6.98 (s, 1H), 5.74 (s, 2H), 4.33 (q, J = 7.2 Hz, 2H), 1.36-1.33 (m, 3H); ES-LCMS m/z 156.0 [M+H]+.
A solution of ethyl lH-imidazole-2-carboxylate (10.0 g, 71.4 mmol) [Combi-Blocks, SS-7811] in N,N-dimethylformamide (357 mL) was treated with potassium tert-butoxide (74.9 mL, 74.9 mmol, 1.0 M in tetrahydrofuran) dropwise and stirred at 20 C for 1 h. The reaction mixture was then treated with a solution of 0-(4-nitrobenzoyl)hydroxylamine (13.7 g, 74.9 mmol) in N,N-dimethylformamide (120 mL) dropwise via an addition funnel and stirred at 20 C for 3 h. The reaction mixture was filtered and the solid was washed with acetonitrile. The filtrate was evaporated to give the crude product as a slightly oily red solid that was used without further purification.

 

Historical Records

Technical Information

Categories