Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 17109-93-2 Chemical Structure| 17109-93-2

Structure of 17109-93-2

Chemical Structure| 17109-93-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

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

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

Alternative Products

Product Details of [ 17109-93-2 ]

CAS No. :17109-93-2
Formula : C9H13NO4
M.W : 199.20
SMILES Code : O=C(OCC)C(CC#N)C(OCC)=O
English Name :Diethyl 2-(cyanomethyl)malonate
MDL No. :MFCD18909214

Safety of [ 17109-93-2 ]

Application In Synthesis of [ 17109-93-2 ]

* 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 [ 17109-93-2 ]

[ 17109-93-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 17109-93-2 ]
  • [ 36821-26-8 ]
YieldReaction ConditionsOperation in experiment
36% With hydrogen In ethanol at 65℃; for 20h; 140 Synthesis of compound 140.3. Into a 3-L pressure tank reactor (80 atm), was placed 140.2 (64 g, 321.28 mmol, 1.00 equiv), EtOH (1 L) and Raney Ni (12 g). The reaction was stirred for 20 h at 65 °C. The solids were filtered out. The resulting mixture was concentrated under vacuum and crude purified by column chromatography to provide 18.5 g (36.0 %) of 140.3 as a white solid.
With ethanol; nickel at 80 - 100℃; Hydrogenation;
  • 2
  • [ 107-14-2 ]
  • [ 105-53-3 ]
  • [ 17109-93-2 ]
YieldReaction ConditionsOperation in experiment
With sodium; benzene
91 % With sodium hydride In acetonitrile at 25℃; Cooling with ice; 1.S4; 4.S4-5.S4 S4. Under ice bath, add 28.8g NaH (60%, dispersed in castor oil), 400ml CH3CN to the reaction bottle, then add 108ml diethyl malonate dropwise, and continue to stir under ice bath for 1h.Then 25ml of chloroacetonitrile was added dropwise, and the mixture was stirred overnight at 25°C.After the completion of the reaction was monitored by TLC (plate polarity: PE:EA=5:1), it was quenched with saturated ammonium chloride solution, then extracted with EA, and washed twice with saturated sodium chloride solution.Dry with anhydrous sodium sulfate, concentrate, install silica gel column, PE: EA = 5: 1, pass through the column.72 g of transparent oily product Compound IV was obtained, and the yield was about 91%.
  • 3
  • [ 17109-93-2 ]
  • [ 353454-94-1 ]
  • [ 426835-40-7 ]
YieldReaction ConditionsOperation in experiment
97% With di-isopropyl azodicarboxylate; triphenylphosphine In 1,4-dioxane at 20℃; for 70h;
  • 4
  • [ 105-53-3 ]
  • [ 590-17-0 ]
  • [ 17109-93-2 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: bromoacetonitrile In tetrahydrofuran at 20℃; for 17h; Further stages.;
64.3% Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: bromoacetonitrile In tetrahydrofuran at 0 - 20℃; for 9h; 140 Synthesis of compound 140.2. Into a 3-L 4-necked round-bottom flask under nitrogen, was placed 140.1 (80 g, 0.50 mol, 1.00 equiv), in THF (800 ml). This was followed by the addition of NaH (12.6 g, 0.54 mol, 1.08 equiv). To this was added 2-bromo-acetonitrile (30 g, 0.25mol, 0.50 equiv) after 30 min. The reaction was stirred for 1 hour at 0 °C, then stirred for 8 h at room temperature, then quenched by the addition of 300 mL of H4C1 (aq). The resulting solution was extracted with 2 x 300 mL of EtOAc, organic layers were combined, dried over anhydrous Na2S04 and concentrated under vacuum. The crude was purified by column chromatography to furnsh 64.0 g (64.3%) of 140.2 as colorless oil.
24% Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.25h; Inert atmosphere; Stage #2: bromoacetonitrile In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2h; Inert atmosphere; General procedure 1 (GP1) General procedure: alkylation: A RBF equipped with a stirring bar was charged with NaH 60% (1.0 equiv) and purged withargon. DMF (V mL) was added and the RBF was cooled to 0 °C (ice/water bath). Malonate 1 (1.1 equiv) was added dropwise with asyringe and the mixture was stirred for 15 min. The alkyl halide 2 (1.0 equiv) was then added dropwise with a syringe. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. Then, the resulting mixture was poured in sat aq NH4Cl (3 V)and the resulting solution was extracted with Et2O (3 × 2 V). The combined organic layers were washed with water (10 V) and brine (5V), dried (Na2SO4), and evaporated. Purification by FC afforded the expected product 3.
64 % Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: bromoacetonitrile In tetrahydrofuran; mineral oil at 0 - 60℃; Inert atmosphere;

  • 5
  • [ 17109-93-2 ]
  • [ 497-23-4 ]
  • [ 126988-49-6 ]
YieldReaction ConditionsOperation in experiment
With NaH In tetrahydrofuran; water; mineral oil 1 Preparation of (Cyanomethyl)(tetrahydro-5-oxo-3-furanyl)propanedioic acid diethyl ester EXAMPLE 1 Preparation of (Cyanomethyl)(tetrahydro-5-oxo-3-furanyl)propanedioic acid diethyl ester A flame-dried flask was charged with a stirred suspension of 1.0 g (0.02 mmol) of NaH (50% dispersion in mineral oil; washed free of oil with 2*20 mL portions of dry pet ether) in 150 mL dry THF under argon at 0° C. To the suspension, 41.2 g (0.20 mol) of ethyl 2-carboethoxy-3-cyano propionate was added dropwise (60 min) and the clear solution stirred for an additional 15 min at 0° C. A solution of 21.0 g (0.25 mol) of freshly distilled crotonolactone in 20 mL dry THF was added dropwise under a period of 30 min. After the addition was complete, the flask was sealed tightly under argon and stirred at 5° C. for 3 days. Water (50 mL) was added and the product extracted with 2*100 mL portions of chloroform. The organic extracts were combined, washed with water, saturated sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The resultant crude white solid was triturated in cold ether and filtered to give 53 g (93%) of the named compound suitable for use in subsequent reactions. It was further purified for analysis by recrystallization in ethyl acetate/ether to give white crystals, mp 77°-78° C. Anal. Calcd, for C13 H17 NO6: C, 55.12; H, 6.05; N, 4.94. Found: C, 55.27; H,, 6.11; N, 4.99.
  • 6
  • [ 873801-17-3 ]
  • [ 17109-93-2 ]
  • [ 1238279-28-1 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: α-cyanomethylmalonic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: diethyl 2-(4-bromobut-2-yn-1-yl)-2-(but-2-yn-1-yl)malonate In tetrahydrofuran; mineral oil at 20℃; for 16h; Inert atmosphere;
 

Historical Records

Technical Information

Categories