tert-Butyl cyanoacetate

Base Information

• Chemical Name: tert-Butyl cyanoacetate
• CAS No.: 1116-98-9
• Deprecated CAS: 57710-63-1,1654002-83-1
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.17
• Hs Code.: 29269090
• European Community (EC) Number: 214-243-7
• NSC Number: 1072
• UNII: PWT31M9VDL
• DSSTox Substance ID: DTXSID8061501
• Nikkaji Number: J203.338K
• Wikidata: Q72502743
• Mol file: 1116-98-9.mol

Synonyms:tert-Butyl cyanoacetate;1116-98-9;tert-butyl 2-cyanoacetate;Acetic acid, cyano-, 1,1-dimethylethyl ester;t-Butyl cyanoacetate;Cyanoacetic Acid tert-Butyl Ester;Acetic acid, cyano-, tert-butyl ester;tert-butylcyanoacetate;MFCD00001938;PWT31M9VDL;1,1-dimethylethyl cyanoacetate;NSC 1072;NSC-1072;EINECS 214-243-7;Acetic acid, 2-cyano-, 1,1-dimethylethyl ester;t-butylcyanoacetate;tert-butyl2-cyanoacetate;tert.-Butyl cyanoacetate;UNII-PWT31M9VDL;tert-butyl-2-cyanoacetate;SCHEMBL182386;Cyanoacetic acid t-butyl ester;NCCH2C(O)OC(CH3)3;DTXSID8061501;BFNYNEMRWHFIMR-UHFFFAOYSA-;AMY3784;NSC1072;cyano-acetic acid tert-butyl ester;CS-D1442;AKOS000121136;AB00182;GS-3781;TERT-BUTYL .ALPHA.-CYANOACETATE;SY007488;tert-Butyl cyanoacetate, >=97.0% (GC);FT-0624128;EN300-27210;D70419;A802398;W-108669;F8889-2500;Z237573790;Benzenepropanoic acid, .alpha.,.beta.-dibromo-4-fluoro-, ethyl ester

Chemical Property of tert-Butyl cyanoacetate

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 107-108oC
• Refractive Index: n20/D 1.420
• Boiling Point: 194.6 °C at 760 mmHg
• PKA: 3.21±0.10(Predicted)
• Flash Point: 79 °C
• PSA: 50.09000
• Density: 1.001 g/cm³
• LogP: 1.24178
• Storage Temp.: 2-8°C
• Solubility.: Difficult to mix.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 141.078978594
• Heavy Atom Count: 10
• Complexity: 170

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl Cyanoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC#N
• General Description: tert-Butyl cyanoacetate is a versatile reagent used in the synthesis of heterocyclic compounds, particularly in reactions with 3-hetero-1,5-dialdehydes to form derivatives such as tetrahydrothiopyran, tetrahydropyran, and C-pyranosyl glycosides. It participates in piperidine-catalyzed reactions under mild conditions (aqueous 1,4-dioxane, room temperature) to yield structurally diverse products, including 3-deoxy-C-glycosyl derivatives and branched glycosides. The reaction outcomes are influenced by reactant ratios and reaction time, demonstrating its utility in generating stereochemically complex molecules for synthetic applications.

Technology Process of tert-Butyl cyanoacetate

There total 8 articles about tert-Butyl cyanoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

cyanoacetic acid (372-09-8) + isobutene (115-11-7,15220-85-6) → cyanoacetic acid tert-butyl ester (1116-98-9)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at 10 ℃; for 0.133333h; under 12001.2 - 14251.4 Torr; Temperature; Solvent;

Reference yield: 86.0%

cyanoacetic acid (372-09-8) + tert-butyl alcohol (75-65-0) → cyanoacetic acid tert-butyl ester (1116-98-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9)

Guidance literature:

With methanol;

DOI:10.1021/ja01262a014

upstream raw materials:

tert-Butyl chloroacetate

potassium cyanide

bromoacetic acid tert-butyl ester

cyanoacetic acid chloride

Downstream raw materials:

5-(4-methoxyphenyl)-5-oxopentanenitrile

2,3-dicyano-3-phenyl-propionic acid tert-butyl ester

tert-butyl 2-cyano-2-(5-nitropyridin-2-yl)acetate

C₃₅H₃₃NO₁₀

Refernces

REACTION OF 3-HETERO-1,5-DIALDEHYDES WITH tert-BUTYL CYANOACETATE

10.1016/S0008-6215(00)90291-X

The study investigates the reaction of various 3-hetero-1,5-dialdehydes with tert-butyl cyanoacetate. The chemicals involved include thiodiglycolaldehyde and diglycolaldehyde, which react with tert-butyl cyanoacetate to yield derivatives of tetrahydrothiopyran and tetrahydropyran, respectively. Other dialdehydes with furan nuclei at the cy-position, such as a-(S)-(3-ethoxycarbonyl-2-methylfur-5-yl)diglycolaldehyde and a-(S)-(3-acetyl-2-methylfur-5-yl)diglycolaldehyde, produce D-xylo and L-arabino C-pyranosyl derivatives. Additionally, a-(S)-methoxy-a’-(R)-hydroxymethyldiglycolaldehyde leads to D-gluco and D-manno glycosides. The reactions are catalyzed by piperidine and carried out in aqueous 1,4-dioxane at room temperature. The products are isolated using column chromatography, and their structures are determined through elemental analysis and spectroscopic data. The study aims to synthesize 3-deoxy-C-glycosyl derivatives and 3-deoxyglycosides branched at C-3, with the relative proportions of products depending on the reaction time and molar ratios of the reactants.

A colorimetric probe based on diketopyrrolopyrrole and tert-butyl cyanoacetate for cyanide detection

10.1039/c5nj01214g

A new colorimetric probe (1) for highly selective and sensitive detection of cyanide anions was designed and synthesized. The probe is based on the diketopyrrolopyrrole (DPP) Michael acceptor. Upon addition of cyanide, the color of the probe rapidly changes from pink to light yellow, while the UV-visible light absorption undergoes a significant blue shift and 94% fluorescence quenching occurs at 640 nm. The detection limit of cyanide using fluorescence spectrum changes is 0.75 mM, which is lower than the detection limit of 1.9 mM specified by the World Health Organization (WHO). The probe also exhibits higher selectivity for cyanide than other anions and biothiols, and the test paper based on the probe can successfully detect cyanide in aqueous solution.