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:

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
• Uses: tert-Butyl cyanoacetate is used in the synthesis of vinylogous urea and tert-butyl phenylcyanoacrylates. It is also used as a new additive for the sugar nucleoside base coupling step en route to DAPD with improved β-selectivity.

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

Cyanoaceton

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

Refernces

• 1、 Ninomiya,Shioiri,Yamada. "Amino acids and peptides. XII. Phosphorus in organic synthesis. VIII. Reaction of malonic acid half esters with diphenyl phosphorazidate". . p. 1398 - 1404. Retrieved 1974.
• 2、 -. "Continuous flow preparation method of tert-butyl cyanoacetate". Paragraph 0027-0038. . Retrieved 2021/04/14.
• 3、 Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Eshghi, Hossein,Salimi, Alireza. "Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions". . . Retrieved 2017/11/23.