tert-Butyl isocyanoacetate

Base Information

• Chemical Name: tert-Butyl isocyanoacetate
• CAS No.: 2769-72-4
• Molecular Formula: C7H11 N O2
• Molecular Weight: 141.17
• Hs Code.: 2926909090
• European Community (EC) Number: 628-840-9
• DSSTox Substance ID: DTXSID70374780
• Nikkaji Number: J704.915C
• Wikidata: Q72503489
• Mol file: 2769-72-4.mol

Synonyms:tert-Butyl isocyanoacetate;2769-72-4;Tert-butyl 2-isocyanoacetate;2-Isocyano Acetic Acid Tert-Butyl Ester;T-butyl isocyanoacetate;tert-butylisocyanoacetate;Acetic acid, 2-isocyano-, 1,1-dimethylethyl ester;SCHEMBL768870;DTXSID70374780;IQSYKHVFMYGJER-UHFFFAOYSA-N;isocyano-acetic acid tert-butyl ester;isocyanoacetic acid tert.-butyl ester;MFCD00042952;AKOS015959163;GS-0319;FT-0695318;EN300-86222;D86355;A852933;J-016864

Chemical Property of tert-Butyl isocyanoacetate

Chemical Property:

• Refractive Index: n20/D 1.422
• Boiling Point: 50 oC (0.1 mmHg)
• Flash Point: 82 °C
• PSA: 26.30000
• Density: 0.97g/cm³
• LogP: 0.47810
• Storage Temp.: −20°C
• 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:

99% ^*data from raw suppliers

tert-Butyl isocyanoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/22
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C[N+]#[C-]

Technology Process of tert-Butyl isocyanoacetate

There total 6 articles about tert-Butyl isocyanoacetate 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: 87.0%

tert-butyl 2-formamidoacetate (51354-15-5) → tert-Butyl isocyanoacetate (2769-72-4)

Guidance literature:

With triethylamine; trichlorophosphate; In dichloromethane; at 0 ℃; for 0.583333h; Inert atmosphere;

DOI:10.1039/c5ob02141c

Reference yield:

Glycine tert-butyl ester (6456-74-2) → tert-Butyl isocyanoacetate (2769-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC, Py / CHCl₃

2: COCl₂, Et₃N / CH₂Cl₂

With pyridine; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; chloroform;

DOI:10.1021/jo00431a046

Reference yield:

tert-Butyl chloroacetate (107-59-5) → tert-Butyl isocyanoacetate (2769-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOMe / 1.) MeOH, 2.) room temperature, 4-6 h

2: 80 percent / Et₃N, POCl₃ / CH₂Cl₂ / 1 h / 0 °C

With sodium methylate; triethylamine; trichlorophosphate; In dichloromethane;

DOI:10.1021/jo980043m

upstream raw materials:

tert-butyl 2-formamidoacetate

tert-Butyl chloroacetate

Glycine tert-butyl ester

bromoacetic acid tert-butyl ester

Downstream raw materials:

2-(S)-amino-3-ethyl-pentanoic acid

acetic acid tert-butyl ester

4-methyl-3-(4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid tert-butyl ester

Refernces

• 1、 Liang, Wenbin,Nakajima, Kazunari,Sakata, Ken,Nishibayashi, Yoshiaki. "Copper-Catalyzed [3+2] Cycloaddition Reactions of Isocyanoacetates with Phosphaalkynes to Prepare 1,3-Azaphospholes". . p. 1168 - 1173. Retrieved 2019.
• 2、 -. "BENZODIAZEPINE DERIVATIVES, COMPOSITIONS, AND METHODS FOR TREATING COGNITIVE IMPAIRMENT". Paragraph 1599. . Retrieved 2018/07/05.