Tert-butyl 2-chloro-2-oxoacetate

Base Information

• Chemical Name: Tert-butyl 2-chloro-2-oxoacetate
• CAS No.: 39061-59-1
• Molecular Formula: C6H9ClO3
• Molecular Weight: 164.589
• Hs Code.: 2918300090
• European Community (EC) Number: 820-434-1
• DSSTox Substance ID: DTXSID00456104
• Nikkaji Number: J1.930.038B
• Wikidata: Q82278320
• Mol file: 39061-59-1.mol

Synonyms:tert-butyl 2-chloro-2-oxoacetate;39061-59-1;Acetic acid, chlorooxo-, 1,1-dimethylethyl ester;MFCD03788742;t-butyl chlorooxalate;SCHEMBL836808;t-butyl 2-chloro-2-oxoacetate;tert-butyl2-chloro-2-oxoacetate;DTXSID00456104;UDACWKHNECHEBB-UHFFFAOYSA-N;chloro-oxo-acetic acid t-butyl ester;Oxochloroacetic acid tert-butyl ester;AKOS025146393;BS-13359;2-chloro-2-oxo-acetic acid tert.butylester;C77511;EN300-101862

Chemical Property of Tert-butyl 2-chloro-2-oxoacetate

Chemical Property:

• Boiling Point: 60-63 °C(Press: 23 Torr)
• PSA: 43.37000
• Density: 1.178±0.06 g/cm3(Predicted)
• LogP: 1.09350
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 164.0240218
• Heavy Atom Count: 10
• Complexity: 157

Purity/Quality:

tert-Butyl2-Chloro-2-oxoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(=O)Cl
• Uses: tert-Butyl 2-chloro-2-oxoacetate is a reagent used in the preparation of (S)?-?3-?(Carboxyformamido)?-?2-?(3-?(carboxymethyl)?ureido)?propanoic Acid for prostate cancer imaging.

Technology Process of Tert-butyl 2-chloro-2-oxoacetate

There total 3 articles about Tert-butyl 2-chloro-2-oxoacetate 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: 77.4%

oxalyl dichloride (79-37-8) + tert-butyl alcohol (75-65-0) → t-butoxalyl chloride (39061-59-1)

Guidance literature:

at 20 ℃; for 1h; Ice-bath; Wrapped in foil;

Reference yield:

oxalic acid tert-butyl ester ethyl ester (50624-94-7) → t-butoxalyl chloride (39061-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hydroxide monohydrate / water; methanol / 4 h / 0 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 4 h / Reflux

With oxalyl dichloride; lithium hydroxide monohydrate; N,N-dimethyl-formamide; In methanol; dichloromethane; water;

DOI:10.1002/asia.201801035

Reference yield:

oxalic acid mono-tert-butyl ester (35448-10-3) → t-butoxalyl chloride (39061-59-1)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 4h; Reflux;

DOI:10.1002/asia.201801035

upstream raw materials:

oxalyl dichloride

tert-butyl alcohol

oxalic acid tert-butyl ester ethyl ester

oxalic acid mono-tert-butyl ester

Downstream raw materials:

(Benzyl-benzyloxycarbonyl-amino)-oxo-acetic acid tert-butyl ester

Refernces

• 1、 -. "PSMA (Prostate-Specific Membrane Antigen) inhibitor, compound and application". Paragraph 0082; 0083; 0084; 0085. . Retrieved 2019/05/28.
• 2、 -. "(2S,4R)-5-(5'-CHLORO-2'-FLUOROBIPHENYL-4-YL)-4-(ETHOXYOXALYLAMINO)-2-HYDROXYMETHYL-2-METHYLPENTANOIC ACID". Paragraph 0257. . Retrieved 2016/09/08.