Tert-butyl 4-chloro-3-oxobutanoate

Base Information

• Chemical Name: Tert-butyl 4-chloro-3-oxobutanoate
• CAS No.: 74530-56-6
• Molecular Formula: C8H13 Cl O3
• Molecular Weight: 192.642
• European Community (EC) Number: 277-910-1
• DSSTox Substance ID: DTXSID60996051
• Nikkaji Number: J349.422E
• Mol file: 74530-56-6.mol

Synonyms:74530-56-6;tert-Butyl-4-chloro-3-oxobutanoate;tert-butyl 4-chloro-3-oxobutanoate;Butanoic acid,4-chloro-3-oxo-, 1,1-dimethylethyl ester;tert-Butyl 4-chloro-3-oxobutyrate;EINECS 277-910-1;tert-butyl 4-chloroacetoacetate;t-butyl 4-chloroacetoacetate;t-butyl-4-chloroacetoacetate;SCHEMBL5604487;t-butyl 4-chloro-3-oxobutanoate;tert.-butyl 4-chloroacetoacetate;DTXSID60996051;DVOUIKQENBFPRS-UHFFFAOYSA-N;ZCA53056;tert.-butyl 4-chloro-3-oxobutyrate;MFCD00052188;AKOS006274345;AC-13976;AS-44356;4-Chloro-3-oxobutyric acid tert-butyl ester;CS-0119530;FT-0777829;EN300-265938;A937406;4-Chloro-3-oxobutanoic acid 1,1-dimethylethyl ester;Butanoic acid, 4-chloro-3-oxo-, 1,1-dimethylethyl ester

Chemical Property of Tert-butyl 4-chloro-3-oxobutanoate

Chemical Property:

• Vapor Pressure: 0.0657mmHg at 25°C
• Boiling Point: 230.5°C at 760 mmHg
• PKA: 9.58±0.46(Predicted)
• Flash Point: 87°C
• PSA: 43.37000
• Density: 1.115g/cm³
• LogP: 1.52610
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 192.0553220
• Heavy Atom Count: 12
• Complexity: 181

Purity/Quality:

98%Min ^*data from raw suppliers

tert-Butyl-4-chloro-3-oxobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(=O)CCl
• Uses: tert-Butyl-4-chloro-3-oxobutanoate acts as a reagent in the synthetic preparation of cephalosporin antibiotics and penicillin derivatives. Also functions as a reagent for the synthesis of Ethyl 4-Chloroacetoacetate.

Technology Process of Tert-butyl 4-chloro-3-oxobutanoate

There total 1 articles about Tert-butyl 4-chloro-3-oxobutanoate 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:

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + tert-butyl alcohol (75-65-0) → tert-butyl 4-chloroacetoacetate (74530-56-6) + tert-butyl 4-chloro-3-hydroxybutanoate (85153-48-6)

Guidance literature:

With pyridine; chlorine; Yield given; Multistep reaction. Yields of byproduct given; 1.) CCl₄, from -25 deg C to -20 deg C, 30 min, 2.) CCl₄, -5 deg C, 1 h;

DOI:10.1016/S0957-4166(99)00126-3

Reference yield: 72.0%

tert-butyl 4-chloroacetoacetate (74530-56-6) → (+/-)-tert-butyl 3,4-epoxybutanoate (108100-50-1,111058-62-9,56936-16-4) + tert-butyl 4-chloro-3-hydroxybutanoate

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 1.5h; Yield given; Ambient temperature;

DOI:10.1016/S0957-4166(99)00126-3

Reference yield:

tert-butyl 4-chloroacetoacetate (74530-56-6) → (3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate (125971-93-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanesulfonic acid / 6 h / 20 - 60 °C

2.1: magnesium; iodine; ethyl bromide / tetrahydrofuran / 50 - 60 °C

2.2: -10 - 45 °C

3.1: nicotinamide adenine dinucleotide phosphate; glucose dehydrogenase; D-glucose / N,N-dimethyl-formamide / 12 h / 25 °C / pH 6.5 / Microbiological reaction; Enzymatic reaction

With glucose dehydrogenase; ethyl bromide; methanesulfonic acid; D-glucose; iodine; nicotinamide adenine dinucleotide phosphate; magnesium; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

4-methyleneoxetan-2-one

tert-butyl alcohol

Downstream raw materials:

tert-Butyl 4-benzyloxy-3-oxobutanoate

(+/-)-tert-butyl 3,4-epoxybutanoate

tert.-butyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-acetoacetate

tert.-butyl (6R,7R)-7-benzoylamino-3-chloro-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Refernces