107-59-5 Usage
Description
Tert-Butyl chloroacetate, also known as 1,1-dimethylethyl chloroacetate, is an organic compound with the chemical formula C6H11ClO2. It is a clear colorless to yellow liquid that is soluble in water and has a distinct chemical structure featuring a tert-butyl group attached to a chloroacetyl group. Upon hydrolysis, it generates tert-butanol and chloroacetic acid, which are useful in various chemical reactions and applications.
Uses
1. Used in the Glycidic Ester Condensation:
Tert-Butyl chloroacetate is used as a reagent in the glycidic ester condensation process, which is a chemical reaction involving the formation of an ester from an epoxide (glycidic ester) and an alcohol or phenol. This process is essential in the synthesis of various organic compounds and polymers.
2. Used in the Synthesis of Imidazol-1-yl-Acetic Acid Hydrochloride:
Tert-Butyl chloroacetate serves as a key intermediate in the synthesis of imidazol-1-yl-acetic acid hydrochloride, a compound with potential applications in the pharmaceutical industry. This synthesis involves the reaction of tert-butyl chloroacetate with imidazole, followed by hydrolysis and deprotection to obtain the desired product.
3. Used in the Synthesis of cis-Disubstituted Aziridine Ester via Aza-Darzens Reaction:
Tert-Butyl chloroacetate is utilized in the aza-Darzens reaction, a type of organic reaction that involves the formation of aziridines from imines and α-haloesters. In this case, the reaction with an appropriate imine leads to the formation of cis-disubstituted aziridines, which are valuable synthetic intermediates and have potential applications in the synthesis of various biologically active compounds.
4. Used in the Synthesis of 1,10-Diaza-18-Crown-6 Based Sensors Bearing a Coumarin Fluorophore:
Tert-Butyl chloroacetate is employed in the synthesis of 1,10-diaza-18-crown-6 based sensors that incorporate a coumarin fluorophore. These sensors are designed for the selective detection of metal ions, which is crucial in various analytical and environmental applications.
Preparation
tert-Butyl chloroacetate synthesis: The tert-butanol was added to the mixture of chloroacetyl chloride and N,N-dimethylaniline, and the temperature was kept below 30°C. The reactant was poured into water, washed and dried, and then fractionated under reduced pressure. The fractions at 48-49°C (1.46kPa) were collected to obtain tert-butyl chloroacetate with a yield of 63%.
Safety Profile
A poison by ingestion.
Moderately toxic by inhalation skin contact.
S severe sluin and moderate eye irritant.
When heated to decomposition it emits
toxic vapors of Cl-.
Purification Methods
Check the NMR spectrum; if satisfactory then distil in a vacuum; if not then dissolve in Et2O, wash with H2O, 10% H2SO4 until the acid extract does not become cloudy when made alkaline with NaOH. Wash the organic layer again with H2O, then saturated aqueous NaHCO3, dry over Na2SO4, evaporate and fractionate it through a carborundum-packed column or a 6-inch Widmer column (p 11, see tert-butyl ethyl malonate for precautions to avoid decomposition during disillation). [Johnson et al. J Am Chem Soc 75 4995 1953, Baker Org Synth Coll Vol III 144 1944, Beilstein 2 III 444.]
Check Digit Verification of cas no
The CAS Registry Mumber 107-59-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 107-59:
(5*1)+(4*0)+(3*7)+(2*5)+(1*9)=45
45 % 10 = 5
So 107-59-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H11ClO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3
107-59-5Relevant articles and documents
General procedure for acylation of 3° alcohols: Scandium triflate/DMAP reagent
Zhao, Hong,Pendri, Annapurna,Greenwald, Richard B.
, p. 7559 - 7562 (1998)
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Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions
Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Eshghi, Hossein,Salimi, Alireza
, (2017/11/23)
In this work, a new Fe3O4/AlFe/Te nanocomposite was synthesized by a one-step sol–gel method. The Fe3O4 magnetic nanoparticles (MNPs) were prepared and then mixed with aluminum telluride (Al2Te3) in an alkali medium to produce the desired catalyst. After characterization of the Fe3O4/AlFe/Te nanocomposite by SEM, TEM, EDS, XRD, and ICP analyses, it was used in the esterification reaction. This heterogeneous catalyst showed high catalytic activity in the esterification of commercially available carboxylic acids with various alcohols to produce the desired esters at high conversions under neat conditions. The Fe3O4/AlFe/Te nanocomposites were separated from the reaction mixture via an external magnet and re-used 8 times without significant loss of catalytic activity.
A PROCESS FOR THE PREPARATION OF [2-(2,6-DICHLORO ANILINO) PHENYL] ACETOXY ACETIC ACID
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Page/Page column 5, (2010/02/13)
Process for manufacture of 2-(2,6-dichlooranilino)phenyl acetoxy acetic acid is provided. The process comprises of acid hydrolysis 2-tert-butoxy-2-oxoethyl {2[(2,6-dichlorophenyl) amino]phenyl)acetate in presence of a strong acid cationic exchange resin with S03H group on -Divinylbenzene copolymer beads in presence of a solvent to yield compounds of formula 1. The compounds so obtained have shown Non-Steroidal anti-inflammatory activity.