49653-47-6

Usage

Uses

Used in Pharmaceutical Industry:
1,1-Dimethylethyl dichloroacetate is used as an intermediate in organic synthesis for the production of various pharmaceutical compounds. It plays a crucial role in the synthesis of drugs, contributing to the development of new medications and therapies.
Used in Organic Synthesis:
1,1-Dimethylethyl dichloroacetate is used as a reagent in organic synthesis, enabling the creation of a wide range of organic compounds. Its versatility in chemical reactions makes it a valuable component in the synthesis of various organic molecules for different applications.

InChI:InChI=1/C6H10Cl2O2/c1-6(2,3)10-5(9)4(7)8/h4H,1-3H3

Upstream product

• 79-36-7 dichloroacethyl chloride 
• 75-65-0 tert-butyl alcohol 
• 79-43-6 dichloro-acetic acid 
• 115-11-7 isobutene 

Downstream Products

• 133270-03-8 tert-butyl (chloro)(2,4-dinitrophenyl)acetate 
• 7633-38-7 di-tert-butyl fumarate 
• 18305-60-7 di-tert-butyl maleate 
• 133270-02-7 tert-butyl (chloro)(5-chloro-2,4-dinitrophenyl)acetate 
• 34619-03-9 tert-butyldicarbonate 
• 694-16-6 1,1-dichloro-2,2-dimethylcyclopropane 
• 102191-67-3 1,1-dimethylethyl 2-chloro-3-(4-chlorophenyl)-oxirane carboxylate 
• 102191-63-9 1,1-dimethylethyl 2-chloro-3-(4-nitrophenyl)-oxirane carboxylate 
• 63139-95-7 3-chloro-2-oxo-3-m-nitrophenyl-propionic acid-t-butyl ester 
• 120823-67-8 tert-butyl (E,E)-5-phenylpenta-2,4-dienoate 
• 955961-39-4 tert-butyl 3-chloro-3-(4-methoxyphenyl)-2-oxopropionate 
• 75814-56-1 (E)-tert-butyl 3-phenylbut-2-enoate 
• 75814-57-2 tert-butyl (Z)-3-phenylbut-2-enoate 

Relevant academic research and scientific papers

Synthesis of substituted 5-bromomethyl-4-nitroimidazoles and use for the preparation of the hypoxia-selective multikinase inhibitor SN29966

5-Bromomethyl-4-nitroimidazoles have utility as bioreductive trigger precursors for the preparation of hypoxia-selective prodrugs. Here we describe an efficient two-step synthesis of 5-(bromomethyl)-1-methyl-4-nitro-1H- imidazole, a preferred precursor, employing an N-bromosuccinimide mediated radical bromination. Use of this precursor to prepare SN29966, a promising hypoxia-selective irreversible pan-ErbB inhibitor is reported along with the preparation of four other prodrug candidates. 5-Bromomethyl-4-nitroimidazole analogues bearing electron-donating and electron-withdrawing substituents at the N-1 and C-2 positions are also described.

PRODRUG FORMS OF KINASE INHIBITORS AND THEIR USE IN THERAPY

The invention provides novel prodrug compounds comprising a kinase inhibitor and a reductively-activated fragmenting aromatic nitroheterocycle or aromatic nitrocarbocycle trigger, where the compound carries a positive charge. In preferred embodiments, the compounds are of Formula I: where: X is any negatively charged counterion; R1 is a group of the formula —(CH2)nTr, where Tr is an aromatic nitroheterocycle or aromatic nitrocarbocycle and —(CH2)nTr acts as a reductively-activated fragmenting trigger; and n is an integer from 0 to 6; R2, R3 and R4 may each independently be selected from aliphatic or aromatic groups of a tertiary amine kinase inhibitor (R2)(R3)(R4)N, or two of R2, R3, and R4 may form an aliphatic or aromatic heterocyclic amine ring of a kinase inhibitor, or one of R2, R3 and R4 may be absent and two of R2, R3 and R4 form an aromatic heterocyclic amine ring of a kinase inhibitor. The compounds of the invention are useful in treating proliferative diseases such as cancer.

The first sequential reaction promoted by manganese: Complete stereoselective synthesis of (E)-α,β-unsaturated esters from 2,2-dichloroesters and aldehydes

(Chemical Equation Presented) α,β-Unsaturated esters were obtained with complete control of stereoselectivity utilizing a sequential reaction of dichloroesters with a variety of aldehydes, promoted by active manganese. This methodology is generally applicable, and the C-C double bond can be di- or trisubstituted. A mechanism based on a successive aldol-type reaction/β-elimination is proposed to explain these results.

Substituted benzaldehydes in the darzens condensation with alkyl dihaloacetates

The Darzens reaction of dihaloacetic acid esters with aromatic aldehydes produces either arylhaloglycidic or arylhalopyruvic esters depending on the nature of the substituent in the aromatic ring. Alkyl p- methoxyphenylchloropyruvates undergo spontaneous intermolecular cyclocondensation to form pyranone or furanone derivatives depending on the character of the alkyl fragment.

A Mild and Efficient Alumina-Promoted Synthesis of t-Butyl Esters

A wide variety of aliphatic acid chlorides including an optically active one has been efficiently converted to their t-butyl esters under very mild reaction conditions by employing activated alumina as a catalyst.

Process for the production of oxazolinone-2-compounds

The condensation of an α-halogen carbonyl compound with carbamic acid esters in the presence of a basic condensing agent and an aprotic solvent enables the production of oxazolinone-2-compounds in a high degree of purity, and in high yields in one step by using simple and readily available starting compounds.