55233-05-1

Basic information

• Product Name: TERT-BUTYL 2-CHLORO-5-NITROBENZOATE
• Synonyms: TERT-BUTYL 2-CHLORO-5-NITROBENZOATE;tert-butyl 2-chloro-5-nitrobenzenecarboxylate
• CAS NO: 55233-05-1
• Molecular Formula: C₁₁H₁₂ClNO₄
• Molecular Weight: 257.67028
• Mol File: 55233-05-1.mol

Chemical Properties

• Boiling Point: 343.3±22.0 °C(Predicted)
• Appearance: /
• Density: 1.283±0.06 g/cm3(Predicted)
• CAS DataBase Reference: TERT-BUTYL 2-CHLORO-5-NITROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 2-CHLORO-5-NITROBENZOATE(55233-05-1)
• EPA Substance Registry System: TERT-BUTYL 2-CHLORO-5-NITROBENZOATE(55233-05-1)

Safety Data

• Hazardous Substances Data: 55233-05-1(Hazardous Substances Data)

Upstream product

• 2516-96-3 2-chloro-5-nitrobenzoic acid 
• 115-11-7 isobutene 
• 865-47-4 potassium tert-butylate 
• 25784-91-2 2-chloro-5-nitrobenzoylchloride 

Downstream Products

• 22156-66-7 2-Phenyl-2-<2-tert.-butoxycarbonyl-4-nitro-phenyl>-propionitril 
• 185433-44-7 2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-5-nitrobenzoic acid 
• 474799-41-2 6-nitroindolin-2-one 

Relevant articles and documents

INDOLINONE DERIVATIVES AND THEIR USE IN TREATING DISEASE-STATES SUCH AS CANCER

The present invention encompasses compounds of general formula (1) wherein R1 to R4 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a pharmaceutical composition having the above-mentioned properties.

NEW COMPOUNDS

The present invention encompasses compounds of general Formula (I) wherein R2, R3, Q, W, X, Y and Z are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation

Synthesis of nitrogen and sulfur analogues of the seco-CI alkylating agent

Two complementary syntheses of amino seco-CI (CI = 1a,2,3,5-tetrahydro-1H-cycloprop[1,2-c]indol-5-one) alkylating agents starting from isomeric chloronitrobenzoic acids are reported. Further reactions of these compounds, including diazotisation to phenol and thiophenol derivatives, and alkylation and acylation reactions relevant to the preparation of pro-drug forms are also described.

Enzyme kinetics and substrate selectivities of rat glutathione S-transferase isoenzymes towards a series of new 2-substituted 1-chloro-4-nitrobenzenes

1. Four different rat glutathione S-transferase (GST) isoenzymes, belonging to three different classes, were examined for their GSH conjugating capacity towards 11 2-substituted 1-chloro-4-nitrobenzene derivatives. Significant differences were found in their enzyme kinetic parameters K(m), k(cat) and k(cat)/K(m). 2. Substrates with bulky substituents on the ortho-position appeared to have high affinities (low K(m)'s) for the active site of the GST-isoenzymes, suggesting that there is sufficient space in this area of the active site. A remarkably high K(m) (low affinity) was found for 2-chloro-5-nitropyridine towards all GST-isoenzymes examined. 3. GST 3-3 catalysed the reaction between GSH and the substrates most efficiently (high k(cat)) compared with the other GST-isoenzymes. Moreover, GST 3-3 showed clear substrate selectivities towards the substrates with a trifluoromethyl-, chlorine- and bromine-substituent. 1-Chloro-2,4-dinitrobenzene and 2-chloro-5-nitrobenzonitrile were most efficiently conjugated by all four GST-isoenzymes examined. 4. When the rate of the conjugation reactions was followed, a linear increase of formation of GS-conjugate could be seen for 2-chloro-5-nitrobenzonitrile during a much longer period of time than for 1-chloro-2,4-dinitrobenzene with all GST-isoenzymes examined. Therefore, it is suggested that 2-chloro-5-nitrobenzonitrile might be recommended as an alternative model substrate in GST-research.

A novel nitro-substituted seco-CI: Application as a reductively activated adept prodrug

An alternative synthesis of seco-CI alkylating agents bearing a nitrogen substituent at C-6 is reported. The nitro compound 3 prepared by this route exhibits a 400-fold increase in cytotoxicity against UV4 cells in the presence of a nitroreductase enzyme from Escherichia coli B, suggesting it as a potential prodrug for use in antibody-directed enzyme prodrug therapy.