74367-78-5

Basic information

• Product Name: 3,5-DINITROBENZYL CHLORIDE
• Synonyms: ALPHA-CHLORO-3,5-DINITROTOLUENE;3,5-DINITROBENZYL CHLORIDE;1-(chloromethyl)-3,5-dinitro-benzen;α-chloro-3,5-dinitrotoluene;1-(Chloromethyl)-3,5-dinitrobenzene;Benzene, 1-(chloromethyl)-3,5-dinitro-;Ccris 3134;Einecs 277-841-7
• CAS NO: 74367-78-5
• Molecular Formula: C₇H₅ClN₂O₄
• Molecular Weight: 216.58
• EINECS: 277-841-7
• Product Categories: Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 74367-78-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 79-82 °C(lit.)
• Boiling Point: 373.4 °C at 760 mmHg
• Flash Point: 179.6 °C
• Appearance: /
• Density: 1.538 g/cm³
• Vapor Pressure: 1.93E-05mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• BRN: 2506587
• CAS DataBase Reference: 3,5-DINITROBENZYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DINITROBENZYL CHLORIDE(74367-78-5)
• EPA Substance Registry System: 3,5-DINITROBENZYL CHLORIDE(74367-78-5)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: CZ0770000
• F: 10-19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 74367-78-5(Hazardous Substances Data)

Usage

Uses

3,5-Dinitrobenzyl chloride was used in the synthesis of double-spanned double cavity calix[4]arenes and 3,5-dinitrobenzylamines. It also was used in fluorescence flow immunoassay for determination of 4-nitrophenol.

InChI:InChI=1/C7H5ClN2O4/c8-4-5-1-6(9(11)12)3-7(2-5)10(13)14/h1-3H,4H2

Upstream product

• 618-85-9 3,5-dinitrotoluene 
• 99-34-3 3,5-dinitrobenzoic acid 
• 71022-43-0 3,5-dinitrobenzyl alcohol 
• 75-62-7 Bromotrichloromethane 

Downstream Products

• 78710-94-8 Phosphoric acid mono-{(2R,3S,4R,5R)-5-[6-amino-8-(3,5-dinitro-benzylsulfanyl)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl} ester 
• 252358-63-7 1-(3,5-Dinitrobenzyl)-2,3,3-trimethylindolium iodide 
• 1021465-71-3 C₂₅H₂₀N₂O₄P⁽¹⁺⁾*Cl^(1-) 

Relevant articles and documents

Preparation method of tazobactam

The invention discloses a preparation method of tazobactam. The method includes: adopting 3, 5-dinitrobenzyl chloride as the carboxyl protection reagent for esterification reaction with 6alpha-bromopenam-3alpha-carboxylic acid-1beta-oxide; then carrying out reduction, thermal cracking, chloromethylation, azidation, double oxidation and cyclization addition to obtain tazobactam3, 5-dinitrobenzyl ester; then taking palladium carbon as the catalyst, and employing hydrogen to remove the protection of tazobactam3, 5-dinitrobenzyl ester so as to obtain tazobactam; and reacting the by-product 3, 5-dinitrotoluene with the chlorinating reagent N-chlorosuccinimide to prepare 3, 5-dinitrobenzyl chloride, thus realizing recycling of the protection reagent. The method provided by the invention uses 3,5-dinitrobenzyl chloride with stable chemical properties, high reaction activity and low price as the carboxyl protection reagent, avoids the use of peracetic acid that has poor stability and easily causes decomposition explosion, and realizes intrinsic safety of the process.

The use of bromotrichloromethane in chlorination reactions

Carbon tetrachloride is no longer used as a common solvent due to its toxicity and harmful environmental impact. The synthesis of gem-dichloroalkenes from aldehydes by using triphenylphosphine typically requires carbon tetrachloride as a solvent. We report that stoichiometric bromotrichloromethane in acetonitrile can be used in place of solvent quantities of carbon tetrachloride in this transformation. Similarly, bromotrichloromethane in dichloromethane can be used for the room-temperature Appel reaction of benzyl alcohols to form benzyl chlorides, which is commonly carried out in refluxing carbon tetrachloride. Georg Thieme Verlag Stuttgart New York.

A pentiptycene-derived light-driven molecular brake

(Chemical Equation Presented) A room-temperature light-driven molecular brake (1), consisting of a pentiptycene rotator, a 3,5-dinitrophenyl brake, and a photoisomerizable ethenyl spacer, is reported. The rotation rates of the rotator differ by about 9 orders of magnitude between the brake-on (cis-1) and brake-off (trans-1) states.