2998-56-3

Basic information

• Product Name: N,N-Bis(2-chloroethyl)carbamoyl chloride
• Synonyms: bis(2-chloroethyl)-carbamicchlorid;bis(2-chloroethyl)-carbamoylchlorid;bis(2-chloroethyl)carbamoylchloride;bischloroethylcarbamoylchloride;tl460;N,N-BIS(2-CHLOROETHYL)CARBAMOYL CHLORIDE;bis-(2-Chloroethyl)carbamic chloride;Bis-(2-chloro ethyl)carbamoyl hydrochloride
• CAS NO: 2998-56-3
• Molecular Formula: C₅H₈Cl₃NO
• Molecular Weight: 204.48
• EINECS: 221-075-8
• Mol File: 2998-56-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 101-103 °C
• Boiling Point: 125°C 3mm
• Flash Point: 129.3 °C
• Appearance: Colorless transparent liquid
• Density: 1,4 g/cm3
• Refractive Index: 1.5060-1.5100
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -2.30±0.70(Predicted)
• CAS DataBase Reference: N,N-Bis(2-chloroethyl)carbamoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Bis(2-chloroethyl)carbamoyl chloride(2998-56-3)
• EPA Substance Registry System: N,N-Bis(2-chloroethyl)carbamoyl chloride(2998-56-3)

Safety Data

• Hazard Codes: T
• Statements: 34-43-25
• Safety Statements: 26-36/37/39-45
• RIDADR: 3265
• RTECS: FD2200000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2998-56-3(Hazardous Substances Data)

Usage

General Description

N,N-Bis(2-chloroethyl)carbamoyl chloride is a chemical compound that is used in the synthesis of various pharmaceuticals and pesticides. It is a carbamate derivative with two 2-chloroethyl groups attached to the carbamoyl chloride group. N,N-Bis(2-chloroethyl)carbamoyl chloride is a potent alkylating agent, meaning it can react with and modify nucleophilic groups in proteins and nucleic acids. Its alkylating properties make it useful in the development of cancer-fighting drugs, as it can disrupt the replication of cancerous cells. However, it is also highly toxic and poses a significant health risk, so it must be handled with extreme caution in a controlled environment.

Upstream product

• 334-22-5 N,N-bis(chloro-2-ethyl)amine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 

Downstream Products

• 2998-57-4 estramustine 
• 62899-40-5 Estromustine 
• 15470-58-3 Diethylstilboestryl-bis--carbamat 
• 1357376-12-5 C₂₇H₂₈ClN₅O₄ 
• 6526-87-0 Bis-(2-chloro-ethyl)-carbamic acid 4-{[1-{4-[bis-(2-chloro-ethyl)-carbamoyloxy]-phenyl}-meth-(E)-ylidene]-amino}-phenyl ester 
• 6526-51-8 4-anilin 
• 110008-67-8 E,Z-1-<4-(N,N-bis-β-chloroethylcarbamoyloxy)-phenyl>-1-(4-acetoxyphenyl)-2-(3-acetoxyphenyl)-but-1-ene 
• 110008-62-3 E,Z-1-<4-(N,N-bis-β-chloroethylcarbamoyloxy)-phenyl>-1-(4-hydroxyphenyl)-2-(3-hydroxyphenyl)-but-1-ene 
• 6526-89-2 2,4'-Bisdiphenylsulfon 
• 6526-81-4 3,3-Di<4-phenyl>pentan 
• 6548-20-5 4,4'-Bis-diphenyl-disulfid 
• 6526-80-3 2,2-Di<4-phenyl>butan 
• 6526-84-7 Bis-(2-chloro-ethyl)-carbamic acid 4-(1-{4-[bis-(2-chloro-ethyl)-carbamoyloxy]-phenyl}-cyclohexyl)-phenyl ester 

Relevant articles and documents

Expanding the Arsenal of PtIV Anticancer Agents: Multi-action PtIV Anticancer Agents with Bioactive Ligands Possessing a Hydroxy Functional Group

Most multi-action PtIV prodrugs have bioactive ligands containing carboxylates. This is probably due to the ease of carboxylating the OH axial ligands and because following reduction, the active drug is released. A major challenge is to expand the arsenal of bioactive ligands to include those without carboxylates. We describe a general approach for synthesis of PtIV prodrugs that release drugs with OH groups. We linked the OH groups of gemcitabine (Gem), paclitaxel (Tax), and estramustine (EM) to the PtIV derivative of cisplatin by a carbonate bridge. Following reduction, the axial ligands lost CO2, rapidly generating the active drugs. In contrast, succinate-linked drugs did not readily release the free drugs. The carbonate-bridged ctc-[Pt(NH3)2(PhB)(Gem-Carb)Cl2] was significantly more cytotoxic than the succinate-bridged ctc-[Pt(NH3)2(PhB)(Gem-Suc)Cl2], and more potent and less toxic than gemcitabine, cisplatin, and co-administration of cisplatin and gemcitabine.

ANTICANCER AGENTS

The invention generally concerns a method for conjugating an active material to a Pt complex.

Selective acylation process

This invention relates to a selective acylation process for the preparation of phenolic N-disubstituted carbamate esters of steroids, comprising reacting in an inert solvent an acylating agent being a carbamoyl halogenide, a 4-(tertiary amino)-pyridine, or a complex thereof, optionally as a part of a polymer and a steroid having at least two free hydroxy groups, where at least one is phenolic and at least one is alcoholic, optionally in the presence of an acid acceptor.