334-22-5

Basic information

• Product Name: Nornitrogen mustard
• Synonyms: Nornitrogen mustard;NOR-N-MUSTARD;1,1'-Iminobis(2-chloroethane);2-Chloro-N-(2-chloroethyl)ethanamine;Nor-mustard
• CAS NO: 334-22-5
• Molecular Formula: C₄H₉Cl₂N
• Molecular Weight: 142.028
• Mol File: 334-22-5.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 231.44°C (rough estimate)
• Flash Point: 77.3°C
• Appearance: /
• Density: 1.3111 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• PKA: 7.02±0.19(Predicted)
• CAS DataBase Reference: Nornitrogen mustard(CAS DataBase Reference)
• NIST Chemistry Reference: Nornitrogen mustard(334-22-5)
• EPA Substance Registry System: Nornitrogen mustard(334-22-5)

Safety Data

• Safety Statements: x and Cl−." target="_blank">Poison by intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive eff
• Hazardous Substances Data: 334-22-5(Hazardous Substances Data)

Usage

Safety Profile

Poison by intraperitoneal,subcutaneous, and intravenous routes. Experimentalreproductive effects. Human mutation data reported.When heated to decomposition it emits very toxic NOxand Cl-.

Upstream product

• 111-42-2 2,2'-iminobis[ethanol] 
• 56-23-5 tetrachloromethane 
• 51-75-2 nitrogen mustard 
• 75-44-5 phosgene 
• 1448-36-8 methyl cholate 
• 1566-15-0 N,N-bis(2-chloroethyl)phosphorodiamidic acid cyclohexylammonium salt 
• 538-07-8 bis(2-chloroethyl)(ethyl)amine 
• 555-77-1 tris-(2-chloro-ethyl)-amine 
• 126-85-2 bis-(2-chloro-ethyl)-methyl-amine oxide 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 

Downstream Products

• 99360-31-3 3-(N,N-bis(2-chloroethyl)carbamoyl)pyridine 
• 5467-15-2 bis(2-chloroethyl)carbamic acid ether 
• 15567-91-6 bis-(2-chloro-ethyl)-methoxymethyl-amine 
• 54533-09-4 N,N-bis(2-chloroethyl)methanesulfonamide 
• 34761-58-5 Ethyl N,N-bis(β-chloroethyl)amidophosphorochloridate 
• 6472-49-7 4-chloro-benzenesulfonic acid-[bis-(2-chloro-ethyl)-amide] 
• 19945-22-3 N,N-bis-(2-chloro-ethyl)-acetamide 
• 2998-56-3 N,N-bis-(2-chloroethyl)carbamoyl chloride 
• 667-82-3 trifluoro-acetic acid-[bis-(2-chloro-ethyl)-amide] 
• 1009-85-4 1,4-bis-(2-chloro-ethyl)-piperazine 
• 5504-55-2 bis-(2-chloro-ethyl)-carbamonitrile 
• 91674-25-8 phosphoric acid-[bis-(2-chloro-ethyl)-amide]-(2-chloro-ethyl ester)-chloride 
• 398-87-8 fluoro-acetic acid-[bis-(2-chloro-ethyl)-amide] 
• 89212-13-5 chloro-methanesulfonic acid-[bis-(2-chloro-ethyl)-amide] 

Relevant articles and documents

Biological evaluation of tetracationic compounds based on two 1,4-diazabicyclo[2.2.2]octane moieties connected by different linkers

A series of 1,4-diazabicyclo[2.2.2]octane derivatives differing by linker moiety was evaluated for activity against several strains of both Gram-positive and Gram-negative bacteria including drug-resistant strains, one strain of fungus and influenza virus A/Puerto Rico/8/34 (H1N1). All compounds exhibited high antibacterial activity against all bacteria except Proteus vulgaris. The minimum inhibitory concentrations (MICs) of compound 1c with an o-phenylenebismethyl linker and compound 1e with a propylene aliphatic linker were found to be low and were comparable or better to the reference drug ciprofloxacin for Pseudomonas aeruginosa and Staphylococcus aureus. Additionally, a time-kill assay was performed to examine the bactericidal kinetics. Compounds 1c and 1e displayed rapid killing effects against St. aureus and Ps. aeruginosa after 2?h. Furthermore, compounds 1a–c with aromatic linkers and compound 1e showed the highest antiviral activity.

Kinetics of phosphoramide mustard hydrolysis in aqueous solution

Hydrolysis of phosphoramide mustard was investigated using HPLC, 31P NMR, and GC-MS with specific deuterium labels. The hydrolysis of phosphoramide mustard in sodium phosphate buffers was found to follow apparent first-order kinetics. The rate of hydrolysis was temperature and pH dependent, being slower under acidic conditions. The hydrolysis was not catalyzed by hydroxyl ion, and its pH dependence appeared to be the result of a change in the mechanism of hydrolysis at different pH values. At a pH value approximately above the pK(a) of the phosphoramide mustard nitrogen, the major hydrolytic pathway of phosphoramide mustard was via the formation of the aziridinium ion, followed by nucleophilic attack. At pH values below its pK(a), cleavage of the P-N bond predominated. At pH 7.4, the formation of an aziridinium ion was followed by a rapid hydrolysis to yield the monohydroxy and, subsequently, the dihydroxy products. The hydrolysis at this pH was adequately described by consecutive first-order kinetics. Seven species in the hydrolytic mixture have been identified as intact phosphoramide mustard, N-(2-chloroethyl)-N-(2-hydroxyethyl)phosphorodiamidic acid, N,N-bis-(2-hydroxyethyl)phosphorodiamidic acid, phosphoramidic acid, phosphoric acid, N,N-bis-(2-chlorethyl)amine, and N-(2-chloroethyl)-N-(2-hydroxyethyl)amine by GC-MS with the aid of deuterium labels. Phosphoramide mustard was found to be stabilized by chloride ion. The stabilization was linearly related to the chloride ion concentration, and the mechanism was found to be via the formation of phosphoramide mustard from the aziridinium and chloride ions. Phosphoramide mustard was significantly more stable in human plasma and in 5% human serum albumin as compared to aqueous buffers, an observation that may be important in vivo.

Novel antitumor agent family of 1H-benzo[c,d]indol-2-one with flexible basic side chains: Synthesis and biological evaluation

A series of mono-1H-benzo[c,d]indol-2-one with different amine side chains and bis-1H-benzo[c,d]indol-2-one as novel family of DNA intercalators were designed and synthesized, the contributions of aromatic chromophores and amine side chains for DNA binding properties, for example, intercalation and electrostatic binding, respectively, were evaluated. Among them, A3 tailed with N,N-dimethylamino-ethyl-ethane-1,2-diamine showed selective anti-tumor activities against cell lines A549 and P388 with IC50 0.428 μm and 1.69 μm.

Synthesis of novel perfluoroalkyl ether derivatives

A series of novel fluoroether-containing monomers has been designed and prepared based on the commercially available perfluoroalkyl ether acid fluoride. Treating acid fluoride with allyl alcohol, 2-hydroxyethyl methacrylate or N-allylmethylamine allowed for the direct formation of corresponding vinyl-containing fluorinated monomers. High yields of the fluorinated epoxy monomers could be obtained from acid chloride with glycidol; meanwhile, fluorinated diol was prepared from diethanolamine or 3-amino-1,2-propanediol. Moreover, fluorinated monoamine, fluorinated monoalcohol and fluorinated dichloride were also obtained. Most of these fluorinated monomers were liquid at room temperature and exhibited good solubility in common organic solvents.

The preparation of 8-[4-[4-(2-pyrimidinyl)-1-piperaziny]butyl]-8- azaspiro[4,5] decane-7,9-dione hydrochloride

8-[4-[4-(2-Pyrimidinyl)-1-piperaziny]butyl]-8-azaspiro [4,5] decane-7,9-dione hydrochloride (buspirone hydrochloride) was obtained in one pot with a 51.8% overall yield. The key intermediate, 1-(2-pyrimidinyl) piperazine, was synthesized through chlorination and cyclization condensation reaction with diethanolamine as initial material. This modified protocol has the notable advantages of mild reaction condition, convenient operation, and high overall yield.