2771-67-7

Basic information

• Product Name: N-(Dichloromethylene)-4-chloroaniline
• Synonyms: (4-Chlorophenyl)imidocarbonic aciddichloride;N-(4-Chlorophenyl)dichloromethanimine;N-(Dichloromethylene)-4-chloroaniline
• CAS NO: 2771-67-7
• Molecular Formula: C₇H₄Cl₃N
• Molecular Weight: 208.47
• Mol File: 2771-67-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 249.7°C at 760 mmHg
• Flash Point: 104.8°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0.0357mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: N-(Dichloromethylene)-4-chloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Dichloromethylene)-4-chloroaniline(2771-67-7)
• EPA Substance Registry System: N-(Dichloromethylene)-4-chloroaniline(2771-67-7)

Safety Data

• Hazardous Substances Data: 2771-67-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H4Cl3N/c8-5-1-3-6(4-2-5)11-7(9)10/h1-4H

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 7719-09-7 thionyl chloride 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 103-70-8 Formanilid 
• 463-71-8 thiophosgene 
• 106-47-8 4-chloro-aniline 
• 2617-79-0 N-(4-chlorophenyl)formamide 

Downstream Products

• 59611-67-5 [(4-chlorophenylamino)methyl]-1,1-bisphosphonic acid 
• 34233-04-0 Benzoic acid N'-[1-(4-chloro-phenylamino)-1-methoxy-meth-(Z)-ylidene]-N-methyl-hydrazide 
• 34257-22-2 5-(4-chloro-anilino)-3-methyl-2-phenyl-[1,3,4]thiadiazolium betaine 
• 1273585-24-2 (Z)-N-(4-chlorophenyl)-4,5-diphenyl-1,3-oxathiol-2-imine 
• 956471-87-7 C₁₀H₁₂ClN₅S 
• 33328-21-1 phenyl-N'-(4-chlorophenyl)-N,N-dimethylcarbamimidothioate 
• 3050-27-9 N-(p-Chlorphenyl)-N',N'-dimethyl-O-methylisoharnstoff 
• 143770-22-3 4-<4-chlorophenyl>-5-imino-6,7,8,9-tetrahydro<1>benzothieno<3,2-e>tetrazolo<1,5-a>pyrimidine 
• 143770-24-5 4-<4-chlorophenyl>-5-imino-6,7-dimethyltetrazolo<1,5-a>thieno<3,2-e>pyrimidine 
• 143770-36-9 2-amino-3-<4-chlorophenyl>-4-imino-5,6,7,8-tetrahydro<1>benzothieno<2,3-d>pyrimidine 
• 52625-27-1 N-(4-chlorophenyl)morpholine-4-carboxamide 

Relevant articles and documents

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Lifetimes of imidinium ions in aqueous solution

Imidinium ions, ArN=CNR2+, were generated in aqueous solution from the solvolysis of fluoro and chloro formamidines at pH 9.3 and 25°C. Rate constants for the hydration of five imidinium ions were determined from a kinetic analysis of their trapping by thiolacetate anion, CH3COS-, in the presence of a pool of competing fluoride anion, and a rate constant of k(AcS)- = 5 x 109 M-1 S-1 for diffusion-controlled trapping of the carbocations with thiolacetate anion. The rate constants, k(s), for hydration of the imidinium ions, XArN=CNC4H8O+ are 3.6 x 105, 5.8 x 105, 1.5 x 106, 1.6 x 106, and 1.8 x 106 s-1 for X = H, 4-Cl, 3-CN, 4-CN, and 3-NO2, respectively. In a similar experiment a rate constant of k(s) = 3.3 x 107 s-1 was obtained for hydration of the imidinium ion 4-NO2-ArN=CNCH3(OCH3)+, by using azide anion to trap the cation and a rate constant of k(az) = 5 x 109 M-1 s-1 for diffusion-controlled trapping of the imidinium ion with azide ion. The partitioning rate constant ratio k(AcS)-/k(s) for 4-ClArN=CNC4H8O+ decreases by approximately 6-fold in 45% v/v glycerol/water in contrast to k(az)/k(s), which remains almost constant, showing that thiolacetate, but not azide anion, combines with the imidinium ion at a diffusion-limited rate. The reactivity of the imidinium ions deviate from behavior predicted by the N+ scale in a manner that may be explained by a difference in the selectivity of the cation when compared to the more stable N+ carbocations.