20265-96-7

Basic information

• Product Name: 4-Chlorobenzenamine hydrochloride
• Synonyms: 4-Chlorobenzemine hydrochloride;1-amino-4-chlorobenzenehydrochloride;4-chloroaniliniumchloride;4-chloro-benzenaminhydrochloride;4-chlorophenylaminehydrochloride;Aniline, p-chloro-, hydrochloride;aniline,p-chloro-,hydrochloride;Benzenamine, 4-chloro-, hydrochloride
• CAS NO: 20265-96-7
• Molecular Formula: C₆H₇ClN*Cl
• Molecular Weight: 164.03
• EINECS: 243-656-5
• Mol File: 20265-96-7.mol

Chemical Properties

• Melting Point: 230°C (subl.)
• Boiling Point: 270.51°C (rough estimate)
• Flash Point: 89.5 °C
• Appearance: /
• Density: 1.3807 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: within almost transparency
• Stability: Hygroscopic
• BRN: 3560964
• CAS DataBase Reference: 4-Chlorobenzenamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorobenzenamine hydrochloride(20265-96-7)
• EPA Substance Registry System: 4-Chlorobenzenamine hydrochloride(20265-96-7)

Safety Data

• Hazard Codes: Xn
• Statements: 23/24/25-33-40-50/53-22
• Safety Statements: 28-36/37-45-60-61
• RIDADR: 2811
• RTECS: BX1394000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 20265-96-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Safety Profile

Suspected carcinogen with carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic vapors of NOx, HCl, and Cl-.

InChI:InChI=1/C6H6ClN.ClH/c7-5-1-3-6(8)4-2-5;/h1-4H,8H2;1H

Upstream product

• 106-47-8 4-chloro-aniline 
• 2617-79-0 N-(4-chlorophenyl)formamide 
• 100-00-5 4-chlorobenzonitrile 
• 3289-75-6 2-chloro-N-(4-chlorophenyl)acetamide 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 15873-72-0 dicyclohexylphosphinoyl chloride 
• 14410-07-2 O-phenyl methylphosphonochloridothioate 
• 52038-84-3 3-chlorophenyl methyl phosphonochloridothioate 
• 27976-53-0 4-methoxyphenyl methyl phosphonochloridothioate 
• 14410-08-3 4-methylphenyl methyl phosphonochloridothioate 
• 1186024-70-3 4-cyanophenyl methyl phosphonochloridothioate 
• 1111-92-8 dimethylphosphinic acid chloride 
• 5761-97-7 methyl(phenyl)phosphinic chloride 
• 2991-84-6 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl chloride 

Downstream Products

• 103853-50-5 N²-(4-chloro-phenyl)-pyrimidine-2,4,6-triyltriamine 
• 16018-61-4 1-(4-chloro-phenyl)-3-(4,6-dimethyl-pyrimidin-2-yl)-urea 
• 5429-13-0 N-(4-chloro-phenyl)-N'-(4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-guanidine 
• 60221-92-3 N¹-(p-Chlorphenyl)-N⁵-methylbiguanide 
• 51835-01-9 5,5'-bis-(4-chloro-phenyl)-1,1'-ethanediyl-bis-biguanide 
• 959-05-7 6-chloro-3-(4'-chlorophenyl)-3,4-dihydroquinazoline 
• 123333-40-4 N-(2-amino-5-chloro-benzyl)-4-chloro-aniline 
• 131762-02-2 1-(4-chloro-phenyl)-6-methyl-6-propyl-1,6-dihydro-[1,3,5]triazine-2,4-diyldiamine; hydrochloride 
• 516-21-2 cycloguanil 
• 104509-37-7 1-(4-chloro-phenyl)-6-ethyl-6-methyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine 
• 95486-92-3 5,5'-bis-(4-chloro-phenyl)-3,3'-ethane-1,2-diyl-bis-[1,3,5]thiadiazinane-2-thione 
• 51835-04-2 5,5'-bis-(4-chloro-phenyl)-1,1'-decanediyl-bis-biguanide 
• 51835-03-1 C₂₄H₃₄Cl₂N₁₀ 
• 51835-05-3 C₂₈H₄₂Cl₂N₁₀ 

Relevant articles and documents

Deoxygenation of Nitrous Oxide and Nitro Compounds Using Bis(N-Heterocyclic Silylene)Amido Iron Complexes as Catalysts

Herein, we report the efficient degradation of N2O with a well-defined bis(silylene)amido iron complex as catalyst. The deoxygenation of N2O using the iron silanone complex 4 as a catalyst and pinacolborane (HBpin) as a sacrificial reagent proceeds smoothly at 50 °C to form N2, H2, and (pinB)2O. Mechanistic studies suggest that the iron–silicon cooperativity is the key to this catalytic transformation, which involves N2O activation, H atom transfer, H2 release and oxygenation of the boron sites. This approach has been further developed to enable catalytic reductions of nitro compounds, producing amino-boranes with good functional-group tolerance and excellent chemoselectivity.

Selective and Additive-Free Hydrogenation of Nitroarenes Mediated by a DMSO-Tagged Molecular Cobalt Corrole Catalyst

We report on the first cobalt corrole that effectively mediates the homogeneous hydrogenation of structurally diverse nitroarenes to afford the corresponding amines. The given catalyst is easily assembled prior to use from 4-tert-butylbenzaldehyde and pyrrole followed by metalation of the resulting corrole macrocycle with cobalt(II) acetate. The thus-prepared complex is self-contained in that the hydrogenation protocol is free from the requirement for adding any auxiliary reagent to elicit the catalytic activity of the applied metal complex. Moreover, a containment system is not required for the assembly of the hydrogenation reaction set-up as both the autoclave and the reaction vessels are readily charged under a regular laboratory atmosphere.

Synthesis method of 4-chlorobenzene cyanoguanidine

The invention provides a synthetic method of 4-chlorobenzene cyanoguanidine. According to the method, diazonium p-chlorobenzene chloride and dicyandiamide are taken as main raw materials, and a targetcompound is synthesized by two steps. The preparation method comprises the following steps: carrying out coupling reaction on the diazonium p-chlorobenzene chloride and the dicyandiamide in the presence of sodium carbonate to obtain an intermediate 4-chlorphenyl azo cyanoguanidine; then putting the intermediate into diluted hydrochloric acid, performing heating and discharging nitrogen to obtaina crude product; and dissolving the crude product in a dilute sodium hydroxide solution, removing color by activated carbon, performing neutralizing by adding acid, carrying out suction filtration andwashing, and performing drying to obtain a final product 4-chlorobenzene cyanoguanidine. Chlorinated diazonium p-chlorobenzene needs to be prepared for immediate use and is prepared by reacting 4-chloroaniline with sodium nitrite under an acidic condition. The preparation method is simple, mild in reaction condition, free of organic solvent, simple and convenient in subsequent treatment, safe andenvironmentally friendly; and meanwhile, the obtained product is relatively good in purity and relatively high in yield, and the method is a relatively good and safe method for synthesizing the aromatic guanidino compound, namely, the 4-chlorobenzene cyanoguanidine.

p-chloroaniline hydrochloride preparation method

The invention provides a p-chloroaniline hydrochloride preparation method, which comprises: in the presence of an organic solvent azeotropic with water, using p-chloronitrobenzene as a starting raw material, adding anti-dehalogenation agent and an acid binding agent, sealing, introducing hydrogen gas, carrying out a hydrogenation reaction under the catalysis of a platinum-carbon catalyst at a hightemperature under a high pressure, cooling, filtering to remove the catalyst, collecting the filtrate, adding concentrated hydrochloric acid to the filtrate, carrying out thermal insulation for 0.5-2h at a temperature of 80-95 DEG C, continuously heating to achieve a boiling state, refluxing by a water separator until no water is separated, filtering, and drying to obtain p-chloroaniline hydrochloride. According to the present invention, the preparation method has characteristics of mild and controllable reaction conditions, simple operation and low cost, performs the two steps through the one-pot method, and provides the advanced preparation method for industrial production.

Sustainable and Scalable Fe/ppm Pd Nanoparticle Nitro Group Reductions in Water at Room Temperature

An operationally simple and general process for the safe and selective reduction of nitro groups utilizing ppm Pd supported on Fe nanomaterials in aqueous solution of designer surfactant TPGS-750-M has been developed and successfully carried out at a 100 mmol scale. Preferred use of KBH4 as the hydride source, at ambient temperature and pressure, lends this process suitable for a standard reaction vessel alleviating the need for specialized hydrogenation equipment. Calorimetry data parallel those expected for a classical nitro group reduction when measuring the heat of reaction (-896 to -850 kJ/mol).

Reversible capture and release of aromatic amines by vicinal tricarbonyl compound

In this paper, we report reversible capture and release of aromatic amines by diphenylpropanetrione (DPPT). Addition of aromatic amines to the central carbonyl group occurred readily at ambient temperature to provide the aromatic amine adducts of DPPT (DPPT-aromatic amines), which has a hemiaminal structure. On the other hand, washing a solution of DPPT-aromatic amine with diluted hydrochloric acid (HCl) enabled successful recovery of DPPT to demonstrate the reversible nature of this system.

Continuous-flow hydrogenation of olefins and nitrobenzenes catalyzed by platinum nanoparticles dispersed in an amphiphilic polymer

A method for the flow hydrogenation of olefins and nitrobenzenes in a continuous-flow reactor containing platinum nanoparticles dispersed on an amphiphilic polystyrene-poly(ethylene glycol) resin (ARP-Pt) was developed. The hydrogenation of olefins and nitrobenzenes was completed within 31 seconds in the continuous-flow system containing ARP-Pt, giving the corresponding hydrogenated products in up to 99% yield with good chemoselectivity. Moreover, long-term (63-70 h) continuous-flow hydrogenation of styrene and nitrobenzene produced more than ten grams of ethylbenzene and aniline, respectively, without significant loss of catalytic activity. The flow hydrogenation system provides an efficient and practical method for the chemoselective reduction of olefins and nitrobenzenes. This journal is

The ortho effect on the acidic and alkaline hydrolysis of substituted formanilides

The kinetics of formanilides hydrolysis were determined under first-order conditions in hydrochloric acid (0.01-8 M, 20-60°C) and in hydroxide solutions (0.01-3 M, 25 and 40°C). Under acidic conditions, second-order specific acid catalytic constants were used to construct Hammett plots. The ortho effect was analyzed using the Fujita-Nishioka method. In alkaline solutions, hydrolysis displayed both first- and second-order dependence in the hydroxide concentration. The specific base catalytic constants were used to construct Hammett plots. Ortho effects were evaluated for the first-order dependence on the hydroxide concentration. Formanilide hydrolyzes in acidic solutions by specific acid catalysis, and the kinetic study results were consistent with the AAC2 mechanism. Ortho substitution led to a decrease in the rates of reaction due to steric inhibition of resonance, retardation due to steric bulk, and through space interactions. The primary hydrolytic pathway in alkaline solutions was consistent with a modified BAC2 mechanism. The Hammett plots for hydrolysis of meta- and para-substituted formanilides in 0.10 M sodium hydroxide solutions did not show substituent effects; however, ortho substitution led to a decrease in rate constants proportional to the steric bulk of the substituent.

1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: New utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst

1,2,3-Trimethoxypropane (1,2,3-TMP) was prepared from glycerol in one step in good yield and selectivity by phase transfer catalysis. According to OECD guidelines, a toxicity study was realized for this compound. It revealed that 1,2,3-TMP has a low acute toxicity, no skin sensitization, no mutagenicity and no ecotoxicity in an aquatic environment. This compound was also used as a solvent for the reduction of organic functions using either aluminium hydride or 1,1,3,3-tetramethyldisiloxane (TMDS) as a benign hydride source. In particular, a new process for the reduction of nitriles to amines in 2-MeTHF and in 1,2,3-TMP was developed, using TMDS in combination with copper triflate (Cu(OTf)2).