4-Chloro-m-phenylenediamine
-
4-Chloro-m-phenylenediamine
structure -
-
CAS No:
5131-60-2
-
Formula:
C6H7ClN2
-
Chemical Name:
4-Chloro-m-phenylenediamine
-
Synonyms:
1,3-Benzenediamine,4-chloro-;m-Phenylenediamine,4-chloro-;4-Chloro-1,3-benzenediamine;C.I. 76027;4-Chloro-m-phenylenediamine;4-Chloro-1,3-phenylenediamine;1-Chloro-2,4-diaminobenzene;4-Chloro-1,3-diaminobenzene;4-Chloro-3-aminoaniline;3-Amino-4-chloroaniline;2,4-Diaminochlorobenzene;NSC 6074;2-Chloro-1,5-phenylenediamine;2,4-Diamino-1-chlorobenzene
- Categories:
-
CAS No:
Description
Crystals. Soluble in ethanol; slightly soluble in water; insoluble in petroleum ether.
4-chloro-m-phenylenediamine appears as gray powder or dark purple solid. (NTP, 1992)
4-chloro-m-phenylenediamine appears as gray powder or dark purple solid. (NTP, 1992)|4-Chloro-meta-phenylenediamine is a member of monochlorobenzenes.
4-Chloro-m-phenylenediamine Basic Attributes
142.59
142.59
225-877-9
46M6FQ5PJK
6074
1673
DTXSID0020282
PLATES OR NEEDLES
2921519090
Characteristics
52
0.8
4-chloro-m-phenylenediamine appears as gray powder or dark purple solid. (NTP, 1992)
1.345 g/cm3
91 °C
298.6°C at 760 mmHg
134.4ºC
1.67
H2O: <0.1 g/100 mL at 19 ºC;SLIGHTLY SOL IN WATER, SOL IN ALCOHOL, INSOL IN PETROLEUM ETHER
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
This compound is sensitive to prolonged exposure to light and air. Insoluble in water.
Aryl Halides
Aryl amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Safety Information
III
6.1
UN 1673 6.1/PG 3
3
36/37/38
26-36
SS8800000
Xi
P261-P305 + P351 + P338
H315-H319-H335
Bioassay of 4-Chloro-m-phenylenediamine for Possible Carcinogenicity (1978) Technical Rpt Series No. 85 DHEW Pub No. (NIH) 78-1335, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
|Warning|H315 (97.87%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicity
A bioassay of 4-chloro-m-phenylenediamine for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. 4-Chloro-m-phenylenediamine was admin in the feed, at either of two concn, to groups of 49 or 50 male and 50 female animals of each species. The dietary concn used in the chronic bioassay for low and high dose rats were 0.2 and 0.4%, respectively. The time weighted avg dietary concn used for low and high dose mice were 0.7 and 1.4%, respectively. After a 78 wk period of cmpd administration, observation of rats continued for an additional 27 wk and observation of mice continued for an additional 17 wk. For each species, 50 animals of each sex were placed on test as untreated controls. ... Under the conditions of this bioassay, dietary administration of 4-chloro-m-phenylenediamine was carcinogenic to the experimental animals causing an increased incidence of hepatocellular tumors in female B6C3F1 mice and an incr incidence of adrenal pheochromocytomas in male Fischer 344 rats. Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Negative; Male Mice: Negative; Female Mice: Positive.
Drug Information
The substituted- benzenediamines appear to be least active when the amino groups are para to one another, whereas activity increases when the para position is occupied by a nonamino substituent. Activity also tends to increase as the two amino groups become ortho to the substituted group. The degree of activity may be explained by the capacity of N-acetyltransferase to interact with particular amino groups of the substituted-benzenediamines, leading to their detoxification.
ACUTE/CHRONIC HAZARDS: This compound is a positive animal carcinogen and suspected human carcinogen. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
4-chloro-1,3-phenylenediamine
4-Chloro-m-phenylenediamine Use and Manufacturing
General procedure: To a mixture ofhalogenated nitroarene (1 mmol), Pd/C(5percent), and MeOH (5mL) was added NH2NH2·H2O (10 mmol), and the resultingsolution was heated at 80 °C reflux condition for 5 min. Thenthe mixture was filtered and concentrated in vacuo. Thecrude material was purified by flash columnMethod 61; 4-Chlorobenzene- 1 , 3-diamine; To a solution of ammonium chloride (1.57g, 29mmol) in HGeneral procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.A mixture of 1-chloro-2, 4-dinitro-benzene (100 mg, 0.5 mmol) and SnClThe amination p-anisidine and p-chloroaniline wasconducted at 40 °C under argon in a custom-madethree-electrode cell [1] which allowed working withboth liquid and solid electrodes. The electrolyses in 8–12 M H2SO4 were performed using a Metrohm AutolabPGSTAT 302N potentiostat/galvanostat (current density–2 mA/cm2) and a mercury cathode (11 cm2); a platinumcathode (8.2 cm2) was used in more acidic media.The catholyte (25 mL) contained an aqueous solution of sulfuric acid, 0.1 mol/L of Ti(IV), 0.2 mol/Lof NH2OH, and 0.2 mol/L of substrate (p-anisidine or p-chloroaniline).When the electrolysis was complete, the catholyte was diluted with water and neutralized by treatmentfirst with a saturated aqueous solution of sodium hydroxide (on cooling) and then with NaHCO3. The products were extracted into chloroform (p-anisidine) or benzene (p-chloroaniline) and quantified by GLCon a Khromatek-Kristall 5000.2 chromatograph equipped with a flame ionization detector [CP-Sil 8CB capillary column, 60 m × 0.25 mm × 0.25 μm; oventemperature 160 °C; carrier gas (helium) inlet pressure 200 kPa]. Qualitative analyses were also performed ona Chrom-5 chromatograph (flame ionization detector; glass column, 3.5 m × 3 mm; stationary phase XE-60 or OV-17).A mixture of 1-chloro-2, 4-dinitro-benzene (100 mg, 0.5 mmol) and SnCl2.2H2O (1.12 g, 5 mmol) in ethanol (2.5 mL) was stirred at room temperature overnight. Water was added and then the mixture was basified to pH 7-8 with saturated NaHCO3 solution. The solution was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to yield 4-chloro-benzene-1, 3-diamine (D-1) (79 mg, quant.). HPLC ret. time 0.38 min, 10-99% CH3CN, 5 min run; ESI-MS 143.1 m/z (MH+).General procedure: PtL1/L2/C (25.0 mg, 1.282 mol of Pt) and the desired amountof substrate were placed in a Teflon-coated stainless steel auto-clave (80.0 mL), equipped with magnetic stirrer, temperature andpressure controller. The autoclave was then sealed and evacu-ated, followed by charging it with deaerated MeOH (10.0 mL)by suction. Afterwards, the autoclave was placed in an oil pathwhich was heated to 30.0C. Once the latter temperature wasreached, the autoclave was pressurized with hydrogen (5.0 bar) and stirred at 800 rpm. After the desired reaction time, the auto-clave was removed from the oil bath and cooled to 20.0C, followedby venting the excess hydrogen. The suspension was centrifugedand the catalytic solution separated from catalyst by decantationin air atmosphere. To the latter solutions n-dodecane (100.0 L, 0.44 mmol) was added as external standard and analyzed by GC.Recycling experiments were conducted by using recovered PtL1/2, applying the above descript protocol. The Ptsurface-atom related TOF(h-1) values were calculated according to the following equation:mmol(converted substrate) × [mmol(Ptsurface) × h]-1.The mmolof Ptsurface(i.e. amount of Pt atoms exposed to the substrate)using 25.0 mg of catalyst for the hydrogenation reactions were0.7179 mol for PtL1and 0.7948 mol for PtL2and PtC, according to the percentage of Pt-atoms localized on the NPs' sur-face (i.e. 56% (PtL1) and 62% for PtL2/C), using a HRTEM-basedcalculation [35].
Used in organic synthesis intermediate
(1975) No Data|(1977) No Data
1,3-Benzenediamine, 4-chloro-: ACTIVE|Dyestuff and pigment intermediates; hair dye coupler.|...BELIEVED TO BE USED AS A DYE INTERMEDIATE AND AS A RUBBER-PROCESSING AGENT.|Description is given for preparation and use of p-phenylenediamine in a hair dye preparation.
...4-CHLORO-META-PHENYLENEDIAMINE CAN BE IDENTIFIED IN HAIR DYES BY THIN-LAYER CHROMATOGRAPHY (KOTTEMANN CM; J ASSOC OFF ANAL CHEM 49: 954 (1966).|Phenylenediamine was determined by high performance liquid chromatography in aq samples.
Computed Properties
Molecular Weight:142.58
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:142.0297759
Monoisotopic Mass:142.0297759
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Learn More Other Chemicals
-
2-Bromophenacyl bromide, 90%
49851-55-0
-
1H-Indazol-7-ol
81382-46-9
-
6-Chloro-4-forMyl-nicotinic acid
1031433-06-3
-
3-Hydroxy-2,4,5-trifluorobenzoic acid Formula
116751-24-7
-
2-Methyl-1-heptene Formula
15870-10-7
-
1-(3,5-Dinitrophenyl)ethanone Formula
14401-75-3
-
α-Amino-3-bromobenzeneacetic acid Structure
79422-73-4
-
6-(BROMOMETHYL)-1,3-BENZOTHIAZOLE,97% Structure
499770-85-3
-
What is Allyl methacrylate
96-05-9
-
What is ethyl 5-hydroxy-2-Methylnicotinate
60390-47-8