5-Chloro-2-methylaniline
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5-Chloro-2-methylaniline
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CAS No:
95-79-4
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Formula:
C7H8ClN
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Chemical Name:
5-Chloro-2-methylaniline
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Synonyms:
Benzenamine,5-chloro-2-methyl-;o-Toluidine,5-chloro-;Fast Red KB Base;5-Chloro-2-methylbenzenamine;Ansibase Red KB;Pharmazoid Red KB;Spectrolene Red KB;5-Chloro-o-toluidine;2-Methyl-5-chloroaniline;5-Chloro-2-methylaniline;3-Chloro-6-methylaniline;2-Amino-4-chlorotoluene;Fast Red KBS salt;Genazo Red KB soln;Fast Red KB salt Supra;Fast Red KB salt;Acco Fast Red KB base;Azoene Fast Red KB base;Red KB base;Fast Red KB amine;Stable Red KB base;Hiltonil Fast Red KB base;Metrogen Red Former KB soln;Naphthosol Fast Red KB base;Fast Red KB-T Base;4-Chloro-2-aminotoluene;5-Chloro-2-toluidine;NSC 7094;5-Chloro-2-methylphenylamine
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CAS No:
Description
clear yellow to light brown liquid after melting The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.
5-Chloro-ortho-toluidine is a member of monochlorobenzenes.
5-Chloro-2-methylaniline Basic Attributes
141.6
141.60
878504
202-452-6
LW5K546DTR
7094
DTXSID5020287
GRAYISH-WHITE SOLID
29214300
Characteristics
26
2.58 (estimated)
Clear yellow to light brown Liquid After Melting
1.177 g/mL at 20 °C(lit.)
26 °C
237 °C @ Press: 722 Torr
320 °F
1.583-1.585
< 1 g/L (22 ºC)
Room temperature.
0.45 hPa (50 °C)
Oral-Rat LD50: 464 mg/kg
Open flame is flammable; high heat emits toxic chloride and nitrogen oxide gas
Henry's Law constant= 1.56X10-6 atm-cu m/mole (estimated)
Safety Information
III
6.1
UN 3429 6.1/PG 3
3
22-36/37/38-40-45-23/24/25
26-45-36/37/39-53
XU5075000
Xn,T
Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives
Stable under normal temperatures and pressures.
P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
Birner G, Neumann H-G; Biomonitoring of Aromatic Amines II: Hemoglobin Binding of Some Monocyclic Aromatic Amines; Arch Toxicol 62 (2/3): 110-155 (1988).|DHEW/NCI; Bioassay of 5-Chloro-o-toluidine for Possible Carcinogenicity (1979) Technical Rpt Series No. 187 DHEW Pub No. (NIH) 79-1743
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 49 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chlorotoluidines; Chlorotoluidines, liquid; Chlorotoluidines, solid/|For more DOT Emergency Guidelines (Complete) data for 5-CHLORO-O-TOLUIDINE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Toxicity
highly toxic
A bioassay for the possible carcinogenicity of 5-chloro-o-toluidine was conducted using Fischer 344 rats and B6C3F1 mice. 5-Chloro-o-toluidine was admin in the feed, at either of two concn, to groups of 50 male and 50 female animals of each species. Twenty animals of each sex and species were placed on test as controls. The high and low dietary concentrations of 5-chloro-o-toluidine were 5,000 and 2,500 ppm for rats and 4,000 and 2,000 ppm for mice. The cmpd was admin for 78 wk to both rats and mice, followed by an observation period of up to 26 wk for rats and 13 wk for mice. Under the conditions of this bioassay, 5-chloro-o-toluidine B6C3F1 mice, inducing hemangiosarcomas and hepatocellular carcinomas in both males and females. There was no conclusive evidence of the carcinogenicity of the cmpd in Fischer 344 rats. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Positive; Female Mice.
5-Chloro-o-toluidine is not likely to occur naturally since an isomer, p-chloro-o-toluidine is not known to occur naturally(1,SRC).
Since 5-chloro-o-toluidine is used in the synthesis of certain organic dyestuffs(1), its release may occur during the manufacture of the dyes(SRC).
TERRESTRIAL FATE: Hydrolysis of 5-chloro-o-toluidine should not be important in soil since it does not contain a hydrolyzable functional group(4,SRC). Based on the UV absorption spectra of m-chloroaniline(5), 5-chloro-o-toluidine should absorb sunlight and therefore, 5-chloro-o-toluidine may undergo some direct photolysis on soil surfaces(SRC). 5-Chloro-o-toluidine may undergo biotransformation in soil(1), but the fact that it was found to pass through bank-filtered water with a retention time of more than one year(2) suggests that it is not readily biotransformable in soil(SRC). The estimated Koc(4) indicates that 5-chloro-o-toluidine like other aromatic amines may be moderately mobile in soil(3). However, 5-chloro-o-toluidine may become increasingly immobilized in soil with the increase in humic matter content in soil due to formation of an irreversible complex(6).|AQUATIC FATE: Hydrolysis of 5-chloro-o-toluidine in water should not be important because it lacks hydrolyzable functional groups(3,SRC). Based on the absorption spectra of m-chloroaniline which shows a second UV absorption maxima at about 295 nm with an absorbance of 0.185(4), direct photolysis of 5-chloro-o-toluidine may become important in clear surface water(SRC). The observed biotransformation in soil(1) suggests that biotransformation may occur in water. However, the detection of 5-chloro-o-toluidine in bank-filtered drinking water(5) suggests that it may not be readily biodegradable in water(SRC). The estimated Henry's Law constant by the bond contribution method(6) suggests volatilization may not be important in water(3). The estimated Koc(3) of 234 indicates that it may moderately adsorb to suspended solid and sediment in water(2). However, 5-chloro-o-toluidine may form an irreversible complex with humic matter in suspended solid and sediment in water and thus may become immobilized(7). The estimated bioconcentration factor(3) of 54 suggests that bioconcentration of 5-chloro-o-toluidine in aquatic organisms should not be important(SRC).|ATMOSPHERIC FATE: Based on an estimation method(1), the rate constant for the reaction of 5-chloro-o-toluidine with hydroxyl radicals has been estimated to be 1.20X10-10 cu-cm/molecule-sec(1,SRC). Assuming the daily average concn of hydroxyl radicals in the atmosphere as 5X10+5/cu-cm(2), the half-life for this reaction has been estimated to be 3.2 hrs(SRC). Based on an estimated water solubility of 832 mg/L(3), wet deposition may partly remove the compound from the atmosphere(SRC).
Hydrolysis of 5-chloro-o-toluidine in the environment should not be important because it lacks hydrolyzable functional groups(1,SRC). Based on the absorption spectra of m-chloroaniline which shows a second UV absorption maxima at about 295 nm with an absorbance of 0.185(2), photolysis of 5-chloro-o-toluidine by sunlight may be important, but rates of photolysis are unknown(SRC). The rate constant for the reaction of vapor phase 5-chloro-o-toluidine with hydroxyl radicals has been estimated to be 1.20X10-10 cu-cm/molecule-sec(3,SRC). Assuming the daily average concn of hydroxyl radicals in the atmosphere of 5X10+5/cu-cm(4), the half-life for this reaction has been estimated to be 3.2 hrs(SRC).
Using an estimation method(2), a log Kow value of 2.58 has been estimated for 5-chloro-o-toluidine. Based on this log Kow and a recommended regression equation(1), the bioconcentration factor for 5-chloro-o-toluidine has been estimated to be 54(SRC). Therefore, bioconcentration of 5-chloro-o-toluidine in aquatic organisms should not be important.
Based on an estimated log Kow of 2.58 and a recommended regression equation(1), a log Koc of 2.37 has been estimated for 5-chloro-o-toluidine(SRC). This value indicates that 5-chloro-o-toluidine may be moderately mobile in soil(2). However, primary aromatic amines can react with humic matter in soil forming an irreversible complex and as a result may be immobilized in soil(3-4). With the increase in humic matter in soil, the tendency of irreversible complex formation may increase and 5-chloro-o-toluidine may become increasingly immobilized. In sandy soil containing a marginal amount of humic matter, 5-chloro-o-toluidine may be mobile(5,SRC).
A Henry's Law constant of 1.56X10-6 atm-cu m/mole has been estimated for 5-chloro-o-toluidine by the bond contribution method(1). Based on this value, the volatilization of 5-chloro-o-toluidine should not be important in water(2).
DRINKING WATER: 5-Chloro-o-toluidine has been detected in tapwater obtained from bankfiltered Rhine water in the Netherlands at a concn 0.3 ug/L(1-2).
Since 5-chloro-o-toluidine is used in solution form for making certain dyestuffs, the most probable route of exposure is by skin absorption(1,SRC).|Workers using 5-chloro-o-toluidine during dye manufacturing are the most likely people for exposure to this compound.
Drug Information
... READILY ABSORBED THROUGH THE SKIN OR BY INHALATION.
IF METHEMOGLOBINEMIA OCCURS & IS SEVERE, THEN TREAT WITH METHYLENE BLUE & OXYGEN.
... HEMATURIA MAY BE OBSERVED IN MEN HANDLING CHLOROTOLUIDINES. ... MAY BE A HEMORRHAGIC CYSTITIS WITH PAINFUL & FREQUENT MICTURITION. THIS ACUTE PROBLEM ... /HAS/ NO LONG TERM SIGNIFICANCE & CLEARS ... ON CESSATION. ... IF ... PERSISTS, OTHER PATHOLOGICAL URINARY TRACT PHENOMENA MUST BE CONSIDERED. /CHLOROTOLUIDINES/|MAY CAUSE METHEMOGLOBIN FORMATION. ... MOST STRIKING FEATURE ... IRRITANT EFFECT ON ... URINARY TRACT.|MICROSCOPIC HEMATURIA MAY BE PRESENT ... BEFORE THE CYSTITIS IS MANIFEST ... .
5-chloroaminotoluene
5-Chloro-2-methylaniline Use and Manufacturing
REDUCTION OF 4-CHLORO-2-NITROTOLUENE
Used in organic synthesis. In the dye industry, it can be used directly to synthesize ice-based dye red base KB and naphthol AS-KB. It is also an important pesticide intermediate.
(1972) 1.14X10+8 G|(1975) PROBABLY GREATER THAN 4.54X10+5 G
Benzenamine, 5-chloro-2-methyl-: ACTIVE
Computed Properties
Molecular Weight:141.60
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:141.0345270
Monoisotopic Mass:141.0345270
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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