4-Chlorbenzol-1,3-diamin

less than 1 mg/mL at 66 °F (NTP, 1992)

SLIGHTLY SOL IN WATER, SOL IN ALCOHOL, INSOL IN PETROLEUM ETHER

196 °F (NTP, 1992)

91 °C

4-chloro-m-phenylenediamine appears as gray powder or dark purple solid. (NTP, 1992)

Gray or dark purple solid; [CAMEO] Brown crystalline solid; [MSDSonline]

Warning

H315 (97.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

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.

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.

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.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=5131-60-2]

4-Chloro-meta-phenylenediamine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 27: (1982) Some Aromatic Amines, Anthraquinones and Nitroso Compounds, and Inorganic Fluorides Used in Drinking-water and Dental Preparations

1987

1987

4-Chloro-m-phenylenediamine

TWO GROUPS OF FISCHER 344 RATS, ONE OF 50 MALES & 50 FEMALES & ONE OF 49 MALES AND 50 FEMALES, 6 WK OF AGE...FED DIETS CONTAINING 2000 OR 4000 MG/KG...FOR 78 WK AND OBSERVED AN ADDITIONAL 26-27 WK...50 RATS OF EACH SEX AS CONTROLS OBSERVED 106 WK. ... BY END OF STUDY 64, 86 & 73% MALES & 72, 78 & 66% FEMALES ALIVE IN CONTROL LOW-DOSE & HIGH-DOSE GROUPS, RESPECTIVELY. ...SIGNIFICANT INCR IN THE INCIDENCES OF ADRENAL PHEOCHROMOCYTOMA & OF INTERSTITIAL-CELL TUMORS OF THE TESTIS OBSERVED IN TREATED MALES. [THE WORKING GROUP NOTED THAT THE OBSERVED DIFFERENCS DO NOT APPEAR TO BE SIGNIFICANT WHEN HISTORICAL CONTROLS ARE TAKEN INTO ACCOUNT.]

TWO GROUPS OF 50 MALE & 50 OR 49 FEMALE B6C3F1 MICE, 6 WK OF AGE, WERE FED... DOSES OF 10000 & 200000 MG/KG OF DIET FOR 29 WK & THEN 5000 & 10000 MG/KG OF DIET FOR 49 WK, WERE OBSERVED FOR AN ADDITIONAL 17 WK... MATCHED CONTROLS...WERE KEPT UNDER OBSERVATION FOR 97 WK. ... AT 78 WK, 5 HIGH-DOSE & 5 CONTROL ANIMALS OF EACH SEX WERE SACRIFICED. BY THE END OF STUDY, 84, 82 & 80%...MALES & 72, 74 & 78%...FEMALES...STILL ALIVE IN CONTROL, LOW-DOSE & HIGH-DOSE GROUPS, RESPECTIVELY. ...SIGNIFICANT... DOSE-RELATED INCR IN INCIDENCE OF HEPATOCELLULAR ADENOMAS PLUS CARCINOMAS...OBSERVED AMONG TREATED FEMALE MICE: CONTROLS 0/46; LOW-DOSE, 11/44...HIGH-DOSE, 8/45... [THE WORKING GROUP NOTED THAT THE INCIDENCE OF LIVER TUMORS IN THE CONTROL GROUP WAS LOWER THAN THAT OBSERVED IN HISTORICAL CONTROLS, & THAT THE INCIDENCE IN THE TREATED GROUPS WAS WITHIN THE NORMAL RANGE SEEN IN HISTORICAL CONTROLS.]

IN 8-WK SUBCHRONIC FEEDING STUDIES, MALE & FEMALE FISCHER 344 RATS & B6C3F1 MICE WERE FED DIETS CONTAINING UP TO 3% OF 4-CHLORO-META-PHENYLENEDIAMINE. ALL RATS FED 3%...DIED, WHEREAS ONLY 1 MOUSE FED 3% OF THE META ISOMER DIED BY THE END OF THE STUDY. A 25% DEPRESSION OF WEIGHT GAIN WAS OBSERVED IN BOTH RATS AND MICE FED 1% OF THE META ISOMER AND OF 10% IN MICE FED 3% OF THE META ISOMER. NO COMPD-RELATED ORGAN LESIONS WERE OBSERVED IN CHRONIC STUDIES IN RATS WITH DOSES OF UP TO...0.4% OF 4-CHLORO-META-PHENYLENEDIAMINE OR IN MICE WITH DOSES OF 1.4%...

Fifty inbred F344 rats of both sexes and 50 inbred C57Bl/6N mice of both sexes were fed ad libitum at 2 dose levels of either 4,000 mg/kg or 2,000 mg/kg of 4-chloro-m-phenylendiamine for a period of 78 weeks. In female mice, there was a statistically significant incidence of liver tumors. Controls were tumor-free, while 17.8% and 25.0% of the animals on the high- and low dose levels, respectively, developed tumors. Thirty percent of male controls, and 30.0% and 39.6% of males on high- and low dose levels, respectively, developed tumors.

In male and female Fischer rats feeding 4-chloro-m-phenylenediamine at 0.2 or 0.4% in the diet led to a significant elevation in the incidence of adrenal pheochromocytoma in male rats. At 1 or 2% levels it caused hepatocellular carcinoma or hepatocellular carcinoma and hepatocellular adenoma in female mice.

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.

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.

Used as a chemical intermediate for dyestuffs and pigments, a hair dye coupler, a rubber-processing agent, and a research chemical; [HSDB]

Dressing Hair [Category: Other]

CHEMICAL RESEARCH

(1975) No Data

(1977) No Data

(1975) No Data

(1977) No Data

(1975) No Data

(1977) No Data

4-CHLORO-META-PHENYLENEDIAMINE WAS FIRST PRODUCED BY BEILSTEIN AND KURBATOW IN 1879 BY THE REDUCTION OF 4-CHLORO-1,3-DINITROBENZENE WITH ZINC CHLORIDE AND HYDROCHLORIC ACID. IT CAN ALSO BE PREPARED BY THE REDUCTION OF 1-CHLORO-2,4-DINITROBENZENE WITH IRON.

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.