2-Aminobiphenyl

Leaflets (dilute alcohol)

Colorless or purplish crystals

less than 0.1 mg/mL at 70 °F (NTP, 1992)

Sol in ethanol, ether, benzene; slightly sol in dimethylsulfoxide, petroleum ether

Insol in water

greater than 235 °F (NTP, 1992)

Flash point > 113 °C

570 °F at 760 mmHg (NTP, 1992)

299 °C

122 to 127 °F (NTP, 1992)

51 °C

5.8 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

5.8 (AIR= 1)

0.000117 [mmHg]

1.2X10-4 mm Hg @ 25 °C /Estimated/

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Status: Cease Manufacture Update: 30-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17706

2-Phenylaniline: Does not have an individual approval but may be used under an appropriate group standard

Emergency treatment: Methemoglobinemia; [HSDB] May cause irritation; [CAMEO] Effects in high-dose animal studies include respiratory depression, coma, hemorrhage, and changes in bone marrow, spleen, and renal tubules; [RTECS] Harmful if ingested; Suspected carcinogen; [Aldrich MSDS] See Biphenyl. See 4-Aminodiphenyl.

2-AMINOBIPHENYL neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Acute Tox. 4 (100%)

Carcinogenicity - category 2

Carcinogenicity - Category 2

Carc. 2

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: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 830(SRC), determined from a log Kow of 2.84(2) and a regression-derived equation(3), indicates that 2-biphenylamine is expected to have low mobility in soil(SRC). Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(6,7), suggesting that 2-biphenylamine may be immobile in some soils. Volatilization of 2-biphenylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Biphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-4 mm Hg(SRC), determined from a fragment constant method(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 830(SRC), determined from a log Kow of 2.84(2) and a regression-derived equation(3), indicates that 2-biphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.5X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 31(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-Biphenylamine, which has an estimated vapor pressure of 1.2X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-biphenylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2(SRC), calculated from its rate constant of 8.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

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. /2-Biphenylamine hydrochloride/ [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2185-92-4]

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-Biphenylamine can be estimated to be 836(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-biphenylamine is expected to have low mobility in soil. Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC).

2-Biphenylamine was shown to be non-toxic to a pure culture of Tetrahymena pyriformis, relative to other mono alkyl-or halogen substituted anilines; loss was not attributed to abiotic processes(1). Using Escherchia coli, 2-biphenylamine was degraded during a seven-day incubation period at an un-specified rate(2).

An estimated BCF of 31 was calculated for 2-biphenylamine(SRC), using a log Kow of 2.84(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Henry's Law constant for 2-biphenylamine is estimated as 1.5X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-biphenylamine is expected to be essentially nonvolatile from water surfaces(2). 2-Biphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-4 mm Hg(SRC), determined from a fragment constant method(2).

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ... Under the conditions of the bioassay, 2-biphenylamine hydrochloride was not carcinogenic for F344/N rats of either sex. 2-Biphenylamine hydrochloride was carcinogenic for B6C3F1 female mice, inducing hemangiosarcomas at various sites. The evidence for an association between the admin of 2-biphenylamine hydrochloride and the incr incidence of hemangiosarcomas in male mice was equivocal. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Equivocal; Female Mice: Positive. /2-Biphenylamine hydrochloride/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Diets containing 0.1 or 0.3% 2-biphenylamine hydrochloride were fed to groups of 50 Fischer 344 rats and 50 B6C3F1 mice of each sex for 104-106 weeks. Mean body weights of high-dose rats of both sexes and of low-dose male rats were slightly lower than those of controls. No significant differences in survival times were observed between dosed and control groups. In dosed male rats there was a compound-related increased incidence of kidneys with inflammatory cells and interstitial fibrosis. No tumors in dosed rats were associated with the chemical. Mean body weights of high-dose male mice were slightly lower than those of controls, and survival of high-dose male mice was also significantly (P<0.01) reduced relative to controls. Hemangiosarcoma of the circulatory system occurred in female mice with a statistically significant (P<0.001) positive trend. The observed incidences of hemangiosarcoma were 0/49 (0%), 1/50 (2%), and 7/50 (14%) in controls, low- and high-dose groups, respectively. In individual group comparisons, the incidence in the high-dose group was significantly (P<0.01) higher than that in the controls. The hemangiosarcoma seen in female mice were quite rare with only 6/816 (0.7%) previously seen in controls at the same laboratory and no more than 3 in any group of 50. Hemangiosarcoma also occurred in male mice with a statistically significant positive trend (P=0.04 by a life table test), with incidences of 0/50 (0%), 2/50 (4%), and 3/50 (6%), in control, low-dose and high-dose groups, respectively. The development of hemangiosarcoma in the high-dose male mice might have been curtailed by the significantly reduced survival time in this group.

/GENOTOXICITY/ Chemically-induced sister chromatid exchange was measured in vivo in bone marrow of Chinese hamsters. Admin either ip or orally and increased sister chromatid exchange frequencies were noted with 6 of 6 direct-acting genotoxins and with 9 of 14 activation-dependent genotoxins.

/GENOTOXICITY/ In the presence of a rat liver 9,000 g supernatant, several aminobiphenyls were assayed for mutagenicity to Salmonella typhimurium. Among the 3 possible aminobiphenyls isomers, only 4-aminobiphenyl was a potent mutagen.

/OTHER TOXICITY INFORMATION/ The effects of carcinogens such as 2-aminobiphenyl, benzo-alpha-pyrene, 3,3'-diaminobenzidine,beta-naphthylamine and rho-dimethylaminoazobenzene were studied on oxidative phosphorylation of rat liver mitochondria. For in vivo experiments, rats were killed by decapitation 6 wk after s.c. injection of the carcinogens, and the isolated liver mitochondria were incubated with standard incubation media. ATP formation and O2 uptake were measured. In the in vitro experiments the carcinogens were added to incubation media containing liver mitochondria isolated from normal rats. With 2-aminobiphenyl, ATP formation and O2 uptake decreased as compared with the control group using succinate as substrate. No noticeable changes in ATP formation or O2 uptake were observed with glutamate as substrate. With benzo-alpha-pyrene, O2 uptake decreased when succinate was used as substrate, but increased if glutamate was the substrate. With 3,3'-diaminobenzidine, ATP formation and O2 uptake decreased with succinate as substrated P:O value decreased with glutamate as substrate. With BETA-naphthylamine, O2 uptake decreased, but the P:O value increased when succinate was used as substrate. Using glutamate as substrate, ATP formation, O2 uptake and P:O value decreased. With rho-dimethylaminoazobenzene, no noticeable changes in ATP formation, O2 uptake and P:O ratio were observed with succinate and glutamate as substrates. The ATP formation and P:O value were depressed by addition of benzo-alpha-pyrene, 3,3'-diaminobenzidine and beta-naphthylamine to incubation media containing mitochondria. O2 uptake was enhanced as compared with controls. ATP formation and O2 uptake were decreased by 2-aminobiphenyl, but the P:O value was not affected. rho-Dimethylaminoazobenzene decreased O2 uptake, but it increased the P:O value. ATP formation was not changed.

The rate constant for the vapor-phase reaction of 2-biphenylamine with photochemically-produced hydroxyl radicals has been estimated as 8.0X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

2-Biphenylamine's production and use in research and analytical chemistry may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.2X10-4 mm Hg at 25 °C indicates 2-biphenylamine will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-biphenylamine will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2 hours. If released to soil, 2-biphenylamine is expected to have low mobility based upon an estimated Koc of 836. Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group, suggesting that 2-biphenylamine may be immobile in some soils. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.5X10-7 atm-cu m/mole. 2-Biphenylamine was shown to be non-toxic using a pure culture of Tetrahymena pyriformis, relative to other mono alkyl-or halogen substituted anilines and utilized to some extent by Escherchia coli strain. If released into water, 2-biphenylamine is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 30.68 suggests the potential for bioconcentration in aquatic organisms is moderate. Occupational exposure to 2-biphenylamine may occur via inhalation and dermal contact with this compound at workplaces where 2-biphenylamine is produced or used. (SRC)

Used as intermediate for carbazole, resins, and synthetic rubbers; [HSDB] Used in research and analytical chemistry; [Hawley]

Chemical intermidiate for carbazole, resins, and synthetic rubbers.

(1972) No Data

(1975) No Data

(1972) No Data

(1975) No Data

(1971) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) No Data