Benzamide

121.14

121.14

385876

200-227-7

6X80438640

3114

DTXSID0021709

Colorless crystals|Monoclinic prisms or plates from water

29242995

43.1

0.818

White to almost white Crystalline Powder

1.341 g/cm³

130 °C

288 °C

180°C

1.547

H2O: 1.35 g/100 mL (20 ºC);ethanol: soluble 50mg/mL, clear to very slightly hazy, colorless to light yellow

Store below +30°C.

0.000056 hPa (20 °C)

Peritoneal-rat LD50: 781 mg/kg; oral-mouse LD50: 1160 mg/kg

Solvent flammable

2.45e-10 atm-m3/mole|Henry's Law constant = 2.45X10-10 atm-cu m/mol @ 25 °C

Dipole moment: 3.6 debyes|Benzamide can be transformed to phenyl isocyanate @ 60 °C & @ normal pressure|Heat of formation: -48.42 kcal/mole @ 25 °C

Insoluble in water.

Amides and Imides

BENZAMIDE reacts with azo and diazo compounds to generate toxic gases. Forms flammable gases with strong reducing agents. Mixing with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. Combustion generates toxic mixed oxides of nitrogen (NOx).

847.6 kcal/g mol wt @ 20 °C

NONH for all modes of transport

1

22-68

22-24/25-36/37

CU8700000

Xn

Ventilated, low temperature and dry

Stable. Combustible. Incompatible with strong oxidizing agents.

P281

H302-H341

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|The following wastewater treatment technology has been investigated for benzamide: Concentration process: Biological treatment.

P281

Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|Aggregated GHS information provided by 100 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound can be extinguished using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Combustible

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzamide is produced, as an intermediate or a final product, by process units covered under this subpart.

moderately toxic

Phorbol ester-induced promotion of initiated NMRI mouse skin keratinocytes to papillomas could be largely prevented when nicotinamide like inhibitors of poly(ADP-ribose)polymerase (nicotinamide, benzamide, 3-aminobenzamide) were applied simultaneously with 12-O-tetradecanoylphorbol-13-acetate. A similar suppression of tumor promotion by nicotinamide analogues was demonstrated in clone 41 JB6 epidermal cells which are promotable by 12-O-tetradecanoylphorbol- 13-acetate to anchorage-independent growth.|Differences in the mode of action of caffeine and benzamide on DNA repair processes were studied in Chinese hamster lung fibroblast line V79 cells treated or not treated with N-methyl-N'-nitro-N-nitrosoguanidine. Post treatment with 2 mM caffeine or benzamide for 24 hr, following N-methyl-N'-nitro-N-nitrosoguanidine treatment, greatly increased cell lethality. In the presence of 50 uM deoxycytidine, caffeine had almost no effect on cell lethality. Benzamide induced cell lethality was not affected by the presence of deoxycytidine. Treatment with 2 mM caffeine or benzamide alone for 24 hours had no effect on cell lethality. When caffeine and benzamide were present simultaneously for 96 hr, cell lethality was greatly increased. This effect was eliminated in the presence of 50 uM deoxycytidine. Poly(ADP-ribose)polymerase activity of the cells was substantially inhibited by 2 mM benzamide; 2 to 5 mM caffeine had no detectable effect on the polymerase activity.

LD50 Rat ip 781 mg/kg|LD50 Mouse oral 1160 mg/kg

Benzamide's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). Benzamide is formed when mepronil, a fungicide, and other benzanilides are exposed to sunlight(2).

TERRESTRIAL FATE: Based on a classification scheme(1), a range of Koc values from 9 to 57(2-5), indicates that benzamide is expected to have high to very high mobility in soil(SRC). Volatilization of benzamide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.45X10-10 atm-cu m/mole(6). Benzamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.4X10-4 mm Hg(SRC), determined from a fragment constant method(7). Benzamide is oxidized by soil bacteria adapted to phenol(8-10). In experiments in which 400 mg/l of benzamide was applied to soil columns, 96% degradation occurred within 3 days in a clay soil and 98% degradation occurred within 13 days in an organic soil(11).|AQUATIC FATE: Based on a classification scheme(1), a range of Koc values from 9 to 57(2-5), indicates that benzamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(6) based upon a Henry's Law constant of 2.5X10-10 atm-cu m/mole(7). According to a classification scheme(8), an estimated BCF of 3(SRC), from its log Kow(9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Benzamide is readily oxidized by activated sludge from a municipal waste water plant(11). However, no information is available concerning biodegradation in aerobic natural waters(SRC). Benzamide undergoes anaerobic biodegradation under both sulfate-reducing and methanogenic conditions(12). When incubated in aquifer slurries from a sulfate-reducing and methanogenic site, respectively, 45% and 40% of the benzamide was biodegraded after one month(12). All the benzamide disappeared within 8 months(12).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzamide, which has an estimated vapor pressure of 9.4X10-4 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(SRC). Vapor-phase benzamide 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 4.2 days(SRC), calculated from its rate constant of 3.8X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of benzamide with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Benzamide is not expected to undergo hydrolysis in the environment since amides hydrolyze very slowly under environmental conditions(2) and will not directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

An estimated BCF of 3 was calculated for benzamide(SRC), using a log Kow of 0.64(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

28.84 L/kg|The Koc of benzamide ranges from 9 to 57(1-4). According to a classification scheme(5), these Koc values suggest that benzamide is expected to have high to very high mobility in soil(SRC). Batch equilibrium studies were conducted on benzamide in two representative soils and a sediment(1). The Koc in an acidic forest soil (4.85% organic carbon, pH 2.8), an agricultural soil (1.25% organic carbon, pH 6.7), and a sediment (1.58% organic carbon, pH 7.1) was 57, 20 and 9, respectively. Koc values for sewage sludges and soils were 40 and 18, respectively(3).

The Henry's Law constant for benzamide is 2.45X10-10 atm-cu m/mole(1). This Henry's Law constant indicates that benzamide is expected to be essentially nonvolatile from water surfaces(2). Benzamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.4X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to benzamide may occur through inhalation and dermal contact with this compound at workplaces where benzamide is produced or used. (SRC)

Treatment of acute lymphoblastic leukaemia, Treatment of non-Hodgkin lymphoma

The percutaneous absorption of the fragrances benzyl acetate and five other benzyl derivatives (benzyl alcohol, benzyl benzoate, benzamide, benzoin and benzophenone) was determined in vivo in monkeys. Absorption through occluded skin was high for all compounds (approximately 70% of the applied dose in 24 hr) and no significant differences between values for the different compounds were observed. No correlations were seen between skin penetration of these compounds and their octanol-water partition coefficients. Under unoccluded conditions skin penetration of the fragrances was reduced and there was great variability between compounds, presumably because of variations in the rates of evaporation from the site of application. The data suggest that humans may have significant systemic exposure to these fragrance.

Benzamide yields benzoic acid in rabbit, guinea pig, dog, pig, & cat. /From table/

SYMPTOMS: This compound may produce gastric pain, nausea, and vomiting. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. Activated charcoal is not effective. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

Treatment of benzamide to HeLa cells resulted in striking alterations of the process of cell division. Studies employing continuous treatment showed that the mitotic index remained almost similar in control and treated cells for up to 48 hr; at 72 hr the mitotic index was lowered considerably. The ratio of metaphase/anaphase plus telophase showed a constant incr, keeping a positive correlation with the dose and duration of benzamide treatment. Abnormal division figures were also /observed/ at high frequency. In recovery experiments, the percentage of abnormally dividing cells became comparable to that of control group by 48 hr of recovery.

benzamide

Grade: Technical

Benzamide: ACTIVE

Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans