Benzamide

Nitrogen Compounds -> Other Aromatics (Nitrogen)

Industrial compound

log Kow= 0.64

0.818

0.67

1.0792 at 266 °F (NTP, 1992) - Denser than water; will sink

1.341

1.341 @25 °C

Colorless crystals

Monoclinic prisms or plates from water

less than 1 mg/mL at 72.5 °F (NTP, 1992)

> 10% in benzene

1 g in 6 ml ethanol; 1 g in 3.3 ml pyridine

Soluble in ammonia

Slightyl soluble in ethyl ether, benzene; very soluble in ethyl alcohol, carbon tetrachloride, carbon disulfide.

In water, 1.35X10+4 mg/l @ 25 °C

554 °F at 760 mmHg (NTP, 1992)

288 °C

290.00 °C. @ 760.00 mm Hg

288 °C @760 [mm Hg]

270 to 271 °F (NTP, 1992)

130 °C

129.1 °C

130 °C

0.000939 [mmHg]

0.000165 [mm Hg]

Warning

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

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

Aggregated GHS information provided per 173 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Benzamide

Benzamide: Does not have an individual approval but may be used under an appropriate group standard

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).

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.

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.

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.

1.9 [mg/m3]

21 [mg/m3]

130 [mg/m3]

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)

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.

LC50 Pimephales promelas (fathead minnow) 661 mg/l/96 hr (confidence limit 590 - 740 mg/l), flow-through bioassay with measured concentrations, 25.1 °C, dissolved oxygen 7.2 mg/l, hardness 47.0 mg/l calcium carbonate, alkalinity 41.3 mg/l calcium carbonate, and pH 7.5.

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 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).

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.

AEROBIC: Benzamide is readily oxidized by activated sludge from a municipal waste water plant(1). However, no information is available concerning biodegradation in aerobic natural waters(SRC). Benzamide is oxidized by soil bacteria adapted to phenol(2-4). 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(5).

ANAEROBIC: Benzamide undergoes anaerobic biodegradation under both sulfate-reducing and methanogenic conditions(1). When incubated in aquifer slurries from a sulfate-reducing and methanogenic site, respectively, 45% and 40% of the benzamide was biodegraded after one month(1). All the benzamide disappeared within 8 months(1).

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).

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).

3-Aminobenzamide and benzamide, two potent inhibitors of poly-(ADP-ribose)-polymerase, incr the frequencies of sister chromatid exchange in Chinese hamster ovary cells in a dose dependent manner. Sister chromatid exchange were studied in cells in which the inhibitors were present either during the first cell cycle or the second cell cycle or both. Most of the induced sister chromatid exchange were formed during the second cell cycle in which BU-containing DNA was used as template for DNA synthesis. ...

The induction of micronucleated erythrocytes in bone marrow by primary thioamides and their metabolites was studied in mice. Female C57B1/6 mice were administered 0 to 3.39 mmol/kg thioacetamide, thiobenzamide, thioacetamide-S-oxide, thiobenzamide-S-oxide, acetamide, or benzamide by oral gavage. Mice were killed 6 or 30 hours later, the femurs were removed, and the bone marrow was flushed out. Polychromatic erythrocytes were isolated and assayed for micronuclei. Thioacetamide, thiobenzamide, thioacetamide-S-oxide, and thiobenzamide-S-oxide induced dose dependent increases in the incidence of micronucleated polychromatic erythrocytes. When compared on an equimolar basis, thioacetamide-S-oxide and thiobenzamide-S-oxide were more effective than the parent compounds. Acetamide and benzamide also induced significant increases in polychromatic erythrocytes containing micronuclei. Thioacetamide and benzamide and their major metabolites cause a significant induction of micronucleated bone marrow cells. The mechanism for these effects is unknown

Benzamides induce sister chromatid exchanges in L1210 cells. This induction is strongly potentiated when the cells are grown in nicotinamide free medium.

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).

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.

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.

Used in organic synthesis; [HSDB]

Organic synthesis

To manufacture benzonitrile