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Home > Encyclopedia > Formamide

Formamide

Formamide structure

Formamide 

structure
  • CAS No:

    75-12-7

  • Formula:

    CH3NO

  • Chemical Name:

    Formamide

  • Synonyms:

    Formamide;Carbamaldehyde;Methanamide;Formimidic acid;NSC 748;23296-41-5;1156543-55-3;1158234-15-1

  • Categories:

    Organic Chemistry  >  Amides

Description

Formamide is an amide derived from formic acid and has been used as solvent for many ionic compounds.


Formamide appears as a colorless liquid with a faint odor of ammonia. Denser than water. Freezing point 36°F. (USCG, 1999)|Liquid|COLOURLESS HYGROSCOPIC VISCOUS LIQUID.|Colorless, oily liquid with a light ammonia-like odor.|Colorless, oily liquid. [Note: A solid below 37°F.]


Formamide appears as a colorless liquid with a faint odor of ammonia. Denser than water. Freezing point 36°F. (USCG, 1999)|Formamide is the simplest monocarboxylic acid amide, obtained by formal condensation of formic acid with ammonia. The parent of the class of formaldehydes. It has a role as a solvent. It is a monocarboxylic acid amide, a one-carbon compound and a member of formamides. It derives from a formic acid. It is a tautomer of a formimidic acid.

Formamide Basic Attributes

45.04060

45.04

200-842-0

4781T907ZS

0891

748

DTXSID8025337

Slightly viscous, colorless liquid|Oily liquid

2924199090

Characteristics

43.09000

-0.8

Formamide appears as a colorless liquid with a faint odor of ammonia. Denser than water. Freezing point 36°F. (USCG, 1999)

1.1334 g/cm3 @ Temp: 20 °C

2.55 °C

210.5 °C @ Press: 760 Torr

175ºC

1.446-1.448

Miscible

2-8ºC

0.08 mm Hg ( 20 °C)

1.55 (vs air)

LD50 in mice, rats (g/kg): 4.6, 5.7 i.p. (Pham-Huu-Chanh)

Class IIIB Combustible Liquid: Fl.P. at or above 200°F.

vol% in air: 2.7 19

Faint ammonia odor

7.1 (0.5 molar aqueous soln)

pKa = - 0.48 @ 20 °C

Dissolves casein, glucose, zein, tannins, starch, lignin, polyvinyl alcohol, cellulose acetate, nylon, chlorides of copper, lead, zinc, tin, iron, cobalt, aluminum, nickel, the acetates of the alkali metals, some inorganic sulfates and nitrates.|Dielectric constant: epsilon= 84; industrial grades may have odor of ammonia|Hygroscopic|Hydrolyzes very slowly at room temperature, hydrolysis is accelerated by acids and bases at elevated temperatures.|For more Other Experimental Properties (Complete) data for FORMAMIDE (8 total), please visit the HSDB record page.

Hygroscopic. Water soluble.

Amides and Imides

FORMAMIDE is incompatible with strong oxidizers, acids and bases. Sensitive to light. Reacts with water very slowly at room temperature, but rate is accelerated by acids and bases at elevated temperatures. Incompatible with iodine, pyridine and sulfur trioxide. Reacts explosively with furfuryl alcohol, H2O2, Tl(NO3)3.H2O, nitromethane and P2O5. An effective solvent: dissolves casein, glucose, tannins, starch, lignin, polyvinyl alcohol, cellulose acetate, nylon, the chlorides of copper, lead, zinc, tin, cobalt, iron, aluminum and nickel, the acetates of the alkali metals, some inorganic sulfates and nitrates. Attacks copper and brass (NTP, 1992).

310 °F (USCG, 1999)|>500 °C

-568.2 kJ/mole

10.20 eV

Class IIIB Combustible Liquid: Fl.P. at or above 200°F.

The vapour is heavier than air.

Copper, brass and even lead are attacked.

64.98 kJ/mole

Safety Information

NONH for all modes of transport

2

R61

S45-S53

LQ0525000

T

Separated from oxidants, acids and bases. Dry.

P201-P281-P308 + P313

H351-H360D-H373

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 technologies have been investigated for formamide: Concentration process: Biological treatment.

Incompatible with iodine, pyridine and sulfur trioxide.|Bottles containing a modified Karl Fischer reagent with formamide replacing methanol developed gas pressure during several months and burst. No reason was apparent, but slow absorption of moisture, formation of sulfuric acid and liberation of carbon monoxide from the formamide seems a likely sequence.|A mixture containing 51% of calcium nitrate and 12% ammonium nitrate with 27% formamide and 10% water is detonable @ -20 °C.|Oxidizers, iodine pyridine, sulfur, trioxide, copper, brass, lead [Note: Hygroscopic (i.e., absorbs moisture from the air)].|Formamide is hydrolyzed very slowly at room temperature. Acids, bases and elevated temperatures accelerate the hydrolysis.

Formamide is an indirect food additive for use only as a component of adhesives.

Special Hazards of Combustion Products: Toxic fumes emitted on decomposition (carbon monoxide and ammonia), beginning at 180 - 210°C. Behavior in Fire: Vapor will burn in air above 310°F. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H360D ***: May damage the unborn child [Danger Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|H351 (28.9%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P260, P281, P308+P313, P314, P405, and P501|Aggregated GHS information provided by 475 companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H360Df: May damage the unborn child; Suspected of damaging fertility [Danger Reproductive toxicity]|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P264, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501|Warning|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P264, P305+P351+P338, P332+P313, and P337+P313

Fire Extinguishing Agents: Dry chemical, water, alcohol foam, or carbon dioxide. (USCG, 1999)|Use water spray, alcohol-resistant foam, powder, carbon dioxide.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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 chemical under refrigerated temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)

Skin: No recommendation is made specifying the need for personal protective equipment for the body. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: No recommendation is made specifying the need for washing the substance from the skin (either immediately or at the end of the work shift). Remove: No recommendation is made specifying the need for removing clothing that becomes wet or contaminated. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Wear rubber gloves, goggles and overalls.|Wear appropriate eye protection to prevent eye contact.|(See protection codes)

Combustible when exposed to heat or flame.

Has exploded while in storage.|Explosive limits , vol% in air: 2.7 - 19

Women of childbearing potential should handle this substance only in a hood and should take precautions to avoid skin contact with the liquid because of the ease with which it passes through the skin.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Moderately irritating to skin, mucous membranes.|An irritant to skin, eyes, and mucous membranes.

Vacated 1989 OSHA PEL TWA 20 ppm (30 mg/cu m); STEL 30 ppm (45 mg/cu m), is still enforced in some states.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (15 mg/cu m)[skin].

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Store and dispose of according to local regulations.

Separated from oxidants, acids and bases. Dry.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

The substance is moderately irritating to the eyes and skin. The substance may cause effects on the central nervous system.

May cause toxicity to human reproduction or development.

NO open flames. See Chemical Dangers.

PREVENT GENERATION OF MISTS! AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective clothing. Protective gloves.

Wear face shield.

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. Formamide is produced, as an intermediate or a final product, by process units covered under this subpart.

| 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.

Formamide has been detected in wastewater from a polyamide production plant(1). Formamide was detected at 2.0 mg/l in gas condensate retort water in oil-shale retort, but was not detected in the processed retort water(2).

Toxicity

FORMAMIDE (3 G/KG IV) HAD LITTLE EFFECT ON CAROTID SINUS REFLEX OR ON HYPERTENSION INDUCED BY EXOGENOUS CATECHOLAMINES, BUT FORMAMIDE DECR HYPERTENSION INDUCED BY INDIRECTLY ACTING AMINES TYRAMINE AND EPHEDRINE.|FORMAMIDE, WHEN ADMIN IP TO MICE IN SUBLETHAL DOSES (3.2, 0.77, 2, 1.2, AND 0.75 G/KG), LENGTHENED /CNS DEPRESSION/ ... INDUCED BY 100 MG HEXOBARBITAL, 350 MG CHLORAL, OR 1.4 G URETHANE/KG.

LD50 Rat oral 6 g/kg|LD50 Rabbit dermal 6 g/kg|LD50 Mouse oral 3.15 g/kg|LD50 Tumor bearing BDF1 mouse oral 400 mg/kg (given daily for 9 days)|For more Non-Human Toxicity Values (Complete) data for FORMAMIDE (8 total), please visit the HSDB record page.

Formamide (FORM) ... was evaluated for reproductive toxicity in CD-1 (Swiss) mice using the Reproductive Assessment by Continuous Breeding Protocol (RACB). Male & female mice were exposed to FORM in drinking water at doses of 0, 100, 350, & 750 ppm (/about/ 20-200 mg/kg/day). A Max Tolerated Dose (MTD) of FORM, based on indices of generalized toxicity, was not reached for F0 animals. However, reproductive toxicity, including reduced fertility & litter size, was observed at 750 ppm FORM. F0 females at 750 ppm FORM exhibited an incr in the avg days to litter, & tended to spend more time in diestrus than in another stage of the cycle. FORM caused no detectable change in the histopathology of kidney, liver, or reproductive organs. Estimated exposure for the F0 generation was 24, 80, & 195 mg/kg/day for the 100, 350, & 750 ppm FORM groups, respectively. Females tended to have higher relative exposure (mg/kg/day) compared to males. F1 postnatal survival was unaffected by treatment. The MTD for the F1 generation was 750 ppm FORM, based on reduced body weight. Mild reproductive toxicity, observed as reduction in litter size & increased days to litter, occurred at 750 ppm. No significant histopathologic changes were observed in either males or females. Estimated exposure to FORM was 26, 87, & 190 mg/kg/day for F1 animals. In summary, the MTD for generalized toxicity was not reached for the F0 generation, but was established at 750 ppm for the F1 generation. The No-Observed-Adverse-Effect-Level (NOAEL) for generalized toxicity was 750 ppm for the F0 generation & 350 ppm for the generation. Reproductive toxicity was observed at 750 ppm in both generations.|... This study was performed due to the lack of data from pregnant rats exposed during the entire embryo/fetal period. Dose selection was based on a screening study in which CD rats were treated by gavage with 0, 62, 125, 250, 500, or 1000 millgrams formamide per kilogram body weight per day on gestational days (gd) 6-19 ... . Maternal toxicity was noted at greater than or equal to 250 mg/kg/day, including morbidity, and reductions in water/food intake, body weight, and weight gain. Fetal body weight was reduced at greater than or equal to 125 mg/kg/day ... . In this study, female Sprague-Dawley-derived (CD® ) rats were dosed by gavage with formamide (50, 100, or 200 mg/kg/day) or its vehicle (deionized/distilled water) on gestational days 6-19. The dose volume was 5 ml/kg. Twenty-five timed-mated rats were assigned to each group. Dams were monitored at regular intervals throughout gestation for clinical signs, food and water intake, and body weight. At necropsy on gestational days 20, the following were recorded: maternal clinical condition; body, liver, and gravid uterine weights; pregnancy status; and number of corpora lutea. In the gravid uterus, the numbers of resorbed, dead, or live fetuses were recorded. All live fetuses were weighed, sexed, and examined for external morphological anomalies. Approximately, one-half of the fetuses were examined for visceral anomalies, including internal head structures, and the remaining fetuses were examined for skeletal anomalies. Pregnancy was confirmed in 88-92% of females/group. No maternal deaths occurred, and there were no dose-related clinical signs. Maternal body weight exhibited significant decreasing trends (gestational days 15-20), with significant reductions at 200 mg/kg/day on gestational days 18, 19, and 20. Maternal body weight gain was also reduced at 200 mg/kg/day from gestational days 6 to 9, from gestational days 15 to 18, for the treatment period as a whole (gestational days 6 to 20), and for the gestational period as a whole (gestational days 0 to 20). However, maternal gestational weight gain, corrected for gravid uterine weight, was not affected. Maternal food and water intake were also unaffected Maternal liver weight (absolute or relative) was not affected by formamide exposure. Gravid uterine weight exhibited a significant decreasing trend (100, 94, and 87% of control weight), and the reduction was significant at 200 mg/kg/day. Prenatal mortality (resorptions and late fetal deaths), live litter size, and percent males/litter were not affected by formamide exposure. Average fetal body weight/litter exhibited a decreasing trend (98, 97, and 85% of average control weight), with significant reductions at greater than or equal to 100 mg/kg/day. No statistically significant differences were observed in the incidences of fetal morphological anomalies (malformations or variations). In summary, CD® rats were dosed by gavage with formamide (0, 50, 100, or 200 mg/kg/day) on gestational days 6-19. Minimal evidence of maternal toxicity was found at 200 mg/kg/day. Gravid uterine weight was reduced at 200 mg/kg/day, and fetal body weight was reduced at greater than or equal to 100 mg/kg/day. Thus, the maternal toxicity NOAEL was 100 mg/kg/day, and the LOAEL was 200 mg/kg/day. The developmental toxicity NOAEL was 50 mg/kg/day, and the LOAEL was 100 mg/kg/day.|... This study was performed due to the potential for human exposure to formamide and the lack of complete developmental toxicity data. Dose selection was based on a developmental toxicity screen in New Zealand White rabbits ... . Naturally-mated female New Zealand White (NZW) rabbits were dosed by gavage with formamide (10, 20, 40, 80 or 120 mg/kg body weight/day) or its vehicle (deionized/distilled water) on gestational days (gd) 6 through 29. Mild maternal toxicity and abortion or early delivery in 3 out of 7 pregnancies were found at 120 mg/kg/day. Although not statistically significant, the reduction in average fetal body weight at the high dose (83% of control weight) was considered to be a biologically relevant response to FORM exposure. In this study, female New Zealand White rabbits were dosed by gavage with formamide (35, 70, or 140 mg/kg/day) or its vehicle (deionized/distilled water) on gestational days 6 through 29. The dose volume was 1 ml/kg. The study was conducted in a two-replicate design. Twenty-four timed naturally-mated female rabbits (12 per replicate) were assigned to each group. Does were monitored at regular intervals throughout gestation for clinical signs, food intake, and body weight. At necropsy on gestational days 30, the following were recorded: maternal clinical condition; body, liver and gravid uterine weights; pregnancy status; and number of corpora lutea. In the gravid uterus, the numbers of resorbed, dead, or live fetuses were recorded. All live fetuses were weighed, sexed, and examined for morphological anomalies (external, visceral, and skeletal). Approximately one-half of the fetuses were examined for anomalies of the internal head structures. Abortions or early deliveries were noted in 0, 2, 2, and 8 females in the 0, 35, 70, and 140 mg/kg/day dose groups, respectively. At necropsy, confirmed pregnancy rates were 86-100% per group. One maternal death and four maternal deaths occurred in the low and high dose groups, respectively. Clinical signs associated with formamide exposure were minimal. Reduced or absent fecal output was more often recorded at the high dose (2-13 animals per day), presumably related to reduced feed consumption. A significant decreasing trend was noted for maternal body weight on gestational days 15, 18, 21, 24, 27, 29, and 30, maternal body weight change for gestational days 12 to 15, 15 to 18, 18 to 21 and 21 to 24, but not for weight change during treatment (gestational days 6 to 29) or gestation (0 to 30). Maternal body weight was significantly depressed in the high dose group on gestational days 21, 24, and 27. Maternal body weight change was significantly depressed at the high dose for gestational days 12 to 15, 18 to 21, and 21 to 24. In addition, maternal body weight change was depressed at the mid dose for gestational days 18 to 21. No significant treatment-related effects were observed for corrected maternal weight gain. Relative maternal food intake (g/kg/day) exhibited a decreasing trend during most of the treatment period treatment (gestational days 9 to 24), and was 34-59% of control intake in the high dose group from gestational days 12 through gestational days 24. Thereafter, no significant differences were noted among treatment groups for maternal relative feed consumption. Maternal liver weight (absolute and relative to body weight) was equivalent among groups. Gravid uterine weight exhibited a dose-related decreasing trend and was 71% of the control value at the high dose (significant). Formamide exposure decreased average litter size at 140 mg/kg/day that was 66% of the control mean. Mean fetal body weight per litter (males, females, and sexes combined) exhibited a decreasing trend. Mean fetal body weight per litter for males and the sexes combined was significantly decreased at the high dose. There was no effect of treatment on the incidence of external, visceral, or skeletal malformations or variations. In summary, maternal mortality and other indices of maternal toxicity were noted in this study at the high dose, and the maternal No Observed Adverse Effect Level (NOAEL) for formamide was 70 mg/kg/day. Formamide caused significant treatment-related developmental toxicity at 140 mg/kg/day, consisting of reduced mean live litter size and fetal body weight per litter. Thus, the developmental toxicity NOAEL was also 70 mg/kg/day.

Formamide's production and use as an intermediate in the chemical industry; to produce heterocyclic compounds, pharmaceuticals, crop protection agents, fungicides, and pesticides; as a solvent in the manufacture and processing of plastics; to produce formic acid; to remove coating from copper conductors; in the spinning of acrylonitrile copolymers; in the antistatic finishing of plastics or formation of conductive coatings on plastic particles(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 3.6(2), indicates that formamide is expected to have very high mobility in soil(SRC). Volatilization of formamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 6.1X10-2 mm Hg(3), and water solubility, 1.0X10+6 mg/l(4). Formamide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.1X10-2 mm Hg(3). Several biodegradation screening studies have observed significant biodegradation of formamide(5-8); although these screening studies are not specific to soil media, they suggest that biodegradation in soil may be important(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 3.6(2), indicates that formamide is not 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 1.4X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 6.1X10-2 mm Hg(4), and water solubility, 1.0X10+6 mg/l(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from a log Kow of -1.51(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Formamide is hydrolyzed very slowly at room temperature; the rate of hydrolysis increases rapidly in the presence of acid or bases and is further accelerated at elevated temperature(9). Biodegradation is an important fate process in water based on its biodegradability in aqueous screening tests(10-13).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), formamide, which has a vapor pressure of 6.1X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase formamide 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 8 days(SRC), calculated from its rate constant of 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of formamide with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Formamide is hydrolyzed very slowly at room temperature; the rate of hydrolysis increases rapidly in the presence of acid or bases and is further accelerated at elevated temperature(2). The rate constant for reaction of formamide with OH radicals in aqueous solution is <5.0X10+8 cu dm/mol s(3).

An estimated BCF of 3 was calculated for formamide(SRC), using a log Kow of -1.51(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 Koc of formamide is 3.6(1). According to a classification scheme(2), this Koc value suggests that formamide is expected to have very high mobility in soil(SRC).

The Henry's Law constant for formamide is estimated as 1.4X10-9 atm-cu m/mole(SRC) based upon its vapor pressure, 6.1X10-2 mm Hg(1), and water solubility, 1.0X10+6 mg/l(2). This Henry's Law constant indicates that formamide is expected to be essentially nonvolatile from water surfaces(3). Formamide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.1X10-2 mm Hg(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2,724 workers (556 of these are female) are potentially exposed to formamide in the US(1). Occupational exposure to formamide may occur through inhalation and dermal contact with this compound at workplaces where formamide is produced or used(SRC). Formamide, a physiological product of N,N-dimethylformamide, was detected in the urine of synthetic leather factory workers(2). Urinary concns ranged from 7-69 mg/l for workers exposed to N,N-dimethylformamide in the workplace(2).

Formamide, a physiological product of N,N-dimethylformamide, was detected in the urine of synthetic leather factory workers(1). Urinary concns ranged from 7-69 mg/l for workers exposed to N,N-dimethylformamide in the workplace(1).

Drug Information

FORMAMIDE IS ABSORBED DIRECTLY THROUGH GUINEA PIG SKIN ... .|After admin of 2-4 g/rabbit orally, 39% of the dose was recovered unchanged ... .

THERE APPEARS TO BE GOOD EVIDENCE FOR HYDROLYSIS /OF ALIPHATIC CARBOXYLIC AMIDES/ ... THE SITE OF HYDROLYSIS IS PROBABLY LIVER, WHERE THERE ARE RELATIVELY NONSPECIFIC AMIDASES. RATE OF HYDROLYSIS INCREASES RAPIDLY AS MOLECULAR WT INCREASES ... /EXCEPT/ ACETAMIDE WAS HYDROLYZED MORE SLOWLY THAN FORMAMIDE ... .|RELATIVE LACK OF IRRITANT EFFECTS /OF SIMPLE CARBOXYLIC AMIDES/ ON SKIN & MUCOUS MEMBRANES INDICATES THAT HYDROLYSIS IS PROBABLY NOT OCCURRING THERE TO ANY EXTENT, OTHERWISE LOWER MOLECULAR WT ACIDS PRODUCED WOULD CAUSE LOCAL DAMAGE.|It is known that dimethylformamide is metabolized in man by sequential N-demethylation to methylformamide & formamide, which are largely eliminated in the urine.|In a study ... the hypothesis was tested that formamide undergoes metabolic hydrolysis in rabbits. Acidic substances were titrated after extraction by ether, before & after hydrolysis of urine samples. The ether-soluble acid determined in hydrolyzed urine was assumed to reflect the amount of formamide excreted unchanged. The difference between the amount of amide admin & the total amount excreted unchanged was considered to represent amide which was metabolically hydrolyzed. After admin of 2-4 g/rabbit orally, 39% of the dose was recovered unchanged using this method.

Methanol, 0.1%; ammonium formate, 0.1%; water, 0.1%; iron, 0.0001%

INHALATION: A moderate irritant to mucous membranes. EYES: Moderately irritating to the eyes. SKIN: A mild to moderate irritant to the skin. (USCG, 1999)

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. 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. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. 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. IMMEDIATELY transport the victim to a hospital. 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. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)|(See procedures)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Moderately irritating to skin, mucous membranes.|An irritant to skin, eyes, and mucous membranes.

formamide

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.|inhalation, ingestion, skin and/or eye contact

irritation eyes, skin, mucous membrane; drowsiness, lassitude (weakness, exhaustion); nausea; acidosis; skin eruptions; In Animals: reproductive effects


Drowsiness. Headache. Nausea. Diarrhoea.


Redness.


Redness.

Eyes, skin, respiratory system, central nervous system, reproductive system

Formamide Use and Manufacturing

Methods of Manufacturing

Prepared on large scale from carbon monoxide and ammonia at high pressure and temp: Meyer, Orthner, Ber 54, 1705 (1921); 55, 857 (1922); Meyer, German patents 390,798 (1924); 392,409 (1924); 414,257 (1925 to BASF); Weitzel, Herbst, US patent 1,843,434 (1932 to IG Farben).|Interaction of ethyl formate and ammonia with subsequent distillation.

Uses

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.Formamide will begin to partially decompose into carbon monoxide and ammonia at 180°C together with traces of hydrogen cyanide (HCN) and water.


Corrosion inhibitors and anti-scaling agents


Water treatment products

Production

500,000 - 1,000,000 lb|(1972) PROBABLY GREATER THAN 4.54X10+5 G|(1975) PROBABLY GREATER THAN 4.54X10+5 G

All other chemical product and preparation manufacturing|Formamide: ACTIVE

A HPLC method with UV detection was used for the determination of low mol wt amides in pharmaceutical matrixes. The method was based on Zorbax C8 or Alltech C18 column, mobile phase consisting of 3-5% MeCN in 0.1M phosphate buffer, & flow rate of 1-1.5 ml/min at the room temperature. By strongly retaining the sample matrix & allowing the amide analyte to elute, the method can be generally applied to many types of org matrix for pharmaceutical & agricultural products. /Amides/|EPA Method 1666: Volatile Organic Compounds Specific to the Pharmaceutical Manufacturing Industry by Isotope Dilution GC/MS. Detection limit = 1000 mg/l.|EPA Method 1671: Volatile Organic Compounds Specific to the Pharmaceutical Manufacturing Industry by GC/FID. Detection limit = 100 mg/l.

Computed Properties

Molecular Weight:45.041
XLogP3:-0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:45.021463719
Monoisotopic Mass:45.021463719
Topological Polar Surface Area:43.1
Heavy Atom Count:3
Complexity:12.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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