HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylacetamide
DMAC · DMA · Dimethyl acetamide · N,N-Dimethylacetamide, 99%, pure · C4H9NO · dimethylacetamid · CH3CON(CH3)2 · Acetic acid dimethylacetamide
Identifiers & Physical Properties
| CAS No. | 127-19-5 |
|---|---|
| Molecular formula | C4H9NO |
| Average molar mass | 87.12 g/mol |
| Monoisotopic mass | 87.06841391 g/mol |
| SMILES | CC(=O)N(C)C |
| InChIKey | FXHOOIRPVKKKFG-UHFFFAOYSA-N |
| PubChem CID | 31374 |
| ChEMBL | CHEMBL11873 |
| ChEBI | CHEBI:84254 |
| EC No. | 204-826-4 |
| DTXSID | DTXSID5020499 |
Chemical & Physical Properties
| XLogP | -0.8 |
|---|---|
| Topological polar surface area | 20.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 58 |
| LogP (partition coefficient) | log Kow= -0.77 |
| Odor | AMINEWeak, ammonia- or fish-like odorFaint ammonia odor |
| Density | 0.943 at 68 °F (USCG, 1999) - Less dense than waterwill float0.937 (USCG, 1999) - Less dense than water0.9366 @ 25 °C/4 °CRelative density (water = 1): 0.940.943 @ 20°C0.937 g/mL at 25 °C (lit.) |
| Viscosity | 0.92 cP @ 25 °C |
| Color/Form | LiquidOILYColorless liquid |
| Solubility | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)SOL IN BENZENESoluble in alcohol, acetone, etherMiscible with most org solventsMISCIBLE WITH AROMATIC CMPD, ESTERS, KETONES, ETHERSMiscible in water.>1000g/l soluble |
| Flash point | 151 °F (NTP, 1992)145 °F (USCG, 1999)70 °C70 °C (OPEN CUP)63 °C c.c.158 °F (open cup) |
| Boiling point | 329 to 331 °F at 760 mmHg (NTP, 1992)331 °F at 760 mmHg (USCG, 1999)163-165 °C329 °F165 °C @760 [mm Hg]164.5-166 °C (lit.) |
| Decomposition | ON DECOMPOSITION CAN EMIT FUMES HIGHLY IRRITATING TO EYES, MUCOUS MEMBRANES.When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Melting point | -4 °F (NTP, 1992)-4 °F (USCG, 1999)-18.59 °C-20 °C-20 °C (lit.) |
| Vapor density | 3.01 (Air= 1)Relative vapor density (air = 1): 3.013.89 (vs air) |
| Odor threshold | Odor Threshold Low: 21.0 [ppm]Odor Threshold High: 47.0 [ppm]Odor threshold from "Quick Guide: The Electronic NIOSH Pocket Guide to Chemical Hazards"ODOR THRESHOLD FOR 50% RESPONSE IS 21.4 PPMFOR 100% RESPONSE, 46.8 PPM.Odor low: 163.8 mg/cu mOdor high: 163.8 mg/cu m0.76ppm |
| Vapor pressure | 40 mm Hg ( 19.4 °C) |
| Refractive index | n20/D 1.439(lit.) |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| pKa (acidity coefficient) | -0.41±0.70(Predicted) |
| Color | Colorless to yellowish |
| pH | 4 (200g/l, H2O, 20℃) |
| PH Range | 4 at 200 g/l at 20 °C |
| Relative polarity | 6.3 |
| Appearance | Solid Powder |
| Explosive limits | 1.7-11.5%(V) |
| Evaporation Rate | <0.17 |
| Thermal conductivity | 0.168 W/(m·K) at 25 ℃ |
| Specific heat capacity | Cp(liquid): 2.02 J/(g·K), at 25℃ |
| λmax | λ: 270 nm Amax: 1.00λ: 280 nm Amax: 0.30λ: 290 nm Amax: 0.15λ: 310 nm Amax: 0.05λ: 320 nm Amax: 0.03λ: 360-400 nm Amax: 0.01 |
| Merck | 14,3227 |
| BRN | 1737614 |
| Henry's law constant | 6.1×101 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| Exposure limits | ACGIH:TLV-TWA 10 ppm (36 mg/m3)OSHA:PEL-TWA 10 ppm (35 mg/m3)NIOSH:REL-TWA 10 ppm |
| Dielectric constant | 37.8(25℃) |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 |
| InChIKey | FXHOOIRPVKKKFG-UHFFFAOYSA-N |
| SMILES | CN(C)C(C)=O |
| LogP (partition coefficient) | -0.77 at 25℃ |
| Surface tension | 37.13mN/m at 293.15K |
| Substances of Very High Concern (SVHC) Candidate List | N,N-dimethylacetamide (127-19-5) |
| REACH Annex XVII Substances List | N,N-dimethylacetamide (DMAC) (127-19-5) |
| CAS DataBase Reference | 127-19-5(CAS DataBase Reference) |
| EWG's Food Scores | 3 |
| FDA UNII | JCV5VDB3HY |
| Proposition 65 List | N,N-Dimethylacetamide |
| IARC | 2B (Vol. 123) 2020 |
| NIST Chemistry Reference | Acetamide, N,N-dimethyl-(127-19-5) |
| EPA Substance Registry System | Dimethylacetamide (127-19-5) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H312+H332-H319-H360D |
| GHS precautionary statements | P201-P280-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313 |
| Hazard symbols | T |
| Risk statements (R) | 11-20/22-61-20/21-36 |
| Safety statements (S) | 16-24-53-45-36-28-26 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 10 ppm (35 mg/m3) [skin] |
| Water hazard class (WGK) | WGK 2 |
| RTECS number | AB7700000 |
| F | 3-10 |
| Autoignition temperature | 914 °F |
| TSCA inventory status | TSCA listed |
| Customs code | 29241900 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazard class | Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Irrit. 2Repr. 1B |
| Hazardous substances data | 127-19-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 5.4 ml/kg (Bartsch) |
| Immediately dangerous to life or health concentration | 300 ppm |
| REACH registrations | Active |
| Excepted quantities | Non-Hazardous |
Safety & Regulations
| GHS classification | DangerH312: Harmful in contact with skin [Warning Acute toxicity, dermal]H332: Harmful if inhaled [Warning Acute toxicity, inhalation]H360D ***: May damage the unborn child [Danger Reproductive toxicity]P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: Acetamide, N,N-dimethyl-Hazard Traits - CarcinogenicityDevelopmental ToxicityReproductive ToxicityAuthoritative List - EC Annex VI CMRs - Cat. 1BIARC Carcinogens - 2BProp 65Report - regardless of intended function of ingredient in the productAcetamide, N,N-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetamide, N,N-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 20-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15266Restricted substance: N,N-dimethylacetamide (DMAC)EC: 204-826-4Restriction condition document: PDF linkSubstance: N,N-dimethylacetamideDate of inclusion: >19-Dec-2011Reason for inclusion: Toxic for reproduction (Article 57c) |
| Other safety information | IMAP assessments - Acetamide, N,N-dimethyl-: Human health tier II assessmentIMAP assessments - Acetamide, N,N-dimethyl-: Environment tier I assessment |
| DOT label | Combustible LiquidPoison |
| Fire hazards | This chemical is combustible. (NTP, 1992)Special Hazards of Combustion Products: Emits carbon oxides, nitrogen oxides, and dimethylamine when heated to decomposition.Behavior in Fire: Sealed closed containers may rupture from pressure from heat of fire. (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 63 °C explosive vapour/air mixtures may be formed. |
| Fire potential | Combustible when exposed to heat or flame. |
| Health hazards | Liquid causes mild irritation of eyes and skin. Ingestion causes depression, lethargy, confusion and disorientation, visual and auditory hallucinations, perceptual distortions, delusions, emotional detachment, and affective blunting. (USCG, 1999)Inhalation may cause nasal and respiratory irritation. May cause systemic poisoning. Ingestion may cause abdominal spasms, vomiting, sweating, weakness, and headache. Large doses may cause lethargy, disorientation, redness, dermatitis, and sensitization. (USCG, 1999) |
| Hazards summary | Toxic hepatitis has been reported in workers after inhalation and dermal exposure. DMAC is fetotoxic and teratogenic when administered at high doses to rabbits and rats. NOAEL = 25 ppm for hepatic and renal toxicity in rats and mice. Humans exposed to high doses may experience mental confusion. [ACGIH] A skin and eye irritantInhalation of high concentrations may cause liver and CNS effects[ICSC] In a study of 440 new elastone fiber workers, 28 cases with elevated liver enzymes were detected in a 31 month period from 2002 to 2004. Using the BEI of 30 mg/g creatinine as a cutoff, the incidence of hepatic injury was about 7 times greater in the high exposure group. [Reference #1] |
| Reactive group | Amides and ImidesWater and Aqueous Solutions |
| EC classification | Note: ESymbol: TR: 61-20/21S: 53-45 |
| Special Reports | CENT CHEM HAZARD ASSESSMENT, SYRACUSEINFORMATION PROFILES ON POTENTIAL OCCUPATIONAL HAZARDS. VOLUME I. SINGLE CHEMICALS. N,N-DIMETHYL ACETAMIDEREPORTORDER NUMBER PB81-148009, 14 PP (1979). REVIEW OF KNOWN & SUSPECTED HEALTH EFFECTS, EXTENTS OF WORKER EXPOSURE, & INDUSTRIAL IMPORTANCE. |
| TSCA requirements | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N,N-Dimethylacetamide is included on this list. |
| OSHA Standards | Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 10 ppm (35 mg/cu m). Skin Designation. |
| Fire fighting | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective.SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. For petroleum crude oil, do not spray water directly into a breached tank car. This can lead to a dangerous boil over. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzlesif this is impossible, withdraw from area and let fire burn. (ERG, 2024)Fire Extinguishing Agents Not to Be Used: Do not use halogenated extinguishing media or water.Fire Extinguishing Agents: Dry chemical, alcohol foam, carbon dioxide (USCG, 1999)Use powder, alcohol-resistant foam, water spray, carbon dioxide. |
| First aid measures | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Seek medical attention if you feel unwell. |
| First aid | 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 areatake 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 usedif 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)Call for medical aid.EYES: Flush with plenty of water for 15 min., lifting lids occasionally.SKIN: Flush with plenty of water for 15 min. Remove contaminated clothing and shoes.INGESTION: Induce vomiting. (USCG, 1999)(General first aid procedures)Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.Skin: Water flush immediately - If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly.Breathing: Respiratory supportSwallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately. |
| Safe storage | Ventilation along the floor. Separated from strong oxidants. |
| Exposure control and personal protection | Biological Exposure Indices (BEI) [ACGIH] - M-Methylacetamide in urine = 30 mg/g creatinineend of shift at end of workweek5.0 [ppm] |
| Fire fighting procedures | EXTINGUISH WITH WATER, DRY CHEMICALS, ALCOHOL FOAM OR CARBON DIOXIDE |
| Storage conditions | MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ... . |
| Cleanup methods | 1. Ventilate the area of spill or leak. 2. For small quantities, absorb on paper towels. Evaporate in safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn paper in suitable location away from combustible materials. |
| Nonfire spill response | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024) |
| Disposal methods | 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.1. By absorbing it in vermiculite, dry sand, earth or a similar material and disposing in sealed containers in secured sanitary landfill. 2. By atomizing in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. |
| Spillage disposal | Personal protection: chemical protection suit. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | 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.The worker should immediately wash the skin when it becomes contaminated.Work clothing that becomes wet or significantly contaminated should be removed or replaced.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. |
| Body burden | N,N-dimethylacetamide was qualitatively found in 8 of 12 breath samples of subjects monitored in Bayonne and Elizabeth, NJ, and Research Triangle Park, NC, 1980(1). |
| Interactions | DAILY INJECTIONS OF PROGESTERONE (5 MG/HAMSTER/DAY, FOR 4 DAYS) BLOCKED ANTIFERTILITY EFFECT OF DMA (ADMIN @ NIDATION) AS DID INJECTIONS OF A LUTEOTROPIC COMPLEX (1 MG/HAMSTER/DAY PROLACTIN PLUS 5.1 IU/HAMSTER/DAY OF PREGNANT MARE SERUM GONADOTROPIN, FOR 4 DAYS.DIMETHYLACETAMIDE LOWERED THE YIELDS AND/OR INCIDENCES OF TOTAL TUMORS, BENIGN PLAQUES, BENIGN HYPERKERATOTIC LESIONS AND ADVANCED TUMORS PROMOTED BY RETINYL ACETATE OR CROTON OIL AFTER INITIATION BY 7,12-DIMETHYLBENZ(A)ANTHRACENE.SINGLE EXPT WITH 45 MG/KG RAT OF PYRIMETHAMINE ISETHIONATE IN 6% DIMETHYLACETAMIDE, 6% DIMETHYL SULFOXIDE OR 95% ETHANOL SHOWED THAT TERATOGENIC EFFECT WAS CUMULATIVE IN DIMETHYL SULFOXIDE OR ETHANOL BUT AFTER ADMIN IN DMA RESPONSE-DOSE RELATION FOLLOWED A PARABOLIC CURVE.PCC4azal embryonal carcinoma tumors were grown in strain 129 mice by sc transplantation. When palpable, the tumors were treated with a combination of retinoic acid and dimethylacetamide. In vitro, this embryonal carcinoma cell line shows minimal spontaneous differentiation and is exquistely sensitive to retinoic acid and/or dimethylacetamide induction of differentiation. Ten daily 20 ul intratumor injections of a solution of 10 mg retinoic acid per ml of dimethylacetamide resulted in nearly complete induction of morphological differentiation mainly into neuropithelial and glandular derivatives. Control tumors showed minor spontaneous differentiation. Differentiation was associated with decreased tumor growth rate, decreased mitotic index, decreased extent of necrosis, and increased survival time of the hosts. In 4 of 18 cases, long-term survival of the hosts was effected by a complete differentiation of the malignant embryonal carcinoma tumors into benign teratomas. Retinoic acid: dimethylacetamide was also effective in inducing differentiation with the same dosage and schedule when admin systemically, ie, ip or sc. |
| Target organs | Skin, liver, central nervous system |
| Ecotoxicity values | LC50 Pimephales promelas (fathead minnow) 1.50 g/l/96 hr (confidence limit 1.21- 1.86 g/l), flow-through bioassay with measured concentrations, 23.1 °C, dissolved oxygen 6.6 mg/l, hardness 45.0 mg/l calcium carbonate, alkalinity 43.5 mg/l calcium carbonate, and pH 7.7. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a log Kow of -0.77(2) and a regression-derived equation(3), indicates that N,N-dimethylacetamide is expected to have very high mobility in soil(SRC). Volatilization of N,N-dimethylacetamide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.31X10-8 atm-cu m/mole(4). The potential for volatilization of N,N-dimethylacetamide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2 mm Hg(5). N,N-Dimethylacetamide is expected to be biodegradable in soil based on aqueous screening tests(6,7).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a log Kow of -0.77(2) and a regression-derived equation(3), indicates that N,N- dimethylacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.31X10-8 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). N,N-Dimethylacetamide, present at 100 mg/l reached 28% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(7). N,N-Dimethylacetamide, present at 30 mg/l, reached 80% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 100 mg/l and the Japanese MITI test(7). In other studies, N,N-dimethylacetamide, present at 400 mg/l, reached 96% of its theoretical TOC in 5 days using industrial activated sludge(8). These results from laboratory studies suggest that N,N-dimethylacetamide will biodegrade in the aquatic environment(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-dimethylacetamide, which has a vapor pressure of 2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase N,N-dimethylacetamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is 28 hours(SRC), calculated from its rate constant of 1.36X10-11 cu cm/molecule-sec at 25 °C(3). |
| Adverse effects | Neurotoxin - Acute solvent syndromeOccupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.ACGIH Carcinogen - Confirmed Animal. |
| Exposure routes | The substance can be absorbed into the body by inhalation and through the skin.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Signs and Symptoms | Headache. Nausea.MAY BE ABSORBED! Redness. Further see Inhalation.Abdominal cramps. Diarrhoea. Further see Inhalation.irritation skinjaundice, liver damagedepression, drowsiness, hallucinations, delusions |
| Medical Surveillance | The determination of urinary N-monomethylacetamide in the end of shift urine sample was used to monitor exposure to dimethylacetamide. Five workers were observed followed for 4 consecutive weeks. Airborne dimethylacetamide appeared to account for the greatest amount of urinary N-monomethylacetamide detected and, at the exposure concentrations encountered (0.5 to 2 ppm), a relationship of 10 ppm urinary N-monomethylacetamide inhaled was observed. Interindividual variation was small and no evidence of build-up in N-monomethylacetamide urinary levels was seen in these subjects. Mean airborne dimethylacetamide concentrations were somewhat higher by the end of the week, but magnitude was such that the differences were not statistically significant. It is concluded that changes in dimethylacetamide exposures can be quantitatively reflected by urinary N-monomethylacetamide.A study of occupational exposure to dimethylactamide was conducted using both biological and environmental monitoring techniques. Personal and area air samples were analyzed for dimethylacetamide at a facililty manufacturing prefabricated synthetic products. Spot urine samples were collected from eight exposed and four unexposed workers for 5 consecutive work days and on the following Monday. These were analyzed for N-methylacetamide, a dimethylacetamide metabolite. Area air dimethylacetamide concentrations were generally constant, ranging from 11.81 to 17.24 ppm with a mean of 14.74 ppm. Personal dimethylacetamide concentrations showed a wide variability. The concentrations were distributed log normally with arithmetic and geometric means of 14.0 and 6.0 ppm, respectively. Urinary N-methylacetamide concentrations were not correlated with personal air dimethylacetamide concentrations. Six of the exposed workers excreted about 18% of the inhaled dimethylacetamide dose, calculated as the 8 hr time weighted average exposure, as N-methylacetamide. The other two exposed workers excreted about 30 percent of the inhaled dose as N-methylacetamide. Urinary N-methylacetamide concentrations the Monday following exposure were negligible or had returned to their preexposure values. Based on these results the half life for urinary excretion of N-methylacetamide was calculated to be 16 hours. The authors conclude that for dimethylacetamide and similar substances that are easily absorbed through the skin, biological monitoring is superior to airborne exposure monitoring for determining total uptake and evaluating potential health risks.the assessment of dimethylacetamide exposure can be accomplished through measurement of either dimethylacetamide, N-methylacetamide (NMAC), or acetamide. Urinary levels of NMAC have been shown to correlate with airborne exposure levels of dimethylacetamide. However, no information was located which showed a correlation between urinary NMAC levels & the onset of adverse health effects. Urine Reference Ranges: Normal- None detectedExposed- BEI (sampling time is end of shift at the end of workweek, measured as N-methylacetamide): 30 mg/g creatinineToxic- Not established.Liver Function Tests: Biochemical tests - Enzymes that reflect cholestasis: alkaline phosphatase (AP), 5'-nucleotidase (5'-NT) & leucine aminopeptidase (LAP)Enzymes that detect direct hepatic damage: aspartate aminotransferase (AST), alanine aminotransferase (ALT) & gammma glutamyl Transpeptidase (GGTP)Clearance tests - indocyanine green, antipyrine test and serum bile acids. |
| Soil Adsorption/Mobility | The Koc of N,N-dimethylacetamide is estimated as 9(SRC), using a measured log Kow of -0.77(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that N,N-dimethylacetamide is expected to have very high mobility in soil(SRC). |
| Atmospheric Concentrations | SOURCE DOMINATED: N,N-Dimethylacetamide was detected in 6 of 6 air samples in 1982 within a mile radius of a hazardous liquid waste impoundment, location not given, at concns ranging from 9.6 ng/cu m to 11 ng/cu m(1). |
| Human Toxicity Excerpts | CERTAIN N-SUBSTITUTED AMIDES ... DIMETHYL ACETAMIDE, MAY PRODUCE CHRONIC LIVER OR RENAL DAMAGE.JAUNDICE HAS BEEN OBSERVED ... IN WORKERS EXPOSED REPEATEDLY AT ... 20-25 PPM ... SKIN PENETRATION UNDOUBTEDLY CONTRIBUTED TO THIS EFFECT.... GIVEN TO HUMANS IN DAILY DOSES OF 400 MG/KG FOR 3 OR MORE DAYS ... DEPRESSION, LETHARGY, CONFUSION & DISORIENTATION ENSUED. IN SOME ... VISUAL & AUDITORY HALLUCINATIONS, PERCEPTUAL DISTORTIONS, DELUSIONS, EMOTIONAL DETACHMENT & AFFECTIVE BLUNTING ... .DIZZINESS, SLEEPINESS, & WEAKNESS RESULTED FROM DMA CONCN OF 109.5-337 MG/CU M IN AIR OF METAL SURFACE FINISHING PROCESSES.For more Human Toxicity Excerpts (Complete) data for N,N-DIMETHYLACETAMIDE (17 total), please visit the HSDB record page. |
| F | 3-10 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 10 ppm (35 mg/m3) [skin] |
| Water hazard class (WGK) | WGK 2 |
| Immediately dangerous to life or health concentration | 300 ppm |
| TSCA inventory status | TSCA listed |
| RTECS number | AB7700000 |
| Customs code | 29241900 |
| Toxicity | LD50 orally in rats: 5.4 ml/kg (Bartsch) |
| Risk statements (R) | 11-20/22-61-20/21-36 |
| Signal word | Danger |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | T |
| Safety statements (S) | 16-24-53-45-36-28-26 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| GHS hazard statements | H312+H332-H319-H360D |
| Excepted quantities | Non-Hazardous |
| REACH registrations | Active |
| Hazard class | Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Irrit. 2Repr. 1B |
| Autoignition temperature | 914 °F |
| GHS precautionary statements | P201-P280-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313 |
| Hazardous substances data | 127-19-5(Hazardous Substances Data) |
Applications & Uses
Uses
N,N-Dimethylacetamide is used as a polar solvent in organic synthesis as well as in reactions involving strong bases such as sodium hydroxide. It is also used as a solvent for fibers like polyacrylonitrile, spandex, as an excipient in drugs viz. vumon, busulfex and in the adhesive industry. It finds application as a reaction medium in the production of pharmaceuticals, agrochemicals, dyes and plasticizers. It is widely used in polymer industry due to its high solving power for high molecular-weight polymers and synthetic resins. It plays an important role as a catalyst in various reactions viz. cyclization, halogenation, cynidation, alkylation and dehydrogenation and increases the yield of main products. It is also used as an extracting agent for oil and gases, in paint removers, in the production of photo-resist stripping compounds and as booster solvent in coatings.
Description
Dimethylacetamide (DMAC) is a synthetic organic compound that is produced from a reaction of dimethylamine and acetic acid or acetic anhydride. It is a colorless to yellow liquid with a faint odor resembling ammonia. DMAC has similar density to water and is miscible with water and organic substances. This organic compound is commonly associated with many industrial uses, either as a starting material or an intermediate. DMAC is a good solvent that is used in polymer dissolution, especially in the fiber industry. Historically, DMAC was also tested as a possible antineoplastic agent in a phase 1 study involving 17 patients. However, liver and central nervous system (CNS) toxicity associated with DMAC was observed and these patients had altered mental states, resulting in no further drug development.
Uses
N,N-dimethylacetamide is an excellent solvent and often acts as a catalyst in halogenation, cyclization, and alkylation reactions. It is an important industrial solvent for polyacrylonitrile, vinyl resins, cellulose derivatives, styrene polymers and linear polyesters. It is also used in all analytical laboratories as a major component of mobile phase in High Performance Liquid Chromatography (HPLC) and in Liquid Chromatography - Mass Spectrometry (LC-MS). N,N-dimethylacetamide lithium chelate complexes intercalate cationic sites in layered silicates.
General Description
Dimethylacetamide appears as a clear colorless liquid with a faint odor similar to ammonia. About the same density as water. Flash point 145°F. Vapors heavier than air. May by toxic by skin absorption. May irritate eyes and skin.
Preparation & Synthesis
Preparation
N,N-Dimethylacetamide is prepared by reaction of dimethylamine with acetic acid, acetic anhydride, or acetate esters. Heating dimethylamine acetate with, or without a catalyst affords N,N-Dimethylacetamide. Reaction of dimethylamine with acetate esters requires a catalyst; sodium methoxide is typically used.