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Acetylthiourea

HCID 2723593
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
591-08-2
Standard SMILES
CC(=O)NC(N)=S
InChIKey
IPCRBOOJBPETMF-UHFFFAOYSA-N
Molecular formula
C3H6N2OS
Average molar mass
118.16 g/mol
Monoisotopic mass
118.02008381

Overview

1-acetyl-2-thiourea is a white crystalline solid. Noncombustible, but decomposes with heating.

Names & identifiers

Preferred name
Acetylthiourea
IUPAC
N-carbamothioylacetamide
English name
N-ACETYLTHIOUREA
Molecular formula
C3H6N2OS
Molecular weight
118.16

Names & synonyms

N-AcetylthioureaAcetylthiourea591-08-21-Acetylthiourea1-ACETYL-2-THIOUREAAcetothioureaN-Acetyl-2-thioureaAcetamide, N-(aminothioxomethyl)-N-AcetylthiocarbamideAcetylthiocarbamideUrea, 1-acetyl-2-thio-Acetyl thiourea
Show more names
N-carbaMothioylacetaMideusafek-4890ACETYLTHOUREAN-Acetylthloureaacetyl-2-thiourea
USAF EK-4890N(Thiocarbamyl)acetamideZNZ5N1H713NSC-7597DTXSID4060446CHEBI:188350N-(AMINOTHIOXOMETHYL)ACETAMIDERefChem:428980

Database identifiers

CAS
591-08-2
PubChem CID
2723593
DTXSID
DTXSID4060446
ChEMBL
CHEMBL4524588
ChEBI
CHEBI:188350
UNII
ZNZ5N1H713
EC Number
209-699-9
Nikkaji
J2.688C

Properties

Computed structural properties

XLogP
-0.1
Topological polar surface area
87.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
7
Formal charge
0
Complexity
101

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Thiourea Compounds
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
Color/FormPRISMS FROM WATER; RHOMBIC CRYSTALS FROM ALCOHOL
Solubility · 2 items

SOL IN DILUTE SODIUM HYDROXIDE, HOT WATER; SLIGHTLY SOL IN WATER, ETHER

Slightly soluble in water and ethyl ether; soluble in ethanol.

DecompositionWhen heated to decomposition it emits very toxic fumes of /nitrogen oxides and sulfur oxides/.
Melting Point · 2 items

329 to 336 °F (NTP, 1992)

165 °C

Vapor Pressure0.000372 [mmHg]
Physical Description · 2 items

1-acetyl-2-thiourea is a white crystalline solid. Noncombustible, but decomposes with heating.

White solid; [CAMEO] White crystalline solid; [Alfa Aesar MSDS]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 57 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

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

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards SummaryAn irritant; [Alfa Aesar MSDS]
Reactive GroupAmides and Imides
RCRA Requirements · 1 item

P002; As stipulated in 40 CFR 261.33, when 1-acetyl-2-thiourea, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Chemistry & industry

Uses & manufacturing

UsesNot manufactured or used as an industrial end-product in the US; [HSDB] One manufacturer in the US (as of 1990); [EPA]
General Manufacturing Information · 2 items

Acetamide, N-(aminothioxomethyl)-: ACTIVE

1-Acetyl-2-thiourea is not manufactured or used as an end-product industrially in the USA.

Applications

UsesN-Acetylthiourea is a derivative of Thiourea (T375450)

General DescriptionWhite crystalline solid. Noncombustible, but decomposes with heating.

Upstream & downstream products

Upstream raw materials

Acetyl chlorideThree-necked flaskThiourea

Downstream products

ACETYLUREA

Additional notes

DefinitionChEBI: N-acetylthiourea is a member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by an acetyl group. It is a member of acetamides and a member of thioureas. It is functionally related to a thiourea.

Related reactions

41 records
New reaction record
HRID 188360 reaction equation
HRID 188360As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 272738 reaction equation
HRID 272738As reactantuspto-grants-2008_11
HRID 287267 reaction equation
HRID 287267As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 414795 reaction equation
HRID 414795As reactantuspto-grants-1988_12
HRID 444884 reaction equation
HRID 444884As reactantuspto-grants-2013_07
HRID 601611 reaction equation
HRID 601611As reactantuspto-grants-2011_03
HRID 652057 reaction equation
HRID 652057As reactantuspto-grants-1987_06
HRID 874162 reaction equation
HRID 874162As reactantuspto-grants-2015_03
Page 1 of 6

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Physicochemical properties

Melting point
165 · 165-169 °C(lit.)
Density
1.24 · 1.240 (estimate)
refractive index
1.7 · 1.7000 (estimate)
storage temp.
30 °C · Store below +30°C.
solubility
12.8 g/l · 12.8g/l
pka
11.24 · 11.24±0.70(Predicted)
form
Crystalline Powder
color
Pale cream
PH
6 · 6.0 (173g/l, H2O, 20℃)
BRN
969960 · 969960
Henry's Law Constant
3.8 · 3.8×105 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C3H6N2OS/c1-2(6)5-3(4)7/h1H3,(H3,4,5,6,7)
InChIKey
IPCRBOOJBPETMF-UHFFFAOYSA-N
SMILES
CC(=O)NC(N)=S
CAS DataBase Reference
591 · 591-08-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
5 N1H713 · ZNZ5N1H713
EPA Substance Registry System
1 · 1-Acetyl-2-thiourea (591-08-2)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
300 · H300
Precautionary statements
264 · P264-P301+P310-P280f-P309-P310
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T
Risk Statements
25 · 25
Safety Statements
36 · 36/37/39-45
RIDADR
2811 · UN 2811 6.1/PG 2
WGK Germany
3 · 3
RTECS
7700000 · YR7700000
Hazard Note
Highly Toxic
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
II
HS Code
2930909899 · 2930909899
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 Oral · Acute Tox. 2 Oral
Hazardous Substances Data
591 · 591-08-2(Hazardous Substances Data)
TSCA Requirements · 1 item

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. Acetamide, N-(aminothioxomethyl)- is included on this list.

Reactivity Profile1-ACETYL-2-THIOUREA is incompatible with strong oxidizing agents, strong acids and strong bases. Decomposes when heated to give toxic oxides of sulfur and nitrogen.
Air and Water ReactionsSlightly soluble in water, soluble in hot water. Hydrolysis occurs rapidly with strong acid/base media.
EPA Hazardous Waste NumberP002; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.
CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Safety & protection

Fire Fighting · 1 item

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

First Aid · 1 item

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.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol 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 alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 2 items

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P002, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for liquid injection incineration at a temperature range of 650 to 1600 °C and a residence time of 0.1 to 2 seconds. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter).

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that 1-acetyl-2-thiourea is expected to have very high mobility in soil(SRC). Volatilization of 1-acetyl-2-thiourea from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1-Acetyl-2-thiourea is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-4 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from an estimation method(2), indicates that 1-acetyl-2-thiourea is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.6X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -0.27(6), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-acetyl-2-thiourea, which has an estimated vapor pressure of 3.7X10-4 mm Hg at 25 °C(2), is expected to exist solely in the vapor phase in the ambient atmosphere. Vapor-phase 1-acetyl-2-thiourea 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 10 hours(SRC), calculated from its rate constant of 3.8X10-11 cu cm/molecule-sec at 25 °C, determined using a structure estimation method(3). 1-Acetyl-2-thiourea (in a methanol solvent) absorbs UV light in the region between 290-330 nm(4); although the absorbance is relatively weak, there may be a potential for direct photolysis in the environment(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1-acetyl-2-thiourea can be estimated to be 22(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-acetyl-2-thiourea is expected to have very high mobility in soil.

Human Toxicity Excerpts · 1 item

In the manufacture of rubber, irritant contact dermatitis may occur from a variety of acids, alkalis, detergents, and solvents used in the process. Allergic contact dermatitis occurs not infrequently and is almost always due to an organic accelerator or antioxidant. While the list of potential sensitizing accelerators and antioxidants is enormous, common allergens include ... thioureas. /Thioureas/

Artificial Pollution Sources1-Acetyl-2-thiourea is not manufactured or used as an end-product industrially in the USA.
Environmental Bioconcentration · 1 item

An estimated BCF of 3.2 was calculated for 1-acetyl-2-thiourea(SRC), using an estimated log Kow of -0.27(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 1-acetyl-2-thiourea is estimated as 2.6X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-acetyl-2-thiourea is expected to be essentially nonvolatile(2). 1-Acetyl-2-thiourea is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-4 mm Hg(3).

Non-Human Toxicity ExcerptsAMONG THE 10 THIOAMIDES TESTED IN VIVO, THIOACETAMIDE & ACYLTHIOUREAS HAVING LESS THAN 10 ATOMS IN THE ACYL GROUP INCREASED ORNITHINE DECARBOXYLASE ACTIVITY IN THE LIVER OF NORMAL & ADRENALECTOMIZED RATS.
Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 1-acetyl-2-thiourea with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Acetyl-2-thiourea has experimentally measured hydrolysis rate constants of 4.7X10-9 and 4.2X10-4 L/mole-sec at pH values of 7 and 11, respectively(2); and 7.1X10-5 L/mole-sec at a pH of 9.65(3). These rate constants correspond to half-lives of 4.6 years(2), 2.7 hours(SRC) and 0.46 hours(SRC) at pH values of 7, 9.65 and 11, respectively. The aqueous hydrolysis products of 1-acetyl-2-thiourea are acetic acid and thiourea(3). 1-Acetyl-2-thiourea (in a methanol solvent) absorbs UV light in the region between 290-330 nm(4); although the absorbance is relatively weak, there may be a potential for direct photolysis in the environment(SRC).

Probable Routes of Human ExposureThere are no data available which suggest that the general population is exposed to 1-acetyl-2-thiourea. (SRC)
Environmental Fate/Exposure Summary · 1 item

1-Acetyl-2-thiourea is not manufactured or used as an end-product industrially in the US. If released to air, an estimated vapor pressure of 3.7X10-4 mm Hg at 25 °C indicates 1-acetyl-2-thiourea will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase 1-acetyl-2-thiourea will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 10 hours. 1-Acetyl-2-thiourea absorbs UV light in the environmental spectrum; although the absorbance is relatively weak, there may be a potential for direct photolysis in the environment. If released to soil, 1-acetyl-2-thiourea is expected to have very high mobility based upon an estimated Koc of 22. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.6X10-11 atm-cu m/mole. No data are available regarding biodegradation in soil. If released into water, 1-acetyl-2-thiourea is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. 1-Acetyl-2-thiourea has experimentally measured hydrolysis rate constants of 4.7X10-9, 7.1X10-5 and 4.2X10-4 L/mole-sec at pH values of 7, 9.65 and 11, respectively; these rate constants correspond to half-lives of 4.6 years, 2.7 hours and 0.46 hours, respectively. There are no data which suggests the general population is exposed to 1-acetyl-2-thiourea. (SRC)

Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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 ... . Anticipate seizures 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. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /SRP: Organic bases/amines and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. 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 TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /SRP: Organic bases/amines and related compounds/

Non-Human Toxicity Values · 2 items

LD50 Rat oral 50 mg/kg

LD50 Mouse ip 100 mg/kg

Regulatory information

RCRA Requirements · 1 item

P002; As stipulated in 40 CFR 261.33, when 1-acetyl-2-thiourea, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

TSCA Requirements · 1 item

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. Acetamide, N-(aminothioxomethyl)- is included on this list.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
YR7700000
ridadr
UN 2811 6.1/PG 2
hs_code
2930909899
risk_code
25
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T
hazard_note
Highly Toxic
safety_code
36/37/39-45
hazard_class
6.1
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H300
Hazard Classifications
Acute Tox. 2 Oral
Precautionary statements
P264-P301+P310-P280f-P309-P310
Hazardous Substances Data
591-08-2(Hazardous Substances Data)