CAS 110-26-9 Methylenebisacrylamide (HCID 8041)

Names & identifiers

Preferred name: Methylenebisacrylamide
IUPAC: N-[(prop-2-enoylamino)methyl]prop-2-enamide
English name: N,N'-Methylenebisacrylamide
Molecular formula: C7H10N2O2
Molecular weight: 154.17

Names & synonyms

N,N'-METHYLENEBISACRYLAMIDE110-26-9MethylenebisacrylamideMethylenediacrylamideN,N'-Methylenebis(acrylamide)2-Propenamide, N,N'-methylenebis-N,N'-MethylidenebisacrylamideAcrylamide, N,N'-methylenebis-N,N'-Methylenebis(2-propenamide)DTXSID8025595EDK4RIE19CDTXCID205595

Show more names

MBABISBISACRYLAMIDEN, N-METHYLENE-BIS-ACRYLAMIDEnappN,N-MethylenebisaMFM6

N,N'-Methylenebis[acrylamide]RefChem:161037n,n'-methylene-bis(acrylamide)2-propenamide, N,N'-methyl-enebisN,N'-METHYLENEBIS-2-PROPENAMIDEmethylene bisacrylamideN,N'-Methylenediacrylamiden,n-methylenebisacrylamide

Database identifiers

CAS: 110-26-9
PubChem CID: 8041
DTXSID: DTXSID8025595
ChEMBL: CHEMBL1401480
UNII: EDK4RIE19C
EC Number: 203-750-9
Nikkaji: J33.815J

Properties

Computed structural properties

XLogP: 0.1
Topological polar surface area: 58.2 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 4
Heavy atoms: 11
Formal charge: 0
Complexity: 167

Experimental & physicochemical properties

Density · 2 items

1.235 at 86 °F (NTP, 1992) - Denser than water; will sink

1.235 @ 30°C

Solubility0.1 to 1 mg/mL at 64 °F (NTP, 1992)

Melting Point365 °F (with decomposition) (NTP, 1992)

Vapor Density5.31 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Physical Description · 3 items

N,n'-methylenebisacrylamide is a white crystalline powder with a neutral odor. (NTP, 1992)

Dry Powder

White solid; [CAMEO]

Collision Cross Section138.1 Å² [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8025595]

Physicochemical properties

Melting point: 300 °C · >300 °C(lit.)
Boiling point: 277.52 °C · 277.52°C (rough estimate)
Density: 1.235 · 1.235
bulk density: 200 kg/m3 · 200kg/m3
vapor density: 5.31 · 5.31 (vs air)
vapor pressure: 0 · 0-0.073Pa at 20-84.85℃
refractive index: 1.488 · 1.4880 (estimate)
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: 20 mg/mL at 20 °C, clear, colorless
form: powder
pka: 13.07 · 13.07±0.46(Predicted)
color: White
Odor: Odorless
PH Range: 5 · >5
PH: 5 · >=5.0 (25g/l, H2O, 20℃)
Water Solubility: 0.01 · 0.01-0.1 g/100 mL at 18 ºC
λmax: 528 nm · 528nm(H2O)(lit.)
Sensitive: Air & Light Sensitive
BRN: 1706297 · 1706297
Stability: Light Sensitive
InChI: 1S/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11)
InChIKey: ZIUHHBKFKCYYJD-UHFFFAOYSA-N
SMILES: C=CC(=O)NCNC(=O)C=C
LogP: -1.52 · -1.52--0.08 at 24-25℃ and pH4-10
Surface tension: 70.2 · 70.2-70.3mN/m at 1g/L and 20℃
Indirect Additives used in Food Contact Substances: N,N'-METHYLENEBIS(ACRYLAMIDE)
FDA 21 CFR: 175.105 · 175.105
CAS DataBase Reference: 110 · 110-26-9(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 4 RIE19C · EDK4RIE19C
NIST Chemistry Reference: 2 · 2-Propenamide, n,n'-methylenebis-(110-26-9)
EPA Substance Registry System: N,N'-Methylenebisacrylamide (110-26-9)
Absorption: 0.2 at · ≤0.2 at 290 at 1%
UNSPSC Code: 41105319 · 41105319
NACRES: 1 · NC.01
Symbol(GHS): 6 · GHS06,GHS08
Signal word: Danger
Hazard statements: 301 · H301-H340
Precautionary statements: 202 · P202-P264-P270-P280-P301+P310-P405
target organs: Peripheral nervous system
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes: Xn,Xi
Risk Statements: 20 · 20/22-20/21/22-36/37/38
Safety Statements: 22 · 22-36/37-36-26
RIDADR: 2811 · UN 2811
WGK Germany: 2 · 2
RTECS: 3678000 · AS3678000
F: 8 · 8
TSCA: TSCA listed
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
HS Code: 29241900 · 29241900
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 OralAcute · Acute Tox. 3 OralAcute Tox. 4 DermalCarc. 1BMuta. 1BRepr. 2STOT RE 1 Oral
Toxicity: 50 orally · LD50 orally in Rabbit: 390 mg/kg
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H340: May cause genetic defects [Danger Germ cell mutagenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Danger

Hazard information

Regulatory Information · 5 items

Chemical: 2-Propenamide, N,N'-methylenebis-

Hazard Traits - Genotoxicity；Authoritative List - EC Annex VI CMRs - Cat. 1B；Report - if used as a fragrance or flavor ingredient

2-Propenamide, N,N'-methylenebis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N,N'-methylenebis- 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: 10-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21036

2-Propenamide, N,N'-methylenebis: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - 2-Propenamide, N,N'-methylenebis- (N,N'-methylenebisacrylamide)

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

Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this type of compound may include irritation and redness of the skin, irritation of the eyes, drowsiness, tingling sensation, fatigue, weakness, stumbling, slurred speech and shaking. Chronic exposure to this type of compound may lead to muscular weakness, incoordination, skin rashes, excessive sweating of the hands and feet, cold hands and peeling of the skin.；ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It may be harmful by inhalation or skin absorption. Solutions may be absorbed through the 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. (NTP, 1992)

Hazards Summary · 1 item

May cause skin and eye irritation and symptoms indicative of nervous system effects; [NTP] May cause irritation; Harmful by ingestion and inhalation; May cause reproductive disorders, based on animal studies; [Sigma-Aldrich MSDS] See Acrylamide.

Reactive GroupAmides and Imides；Hydrocarbons, Aliphatic Unsaturated

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (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.；SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.；INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.；INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.；STORAGE PRECAUTIONS: You should store this material under ambient temperatures away from oxidizers, acids and bases. (NTP, 1992)

Protective Action Criteria (PAC) · 3 items

1.2 [mg/m3]

13 [mg/m3]

77 [mg/m3]

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 an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Toxicity DataLC (rat) > 41 ppm/6hr

Regulatory information

Regulatory Information · 5 items

Chemical: 2-Propenamide, N,N'-methylenebis-

Hazard Traits - Genotoxicity；Authoritative List - EC Annex VI CMRs - Cat. 1B；Report - if used as a fragrance or flavor ingredient

2-Propenamide, N,N'-methylenebis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N,N'-methylenebis- 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: 10-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21036

2-Propenamide, N,N'-methylenebis: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F: 8
PPE: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk: 2
tsca: TSCA listed
rtecs: AS3678000
ridadr: UN 2811
hs_code: 29241900
Toxicity: LD50 orally in Rabbit: 390 mg/kg
risk_code: 20/22-20/21/22-36/37/38
Signal word: Danger
Symbol(GHS): GHS06,GHS08
hazard_code: Xn,Xi
safety_code: 22-36/37-36-26
hazard_class: 6.1(b)
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group: III
target organs: Peripheral nervous system
Hazard statements: H301-H340
REACH Registrations: Active
Hazard Classifications: Acute Tox. 3 OralAcute Tox. 4 DermalCarc. 1BMuta. 1BRepr. 2STOT RE 1 Oral
Precautionary statements: P202-P264-P270-P280-P301+P310-P405

Chemistry & industry

Uses & manufacturing

UsesUsed as an organic intermediate, cross-linking agent, for making polyacrylamides, and for preparing polyacrylamide gel for electrophoresis, chemical grouting, and other uses; [NTP]

U.S. Production2023: <50,000 lb；2021: 50,000 - <250,000 lb；2020: <50,000 lb

Industry UsesMonomers

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

2-Propenamide, N,N'-methylenebis-: ACTIVE

Applications · 4 items

UsesOrganic intermediate, cross-linking agent.

UsesN,N-Methylene-bis-acrylamide is an organic intermediate; cross-linking agent for preparation of polyacrylamides; in preparing poly-acrylamide gel for e1ectrophoresis, chemical grouting and other purposes; in NAPP and Nyloprint UV-cured printing plates.

UsesN,N'-Methylenebisacrylamide is used in the preparation of polyacrylamide gels for electrophoretic separation of nucleic acids and proteins. It has also been used as a test compound for studying the biochemical isolation of insoluble Tau in transgenic mouse models of tauopathy by examining the two main isolation methods sarkosyl and formic acid extraction.

General DescriptionWhite crystalline powder with a neutral odor.

Preparation methods · 1 item

PreparationA method for preparing N,N'-Methylenebisacrylamide, the steps of which are as follows: (1). Add 245 kg of water to a reaction vessel, start stirring, and heat to 70°C; (2). Then add 75 kg of acrylamide and 105 kg of formaldehyde, and simultaneously add the polymerization inhibitor p-hydroxyanisole at a dosage of 100-500 ppm. Stir at 40°C for 1 hour to allow the reaction to proceed fully; (3). Then add 75 kg of acrylamide and 45 kg of hydrochloric acid catalyst. Heat to 70°C with stirring and react for 2 hours. Cool and stand for 48 hours; (4). Filter out the product and dry at 80°C to obtain the N,N'-Methylenebisacrylamide product.