CAS 110-26-9 Methylenebisacrylamide (HCID 8041)

名称と識別子

優先名称: Methylenebisacrylamide
IUPAC: N-[(prop-2-enoylamino)methyl]prop-2-enamide
現地名: N,N'-メチレンビスアクリルアミド
英語名: N,N'-Methylenebisacrylamide
分子式: C7H10N2O2
分子量: 154.17

名称と別名

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

名称をさらに表示

N,N'-メチレンビスアクリルアミドN,N'-メチレンジアクリルアミドN,N'-メチレンビスプロペンアミドメチレンビスアクリルアミドN,N'-メチレンビス(アクリルアミド)N,N'-メチレンビス(プロペンアミド)1,1'-[メチレンビス(イミノカルボニル)]ビスエテンN,N'-(メチレン)ビス(プロペンアミド)N,N'-メチレンビス(2-プロペンアミド)Ｎ，Ｎ’－メチレンビスアクリルアミドN，N’メチレンビス（アクリルアミド）N,N′-メチレンジアクリルアミドN,N′-メチレンジアクリルアミドHGXN,N′-メチレンビスアクリルアミドN,N′-メチレンビスアクリルアミドHGXＮ，ＮVメチレンビスアクリルアミドN,N´-メチレンビスアクリルアミドN,N′‐メチレンビスアクリルアミドN,N′‐メチレンビスアクリルアミドHGXN,N-メチレンビスアクリルアミド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

データベース識別子

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

物性

構造計算による物性

XLogP: 0.1
極性表面積: 58.2 Å²
水素結合供与体数: 2
水素結合受容体数: 2
回転可能結合数: 4
重原子数: 11
形式電荷: 0
複雑度: 167

実験および物理化学的性質

Density · 2 件

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 件

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]

物理化学的性質

融点: 300 °C · >300 °C(lit.)
沸点: 277.52 °C · 277.52°C (rough estimate)
比重(密度): 1.235 · 1.235
蒸気密度: 5.31 · 5.31 (vs air)
蒸気圧: 0 · 0-0.073Pa at 20-84.85℃
屈折率: 1.488 · 1.4880 (estimate)
貯蔵温度: 2 · 2-8°C
溶解性: 2 O: · H2O: 20mg/mL at20℃ 無色透明
外見: 粉
酸解離定数(Pka): 13.07 · 13.07±0.46(Predicted)
色: 白い
臭い (Odor): 無臭
PH: 5 · >=5.0 (25g/l, H2O, 20℃)
水溶解度: 18 ℃で0.01～0.1g/100mL · 18℃で0.01～0.1g/100mL
BRN: 1706297 · 1706297
安定性: 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
表面張力: 70.2 · 70.2-70.3mN/m at 1g/L and 20℃
CAS データベース: 110 · 110-26-9(CAS DataBase Reference)
NISTの化学物質情報: 2 · 2-Propenamide, n,n'-methylenebis-(110-26-9)
EPAの化学物質情報: N,N'-Methylenebisacrylamide (110-26-9)
Absorption: 0.2 at · ≤0.2 at 290 at 1%

化学的性質

化学的特性white crystalline powder

安全と法規制

GHS分類

GHS Classification · 6 件

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

危険有害性情報

Regulatory Information · 5 件

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 件

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 件

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

安全と保護具

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 件

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 件

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 件

1.2 [mg/m3]

13 [mg/m3]

77 [mg/m3]

Personal Protective Equipment (PPE) · 1 件

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)

毒性情報

Toxicity DataLC (rat) > 41 ppm/6hr

法規制情報

Regulatory Information · 5 件

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

安全データ

F: 8
wgk: 2
tsca: TSCA listed
rtecs: AS3678000
ridadr: UN 2811
毒性: LD50 orally in Rabbit: 390 mg/kg
hs_code: 29241900
risk_code: 20/22-20/21/22-36/37/38
化審法: (2)-1020
安衛法: 変異原性物質
hazard_code: Xn,Xi
safety_code: 22-36/37-36-26
hazard_class: 6.1(b)
packing_group: III
Hazard Classifications: Acute Tox. 3 OralAcute Tox. 4 DermalCarc. 1BMuta. 1BRepr. 2STOT RE 1 Oral
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

用途と製造

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 件

All Other Basic Organic Chemical Manufacturing

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

応用分野 · 3 件

用途電気泳動用ポリアクリルアミドゲルの作成添加剤。

使用N,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.

一般的な説明White crystalline powder with a neutral odor.

調製方法 · 1 件

純化方法Recrystallise the amide from MeOH (100g dissolved in 500mL boiling MeOH) and filter without suction in a warmed funnel. Allow to stand at room temperature and then at -15oC overnight. The crystals are collected with suction in a cooled funnel and washed with cold MeOH. The crystals are air-dried in a warm oven. [Beilstein 2 IV 1472.] VERY TOXIC (neurotoxic).