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Methacrylamide

HCID 6595
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
79-39-0
Standard SMILES
C=C(C)C(N)=O
InChIKey
FQPSGWSUVKBHSU-UHFFFAOYSA-N
Molecular formula
C4H7NO
Average molar mass
85.1 g/mol
Monoisotopic mass
85.05276384

Overview

Methacrylamide is a primary carboxamide and a member of acrylamides.

Names & identifiers

Preferred name
Methacrylamide
IUPAC
2-methylprop-2-enamide
English name
Methacrylamide
Molecular formula
C4H7NO
Molecular weight
85.1

Names & synonyms

METHACRYLAMIDE79-39-02-Methylacrylamide2-methylprop-2-enamideMethacrylic amideMethacrylic acid amide2-Methylpropenamide2-Propenamide, 2-methyl-Methylacrylic amideMhoromer BM801alpha-Methyl acrylic amideAmid kyseliny methakrylove
Show more names
Methylacrylamide2-methyl-2-Propenamideusafrh-1USAF rh-1mhoromerbm801
DTXSID8029600CHEBI:51759K67NG89J77NSC-23772DTXCID109600RefChem:156839201-202-3Methacryamide

Database identifiers

CAS
79-39-0
PubChem CID
6595
DTXSID
DTXSID8029600
ChEMBL
CHEMBL158237
ChEBI
CHEBI:51759
UNII
K67NG89J77
EC Number
201-202-3
Nikkaji
J38.885H

Properties

Computed structural propertiesFilling in

XLogP
0.1
Topological polar surface area
43.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
6
Formal charge
0
Complexity
85.5

Experimental & physicochemical properties

Chemical ClassesIndustrial compound
PolymersPlastics & Rubber -> Other Monomers
SpringerMaterials PropertiesBoiling point
Boiling Point215 °C @760 [mm Hg]
Vapor Pressure0.1 [mmHg]
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionWhite crystalline solid; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
106 · 106-110 °C (lit.)
Boiling point
215 °C · 215 °C
Density
1 · 1,115 g/cm3

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 · 6 items

This chemical does not meet GHS hazard criteria for 0.9% (7 of 803) of reports.

Warning

H302 (99.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P304+P340, P305+P351+P338, P308+P316, P319, P330, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 803 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Regulatory Information · 3 items

Chemical: 2-Propenamide, 2-methyl-

Status: Active Update: 14-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15801

Methacrylamide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - 2-Propenamide, 2-methyl- (methacrylamide)
Hazards Summary · 1 item

An eye irritant in rabbits; No to mild skin sensitization reactions seen in guinea pigs; Neurotoxicity observed in repeated-dose animal studies; [IUCLID] Marked developmental toxicity observed in mice at doses only slightly maternally toxic; [NTP] An irritant; Moderately toxic by ingestion and inhalation (degenerative changes of the liver, kidney, and brain); Reproductive effects observed in experimental animals; [Alfa Aesar MSDS] See Acrylamide.

Hazard Classes and Categories · 2 items

Acute Tox. 4 (99.1%)

Acute toxicity (Oral) - Category 4

Safety & protection

Chemistry & industry

Uses & manufacturing

Uses · 2 items

A congener of acrylamide; [NTP] Used in the chemical, leather processing, paper-pulp-board, polymers, textile processing, and paints-lacquers-varnishes industries; Used as an adhesive, binding agent, corrosion inhibitor, and intermediate; [IUCLID]

Pulp and Paper Processing [Category: Industry]

General Manufacturing Information2-Propenamide, 2-methyl-: ACTIVE
Applications · 2 items

UsesA monomer for acrylic resins.

UsesMethacrylamide is a reagent used in the production of polymers and copolymers. It is also used as a raw material in the production of chemicals for industrial and professional use such as textiles, leather, fur, bulk, large scale chemicals (including petroleum products), fine chemicals, formulation [mixing] of preparations and/or re-packaging (excluding alloys), building and construction work, electricity, steam, gas, water supply and sewage treatment.

Upstream & downstream products

Upstream raw materials

Acetone cyanohydrinmethacrylammonium hydrogen sulphateSodium cyanideHydrogen cyanideMethacrylic acidACETONE SEMICARBAZONEMethacrylonitrileMethacrylic anhydride

Related reactions

58 records
New reaction record
HRID 111348 reaction equation
HRID 111348As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 196719 reaction equation
HRID 196719As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 255905 reaction equation
HRID 255905As reactantuspto-grants-1987_10
HRID 412836 reaction equation
HRID 412836As reactantuspto-grants-2003_05
HRID 495317 reaction equation
HRID 495317As productuspto-grants-2005_09
HRID 622228 reaction equation
HRID 622228As reactantuspto-grants-1988_09
HRID 750430 reaction equation
HRID 750430As productuspto-grants-2008_07
HRID 805191 reaction equation
HRID 805191As reactantTest data from https://doi.org/10.1039/C8SC04228D
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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bulk density
550 kg/m3 · 550kg/m3
vapor pressure
0.0015 hPa · 0.0015 hPa (20 °C)
refractive index
1.3992 · 1.3992 (estimate)
Flash point
215 °C · 215°C
storage temp.
30 °C · Store below +30°C.
solubility
202 g/l · 202g/l
form
Crystals
pka
15.46 · 15.46±0.50(Predicted)
color
White to very slightly yellow
PH
7.1 · 7.1 (100g/l, H2O, 20℃)
explosive limit
2 · 2-15%(V)
Water Solubility
202 g/L · 202 g/L (20 ºC)
BRN
605397 · 605397
Henry's Law Constant
8.8 · 8.8×103 mol/(m3Pa) at 25℃, Ebert et al. (2023)
InChI
1S/C4H7NO/c1-3(2)4(5)6/h1H2,2H3,(H2,5,6)
InChIKey
FQPSGWSUVKBHSU-UHFFFAOYSA-N
SMILES
CC(=C)C(N)=O
CAS DataBase Reference
79 · 79-39-0(CAS DataBase Reference)
Indirect Additives used in Food Contact Substances
METHACRYLAMIDE
FDA 21 CFR
177.101 · 177.1010; 177.1630
EWG's Food Scores
1 · 1
FDA UNII
67 NG89J77 · K67NG89J77
NIST Chemistry Reference
Methacrylamide(79-39-0)
EPA Substance Registry System
Methacrylamide (79-39-0)
UNSPSC Code
12352111 · 12352111
NACRES
23 · NA.23
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
302 · H302-H319-H335-H371-H373
Precautionary statements
260 · P260-P264-P270-P301+P312-P305+P351+P338-P308+P311
target organs
Respiratory system
Hazard Codes
Xn
Risk Statements
22 · 22-36/37/38
Safety Statements
26 · 26-36/37
RIDADR
3263 · 3263
WGK Germany
1 · 1
RTECS
6475000 · UC6475000
Autoignition Temperature
510 °C · 510 °C
TSCA
TSCA listed
HS Code
2924 · 2924 19 00
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Irrit. 2STOT RE 2STOT SE 2STOT SE 3
Toxicity
50 orally · LD50 orally in Rabbit: 1815 mg/kg LD50 dermal Rat > 5000 mg/kg
REACH Registrations
Active
Protective Action Criteria (PAC) · 3 items

3.0 [mg/m3]

15 [mg/m3]

91 [mg/m3]

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Safety data

wgk
1
tsca
TSCA listed
rtecs
UC6475000
ridadr
3263
hs_code
2924 19 00
Toxicity
LD50 orally in Rabbit: 1815 mg/kg LD50 dermal Rat > 5000 mg/kg
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn
safety_code
26-36/37
hazard_class
6.1(b)
Storage Class
11 - Combustible Solids
packing_group
III
target organs
Respiratory system
Hazard statements
H302-H319-H335-H371-H373
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2STOT RE 2STOT SE 2STOT SE 3
Autoignition Temperature
510 °C
Precautionary statements
P260-P264-P270-P301+P312-P305+P351+P338-P308+P311
N-Phenyl-1-naphthylamine
Methacryloyl chloride
Ammonium hydroxide

Downstream products

methylene polyacrylamideEthyl methacrylate2-methyl-2-(sulphooxy)propionamideButyramide4-Amino-2,6-dimethylpyrimidine2-chloro-2-methylpropiononitrileN-N-Butoxymethyl methacrylamide

Additional notes

DefinitionChEBI: Methacrylamide is a member of acrylamides and a primary carboxamide.