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Methacrylamide

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Name

Methacrylamide

EINECS 201-202-3
CAS No. 79-39-0 Density 0.942 g/cm3
PSA 43.09000 LogP 0.74810
Solubility water: 202 g/L (20 °C) Melting Point 108 °C
Formula C4H7NO Boiling Point 211.5 °C at 760 mmHg
Molecular Weight 85.1057 Flash Point 81.7 °C
Transport Information N/A Appearance white to very slightly yellow crystals
Safety 26-36/37 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 79-39-0 (2-Methylacrylamide) Hazard Symbols HarmfulXn
Synonyms

Methacrylamide(8CI);2-Methyl-2-propenamide;2-Methylacrylamide;2-Methylpropenamide;Methacrylic acid amide;Methacrylic amide;NSC 23772;NSC 24147;

Article Data 54

Methacrylamide Synthetic route

126-98-7

methacrylonitrile

79-39-0

Methacrylamide

Conditions
ConditionsYield
With C29H46NiOP2; water In isopropyl alcohol at 80℃; for 6h; Reagent/catalyst; Sealed tube;100%
With (η6-p-cymene)RuCl2(κ1-P-PPh2OH); water In ethanol at 80℃; Inert atmosphere; Sealed tube;99%
With water; tricyclohexylphosphine; {Rh(OMe)(cod)}2 In isopropyl alcohol at 25℃; for 24h;96%
760-93-0

methacryloyl anhydride

79-39-0

Methacrylamide

Conditions
ConditionsYield
With ammonia at 0 - 5℃; for 1h; Green chemistry;85%
97-63-2

methyl methacrylate

79-39-0

Methacrylamide

Conditions
ConditionsYield
With ammonia for 288h;54%
126-98-7

methacrylonitrile

A

79-41-4

poly(methacrylic acid)

B

79-39-0

Methacrylamide

Conditions
ConditionsYield
With potassium phosphate buffer at 30℃; for 0.5h; Rhodococcus sp. AJ270 cells;A 44.5%
B 43.4%
79-41-4

poly(methacrylic acid)

79-39-0

Methacrylamide

Conditions
ConditionsYield
With diphenyl-phosphinic acid; triethylamine In THF-n-hexane; chloroform; N,N-dimethyl-formamide35%
109-75-1

but-3-enenitrile

A

541-35-5

butanamide

B

79-39-0

Methacrylamide

Conditions
ConditionsYield
Stage #1: but-3-enenitrile With rhodium(III) chloride; borane-THF In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 0℃; for 4h;
75-86-5

2-hydroxy-2-methylpropanenitrile

A

49562-37-0

2-methyl-2-sulphatopropionamide

B

13027-88-8

2-hydroxyisobutyramide

C

79-39-0

Methacrylamide

Conditions
ConditionsYield
With sulfuric acid at 85 - 101℃; for 0.666667h; Product distribution / selectivity; CSTR reactor;
With sulfuric acid; 10H-phenothiazine In acetone at 79 - 101℃; for 1.83333h; Product distribution / selectivity; Continuous process;

copper(II) nitrate

126-98-7

methacrylonitrile

79-39-0

Methacrylamide

Conditions
ConditionsYield
With nitric acid In water
110-20-3

acetone semicarbazone

A

79-39-0

Methacrylamide

B

2-imino-5,5-dimethyl-Δ3-1,3,4-oxadiazoline

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate at 20℃; for 0.333333h;
96-96-8

4-methoxy-2-nitroaniline

A

hydrogen azide

B

565-69-5

ethyl isopropyl ketone

C

589-38-8

n-hexan-3-one

D

28446-58-4

but-3-enamide

E

1789-46-4

(2E,4Z)-3-methoxyhexa-2,4-dienedinitrile

F

64-19-7

acetic acid

G

372-09-8

cyanoacetic acid

H

79-06-1

2-propenamide

I

79-39-0

Methacrylamide

J

627-48-5

ethyl cyanate

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; dihydrogen peroxide at 25℃; for 0.0833333h; pH=6.12; Kinetics; pH-value;

Methacrylamide Consensus Reports

Reported in EPA TSCA Inventory.

Methacrylamide Specification

The Methacrylic acid amide is an organic compound with the formula C4H7NO. The IUPAC name of this chemical is 2-methylprop-2-enamide. With the CAS registry number 79-39-0, it is also named as 2-propenamide, 2-methyl-. The product's categories are Acrylamide and Methacrylamide; Acrylic Monomers; Monomers; Amides; Carbonyl Compounds; Organic Building Blocks. Besides, it is a white to very slightly yellow crystal, which should be stored in a dark and cool place. It is the intermediate of methyl methacrylate.

Physical properties about Methacrylic acid amide are: (1)ACD/LogP: -0.23; (2)ACD/LogD (pH 5.5): -0.23; (3)ACD/LogD (pH 7.4): -0.23; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 17.91; (7)ACD/KOC (pH 7.4): 17.91; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 20.31 Å2; (12)Index of Refraction: 1.438; (13)Molar Refractivity: 23.71 cm3; (14)Molar Volume: 90.2 cm3; (15)Polarizability: 9.4×10-24cm3; (16)Surface Tension: 29.6 dyne/cm; (17)Density: 0.942 g/cm3; (18)Flash Point: 81.7 °C; (19)Enthalpy of Vaporization: 44.78 kJ/mol; (20)Boiling Point: 211.5 °C at 760 mmHg; (21)Vapour Pressure: 0.182 mmHg at 25°C.

Uses of Methacrylic acid amide: it can be used to produce N-(2-methyl-acryloyl)-3-oxo-butyramide at temperature of 50 °C. It will need reagent chlorotrimethylsilane, lithium bromide and solvent acetonitrile with reaction time of 3 hours. The yield is about 82%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(\C(=C)C)N
(2)InChI: InChI=1/C4H7NO/c1-3(2)4(5)6/h1H2,2H3,(H2,5,6)
(3)InChIKey: FQPSGWSUVKBHSU-UHFFFAOYAG
(4)Std. InChI: InChI=1S/C4H7NO/c1-3(2)4(5)6/h1H2,2H3,(H2,5,6)
(5)Std. InChIKey: FQPSGWSUVKBHSU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TCLo inhalation 3mg/m3 (3mg/m3) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 74, 1980.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 451mg/kg (451mg/kg)   Archives of Toxicology. Vol. 47, Pg. 179, 1981.
mouse LD50 skin > 6gm/kg (6000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 74, 1980.
rat LD50 oral 459mg/kg (459mg/kg) BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 74, 1980.
rat LD50 skin > 6gm/kg (6000mg/kg)   Gigiena i Sanitariya. For English translation

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