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Methacrolein
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Name

Methacrolein

 EINECS 201-150-1
CAS No. 78-85-3 Density 0.807 g/cm3
PSA 17.07000 LogP 0.76140
Solubility Water: 6 g/100 mL (20 °C) Melting Point -81 °C
Formula C4H6O Boiling Point 68 °C at 760 mmHg
Molecular Weight 70.091 Flash Point -15 °C
Transport Information UN 2396 3/PG 2 Appearance Colourless to light yellow liquid
Safety 16-26-36/37/39-45-28A Risk Codes 11-24/25-34-26
Molecular Structure Molecular Structure of 78-85-3 (2-Methylacrolein) Hazard Symbols FlammableF,ToxicT
Synonyms

Methacrylaldehyde(8CI);2-Formyl-1-propene;2-Methacrolein;2-Methyl-2-propen-1-al;2-Methyl-2-propenal;2-Methylacrolein;2-Methylenepropanal;2-Methylpropenal;Isobutenal;Methacrylic aldehyde;NSC 8260;a-Methylacrolein;a-Methylacrylaldehyde;

Article Data 266

Methacrolein Synthetic route

50-00-0

formaldehyd

123-38-6

propionaldehyde

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With acetic acid; dimethyl amine at 170 - 180℃; under 52505.3 Torr; for 0.00277778h; Flow reactor;98.1%
With secondary amine salt In water at 15 - 44℃; for 1h;96.6%
With L-proline In water at 42.84℃; for 0.5h; Kinetics; Mechanism; Reagent/catalyst; Temperature; Green chemistry;91.1%
513-42-8

3-hydroxy-2-methyl-1-propene

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With aluminum oxide; pyridinium chlorochromate In hexane for 0.2h; Ambient temperature;98%
With manganese(IV) oxide In diethyl ether Oxidation;76%
at 500℃; beim Leiten ueber Messing;
79-41-4

poly(methacrylic acid)

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h;94%
75-65-0

tert-butyl alcohol

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With oxygen In water at 350℃; under 750.075 Torr;91.1%
With air; cobalt molybdenum at 319.9 - 379.9℃; Rate constant; Product distribution;88.1%
With silicsa-alumina supported Mo12Bi1.7Fe2.0Co6.75Ni1.0Cs0.2Ox In water at 345℃; for 200h; Temperature; Inert atmosphere;81.07%
5658-46-8

((2-methylallyloxy)methyl)benzene

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With water; iodine In 1,4-dioxane for 24h; Reflux;91%
115-11-7

isobutene

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With oxygen; Bi-Mo oxide (1/1) at 400℃; Rate constant; Kinetics; also without O2; other temperature;90%
With oxygen; Mo-Bi-Fe-Co-Ni-K based mixed metal oxide In water at 340 - 360℃; under 760.051 Torr; for 100h;89.9%
With Mo12Bi0.5Fe2.4Co7.2Zn1.1Sb0.7Si7W0.3K0.5O(x); water; oxygen at 340℃; for 0.001h; Sealed tube; Inert atmosphere;88.8%
106-98-9

1-butylene

115-11-7

isobutene

A

78-85-3

2-methylpropenal

B

106-99-0

buta-1,3-diene

Conditions
ConditionsYield
With nitrogen; Mo12Co5.7Fe3.8Bi0.5Ce0.1Tl0.3Sb0.5O49.1; water; oxygen at 380℃; for 10005h; Reagent/catalyst;A 65%
B 89%
115-11-7

isobutene

A

78-85-3

2-methylpropenal

B

124-38-9

carbon dioxide

C

201230-82-2

carbon monoxide

Conditions
ConditionsYield
With air; pelleted Fe-Te-Mo-O at 430℃; Yields of byproduct given;A 83.8%
B n/a
C n/a
With air; pelleted Fe-Te-Mo-O at 430℃; Product distribution; further temperatures: 370, 400 deg C; effect of various catalyst supports investigated;A 83.8%
B n/a
C n/a
With oxygen multicomponent oxide catalyst(Co, Mo, Bi, Sb, Fe, K);
78-84-2

isobutyraldehyde

78-85-3

2-methylpropenal

Conditions
ConditionsYield
With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; 3-amino propanoic acid In acetonitrile at 60℃; for 24h; Sealed tube;82%
With oxygen; C4H8N3O2Pb(1+)*CF3O3S(1-) In various solvent(s) under 760 Torr; Ambient temperature; Yield given;
at 400℃; Dehydrierung an einem Cu-Cr-Zn-Cd-Oxydkatalysator;
75-65-0

tert-butyl alcohol

A

78-85-3

2-methylpropenal

B

79-41-4

poly(methacrylic acid)

C

115-11-7

isobutene

Conditions
ConditionsYield
With oxygen; silica-alumina In water at 355℃; Product distribution / selectivity;A 78.4%
B 1.9%
C 1.1%
With oxygen; silica-alumina In water at 355℃; Product distribution / selectivity;A 78.1%
B 2.2%
C 1%
With oxygen; 5% Pd/zirconia In water at 130℃; under 36003.6 Torr; Product distribution / selectivity; autoclave;
With oxygen; palladium on silica gel In water at 130℃; under 36003.6 Torr; Product distribution / selectivity; autoclave;

Methacrolein Consensus Reports

Reported in EPA TSCA Inventory.

Methacrolein Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid, Poison

Methacrolein Specification

The Methylacrylaldehyde with CAS registry number of 78-85-3 is also known as 2-Methyl-2-propen-1-al. The IUPAC name is 2-Methylprop-2-enal. Its EINECS registry number is 201-150-1. In addition, the formula is C4H6O and the molecular weight is 70.09. This chemical is a colourless to light yellow liquid and should be sealed in dry and cool place.

Physical properties about Methylacrylaldehyde are: (1)ACD/LogP: 0.54; (2)ACD/LogD (pH 5.5): 0.54; (3)ACD/LogD (pH 7.4): 0.54; (4)ACD/BCF (pH 5.5): 1.52; (5)ACD/BCF (pH 7.4): 1.52; (6)ACD/KOC (pH 5.5): 46.99; (7)ACD/KOC (pH 7.4): 46.99; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.384; (11)Molar Refractivity: 20.33 cm3; (12)Molar Volume: 86.7 cm3; (13)Surface Tension: 20.8 dyne/cm; (14)Density: 0.807 g/cm3; (15)Enthalpy of Vaporization: 30.98 kJ/mol; (16)Boiling Point: 68 °C at 760 mmHg; (17)Vapour Pressure: 142 mmHg at 25 °C.

Preparation of Methylacrylaldehyde: it is prepared by reaction of at least one of isobutylene and tert-butyl alcohol. The gas containing molecular oxygen is oxidated in presence of oxidation catalyst Mo12BiaCebKcFedAeBfOg.

Uses of Methylacrylaldehyde: it is used for the manufacture of copolymers and resins, and also is the raw material of methylmalonic acid and thermoplastic fuel. It is used to produce 2,3-dibromo-2-methyl-propionaldehyde. The reaction occurs with reagent bromine at 50 °C for 2 hours. The yield is about 60%.

Methylacrylaldehyde is used to produce 2,3-dibromo-2-methyl-propionaldehyde.

When you are using this chemical, please be cautious about it. As a chemical, it is toxic in contact with skin and if swallowed and very toxic by inhalation. What's more, it is highly flammable that can cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition. If accident happens or you feel unwell seek medical advice immediately. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=C)C=O
2. InChI: InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
3. InChIKey: STNJBCKSHOAVAJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin 430uL/kg (0.43mL/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 60, 1949.
rat LCLo inhalation 125ppm/4H (125ppm)   Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 343, 1949.
rat LD50 oral 140mg/kg (140mg/kg)   Union Carbide Data Sheet. Vol. 7/21/1965,

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