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CAS No.: | 78-98-8 |
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Name: | Methylglyoxal |
Article Data: | 342 |
Molecular Structure: | |
Formula: | C3H4O2 |
Molecular Weight: | 72.0636 |
Synonyms: | Pyruvaldehyde(8CI);2-Ketopropionaldehyde;2-Oxopropanal;2-Oxopropionaldehyde;Acetylformaldehyde;Acetylformyl;NSC 626580;NSC 79019;Pyroracemic aldehyde;Pyruvic aldehyde;a-Ketopropionaldehyde;Methylglyoxal; |
EINECS: | 201-164-8 |
Density: | 0.994 g/cm3 |
Melting Point: | 25 ºC |
Boiling Point: | 71.999 ºC at 760 mmHg |
Flash Point: | 2.468 ºC |
Solubility: | >=10 g/100 mL at 17 ºC in water |
Appearance: | Clear yellow slightly viscous liquid with a pungent odor |
Hazard Symbols: | Xn, Xi |
Risk Codes: | 22-36 |
Safety: | 26-36 |
PSA: | 34.14000 |
LogP: | -0.22570 |
Conditions | Yield |
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With oxygen at 300℃; | A 5.79% B 92.17% C 2.04% |
Conditions | Yield |
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With iron(III) phosphate; oxygen In water at 200℃; Oxidation; | 88% |
With oxygen In methanol at 60℃; under 15001.5 Torr; for 6h; | 18% |
With copper (I) acetate |
Conditions | Yield |
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With sulfuric acid In water at 109.84℃; for 2h; Time; Reagent/catalyst; | 80% |
Conditions | Yield |
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With selenium(IV) oxide at 80℃; for 12h; | 74% |
With sodium periodate; perchloric acid In water at 60℃; Rate constant; | |
With ruthenium trichloride; sodium periodate; perchloric acid In water at 40 - 60℃; Thermodynamic data; Mechanism; ΔE(excit.), ΔH(excit.), ΔS(excit.); |
Conditions | Yield |
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With methyl nitrite; nitrogen(II) oxide at 24.84℃; under 740 Torr; Inert atmosphere; Photolysis; | 65.2% |
With ozone |
Conditions | Yield |
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With tert.-butylhydroperoxide; vanadyl(IV) sulphate pentahydrate In water; acetonitrile at 20℃; for 6h; Green chemistry; | 65% |
With air; silver contact at 390℃; | |
With bromine; potassium carbonate |
Conditions | Yield |
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at 400℃; under 0.01 Torr; for 2.77778E-06h; Kinetics; Temperature; | A 60% B 14% |
Conditions | Yield |
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In water at 400℃; | A 60% B 10% C 30% |
Conditions | Yield |
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With methyl nitrite; nitrogen(II) oxide at 24.84℃; under 740 Torr; Inert atmosphere; Photolysis; | A 11.3% B 56.8% |
D-Xylose
A
furfural
B
dihydroxyacetone
C
Glycolaldehyde
D
2-oxopropanal
Conditions | Yield |
---|---|
With SO4(2-)/12 wt percent ZrO2-Al2O3/SBA-15 In water; toluene at 160℃; for 4h; | A 52.7% B n/a C n/a D n/a |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 51 ,1991,p. 443.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 51 ,1991,p. 443.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human No Available Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 51 ,1991,p. 443.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.
The Methylglyoxal, with the CAS registry number 78-98-8, is also known as Acetylformaldehyde. It belongs to the product categories of Aldehydes; Blocks; Building Blocks; Aliphatics. Its EINECS registry number is 201-164-8. This chemical's molecular formula is C3H4O2 and molecular weight is 72.06. What's more, both its IUPAC name and systematic name are the same which is called 2-Oxopropanal. It is the aldehyde form of pyruvic acid. It has two carbonyl groups, so it is a dicarbonyl compound. In organisms, this chemical is formed as a side-product of several metabolic pathways. It may form from 3-amino acetone, which is an intermediate of threonine catabolism, as well as through lipid peroxidation. However, the most important source is glycolysis.
Physical properties about Methylglyoxalare:
(1) # of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 14.181; (5)ACD/KOC (pH 7.4): 14.181; (6)#H bond acceptors: 2; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 1; (9)Polar Surface Area: 34.14 Å2; (10)Index of Refraction: 1.364; (11)Molar Refractivity: 16.164 cm3; (12)Molar Volume: 72.494 cm3; (13)Surface Tension: 27.133 dyne/cm; (14)Density: 0.994 g/cm3; (15)Flash Point: 2.468 °C; (16)Enthalpy of Vaporization: 31.343 kJ/mol; (17)Boiling Point: 71.999 °C at 760 mmHg; (18)Vapour Pressure: 120.93 mmHg at 25 °C.
Preparation of Methylglyoxal:
Methylglyoxal can be prepared by 1-Hydroxy-propan-2-one. This reaction needs reagents O2, FePO4 and solvent H2O at temperature of 200 °C. The yield is 88 %.
Uses of Methylglyoxal:
(1) it is used as medicine, pesticide intermediates and biochemical reagents; (2) it is used to produce other chemicals. For example, it can react with Hydroxyacetaldehyde to get (4-Methyl-1(3)H-imidazol-2-yl)-methanol. The reaction occurs with reagent NH3 and solvent ethanol at temperature of 40 °C . The yield is 35 %.
Safety Information of Methylglyoxal:
When you are dealing with Methylglyoxal, you should be very careful. This chemical may cause damage to health and cause inflammation to the skin or other mucous membranes. It is irritating to eyes and it is harmful if swallowed. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: CC(=O)C=O
(2) InChI: InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3
(3) InChIKey: AIJULSRZWUXGPQ-UHFFFAOYSA-N
The toxicity data of Methylglyoxal is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 179mg/kg (179mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | intravenous | 252mg/kg (252mg/kg) | Cesko-Slovenska Farmacie. Vol. 15, Pg. 300, 1966. | |
rat | LD50 | oral | 1165mg/kg (1165mg/kg) | Ecotoxicology and Environmental Safety. Vol. 2, Pg. 369, 1978. |