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CAS Number: 95-71-6
EC Number : 202-443-7
PubChem CID : 7253
Molecular Formula : C7H8O2
Molecular Weight : 124.14
Methylhydroquinone is used as a stabilizer in acrylics and as an antioxidant for fatty esters, linseed oil and other inedible fats and oils.
Further research may identify additional product or industrial usages of this chemical.
Methylhydroquinone is a natural product found in Hydropisphaera erubescens, Pyrola rotundifolia, and other organisms with data available.
Toluquinol is a member of the class of hydroquinones that is hydroquinone in which one of the benzene hydrogens has been replaced by a methyl group.
Methylhydroquinone has a role as an angiogenesis inhibitor, an anti-inflammatory agent and a Penicillium metabolite.
Application of Methylhydroquinone
Methylhydroquinone can be used as a reactant to prepare:
-A semiflexible thermotropic polyester via polycondensation reaction with 4,4′-sebacoyldioxydibenzoyl chloride.
-A sesquiterpene (±)-helibisabonol A.
-poly{hexakis[(methyl)(4-hydroxyphenoxy)]cyclotriphosphazene} by reacting with hexachlorocyclotriphosphazene.
-6-Hydroxy-4,7-dimethyl-2H-1-benzopyran-2-one by treating with ethyl acetoacetate in the presence of H2SO4 as a catalyst.
Methylhydroquinone (MeHQ) or methyl ether derivative thereof is prepared by contacting paramethoxyphenol or para-dimethoxybenzene with an acid catalyst, preferably a solid acid catalyst, at a temperature ranging from 100° to 300° C.
Methylhydroquinone is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway.
Allows for screening of novel inhibitors of angiogenesis.
Application Area of Methylhydroquinone
Methylhydroquinone is used as a stabilizer for unsaturated polyesters and as an antioxidant for fatty esters, linseed oil, and other nonfood fats and oils
Methylhydroquinone is used as a stabilizer to inhibit peroxide formation in ethers, chlorinated hydrocarbons and ethyl cellulose
Methylhydroquinone is also used as an intermediate to manufacture other stabilizers, dyes, pharmaceuticals and plasticizers
Methylhydroquinone is a reactive oxygen species (ROS) that can bind to DNA, forming covalent adducts.
It has been shown to have an optimum concentration of 10 μM, and the hydroxyl group on its phenolic ring enables it to form hydrogen bonding interactions with nucleic acids.
Methylhydroquinone has been shown to inhibit angiogenic process in vitro and in vivo, as well as inhibiting the growth of tumor cells by binding to DNA.
This compound also inhibits the transfer of methyl groups from methyl donors such as S-adenosylhomocysteine and methionine to acceptor molecules such as p-hydroxybenzoic acid.
Methylhydroquinone is a versatile compound.
Methylhydroquinone finds many applications in the field of polymer science due to its good binding properties as well as its strength.
Methylhydroquinone is an off-white crystalline solid with a molecular weight of 124.137 g/mol.
Methylhydroquinone has a characteristic odor and its melting point is 262.4°F.
Synthesis of Methylhydroquinone
The easiest way to prepare methylhydroquinone is by the reaction of 2-methylphenol and potassium persulfate in equimolar quantities.
This method is called Elbs persulfate oxidation.
Mechanism
-The mechanism of the synthesis of Methylhydroquinone can be understood better with the resonance structure.
-The OH group from water abstracts a proton from the hydroxy group of the 2-methylphenol.
-Subsequent electron rearrangement takes place, as shown and 2-methylphenol changes to its quinonoid form
-The negative charge on the quinonoid form attacks the electron-deficient oxygen on the potassium persulphate to form , which on subsequent changes gives rise to.
-gets protonated to form .
-The oxygen atom of another water molecule now attacks the Sulphur atom present in the molecule to give
-Finally, the sulfate group is released to form methylhydroxyquinone.
Applications of Methylhydroquinone
Methylhydroquinone has the following applications.
-It is used as a general adhesive and binding agent in various preparations.
-In the automotive industry, methylhydroquinone is widely used for repair as well as maintenance and also caring for automobiles viz, auto shampoo, wax, polish, brake grease.
-Binders are the main ingredient of any paint. Binders are polymers that form a continuous film on a solid surface. Binders ensure that the coating is evenly spread and well adsorbed on to the surface. The binders also have the major role of holing the pigment molecules responsible for color evenly across the coating. Methylhydroquinone is one of the most widely used a binder for paints.
-The technology of thermal insulation of buildings is one of the many steps that men have taken for a sustainable future. Thermal insulation of buildings reduces energy consumption and prevent heat loss or gain by buildings. Methylhydroquinone is used for thermal insulation as well as soundproofing.
-In the construction of buildings and ships, Methylhydroquinone is used for plumbing, electrical work, and also bricklaying. It is also used to repair sporting boats.
First Aid of Methylhydroquinone
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.
Substance identity
EC / List no.: 202-443-7
CAS no.: 95-71-6
Mol. formula: C7H8O2
Hazard classification & labelling of Methyl Hydroquinone
Danger! According to the classification provided by companies to ECHA in REACH registrations this substance causes severe skin burns and eye damage, is very toxic to aquatic life, is very toxic to aquatic life with long lasting effects, causes serious eye damage, is harmful if swallowed, is suspected of causing genetic defects, is suspected of causing cancer, may cause an allergic skin reaction and may cause respiratory irritation.
About Methyl Hydroquinone
Methyl Hydroquinone is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Methyl Hydroquinone is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.
Consumer Uses of Methyl Hydroquinone
Methyl Hydroquinone is used in the following products: coating products.
Other release to the environment of Methyl Hydroquinone is likely to occur from: indoor use and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).
Article service life of Methyl Hydroquinone
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers of Methyl Hydroquinone
Methyl Hydroquinone is used in the following products: coating products, fillers, putties, plasters, modelling clay and polymers.
Methyl Hydroquinone is used in the following areas: building & construction work.
Methyl Hydroquinone is used for the manufacture of: plastic products.
Other release to the environment of Methyl Hydroquinone is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).
Formulation or re-packing of Methyl Hydroquinone
Methyl Hydroquinone is used in the following products: polymers, coating products, fillers, putties, plasters, modelling clay, adhesives and sealants and laboratory chemicals.
Release to the environment of Methyl Hydroquinone can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites of Methyl Hydroquinone
Methyl Hydroquinone is used in the following products: coating products, laboratory chemicals, polymers, fillers, putties, plasters, modelling clay and adhesives and sealants.
Methyl Hydroquinone is used for the manufacture of: chemicals and plastic products.
Release to the environment of Methyl Hydroquinone can occur from industrial use: as processing aid, as processing aid, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and for thermoplastic manufacture.
Manufacture of Methyl Hydroquinone
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Synonyms:
Methylhydroquinone
2-Methylhydroquinone
95-71-6
2-methylbenzene-1,4-diol
2,5-Dihydroxytoluene
Toluhydroquinone
p-Toluhydroquinone
Toluquinol
p-Toluquinol
Tolylhydroquinone
p-Toluhydroquinol
2,5-Toluenediol
Methyl-p-hydroquinone
1,4-Benzenediol, 2-methyl-
1,4-Dihydroxy-2-methylbenzene
2-Methyl-1,4-benzenediol
METHYL HYDROQUINONE
Hydroquinone, methyl-
Hydroquinone, tolyl-
Pyrolin
2-Methyl-1,4-hydroquinone
NSC 4962
UNII-332W51E0OC
MFCD00002345
NSC4962
332W51E0OC
EINECS 202-443-7
BRN 2041489
2-Methyl-benzene-1,4-diol
methylhydroquinon
3-methyl-1,4-dihydroxybenzene
AI3-14932
2-methylhydroquinol
methyl-p-hydroquinol
monomethylhydroquinone
2-methyl hydroquinone
2-Methyl-hydroquinone
monomethyl hydroquinone
2-Methyl-p-hydroquinone
DSSTox_CID_876
Methylhydroquinone, 99%
3-methyl-4-hydroxyphenol
4-hydroxy-2-methylphenol
EC 202-443-7
2-Methylbenzene-1,4-diole
DSSTox_RID_75840
Methylhydroquinone, >=99%
WLN: L6V DVJ X1
DSSTox_GSID_20876
SCHEMBL36349
2,5-Dihydroxytoluene polymer
2,5-DHTOP
4-06-00-05866 (Beilstein Handbook Reference)
2-methyl-1,4-dihydroxybenzene
CHEMBL450917
WLN: L6V DVJ XR X1
3-metyl-1,4-dihydroxy benzene
DTXSID4020876
2-methyl-1,4-dihydroxy benzene
CHEBI:133842
BDBM176768
ZINC388086
NSC-4962
Tox21_200506
AKOS015856210
AC-4660
CS-W013533
MCULE-7035325950
CAS-95-71-6
NCGC00248664-01
NCGC00258060-01
AS-15442
CAS# 95-71-6
P353
FT-0613052
M0342
Methylhydroquinone, purum, >=98.0% (HPLC)
E83005
US9688816, 8
Q1925586
W-109360
F0001-2277
N-a-Fmoc-N-?-allyloxycarbonyl-L-2,3-diaminopropionicacid
7DV
2-methylhydroquinone
2-methylhydroquinone
1,4-Benzenediol, 2-methyl-
2-METHYL HYDROQUINONE
2-Methyl-1,4-benzenediol
2-methylbenzene-1,4-diol
2-Methylhydroquinone
2-methylhydroquinone
Methylhydroquinone
methylhydroquinone
135648-79-2
140627-29-8
29763-99-3
65916-21-4
78446-96-5
95-71-6
96937-50-7
