TOLUENE-2,5-DIOL

Toluene-2,5-diol is a versatile compound that finds many applications in polymer science due to its good binding properties and strength.
Toluene-2,5-diol is an off-white crystalline solid with a molecular weight of 124.137 g/mol and a melting point ranging around 110-112°C.
Additionally, Toluene-2,5-diol is used as a stabilizer in acrylics and as an antioxidant for fatty esters, linseed oil, and other inedible fats and oils.

CAS Number: 95-71-6
EC number: 202-443-7
Molecular Formula: CH3C6H3-1,4-(OH)2
Molecular Weight: 124.14

Synonyms: Toluhydroquinone, 2-Toluhydroquinone, 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, monoToluhydroquinone, 2-methyl hydroquinone, 2-Methyl-hydroquinone, monomethyl hydroquinone, 2-Methyl-p-hydroquinone, DSSTox_CID_876, Toluhydroquinone, 99%, 3-methyl-4-hydroxyphenol, 4-hydroxy-2-methylphenol, EC 202-443-7, 2-Methylbenzene-1,4-diole, DSSTox_RID_75840, Toluhydroquinone, >=99%, WLN: L6V DVJ X1, DSSTox_GSID_20876, SCHEMBL36349, 2,5-Dihydroxytoluene polymer, 2,5-DHTOP, 4-06-00-05866, 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, Toluhydroquinone, purum, >=98.0% (HPLC), E83005, US9688816, 8, Q1925586, W-109360, F0001-2277, N-a-Fmoc-N-?-allyloxycarbonyl-L-2,3-diaminopropionicacid, 7DV, 2-Methyl-p-hydroquinone, 1,4-Benzenediol, 2-methyl-, 202-443-7, 2041489, 2-Methyl-1,4-benzenediol, 2-Méthyl-1,4-benzènediol, 2-Methyl-1,4-benzoldiol, 2-Methylbenzene-1,4-diol, 2-Toluhydroquinone, 95-71-6, Toluhydroquinone, MFCD00002345, MX6700000, QR DQ B1, "1,4-BENZENEDIOL, 2-METHYL-", "1,4-BENZENEDIOL, 2-METHYL-"|"2-METHYLBENZENE-1,4-DIOL", "2-METHYLBENZENE-1,4-DIOL", p-toluquinol, 1-(3,4-Dihydroxyphenyl)-2-propanone, 1,4-Dihydroxy-2-methylbenzene, 135648-79-2, 140627-29-8, 2,4-DCT, 2,5-DHTOP, 2,5-Dihydroxytoluene, 2,5-Dihydroxytoluene, Toluhydroquinone, 2,5-Toluenediol, 202-443-7MFCD00002345, 202-445-8, 29763-99-3, 2-METHYLHYDROQUI, 2-Toluhydroquinone;2,5-Dihydroxytoluene, 4-05-00-00815, 4-06-00-05866, 437-50-3, 65916-21-4, 78446-96-5, 7DV, 95-73-8, 96937-50-7, EINECS 202-443-7, Gentisin, Hydroquinone, methyl-, Toluhydroquinone, Toluhydroquinone|2,5-Dihydroxytoluene, Methyl-p-hydroquinone, PHENOXY, 4-HYDROXY-2-METHYL-, S1, THQ (VAN), WLN: L6V DVJ X1, WLN: L6V DVJ XR X1

Toluene-2,5-diol typically appears as white to off-white crystals or a powder.
Toluene-2,5-diol has a melting point ranging around 110-112°C and is sparingly soluble in water but more soluble in organic solvents like ethanol and chloroform.

Toluene-2,5-diol is a versatile compound.
Toluene-2,5-diol finds many applications in the field of polymer science due to Ant good binding properties as well as Toluene-2,5-diol strength.

Toluene-2,5-diol is an off-white crystalline solid with a molecular weight of 124.137 g/mol.
Toluene-2,5-diol has a characteristic odor and Toluene-2,5-diol melting point is 262.4°F.

Toluene-2,5-diol is a reactive oxygen species (ROS) that can bind to DNA, forming covalent adducts.
Toluene-2,5-diol has been shown to have an optimum concentration of 10 μM, and the hydroxyl group on Toluene-2,5-diol phenolic ring enables Toluene-2,5-diol to form hydrogen bonding interactions with nucleic acids.

Toluene-2,5-diol 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.
Toluene-2,5-diol also inhibits the transfer of methyl groups from methyl donors such as S-adenosylhomocysteine and methionine to acceptor molecules such as p-hydroxybenzoic acid.

Toluene-2,5-diol Chemical which is a tan to white crystalline solid.
Toluene-2,5-diol is a highly active inhibitor in the free radical polymerization of vinyl monomers and unsaturated polyesters.

Toluene-2,5-diol undergoes chemical reactions similar to those of hydroquinone.
The presence of a methyl group in the ortho position in the Toluene-2,5-diol molecule is the slight structural and behavioral difference between Toluene-2,5-diol and hydroquinone.

Toluene-2,5-diol or Toluquinol belongs to a class of compounds called Hydroquinones with one of the benzene hydrogens replaced by a methyl group.
Toluene-2,5-diol is produced by the oxidation of o-cresol by the mutants G103S, G103S/A107G, and G103S/A107T.

Toluene-2,5-diol 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.
Toluene-2,5-diol is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Toluene-2,5-diol 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.

Toluene-2,5-diol is an organic compound with the molecular formula C7H8O2.
Toluene-2,5-diol is a derivative of hydroquinone, featuring a methyl group attached to the benzene ring at the 2-position.
This structural modification alters Toluene-2,5-diol's properties compared to hydroquinone.

Toluene-2,5-diol typically appears as white to off-white crystals or powder.
Toluene-2,5-diol has a melting point ranging around 110-112°C.
While sparingly soluble in water, Toluene-2,5-diol is more soluble in organic solvents such as ethanol, ether, and chloroform.

Toluene-2,5-diol finds application in various industries:

Photography:
Toluene-2,5-diol serves as a developing agent in black-and-white photographic developers, facilitating the reduction of silver ions to metallic silver for image formation.

Polymerization Inhibition:
Toluene-2,5-diol acts as an inhibitor in the polymerization of monomers like acrylic acid and styrene, preventing unwanted polymerization during storage and transportation.

Chemical Synthesis:
Toluene-2,5-diol is used as a precursor or intermediate in the synthesis of dyes, pharmaceuticals, fragrances, and other organic compounds.

Antioxidant:
Toluene-2,5-diol exhibits antioxidant properties due to its phenolic structure, aiding in stabilizing materials against oxidative degradation.
While considered to have low acute toxicity, Toluene-2,5-diol may pose health risks upon prolonged or repeated exposure and can cause skin sensitization in sensitive individuals.
Toluene-2,5-diol should be handled with appropriate precautions and stored away from incompatible materials and ignition sources.

In the environment, Toluene-2,5-diol is expected to biodegrade, although the rate of degradation may vary depending on environmental conditions.
Limited data are available on Toluene-2,5-diol's ecotoxicity, emphasizing the importance of proper handling and disposal to minimize environmental impact.

Toluene-2,5-diol's versatility and utility in various industrial processes make it a valuable compound, but careful management is essential to ensure both safety and environmental responsibility.

Applications of Toluene-2,5-diol:
Toluene-2,5-diol is used as a stabilizer for unsaturated polyesters and as an antioxidant for fatty esters, linseed oil, and other nonfood fats and oils.
Toluene-2,5-diol is used as a stabilizer to inhibit peroxide formation in ethers, chlorinated hydrocarbons and ethyl cellulose.
Toluene-2,5-diol is also used as an intermediate to manufacture other stabilizers, dyes, pharmaceuticals and plasticizers.

Toluene-2,5-diol is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway.
Allows for screening of novel inhibitors of angiogenesis.

Toluene-2,5-diol is used as a general adhesive and binding agent in various preparations.
In the automotive industry, Toluene-2,5-diol is widely used for repair as well as maintenance and also caring for automobiles viz, auto shampoo, wax, polish, brake grease.

Toluene-2,5-diol is the main ingredient of any paint.
Toluene-2,5-diol is polymers that form a continuous film on a solid surface.
Toluene-2,5-diol ensure that the coating is evenly spread and well adsorbed on to the surface.

Toluene-2,5-diol also have the major role of holing the pigment molecules responsible for color evenly across the coating.
Toluene-2,5-diol 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.
Toluene-2,5-diol is used for thermal insulation as well as soundproofing.

In the construction of buildings and ships, Toluene-2,5-diol is used for plumbing, electrical work, and also bricklaying.
Toluene-2,5-diol is also used to repair sporting boats.

Toluene-2,5-diol 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.

Uses of Toluene-2,5-diol:
Toluene-2,5-diol finds application in various industries due to its properties.

Some of Toluene-2,5-diol's common uses include:

1. Photography:
Toluene-2,5-diol serves as a developing agent in black-and-white photographic developers.
Toluene-2,5-diol facilitates the reduction of silver ions to metallic silver, aiding in the formation of photographic images.

2. Polymerization Inhibition:
Toluene-2,5-diol acts as an inhibitor in the polymerization of monomers such as acrylic acid and styrene.
By preventing unwanted polymerization during storage and transportation, Toluene-2,5-diol helps maintain the stability of monomeric solutions.

3. Chemical Synthesis:
Toluene-2,5-diol is utilized as a precursor or intermediate in the synthesis of various organic compounds.
Toluene-2,5-diol is employed in the production of dyes, pharmaceuticals, fragrances, and other specialty chemicals.

4. Antioxidant:
Due to its phenolic structure, Toluene-2,5-diol exhibits antioxidant properties.
Toluene-2,5-diol is used to stabilize materials against oxidative degradation in industries such as plastics, rubber, and personal care products.

5. Chemical Analysis:
In analytical chemistry, Toluene-2,5-diol is employed as a reagent for the determination of certain metals, such as iron and copper.

6. Research and Development:
Toluene-2,5-diol is used in laboratory research and development for its reactivity and ability to modify organic compounds.

These applications highlight the versatility and utility of Toluene-2,5-diol in various industrial processes, ranging from photography and polymerization inhibition to chemical synthesis and antioxidant protection.

Toluene-2,5-diol is antioxidant, polymerization inhibitor.
Toluene-2,5-diol is used as stabilizer and antioxidant in aerylic monomers to prevent polymerization.

Toluene-2,5-diol is a marine fungus metabolite, showing activity as an angiosupressor that interferes with the Akt pathway.
Allows for screening of novel inhibitors of angiogenesis.

Consumer Uses:
Toluene-2,5-diol is used in the following products: coating products.
Other release to the environment of Toluene-2,5-diol 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).

Uses at industrial sites:
Toluene-2,5-diol is used in the following products: coating products, laboratory chemicals, polymers, fillers, putties, plasters, modelling clay and adhesives and sealants.
Toluene-2,5-diol is used for the manufacture of: chemicals and plastic products.
Release to the environment of Toluene-2,5-diol 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.

Widespread uses by professional workers:
Toluene-2,5-diol is used in the following products: coating products, fillers, putties, plasters, modelling clay and polymers.
Toluene-2,5-diol is used in the following areas: building & construction work.

Toluene-2,5-diol is used for the manufacture of: plastic products.
Other release to the environment of Toluene-2,5-diol 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).

Synthesis of Toluene-2,5-diol:
Toluene-2,5-diol can be synthesized through various methods, including the alkylating hydroquinone with methyl iodide in the presence of a base, or the oxidation of 2-methylphenol (o-cresol) using oxidizing agents such as nitric acid or potassium permanganate.

Manufacturing of Toluene-2,5-diol:
Toluene-2,5-diol 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.

Biochem/physiol Actions of Toluene-2,5-diol:
Toluene-2,5-diol inhibits the growth of endothelial and tumor cells in culture in the micromolar range and is a promising drug candidate in the treatment of cancer and other angiogenesis-related pathologies.

Identifiers of Toluene-2,5-diol:
CAS: 95-71-6
Molecular Formula: C7H8O2
Molecular Weight (g/mol): 124.14
MDL Number: MFCD00002345
InChI Key: CNHDIAIOKMXOLK-UHFFFAOYSA-N
PubChem CID: 7253
IUPAC Name: 2-methylbenzene-1,4-diol
SMILES: CC1=CC(O)=CC=C1O

IUPAC Name: 1-Methyl-4-(2-methylbenzene-1,4-diol)
CAS Number: 2468-81-9
Molecular Formula: C7H8O2
SMILES: CC1=CC(=C(C=C1)O)C(O)=C
InChI: InChI=1S/C7H8O2/c1-5-2-4-7(9)6(8)3-5/h2-4,9H,1H3
InChI Key: CHUINQENSVKLOM-UHFFFAOYSA-N

Properties of Toluene-2,5-diol:
Molecular Weight: 124.14
XLogP3: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 124.052429494
Monoisotopic Mass: 124.052429494
Topological Polar Surface Area: 40.5 Ų
Heavy Atom Count: 9
Complexity: 92.9
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Quality Level: 100
Assay: 99%
Form: solid
Autoignition temp.: 851 °F
mp: 128-130 °C (lit.)
SMILES string: Cc1cc(O)ccc1O
InChI: 1S/C7H8O2/c1-5-4-6(8)2-3-7(5)9/h2-4,8-9H,1H3
InChI key: CNHDIAIOKMXOLK-UHFFFAOYSA-N
Product Number: M0342
Purity / Analysis Method: >98.0%(T)
Molecular Formula / Molecular Weight: C7H8O2 = 124.14
Physical State (20 deg.C). Solid
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive
CAS RN: 95-71-6
Reaxys Registry Number: 2041489
PubChem Substance ID: 87572412
SDBS (AIST Spectral DB): 3439
MDL Number: MFCD00002345

Melting point: 128-130 °C(lit.)
Boiling point: 285°C
Density: 1.1006 (rough estimate)
refractive index: 1.4922 (estimate)
Flash point: 172 °C
storage temp.: Store below +30°C.
solubility: 77g/l
form: Crystalline Powder
pka: pK1:10.03;pK2:11.62 (25°C)
color: Grayish-white to light beige
Water Solubility: 77 g/L (25 ºC)
BRN: 2041489
Stability: Stable. Combustible. Incompatible with oxidizing agents, strong bases.
InChIKey: CNHDIAIOKMXOLK-UHFFFAOYSA-N
CAS DataBase Reference: 95-71-6(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 332W51E0OC
NIST Chemistry Reference: 1,4-Benzenediol, 2-methyl-(95-71-6)
EPA Substance Registry System: 2-Toluene-2,5-diol (95-71-6)

Physicochemical Information of Toluene-2,5-diol:
Flash point: 172 °C
Ignition temperature: 468 °C
Melting Point: 128 - 130 °C
Solubility: 77 g/l

Specifications of Toluene-2,5-diol:
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Melting range (lower value): ≥ 125 °C
Melting range (upper value): ≤ 128 °C
Identity (IR): passes test
Purity: >98.0%(T)

Names of Toluene-2,5-diol:

Regulatory process names:
2-Toluene-2,5-diol
2-Toluene-2,5-diol

CAS names:
1,4-Benzenediol, 2-methyl-

IUPAC names:
2-METHYL HYDROQUINONE
2-Methyl-1,4-benzenediol
2-methylbenzene-1,4-diol
2-Toluene-2,5-diol
2-Toluene-2,5-diol
Toluene-2,5-diol
Toluene-2,5-diol

Other identifiers:
135648-79-2
140627-29-8
29763-99-3
65916-21-4
78446-96-5
95-71-6
96937-50-7