| Identification | More | [Name]
1,4-DIMETHYLNAPHTHALENE | [CAS]
571-58-4 | [Synonyms]
1,4-DIMETHYLNAPHTHALENE
1,4-Dimethylnapthalene
naphthalene,1,4-dimethyl-
1,4-DIMETHYLNAPHTHALENE OEKANAL
1 4-DIMETHYLNAPHTHALENE OEKANAL 250 MG
1,4-Dimethylnaphthalene,~99%
1,4-DIMETHYLNAPHTHALENE 95+% | [EINECS(EC#)]
209-335-9 | [Molecular Formula]
C12H12 | [MDL Number]
MFCD00004037 | [Molecular Weight]
156.22 | [MOL File]
571-58-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
-18 °C (lit.) | [Boiling point ]
262-264 °C/751 mmHg (lit.) | [density ]
1.016 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.613(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [form ]
neat | [color ]
Colorless to Light yellow to Light orange | [Water Solubility ]
9.634mg/L(25 ºC) | [BRN ]
2039842 | [Henry's Law Constant]
2.6×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [InChI]
InChI=1S/C12H12/c1-9-7-8-10(2)12-6-4-3-5-11(9)12/h3-8H,1-2H3 | [InChIKey]
APQSQLNWAIULLK-UHFFFAOYSA-N | [SMILES]
C1(C)=C2C(C=CC=C2)=C(C)C=C1 | [LogP]
4.370 | [CAS DataBase Reference]
571-58-4(CAS DataBase Reference) | [EPA Substance Registry System]
1,4-Dimethylnaphthalene (571-58-4) |
| Hazard Information | Back Directory | [Description]
1,4-dimethylnaphthalene is a growth inhibitor used on potatoes. It has a very low aqueous solubility and is highly volatile. | [Uses]
1,4-Dimethylnaphthalene is a polycyclic aromatic hydrocarbon (PAH) that has been found in dust particulate matter and is associated with activation of aryl hydrocarbon receptor as a major toxic mode of action in WB-F344 cell line. 1,4-Dimethylnaphthalene has been found to retard the development of epidermoid carcinomas in hamster buccal pouch. 1,4-Dimethylnaphthalene alters the genes associated with the maintenance of a G1/S phase block possibly through the induction of the cell cycle inhibitors KRP1 and KRP2 in potatoes. | [Definition]
ChEBI: A dimethylnaphthalene carrying methyl groups at positions 1 and 4. | [Production Methods]
The commercial production of 1,4-dimethylnaphthalene typically involves a multi-step chemical process. One industrial method begins with the cyclization of 5-phenyl-2-hexene in the presence of acid catalysts to form crude 1,4-dimethyl-1,2,3,4-tetrahydronaphthalene. This intermediate is then subjected to dehydrogenation to yield crude 1,4-dimethylnaphthalene, which is subsequently purified through distillation to remove isomeric impurities like 1,3-dimethylnaphthalene. An alternative synthesis route uses 1,4-dichloronaphthalene and a methyl Grignard reagent in the presence of a nickel-phosphine catalyst, followed by distillation and solvent recovery, achieving high conversion efficiency and selectivity. Extraction from potato skins is also possible and has been explored as a more natural alternative for use as a sprout suppressant in stored potatoes. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 46, p. 1251, 1981 DOI: 10.1021/jo00320a005 | [Mechanism of action]
Inhibits potato sprouting by mimicking natural plant hormones | [Pesticide Type]
Plant Growth Regulator |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
|