Bis(isopropyl)naphthalene is used in carbonless copy paper, coatings, colours, lacquers, inks, casting resins, adhesives, scintillation cocktails, heat-transfer oils, foundry/steelworks applications, and manufacturing oils.
Due to its hydrophobic nature, Bis(isopropyl)naphthalene serves as a solvent in chemical processes.
CAS Number: 38640-62-9
EC Number / EINECS Number: 254-052-6
Molecular Formula: C16H20
Molecular Weight: 212.33 g/mol
SYNONYMS:
Bis(isopropyl)naphthalene, Diisopropylnaphthalene, Diisopropylnaphtalene, Diisopropylnaphthalin, 1,2-bis(propan-2-yl)naphthalene, 1,2-diisopropylnaphthalene, Naphthalene, bis(1-methylethyl)-, Bis(isopropyl)naphthalene [mixture of isomers], Diisopropylnaphthalene [mixture of isomers], bis(1-methylethyl)naphthalene, bis(1-methylethyl)-naphthalene, bis(1-methylethyl)-Naphthalene, DIPN, KMC, KMC-113, KMC-R113, KSK-OIL 280, RUETASOLU DI, RUETASOLV, Di-Iso-Propylnaphthalene, 1,5-Diisopropylnaphthalene, 1,2-Bis(isopropyl)naphthalene, A6E49MJJ2X, 94133-79-6, DTXSID60240682, 1,2-DIISOPROPYLNAPHTHALENE, RefChem:1052276, DTXCID90163173, 302-742-3, 1,2-di(propan-2-yl)naphthalene, EINECS 302-742-3, UNII-A6E49MJJ2X, 1,2-Bis(1-methylethyl)naphthalene, diiso-propylnaphthalene, Diisopropyl naphthalene, SCHEMBL79572, Naphthalene, 1,2-diisopropyl, orb1986116, AKOS040751582, Naphthalene, 1,2-bis(1-methylethyl)-, T31480, Bis(isopropyl)naphthalene, Naphthalene, bis(1-methylethyl)-, 1,5-Diisopropylnaphthalene, bis(isopropyl)naphthalene, Diisopropylnaphtalene, Bis(isopropyl)naphthalin
Bis(isopropyl)naphthalene, or diisopropylnaphthalene, is a colorless and odorless transparent liquid.
Bis(isopropyl)naphthalene has a pure carbon structure and has excellent compatibility with the resin base material.
Bis(isopropyl)naphthalene, commonly abbreviated as DIPN, is a hydrophobic aromatic hydrocarbon consisting of a naphthalene ring substituted with two isopropyl groups.
An important point concerning this substance is that “Bis(isopropyl)naphthalene” with CAS No. 38640-62-9 is not a single positional isomer.
Bis(isopropyl)naphthalene is a multi-constituent substance / mixture of diisopropylnaphthalene isomers.
The registered substance contains several positional isomers, including 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 2,6-, and 2,7-diisopropylnaphthalene.
Therefore, physical properties such as melting point can differ depending on the exact isomer composition.
Bis(isopropyl)naphthalene is an industrial aromatic hydrocarbon used primarily as a specialty solvent, functional fluid, heat-transfer medium, component of carbonless copy-paper systems, and ingredient in various industrial formulations.
The exact mass of Bis(isopropyl)naphthalene is 212.16 and the complexity rating of the compound is unknown.
The solubility of Bis(isopropyl)naphthalene has been described as Soluble in DMSO.
The storage condition of Bis(isopropyl)naphthalene is described as Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years)..
Bis(isopropyl)naphthalene is an organic compound with the molecular formula C16H20 and a molar mass of 212.3 g/mol.
Bis(isopropyl)naphthalene consists of a naphthalene core with two isopropyl groups attached to the first and second carbon atoms of the naphthalene structure.
Bis(isopropyl)naphthalene is known for its unique physical and chemical properties, including its relatively high boiling point and low solubility in water, which are typical characteristics of polycyclic aromatic hydrocarbons.
Bis(isopropyl)naphthalene is a solvent used in carbonless copy paper.
Bis(isopropyl)naphthalene consists of a mixture of constitutional isomers having two isopropyl groups at various locations on a naphthalene core.
USES and APPLICATIONS of BIS(ISOPROPYL)NAPHTHALENE:
Foundry and steel industry: Bis(isopropyl)naphthalene can be incorporated into specialized materials and formulations used in industrial metal-processing environments.
Application in Organic Light Emitting Diodes (OLEDs): Bis(isopropyl)naphthalene derivatives have been used in the development of organic semiconductor materials for OLEDs.
Industrial Solvent: Due to its hydrophobic nature, Bis(isopropyl)naphthalene serves as a solvent in chemical processes.
Chemical Intermediate: Bis(isopropyl)naphthalene is used in the synthesis of other organic compounds and materials.
Additive in Lubricants: Its thermal stability makes Bis(isopropyl)naphthalene suitable for use in lubricants and greases.
Application in Organic Solar Cells: Bis(isopropyl)naphthalene derivatives have been used in the development of organic semiconductor materials for organic solar cells.
Application of Bis(isopropyl)naphthalene in the Production of Dyes: Naphthalene and its derivatives, including 1,2-Bis(isopropyl)naphthalene, are used in the production of dyes.
Bis(isopropyl)naphthalene is used in carbonless copy paper, coatings, colours, lacquers, inks, casting resins, adhesives, scintillation cocktails, heat-transfer oils, foundry/steelworks applications, and manufacturing oils.
-Application of Bis(isopropyl)naphthalene in Field-Effect Transistors:
1,2-Bis(isopropyl)naphthalene derivatives have been used in the development of organic semiconductor materials for ambipolar field-effect transistors.
Bis(isopropyl)naphthalene derivatives were designed and synthesized by a “building-blocks approach” connected through a-bond, double bond, and triple bond, respectively.
-Carbonless copy paper uses of Bis(isopropyl)naphthalene:
One of the most established applications of Bis(isopropyl)naphthalene is in carbonless copy paper.
Bis(isopropyl)naphthalene functions as an organic solvent in microencapsulated systems used to produce pressure-sensitive copies.
Bis(isopropyl)naphthalene is particularly associated with KMC (Kureha Micro Capsule) oil, a formulation based on diisopropylnaphthalene isomer mixtures.
When pressure is applied to the paper, microcapsules containing the solvent and colour-forming system rupture, allowing the colour-development process to occur on the receiving sheet.
This application is one of the best-known uses of mixed-isomer Bis(isopropyl)naphthalene.
-Application of Bis(isopropyl)naphthalene as Fluorescence Probes:
Naphthalene and its derivatives, including 1,2-Bis(isopropyl)naphthalene, are used as fluorescence probes for detecting and imaging purposes.
Naphthalene-based fluorescence probes exhibit excellent sensing and selectivity properties towards anions and cations and are also used as a part of target biomolecules.
-Application of Bis(isopropyl)naphthalene in Coal Tar Production:
Summary of the Application: Naphthalene and its derivatives, including 1,2-Bis(isopropyl)naphthalene, are the most abundant single component of coal tar.
In industrial practice, distillation of coal tar yields an oil containing about 50% naphthalene, along with twelve other aromatic compounds.
The composition of coal tar varies with coal type and processing, but typical coal tar is about 10% naphthalene by weight.
-Heat-transfer fluids uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene can be used as a component of high-temperature heat-transfer fluids.
Bis(isopropyl)naphthalene's relatively high boiling point, low vapour pressure, high flash point, and low-temperature fluidity make it useful for liquid-phase heating systems.
Bis(isopropyl)naphthalene can be used in industrial heating systems where a stable organic heat-transfer medium is required.
Applications described for Bis(isopropyl)naphthalene-based heat-transfer fluids include chemical processing, petrochemical processing, synthetic materials, resins, textiles, coatings, plastics, and other high-temperature industrial processes.
-Coatings uses Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene is used in formulations for industrial coatings.
Its hydrophobicity and solvent properties make Bis(isopropyl)naphthalene useful as an organic component in coating formulations.
Bis(isopropyl)naphthalene can contribute to formulation viscosity, solvency, film formation and compatibility with hydrophobic components.
-Paints, colours and lacquers uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene is used in certain paints, colours and lacquer formulations.
Its relatively high boiling point allows Bis(isopropyl)naphthalene to function as a slow-evaporating organic solvent or solvent component.
Its hydrophobic character makes Bis(isopropyl)naphthalene particularly suitable for formulations containing non-polar or hydrophobic organic ingredients.
-Printing inks uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene can be used in industrial printing-ink formulations.
Bis(isopropyl)naphthalene's solvent characteristics and relatively low volatility can be useful when controlled evaporation is required.
-Adhesives uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene is used in certain adhesive formulations.
Bis(isopropyl)naphthalene can act as a solvent or formulation component for hydrophobic polymeric materials.
Adhesives among the registered formulation, industrial and professional uses of Bis(isopropyl)naphthalene.
-Casting resins uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene is used in casting resin systems.
Bis(isopropyl)naphthalene can serve as an organic formulation component in resin systems used in industrial applications.
-Scintillation cocktails uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene is also used as a solvent in liquid scintillation and organic scintillator systems.
Scientific studies have used mixed-isomer Bis(isopropyl)naphthalene as the solvent in liquid organic scintillators for radiation and neutron-detection research.
Its optical and physical properties make Bis(isopropyl)naphthalene suitable for formulations containing fluorescent or wavelength-shifting compounds.
-Manufacturing oils uses of Bis(isopropyl)naphthalene:
Bis(isopropyl)naphthalene is also used in certain manufacturing oils and industrial formulations.
Bis(isopropyl)naphthalene's relatively high boiling point and hydrophobic character can be useful where a stable aromatic organic liquid is required.
-Rubber and tyre applications of Bis(isopropyl)naphthalene:
Formulation and industrial uses involving rubber materials for tyre production and tread preparations.
In these applications, Bis(isopropyl)naphthalene may function as a formulation ingredient or processing medium in specialized rubber-related preparations.
BENEFITS AND ADVANTAGES of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene offers several useful technical characteristics.
Its high boiling point makes Bis(isopropyl)naphthalene suitable for high-temperature applications.
Bis(isopropyl)naphthalene's low vapour pressure reduces evaporation compared with many conventional organic solvents.
Bis(isopropyl)naphthalene's high flash point is advantageous in applications where reduced flammability risk relative to low-flash-point solvents is desirable.
Its low pour point allows Bis(isopropyl)naphthalene to remain fluid at relatively low temperatures.
Its high hydrophobicity makes Bis(isopropyl)naphthalene suitable for non-aqueous formulations.
Its solvent properties allow Bis(isopropyl)naphthalene to dissolve or carry various hydrophobic organic components.
Its chemical stability makes Bis(isopropyl)naphthalene suitable for applications involving prolonged thermal or chemical exposure.
Its ability to function as both a specialty solvent and a functional fluid gives Bis(isopropyl)naphthalene a relatively broad industrial application range.
Bis(isopropyl)naphthalene's mixed-isomer nature can also provide a useful combination of physical properties that differs from those of individual purified isomers.
CHARACTERISTICS of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene is a high-boiling, low-volatility, strongly hydrophobic aromatic liquid with a broad range of industrial applications.
Its combination of a high boiling point, low vapour pressure, relatively high flash point, low-temperature fluidity and strong organic-phase affinity makes Bis(isopropyl)naphthalene useful in specialty solvent and functional-fluid applications.
Its most distinctive commercial application is its use in carbonless copy paper, where mixed-isomer Bis(isopropyl)naphthalene is used as a solvent in microencapsulated systems.
Bis(isopropyl)naphthalene is also important as a heat-transfer fluid component, particularly in high-temperature liquid-phase heating systems.
In addition, Bis(isopropyl)naphthalene is used in coatings, inks, adhesives, casting resins, scintillation cocktails, rubber-related formulations and several other industrial systems.
MOLECULAR STRUCTURE of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene consists of a fused two-ring naphthalene aromatic system bearing two isopropyl substituents.
The general molecular formula is: C16H20
Bis(isopropyl)naphthalene portion provides the aromatic hydrocarbon framework, while the two isopropyl groups increase the molecular size, hydrophobicity, and liquid-phase character compared with unsubstituted naphthalene.
Because the two isopropyl groups can occupy different positions on Bis(isopropyl)naphthalene ring, numerous positional isomers are possible.
For the registered CAS 38640-62-9 material, ECHA identifies Bis(isopropyl)naphthalene as a multi-constituent substance rather than a single pure structural isomer.
ISOMER COMPOSITION of BIS(ISOPROPYL)NAPHTHALENE:
The following constituents within the registered mixed-isomer substance:
1,3-Diisopropylnaphthalene — EC 260-571-9
1,4-Diisopropylnaphthalene — EC 246-044-6
1,5-Diisopropylnaphthalene — EC 248-424-7
1,6-Diisopropylnaphthalene — EC 256-971-8
1,7-Diisopropylnaphthalene — EC 302-743-9
2,6-Diisopropylnaphthalene — EC 246-045-1
2,7-Diisopropylnaphthalene — EC 254-929-3
2,6- and 2,7-diisopropylnaphthalene are each reported at less than 45% w/w, while several other isomers are reported below 25% w/w.
This is an important reason why different commercial Bis(isopropyl)naphthalene products can have somewhat different physical properties.
CHEMICAL CHARACTERISTICS of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene is a non-polar aromatic hydrocarbon.
Bis(isopropyl)naphthalene contains only carbon and hydrogen and therefore does not contain heteroatoms such as oxygen, nitrogen, sulfur, or halogens.
The absence of strongly polar functional groups gives Bis(isopropyl)naphthalene a very low affinity for water.
Bis(isopropyl)naphthalene's calculated Log Kow of approximately 6.08–6.17 indicates strong hydrophobicity.
Bis(isopropyl)naphthalene's low water solubility, approximately 125 µg/L at 25 °C, is consistent with this hydrophobic character.
Bis(isopropyl)naphthalene has a relatively high boiling point and low vapour pressure compared with many conventional organic solvents.
The relatively high flash point also makes Bis(isopropyl)naphthalene suitable for applications requiring a high-boiling aromatic liquid.
The aromatic naphthalene structure provides chemical and thermal stability, while the isopropyl substituents modify the physical properties and help keep Bis(isopropyl)naphthalene liquid over a broad temperature range.
SOLUBILITY AND PARTITIONING CHARACTERISTICS of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene is very poorly soluble in water, approximately 125 µg/L at 25 °C in distilled water.
Bis(isopropyl)naphthalene has a high calculated octanol/water partition coefficient, with Log Kow values around 6.08–6.17.
This means Bis(isopropyl)naphthalene strongly prefers non-polar or organic environments over water.
Bis(isopropyl)naphthalene also has a predicted Log Koc of approximately 4.6–5.3, indicating strong partitioning toward organic carbon-containing environmental materials such as soil and sediment.
These characteristics are important both for industrial formulation and for environmental risk assessment.
THERMAL CHARACTERISTICS of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene has a relatively high boiling temperature of approximately 292–295 °C.
Bis(isopropyl)naphthalene's pour point is below −30 °C, which is particularly useful for applications where a liquid needs to remain mobile at relatively low temperatures.
Bis(isopropyl)naphthalene's flash point of approximately 152–156 °C is substantially higher than that of many common low-boiling organic solvents.
These characteristics make Bis(isopropyl)naphthalene useful as a high-temperature organic fluid and specialty solvent.
The combination of low-temperature fluidity, high boiling temperature, relatively low vapour pressure, and high flash point is particularly advantageous for heat-transfer applications.
CHEMICAL REACTIONS of BIS(ISOPROPYL)NAPHTHALENE:
Typical of aromatic compounds.
These include:
Electrophilic Substitution:
The presence of isopropyl groups can direct electrophiles to the ortho and para positions on the naphthalene ring.
Hydrogenation:
Under specific conditions, it can be hydrogenated to form saturated derivatives.
Oxidation:
Bis(isopropyl)naphthalene may also be oxidized to form ketones or carboxylic acids.
The reactivity is influenced by the steric hindrance provided by the isopropyl groups, which can affect both the rate and selectivity of these reactions .
SYNTHESIS METHODS of BIS(ISOPROPYL)NAPHTHALENE:
Bis(isopropyl)naphthalene can be synthesized through several methods:
Friedel-Crafts Alkylation:
This method involves reacting naphthalene with isopropylating agents (like isopropyl bromide) in the presence of a Lewis acid catalyst (e.g., aluminum chloride).
The reaction conditions can influence the yield and isomeric composition of the product .
Direct Isopropylation:
Using isopropanol as a reagent in a high-pressure reactor has been explored to achieve higher yields and selectivity towards desired isomers .
PHYSICAL and CHEMICAL PROPERTIES of BIS(ISOPROPYL)NAPHTHALENE:
Chemical Name: Bis(isopropyl)naphthalene
Common Name: Diisopropylnaphthalene
Abbreviation: DIPN
CAS Number: 38640-62-9
EC Number / EINECS Number: 254-052-6
Molecular Formula: C16H20
Molecular Weight: 212.33 g/mol
Molecular Type: Multi-constituent substance / mixture of isomers
Chemical Class: Alkylated polycyclic aromatic hydrocarbon
Parent Hydrocarbon: Naphthalene
Substituents: Two isopropyl groups
Physical State at 20 °C: Liquid
Appearance: Colourless, odourless liquid
Main abbreviation in industry: DIPN
Molecular Formula: C16H20
Molecular Weight: 212.33 g/mol
Exact Molecular Mass: approximately 212.1565 g/mol
Physical State: Liquid at ordinary room temperature
Appearance: Colourless liquid
Odour: Odourless according to the ECHA substance-evaluation data
Pour Point: below −30 °C
Boiling Point: approximately 292–295 °C at 101.3 kPa according to the ECHA substance evaluation.
Density / Relative Density: 0.9574–0.9584 g/cm³ at 20 °C, based on two different batches.
Viscosity: 12.1–13.2 mm²/s at 20 °C
Viscosity at 40 °C: 6.25–6.42 mm²/s
Vapour Pressure: approximately 0.965 Pa at 20 °C; another reported value is 0.3–0.4 Pa depending on measurement/model.
Water Solubility: approximately 125 µg/L at 25 °C in distilled water and approximately 144 µg/L in artificial saltwater medium.
Log Kow: approximately 6.08–6.17
Log Koc: approximately 4.56–5.28
Log Koa: approximately 7.365
Flash Point: approximately 152–156 °C
Flammability: ECHA evaluation reports the substance as not flammable under the relevant test conditions.
Explosive Properties: Not explosive according to the ECHA evaluation.
Refractive Index: approximately 1.5774
Molecular Weight: 212.33 g/mol
XLogP3-AA: 5.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 2
Exact Mass: 212.156500638 Da
Monoisotopic Mass: 212.156500638 Da
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 16
Formal Charge: 0
Complexity: 216
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
CAS Number: 38640-62-9
Product Name: 1,2-Bis(isopropyl)naphthalene
IUPAC Name: 1,2-di(propan-2-yl)naphthalene
Molecular Formula: C16H20
Molecular Weight: 212.33 g/mol
InChI: InChI=1S/C16H20/c1-11(2)14-10-9-13-7-5-6-8-15(13)16(14)12(3)4/h5-12H,1-4H3
InChI Key: IAUKWGFWINVWKS-UHFFFAOYSA-N
SMILES: CC(C)C1=C(C2=CC=CC=C2C=C1)C(C)C
solubility: Soluble in DMSO
Synonyms: Bis(isopropyl)naphthalene, Naphthalene, bis(1-methylethyl)-
Canonical SMILES: CC(C)C1=C(C2=CC=CC=C2C=C1)C(C)C
Chemical formula: C16H20
Molar mass: 212.336 g·mol−1
Density: 0.96 g/cm3
Melting point: 38 °C
Boiling point: 290–299 °C
FIRST AID MEASURES of BIS(ISOPROPYL)NAPHTHALENE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of BIS(ISOPROPYL)NAPHTHALENE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of BIS(ISOPROPYL)NAPHTHALENE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of BIS(ISOPROPYL)NAPHTHALENE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of BIS(ISOPROPYL)NAPHTHALENE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of BIS(ISOPROPYL)NAPHTHALENE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
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