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1,5-diisocyanatonaphthalene

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Identification
Molecular formula
C12H6N2O2
CAS number
3173-72-6
IUPAC name
1,5-diisocyanatonaphthalene
State
State

At room temperature, 1,5-diisocyanatonaphthalene is a solid. It must be handled with care due to its reactive nature, especially in the presence of moisture.

Melting point (Celsius)
35.00
Melting point (Kelvin)
308.20
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.20
General information
Molecular weight
210.19g/mol
Molar mass
210.2140g/mol
Density
1.3558g/cm3
Appearence

1,5-Diisocyanatonaphthalene is typically a pale yellow to light brown solid. It may appear crystalline and is known for its reactivity with water, producing amines and carbon dioxide.

Comment on solubility

Solubility of 1,5-Diisocyanatonaphthalene

The solubility of 1,5-diisocyanatonaphthalene (C12H8N2O2) can be characterized by several key factors:

  • Solvent Compatibility: This compound is generally considered to be poorly soluble in water due to its hydrophobic aromatic structure.
  • Common Solvents: It exhibits better solubility in organic solvents such as:
    • Dimethyl sulfoxide (DMSO)
    • Acetone
    • Tetrahydrofuran (THF)
  • Temperature Influence: Like many organic compounds, solubility may increase with temperature, making higher temperatures favorable for dissolution.
  • Chain Length and Structure: The addition of isocyanate groups generally influences solubility, leading to reduced solubility compared to non-functionalized aromatic compounds.

In summary, while 1,5-diisocyanatonaphthalene is not readily soluble in water, it can dissolve in certain organic solvents, which opens up possibilities for various applications and reactions in organic chemistry.

Interesting facts

Interesting Facts about 1,5-Diisocyanatonaphthalene

1,5-Diisocyanatonaphthalene is a fascinating compound due to its unique structural characteristics and various applications in industrial chemistry. Here are some key insights:

  • Structural Composition: This compound belongs to the family of isocyanates and is derived from naphthalene. Its structure contains two isocyanate groups (-N=C=O) positioned at the 1 and 5 positions of the naphthalene ring, which is critical for its reactivity.
  • Application in Polyurethanes: 1,5-Diisocyanatonaphthalene is often used as an intermediate in the production of polyurethanes, which have widespread use in foams, elastomers, and coatings.
  • Crosslinking Agent: Due to its multiple isocyanate functionalities, it can serve as a crosslinking agent in polymer chemistry, enhancing the mechanical properties of materials.
  • Research Significance: This compound is of interest in research related to polymer modification and the development of new materials with specific properties.
  • Toxicity Considerations: Like many isocyanates, 1,5-diisocyanatonaphthalene can be hazardous. It's important to handle it with appropriate safety measures due to its potential health effects upon exposure.

In summary, the unique properties and applications of 1,5-diisocyanatonaphthalene make it a subject of ongoing interest in both academic and industrial settings. Its fascinating interplay of structure and function exemplifies the complexity found within organic compounds.

Synonyms
1,5-Diisocyanatonaphthalene
3173-72-6
1,5-Naphthalene diisocyanate
1,5-Naphthylene diisocyanate
Naphthalene, 1,5-diisocyanato-
1,5-Naphthylene di-isocyanate
CCRIS 8920
UNII-0ORB22ST7M
EINECS 221-641-4
0ORB22ST7M
ISOCYANIC ACID, 1,5-NAPHTHYLENE ESTER
NSC 240728
BRN 2212353
NSC-240728
DTXSID8040145
1,5-NDI
EC 221-641-4
4-13-00-00342 (Beilstein Handbook Reference)
NAPHTHALENE DIISOCYANATE, 1,5-
1,5-NAPHTHALENEDIOL, DIISOCYANATE
1,5-NAPHTHALENE DIISOCYANATE [IARC]
1,5-NAPHTHALENE DIISOCYANATE (IARC)
1,5diisocyanatonaphthalene
1,5-naphthene diisocyanate
1,5naphthalene diisocyanate
DTXCID6020145
1,5Naphthalene ester of isocyanic acid
Naphthalene, 1,5-diisocyanato-(9CI)
221-641-4
1,5-Naphthyl diisocyanate
MFCD00039588
1,5-Naphthalene diisocyanate [Diisocyanates]
Naphthalene,5-diisocyanato-
SCHEMBL22210
Naphthalene 1,5-Diisocyanate
CHEBI:82496
Isocyanic acid,5-naphthylene ester
NSC240728
AKOS015900717
FN33948
GS-3153
DB-005648
N0168
NS00006855
C19464
D91652
Q2786152