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1,5-Naphthalene diisocyanate

HCID 18503
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
25551-28-4
Standard SMILES
O=C=Nc1cccc2c(N=C=O)cccc12
InChIKey
SBJCUZQNHOLYMD-UHFFFAOYSA-N
Molecular formula
C12H6N2O2
Average molar mass
210.19 g/mol
Monoisotopic mass
210.04292743

Overview

1,5-naphthalene diisocyanate is a white to light-yellow crystalline flakes. (NIOSH, 2024)

Names & identifiers

Preferred name
1,5-Naphthalene diisocyanate
IUPAC
1,5-diisocyanatonaphthalene
English name
Naphthalene diisocyanate
Molecular formula
C12H6N2O2
Molecular weight
210.18824

Names & synonyms

3173-72-61,5-Naphthalene diisocyanate1,5-Naphthylene diisocyanateNaphthalene, 1,5-diisocyanato-1,5-Naphthyl diisocyanate1,5-Naphthylene di-isocyanate0ORB22ST7MDTXSID8040145NSC-240728RefChem:73516DTXCID6020145221-641-4
Show more names
Naphthalene diisocyanate1,5-Diisocyanatonaphthalene1,5-naphthalenediisocyanateISOCYANIC ACID, 1,5-NAPHTHYLENE ESTERMFCD00039588CCRIS 8920EINECS 221-641-4UNII-0ORB22ST7M

Database identifiers

CAS
25551-28-4、3173-72-6
PubChem CID
18503
DTXSID
DTXSID8040145
ChEBI
CHEBI:82496
UNII
0ORB22ST7M
EC Number
221-641-4
Nikkaji
J41.091H

Properties

Computed structural propertiesFilling in

XLogP
4.8
Topological polar surface area
58.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
16
Formal charge
0
Complexity
309

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Diisocyanates
DensityRelative density (water = 1): 1.42
Flash Point · 4 items

311 °F (NIOSH, 2024)

192 °C c.c.

311 °F

(oc) 311 °F

Boiling Point · 4 items

505 °F at 760 mmHg (NIOSH, 2024)

at 0.7kPa: 167 °C

505 °F

505 °F

Melting Point · 4 items

261 °F (NIOSH, 2024)

130 °C

261 °F

261 °F

Vapor Pressure · 5 items

0.003 mmHg at 75 °F (NIOSH, 2024)

0.003 [mmHg]

Vapor pressure, Pa at 20 °C:

0.003 mmHg

(75 °F): 0.003 mmHg

Physical Description · 6 items

1,5-naphthalene diisocyanate is a white to light-yellow crystalline flakes. (NIOSH, 2024)

Large Crystals

White to light-yellow, crystalline flakes; [NIOSH]

WHITE-TO-LIGHT-YELLOW CRYSTALS.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P233, P260, P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: Naphthalene, 1,5-diisocyanato-

Hazard Traits - Respiratory Toxicity

Naphthalene, 1,5-diisocyanato- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Naphthalene, 1,5-diisocyanato- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/10913

Restricted substance: 1,5-naphthylene diisocyanate

1,5-Naphthylene diisocyanate: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire Hazards · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsExcerpt from NIOSH Pocket Guide for Naphthalene diisocyanate:

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Occupational asthma reported in rubber manufacturing; [Malo]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

U.S. Production2023: 1,000,000 - <5,000,000 lb
Industry UsesMonomers
General Manufacturing Information · 2 items

Paint and Coating Manufacturing

Naphthalene, 1,5-diisocyanato-: ACTIVE

Related reactions

9 records
New reaction record
HRID 327381 reaction equation
HRID 327381As reactantuspto-grants-1993_12
HRID 372943 reaction equation
HRID 372943As reactantuspto-grants-1992_11
HRID 436725 reaction equation
HRID 436725As reactantuspto-grants-1977_06
HRID 466956 reaction equation
HRID 466956As reactantuspto-grants-1992_10
HRID 486855 reaction equation
HRID 486855As reactantuspto-grants-1994_03
HRID 1065609 reaction equation
HRID 1065609As productuspto-grants-1982_05
HRID 1729005 reaction equation
HRID 1729005As reactantuspto-grants-1994_07
HRID 2248077 reaction equation
HRID 2248077As reactantuspto-grants-1991_08
Page 1 of 2

Compound notes

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White to light-yellow, crystalline flakes.

White to light-yellow, crystalline flakes.

Physicochemical properties

EPA Substance Registry System
Naphthalene diisocyanate (25551-28-4)
Hazards SummaryMay cause skin sensitization; [ICSC] Biological monitoring of exposure to 1,5-naphthalene diisocyanate and 4,4'-methylenediphenyl diisocyanate. [PMID 16506043] See DIISOCYANATES.
Reactive GroupIsocyanates and Isothiocyanates
EC ClassificationSymbol: Xn; R: 20-36/37/38-42-52/53; S: (2)-26-28-38-45-61
Reactivity Profile · 1 item

Isocyanates and thioisocyanates, such as 1,5-NAPHTHALENE DIISOCYANATE, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Chemical DangersDecomposes on heating. This produces toxic fumes of nitrogen oxides, carbon monoxide, isocyanates and hydrogen cyanide. Reacts with acids, alcohols, amines, bases, strong oxidants, strong reducing agents and water.
Flammable LimitsCombustible Solid
Packaging and LabellingDo not transport with food and feedstuffs.
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Use foam, powder, carbon dioxide. NO water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Rest. Refer for medical attention .

First Aid · 2 items

Excerpt from NIOSH Pocket Guide for Naphthalene diisocyanate:

(General first aid procedures)

Safe StorageSee Chemical Dangers. Well closed.
Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Spillage Disposal · 1 item

Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

Isolation and EvacuationExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Eye PreventionWear safety spectacles or eye protection in combination with breathing protection if powder.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT DISPERSION OF DUST! STRICT HYGIENE!

Toxicology

Target OrgansEyes, respiratory system
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 items

Cough. Laboured breathing. Sore throat.

Redness. Pain.

Redness. Pain.

Abdominal pain. Sore throat.

irritation eyes, nose, throat; resp sensitization, cough, pulmonary secretions, chest pain, dyspnea (breathing difficulty); asthma

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Carcinogen Classification · 5 items

1,5-Naphthalene diisocyanate

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 19: (1979) Some Monomers, Plastics and Synthetic Elastomers, and Acrolein

1999

1998