• Name

  1,5-Naphthalene diisocyanate

• EINECS 221-641-4
• CAS No. 3173-72-6
• Article Data17
• CAS DataBase
• Density 1.21 g/cm³
• Solubility soluable in water
• Melting Point 130 °C
• Formula C₁₂H₆N₂O₂
• Boiling Point 314.7 °C at 760 mmHg
• Molecular Weight 210.192
• Flash Point 128.6 °C
• Transport Information UN 2206
• Appearance White to light-yellow crystalline flakes
• Safety 26-28-38-45-61
• Risk Codes 20-36/37/38-42-52/53
• Molecular Structure
• Hazard Symbols Xn
• Synonyms 1,5-Naphthalenediol,diisocyanate (5CI);Isocyanic acid, 1,5-naphthylene ester (6CI,8CI);1,5-Diisocyanatonaphthalene;1,5-NDI;1,5-Naphthyl diisocyanate;1,5-Naphthylene diisocyanate;NDI;NSC 240728;
• PSA 58.86000
• LogP 2.77440

Synthetic route

124244-58-2

1,5-bis-(butoxycarbonylamino)-naphthalene

3173-72-6

1,5-diisocyanatonaphthalene

Conditions

Conditions	Yield
1,2-dimethyl-3-ethylimidazole perchloric acid at 190 - 240℃; under 37.5038 Torr; for 2.16667h;	91%

51977-17-4

1,5-bis-(ethoxycarbonylamino)naphthalene

3173-72-6

1,5-diisocyanatonaphthalene

Conditions

Conditions	Yield
1-ethyl-3-methylimidazolium tetrafluoroborate at 190 - 240℃; under 37.5038 Torr; for 2.16667h;	85%
With boron trichloride; triethylamine In benzene for 0.5h; Heating;	100 % Chromat.

63896-10-6

dimethyl 1,5-naphthalenedicarbamate

3173-72-6

1,5-diisocyanatonaphthalene

Conditions

Conditions	Yield
1-butyl-3-methylimidazolium Tetrafluoroborate at 200 - 240℃; under 37.5038 Torr; for 2.16667h;	85%
With boron trichloride; triethylamine In benzene for 0.5h; Heating;	98 % Chromat.
With nitrogen; cobalt(II) acetate In bisbenzyltoluene
at 250℃; Inert atmosphere;

75-44-5

phosgene

2243-62-1

1,5-diaminonaphthalene

3173-72-6

1,5-diisocyanatonaphthalene

Conditions

Conditions	Yield
In various solvent(s) for 1.5h; Condensation; Heating;	23%

75-44-5

phosgene

1.5-diamino-naphthalene dihydrochloride

1.5-diamino-naphthalene dihydrochloride

3173-72-6

1,5-diisocyanatonaphthalene

75-44-5

phosgene

naphthalene-1,5-diyldiamine dihydrochloride

naphthalene-1,5-diyldiamine dihydrochloride

3173-72-6

1,5-diisocyanatonaphthalene

Conditions

Conditions	Yield
With chlorobenzene; 1,2-dichloro-benzene at 140 - 160℃;
With phenylsulfonyl fluoride at 90℃;
With benzene at 140℃; under 19858.7 Torr;

3173-72-6

1,5-diisocyanatonaphthalene

109-89-7

diethylamine

41915-94-0

1,5-bis(3,3-diethylureido)naphthalene

Conditions

Conditions	Yield
In toluene	98%

3173-72-6

1,5-diisocyanatonaphthalene

1,5-bis(3,3-dimethylureido)naphthalene

Conditions

Conditions	Yield
With dimethyl amine In toluene	97%

3173-72-6

1,5-diisocyanatonaphthalene

2-(4-hydroxyphenyl)ethyl prop-2-enoate

C34H30N2O8

Conditions

Conditions	Yield
Stage #1: 1,5-diisocyanatonaphthalene With dibutyltin(II) dilaurate; 4-methoxy-phenol In toluene at 40℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(4-hydroxyphenyl)ethyl prop-2-enoate In toluene at 80℃; for 7h; Inert atmosphere;	86%

3173-72-6

1,5-diisocyanatonaphthalene

818-61-1

2-hydroxyethyl acrylate

C22H22N2O8

Conditions

Conditions	Yield
Stage #1: 1,5-diisocyanatonaphthalene With dibutyltin(II) dilaurate; 4-methoxy-phenol In toluene at 40℃; for 0.166667h; Inert atmosphere; Stage #2: 2-hydroxyethyl acrylate In toluene at 40℃; for 4h; Inert atmosphere;	85%

3173-72-6

1,5-diisocyanatonaphthalene

57709-67-8

1-(4-nitrophenyl)-3-(2-amino-phenyl)urea

1,19-(naphthalene-1,2-diyl)bis(3-(2-(3-(4-nitrophenyl)ureido)phenyl)urea)

Conditions

Conditions	Yield
In tetrahydrofuran Reflux;	80%

3173-72-6

1,5-diisocyanatonaphthalene

4-(hexyloxy)pyridin-3-amine

1,1'-(naphthalene-1,5-diyl)bis(3-(4-(hexyloxy)pyridin-3-yl)urea)

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In dichloromethane Inert atmosphere;	73%

462-08-8

pyridin-3-ylamine

3173-72-6

1,5-diisocyanatonaphthalene

1-pyridin-3-yl-3-[5-(3-pyridin-3-yl-ureido)naphthalen-1-yl]urea

Conditions

Conditions	Yield
In dichloromethane Inert atmosphere;	73%

3173-72-6

1,5-diisocyanatonaphthalene

693-57-2

12-Aminododecanoic acid

C36H56N4O6

Conditions

Conditions	Yield
In dimethyl sulfoxide at 20℃; Inert atmosphere;	67%

3173-72-6

1,5-diisocyanatonaphthalene

N-(2-(cyclopropylidenemethyl)phenyl)-1,1,1-triphenyl-λ5-phosphanimine

1-(2-(cyclopropylidenemethyl)phenyl)-2,3-dihydro-1H-pyrrolo[2,3-b]quinoline

Conditions

Conditions	Yield
In toluene at 65℃; for 4h; Schlenk technique; Inert atmosphere;	59%

67-56-1

methanol

3173-72-6

1,5-diisocyanatonaphthalene

63896-10-6

dimethyl 1,5-naphthalenedicarbamate

64-17-5

ethanol

3173-72-6

1,5-diisocyanatonaphthalene

51977-17-4

1,5-bis-(ethoxycarbonylamino)naphthalene

Conditions

Conditions	Yield
With 1,4-dioxane at 105℃;
In toluene at 40℃;

3173-72-6

1,5-diisocyanatonaphthalene

141-97-9

ethyl acetoacetate

114400-15-6

2,2'-diacetyl-N,N'-naphthalene-1,5-diyl-bis-malonamic acid diethyl ester

Conditions

Conditions	Yield
With sodium; benzene

3173-72-6

1,5-diisocyanatonaphthalene

107-21-1

ethylene glycol

N,N'-naphthalene-1,5-diyl-bis-carbamic acid bis-(2-hydroxy-ethyl ester)

Conditions

Conditions	Yield
With 1,4-dioxane at 105℃;

3173-72-6

1,5-diisocyanatonaphthalene

141-43-5

ethanolamine

30042-58-1

1-(2-Hydroxy-ethyl)-3-{5-[3-(2-hydroxy-ethyl)-ureido]-naphthalen-1-yl}-urea

Conditions

Conditions	Yield
In chloroform

303-45-7

(rac)-gossypol

3173-72-6

1,5-diisocyanatonaphthalene

((8Z,8′Z)-1,1′,6,6′-tetrahydroxy-5,5′-diisopropyl-3,3′-dimethyl-7,7′-dioxo-[2,2′-binaphthalene]-8,8′(7H,7′H)-diylidene)bis(methaneylylidene) bis((5-aminonaphthalen-1-yl)carbamate)

Conditions

Conditions	Yield
In toluene at 85℃; Inert atmosphere;

1,5-Naphthalene diisocyanate Consensus Reports

1,5-Naphthalene diisocyanate Standards and Recommendations

1,5-Naphthalene diisocyanate Specification

1. Introduction of 1,5-Naphthalene diisocyanate
1,5-Naphthalene diisocyanate is also called 1,5-Naphthylene di-isocyanate ; 1,5-Diisocyanatonaphthalene ; 1,5-Naphthyl diisocyanate ; 1,5-Naphthylene diisocyanate ; 4-13-00-00342 (Beilstein Handbook Reference) ; BRN 2212353 ; CCRIS 8920 ; EINECS 221-641-4 ; NSC 240728 ; Isocyanic acid, 1,5-naphthylene ester ; Naphthalene, 1,5-diisocyanato- ; 1,5-Naphthalene diisocyanate [Diisocyanates]. The IUPAC Name of 1,5-Naphthalene diisocyanate is 1,5-Diisocyanatonaphthalene.

2. Properties of 1,5-Naphthalene diisocyanate
Melting Point: 130°C
Polar Surface Area: 58.86 Å²
Index of Refraction: 1.618
Molar Refractivity: 60.56 cm³
Molar Volume: 172.7 cm³
Surface Tension: 49.8 dyne/cm
Density: 1.21 g/cm³
Flash Point: 128.6 °C
Enthalpy of Vaporization: 55.59 kJ/mol
Boiling Point: 314.7 °C at 760 mmHg
Vapour Pressure: 0.000459 mmHg at 25°C
Classification Code: Tumor data

3. Toxicity of 1,5-Naphthalene diisocyanate

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LC50	inhalation	270mg/m3/4H (270mg/m3)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS	National Technical Information Service. Vol. OTS0572846,

4. Safety Information of 1,5-Naphthalene diisocyanate
A powerful allergen. An irritant. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NO_x. See also ISOCYANATES.
Hazard Codes of 1,5-Naphthalene diisocyanate (CAS NO.3173-72-6): Xn
Risk Statements: 20-36/37/38-42-52/53 
R20: Harmful by inhalation. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R42: May cause sensitization by inhalation. 
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-28-38-45-61 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S28: After contact with skin, wash immediately with plenty of soap-suds. 
S38: In case of insufficient ventilation, wear suitable respiratory equipment. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: 2206
RTECS: NQ9600000
HazardClass: 6.1(b)
PackingGroup: III

5. Use of 1,5-Naphthalene diisocyanate
1,5-Naphthalene diisocyanate is used as intermediate.

6. Other details of 1,5-Naphthalene diisocyanate
1,5-Naphthalene diisocyanate should be keep away from heat, sparks, and flame. keep away from sources of ignition. and stored in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.