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3173-72-6

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3173-72-6 Usage

Description

Naphthalene diisocyanate (NDI) occurs as white to lightyellow crystalline flakes with a characteristic odor. NDI is 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. NDI can react with water to form amines and liberate carbon dioxide.

Chemical Properties

Naphthylene 1,5-diisocyanate is a solid, m.p. 128°C. It has a lower vapour pressure than tolylene diisocyanate and is therefore less toxic in use; it does, however, have sensitizing properties.

Uses

Different sources of media describe the Uses of 3173-72-6 differently. You can refer to the following data:
1. Manufacture of polyurethane solid elastomers.
2. Naphthylene 1,5-diisocyanate is mainly used for the production of elastomers.
3. NDI is used as a curing agent in the manufacture of elastomers.

Preparation

Naphthylene 1,5-diisocyanate (NDI) is prepared from naphthalene as follows:

General Description

White to light-yellow crystalline flakes.

Reactivity Profile

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)].

Flammability and Explosibility

Nonflammable

Safety Profile

A powerful allergen. An irritant. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NOx.

Environmental Fate

NDI is a synthetic organic chemical. It is a natural derivative of primary amines with the general formula R–N]C]O which does not occur naturally in the environment. At room temperature it can be a liquid or crystal. It is miscible with alcohol, diglycol, monoethyl ether, ether, acetone, carbon tetrachloride, benzene, chlorobenzene, kerosene, and olive oil; however, it may react violently with alcohol, water, acid, bases, and strong alkaline materials and tertiary amines and generate enough heat to self-ignite and release toxic combustion products. NDI is not readily biodegradable; however, it reacts with water and most acids producing unstable carbonic acids, which subsequently decarboxylate yielding relatively chemically inert and insoluble polymeric urea. While these polyureas are persistent, studies have indicated that they pose virtually no potential for adverse impacts on the aquatic environment. Due to hydrolysis in water, bioaccumulation of NDI is not expected. Since the hydrolysis products formed are irritants, there is a potential for inhalation exposure. The degree stability is a function of humidity.

Toxicity evaluation

The toxicological properties of isocyanates are attributed to the –N=C=O group. It is thought to react vigorously and exothermically with water forming an unstable carbamic acid that dissociates to form a primary amine with liberation of CO2. Hence, the primary amine will react further generating a urea derivative. Isocyanates also react readily with all organic compounds resulting in polymerization. Such reactions denature proteins, form abnormal crosslinkages, and generally disorganize the protein resulting in alteration of its normal function. This reactivity with proteins can account for its potency as a sensitizing agent. An IgE- or IgG-mediated mechanism has been proposed, but has not been definitively linked to isocyanate exposure. There is also evidence that inflammation and morphological changes of the bronchia mucosa and direct neurogenic mechanisms could be involved in the mechanics of toxicity. Thus, more than one reaction may occur in a system at a given time.

Check Digit Verification of cas no

The CAS Registry Mumber 3173-72-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,7 and 3 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 3173-72:
(6*3)+(5*1)+(4*7)+(3*3)+(2*7)+(1*2)=76
76 % 10 = 6
So 3173-72-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H6N2O2/c15-7-13-11-5-1-3-9-10(11)4-2-6-12(9)14-8-16/h1-6H

3173-72-6 Well-known Company Product Price

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  • TCI America

  • (N0168)  1,5-Diisocyanatonaphthalene  >98.0%(GC)

  • 3173-72-6

  • 25g

  • 220.00CNY

  • Detail
  • TCI America

  • (N0168)  1,5-Diisocyanatonaphthalene  >98.0%(GC)

  • 3173-72-6

  • 100g

  • 690.00CNY

  • Detail

3173-72-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,5-Naphthalene diisocyanate

1.2 Other means of identification

Product number -
Other names 1,5-Naphthalene diis

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Paint additives and coating additives not described by other categories
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3173-72-6 SDS

3173-72-6Synthetic route

1,5-bis-(butoxycarbonylamino)-naphthalene
124244-58-2

1,5-bis-(butoxycarbonylamino)-naphthalene

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

Conditions
ConditionsYield
1,2-dimethyl-3-ethylimidazole perchloric acid at 190 - 240℃; under 37.5038 Torr; for 2.16667h;91%
1,5-bis-(ethoxycarbonylamino)naphthalene
51977-17-4

1,5-bis-(ethoxycarbonylamino)naphthalene

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

Conditions
ConditionsYield
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.
dimethyl 1,5-naphthalenedicarbamate
63896-10-6

dimethyl 1,5-naphthalenedicarbamate

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

Conditions
ConditionsYield
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;
phosgene
75-44-5

phosgene

1,5-diaminonaphthalene
2243-62-1

1,5-diaminonaphthalene

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

Conditions
ConditionsYield
In various solvent(s) for 1.5h; Condensation; Heating;23%
phosgene
75-44-5

phosgene

1.5-diamino-naphthalene dihydrochloride

1.5-diamino-naphthalene dihydrochloride

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

phosgene
75-44-5

phosgene

naphthalene-1,5-diyldiamine dihydrochloride

naphthalene-1,5-diyldiamine dihydrochloride

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

Conditions
ConditionsYield
With chlorobenzene; 1,2-dichloro-benzene at 140 - 160℃;
With phenylsulfonyl fluoride at 90℃;
With benzene at 140℃; under 19858.7 Torr;
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

diethylamine
109-89-7

diethylamine

1,5-bis(3,3-diethylureido)naphthalene
41915-94-0

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

Conditions
ConditionsYield
In toluene98%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

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

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

Conditions
ConditionsYield
With dimethyl amine In toluene97%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

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

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

C34H30N2O8

C34H30N2O8

Conditions
ConditionsYield
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%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

2-hydroxyethyl acrylate
818-61-1

2-hydroxyethyl acrylate

C22H22N2O8

C22H22N2O8

Conditions
ConditionsYield
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%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

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

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

Conditions
ConditionsYield
In tetrahydrofuran Reflux;80%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

4-(hexyloxy)pyridin-3-amine

4-(hexyloxy)pyridin-3-amine

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

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

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In dichloromethane Inert atmosphere;73%
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

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

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

Conditions
ConditionsYield
In dichloromethane Inert atmosphere;73%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

12-Aminododecanoic acid
693-57-2

12-Aminododecanoic acid

C36H56N4O6

C36H56N4O6

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; Inert atmosphere;67%
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

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

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

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

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

Conditions
ConditionsYield
In toluene at 65℃; for 4h; Schlenk technique; Inert atmosphere;59%
methanol
67-56-1

methanol

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

dimethyl 1,5-naphthalenedicarbamate
63896-10-6

dimethyl 1,5-naphthalenedicarbamate

ethanol
64-17-5

ethanol

1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

1,5-bis-(ethoxycarbonylamino)naphthalene
51977-17-4

1,5-bis-(ethoxycarbonylamino)naphthalene

Conditions
ConditionsYield
With 1,4-dioxane at 105℃;
In toluene at 40℃;
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

2,2'-diacetyl-N,N'-naphthalene-1,5-diyl-bis-malonamic acid diethyl ester
114400-15-6

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

Conditions
ConditionsYield
With sodium; benzene
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

ethylene glycol
107-21-1

ethylene glycol

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

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

Conditions
ConditionsYield
With 1,4-dioxane at 105℃;
1,5-diisocyanatonaphthalene
3173-72-6

1,5-diisocyanatonaphthalene

ethanolamine
141-43-5

ethanolamine

1-(2-Hydroxy-ethyl)-3-{5-[3-(2-hydroxy-ethyl)-ureido]-naphthalen-1-yl}-urea
30042-58-1

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

Conditions
ConditionsYield
In chloroform
(rac)-gossypol
303-45-7

(rac)-gossypol

1,5-diisocyanatonaphthalene
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)

((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
ConditionsYield
In toluene at 85℃; Inert atmosphere;

3173-72-6Relevant articles and documents

Method for synthesizing 1,5-naphthalene diisocyanate

-

Paragraph 0034; 0037-0038; 0041-0042, (2019/10/04)

The invention discloses a method for synthesizing 1,5-naphthalene diisocyanate. The method comprises the following steps: 1) synthesizing 1,5-naphthalene dicarbamate from 1,5-naphthalene diamine and an auxiliary material A; 2) pyrolyzing the 1,5-naphthale

Process for the preparation of 5-nitro-3,4-dihydro-1(2H)-naphthalenone, 1,5-naphthalendiamine and 1,5-naphthalendiisocyanate

-

Page 8, (2008/06/13)

A process for the production of 1,5-naphthalene diamine (I) comprises reaction of 4-(2-nitrophenyl)-n-butyronitrile to 4-(2-nitrophenyl)-n-butyric acid. Independent claims are included for: (1) a process for the production of 5-nitro-3,4-dihydro-1(2H)-naphthalinone by reaction of 4-(2-nitrophenyl)-n-butyronitrile to 4-(2-nitrophenyl)-n-butyric acid and; (2) a process for the production of 1,5-naphthalene diisocyanate by phosgenation of 1,5-naphthalene diamine (I).

Linking metal centres with diimido ligands: Synthesis, electronic and molecular structure and electrochemistry of organometallic ditungsten complexes [{WCl2(Ph2PMe)2(CO)}2(N-X-N)] (X = π-conjugated organic)

Hogarth, Graeme,Humphrey, David G.,Kaltsoyannis, Nikolas,Kim, Woo-Sung,Lee, Mo-Yin,Norman, Tim,Redmond, Simon P.

, p. 2705 - 2723 (2007/10/03)

Tungsten(IV) diimido-bridged complexes [{WCl2(Ph2PMe)2(CO)}(μ-N-X-N)] have been prepared via oxidative addition of diisocyanates to two equivalents of [WCl2(Ph2PMe)4]. para-Substituted monoimido complexes [WCl2(Ph2PMe)2(CO)(NC6H 4X-p)] (X = I, Br or C≡CPh) have also been prepared but attempts to couple the X = I complex as a route to diimido-bridged complexes were unsuccessful. All complexes are air-stable crystalline solids and five diimido (N-X-N = p-NC6H4N, p-N-o-MeC6H3N, p-N(o-MeOC6H3C6H3OMe-o)N, 1,5-NC10H6N or m-NC6H4N) and one monoimido complex (X = I) have been characterised crystallographically. All show the same gross structural features, namely a trans arrangement of phosphines and cis chlorides. The central aryl ring generally lies approximately in the Cl2(CO) plane (torsional angles 4.1-26.1°) except for one complex in which the ring lies almost perpendicular to this (torsional angle 80.2°). A series of density functional calculations conducted on model mono- and di-imido tungsten-(VI) and -(V) compounds indicated that the most stable aryl ring orientation is perpendicular to the plane containing the trans phosphines, i.e. as found in all cases except one (N-X-N = p-NC6H4N). The anomaly in the latter may be due to cocrystallisation with chlorobenzene. In order to assess the degree of communication between the tungsten(IV) centres through the highly π-conjugated diimido linkages, electrochemical studies have been carried out. All diimido-bridged complexes show two closely spaced oxidative processes at low temperature indicative of weak electronic communication. The reductive chemistry of the para-phenylene bridged complexes is different from other diimido complexes, displaying two closely spaced reductive processes. Spectro-electrochemical studies have also been carried out on N-X-N = p-NC6H4N, oxidation at +1.2 V leading to CO loss. In order to gain further insight into the nature of the electronic communication between metal centres density functional calculations were carried out and were generally in agreement with the electrochemical results, suggesting that there is at best a weak interaction between the metal centres in these π-conjugated diimido-bridged complexes.

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