112-96-9

Basic information

• Product Name: Octadecyl isocyanate
• Synonyms: 1-isocyanato-octadecan;75%;Baykanol OI;baykanoloi;Bykanol OI;millionateo;Mondur O;monduro
• CAS NO: 112-96-9
• Molecular Formula: C₁₉H₃₇NO
• Molecular Weight: 295.5
• EINECS: 204-019-7
• Product Categories: Intermediates of Dyes and Pigments;Isocyanates;Nitrogen Compounds;Organic Building Blocks;Wool softener, polyurethane additives;organic chemical;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 112-96-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 15-16 °C(lit.)
• Boiling Point: 172-173 °C5 mm Hg(lit.)
• Flash Point: 365 °F
• Appearance: Colorless and slightly turbid liquid
• Density: 0.847 g/mL at 25 °C(lit.)
• Vapor Pressure: 1 mm Hg ( 154 °C)
• Refractive Index: n20/D 1.45(lit.)
• Storage Temp.: 2-8°C
• Solubility: soluble in Benzene,Toluene
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Octadecyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecyl isocyanate(112-96-9)
• EPA Substance Registry System: Octadecyl isocyanate(112-96-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-43
• Safety Statements: 26-36/37-45
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 1
• RTECS: NR0140000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 112-96-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 112-96-9 differently. You can refer to the following data:
1. Octadecyl Isocyanate is a useful reagent for the surface modification of poly(Me methacrylate) (PMMA) to form PMMA surfaces terminated with well-ordered and highly crystalline octadecane chains.
2. Octadecyl isocyanate can be used as a modifier:For cellulose nanocrystals in the synthesis of poly(butylene adipate-co-terephthalate) (PBAT) based nanocomposites with improved mechanical and rheological properties.For lignin to effectively incorporate the lignin fillers in polyurethane matrix to prepare composites.It can be reacted with various amines to synthesize variety of unsymmetrical urea derivatives.
3. Octadecyl isocyanate (n-octadecyl isocyanate) was employed for chemical modification of:surface of cellulose nanocrystals to promote interfacial filler/matrix interactionspoly (2-hydroxyethyl methacrylate) (pHEMA) films, to investigate in vitro hemocompatibility assay using freshly drawn human whole bloodcellulose nanocrystals (or whiskers) and microfibrillated cellulose (MFC)

Safety Profile

Poison by intravenous route. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx. See also ISOCYANATES.

InChI:InChI=1/C19H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-19-21/h2-18H2,1H3

Synthetic route

bis(trichloromethyl) carbonate (32315-10-9) + 1-aminooctadecane (124-30-1) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With sodium carbonate In dichloromethane at 20℃; for 2h;	60%
In toluene at 20℃;

carbon disulfide (75-15-0) + 1-aminooctadecane (124-30-1) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With dihydrogen peroxide; diethylamine In tetrahydrofuran	29%

phosgene (75-44-5) + octadecylamine hydrochloride (1838-08-0) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With chlorobenzene
With xylene
With toluene
With chlorobenzene

toluene (108-88-3) + 1-aminooctadecane (124-30-1) + trichloromethyl chloroformate (503-38-8) → octadecyl isocyanate (112-96-9)

Conditions	Yield
at 60 - 70℃;

phosgene (75-44-5) + 1-aminooctadecane (124-30-1) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With toluene at 340℃;
With toluene at 340℃;

1-aminooctadecane (124-30-1) + trichloromethyl chloroformate (503-38-8) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With toluene anfangs bei 60-70grad,zuletzt bei Siedetemperatur;

octadecylamine hydrochloride (1838-08-0) + trichloromethyl chloroformate (503-38-8) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With toluene anfangs bei 60-70grad,zuletzt bei Siedetemperatur;

nonadecanoic acid (646-30-0) → octadecyl isocyanate (112-96-9)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In toluene

octadecanoyl azide (77165-65-2) → octadecyl isocyanate (112-96-9) + stearamide (124-26-5)

Conditions	Yield
With anthracene at 20℃; Kinetics; Reagent/catalyst; Photolysis;

octadecyl isocyanate (112-96-9) + 2-amino-1,6-dihydro-4-(4'-nitrophenyl)-6-oxopyrimidine (168430-11-3) → 1-[6-(4-Nitro-phenyl)-4-oxo-1,4-dihydro-pyrimidin-2-yl]-3-octadecyl-urea

Conditions	Yield
With pyridine for 4h; Heating;	100%

3-aminopropyltriethoxysilane (919-30-2) + octadecyl isocyanate (112-96-9) → N-octadecyl-N'-(3-triethoxysilyl)propyl urea (106868-86-4)

Conditions	Yield
	100%
In chloroform for 12h; Reflux;	82%

3-(3,5,7,9,11,13,15-heptaisobutylpentacyclo[9,5,1,1(3,9),1(7,13),1(5,15)]octasiloxane-1-yl)propylamine (444315-15-5) + octadecyl isocyanate (112-96-9) → C50H108N2O13Si8 (1021693-08-2)

Conditions	Yield
In toluene at 20℃; for 2h;	100%

octadecyl isocyanate (112-96-9) + allyl alcohol (107-18-6) → allyl octadecylcarbamate (114320-46-6)

Conditions	Yield
With dibutyltin(II) dilaurate at 70℃; for 24h;	99%

octadecyl isocyanate (112-96-9) + ((1R,2S,3S,4S)-3-Methoxymethoxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)-methanol → Octadecyl-carbamic acid (1S,2R,3R,4R)-3-methoxymethoxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Conditions	Yield
With pyridine	98%

5-methylene-1,3-thiazolidine-2-thione (52829-72-8) + octadecyl isocyanate (112-96-9) → 5-methylene-2-thioxo-thiazolidine-3-carboxylic acid octadecylamide

Conditions	Yield
With potassium carbonate; triethylamine In toluene at 20℃; for 24h;	98%
With Yb(C8F17SO3)3 In toluene at 20℃; for 24h;	97%

octadecyl isocyanate (112-96-9) + [1-(hydroxymethyl)cyclobutyl]methanol (4415-73-0) → 2-[[N-Acetyl-N-[[[1-[[(octadecylcarbamoyl)oxy]methyl]-1-cyclobutyl]methoxy]carbonyl]amino]methyl]-1-ethyl-pyridinium iodide (156719-61-8)

Conditions	Yield
With di(n-butyl)tin oxide In tetrahydrofuran	98%

toluene-ethyl acetate + 3-benzyloxy-2-methoxypropylthioalcohol + octadecyl isocyanate (112-96-9) → 3-benzyloxy-2-methoxy-1-octadecylcarbamoylthiopropane (126271-17-8)

Conditions	Yield
In pyridine	98%

octadecyl isocyanate (112-96-9) + 5-methylene-1,3-oxazolidin-2-one (369650-98-6) → 5-methylene-2-oxo-oxazolidine-3-carboxylic acid octadecylamide

Conditions	Yield
With Yb(C8F17SO3)3 In toluene at 20℃;	97%
With triethylamine In toluene at 20℃; for 24h;	97%

octadecyl isocyanate (112-96-9) + 3-tert-butylaniline (5369-19-7) → C29H52N2O

Conditions	Yield
In 1,2-dichloro-ethane at 70℃; for 20h; Inert atmosphere;	96%

octadecyl isocyanate (112-96-9) + C27H55N3O6Si3 → C46H92N4O7Si3

Conditions	Yield
In dichloromethane at 20℃; for 6h; Inert atmosphere;	95%
In dichloromethane at 20℃; for 6.03333h; Inert atmosphere;	95%

octadecyl isocyanate (112-96-9) + oxiranyl-methanol (556-52-5) → O-(Octadecylcarbamoyl)glycidol

Conditions	Yield
With pyridine In dichloromethane Ambient temperature;	93%

octadecyl isocyanate (112-96-9) + Nε-lauroyl-L-lysine ethyl ester (292140-08-0) → Nε-lauroyl-Nα-stearylaminocarbonyl-L-lysine ethyl ester

Conditions	Yield
In toluene at 90℃;	93%

octadecyl isocyanate (112-96-9) + cyclohexanecarboxylic acid(3-aminophenyl)amide (43096-46-4) → cyclohexanecarboxylic acid[3-(3-octadecylureido)phenyl]amide

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	91%

piperazine + octadecyl isocyanate (112-96-9) → N-octadecylaminocarbonylpiperazine (540527-76-2)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	91%
In dichloromethane at 20℃; for 1h;	91%

4'-aminobenzo-15-crown-5-ether (60835-71-4) + octadecyl isocyanate (112-96-9) → 4-octadecylurea-benzo-15-crown-5

Conditions	Yield
In acetonitrile for 12h; Reflux;	90%
In acetonitrile for 5h; Heating;	85.8%

octadecyl isocyanate (112-96-9) + 1-O-benzyl-2-O-methyl-sn-glycerol (70259-28-8) → 1-O-benzyl-2-O-methyl-3-O-(octadecylcarbamoyl)-sn-glycerol (116953-51-6)

Conditions	Yield
With pyridine In dichloromethane for 20h; Ambient temperature;	89%

octadecyl isocyanate (112-96-9) + N-acetyl-3-(1,1-dimethylethyl)-4-hydroxy-N-(2-pyridinylmethyl)benzamide (147236-25-7) → 4--2-(1,1-dimethylethyl)phenyl octadecylcarbamate (147219-66-7)

Conditions	Yield
With triethylamine In tetrahydrofuran for 22h; Ambient temperature;	88%

2-(2-benzoyloxypropan-1-yl)-3-hydroxypropyl benzoate + octadecyl isocyanate (112-96-9) → 2-(2-benzoyloxypropan-1-yl)-3-octadecylcarbamoyloxypropyl benzoate (126271-86-1)

Conditions	Yield
With hydrogenchloride In pyridine	87.8%

octadecyl isocyanate (112-96-9) + aniline (62-53-3) → N-octadecyl-N'-phenyl-urea (4128-43-2)

Conditions	Yield
In acetonitrile at 90℃; for 17h; Time; Inert atmosphere;	87%
In benzene

octadecyl isocyanate (112-96-9) + 4-aminobenzo-18-crown-6 (68941-06-0) → 4-octadecylurea-benzo-18-crown-6

Conditions	Yield
In acetonitrile for 5h; Heating;	87%

octadecyl isocyanate (112-96-9) → 1-(3-Octadecylcarbamoyloxy-2-methoxypropyl)-3-(2-benzyloxyethyl)uracil (100489-11-0)

Conditions	Yield
In pyridine	87%

ferrocene (102-54-5) + octadecyl isocyanate (112-96-9) → N-octadecylferrocenecarboxamide

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; for 6h; Inert atmosphere;	87%
With aluminium trichloride	58%
With AlCl3	58%

octadecyl isocyanate (112-96-9) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → Octadecyl-carbamic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Conditions	Yield
With pyridine In chloroform at 50 - 60℃; for 72h;	86%
With pyridine; dmap at 50℃;

3-Amino-1,2-propanediol (616-30-8, 13552-31-3) + octadecyl isocyanate (112-96-9) → (+/-)-3-(3-octadecylureido)-1,2-propanediol (112989-05-6)

Conditions	Yield
In pyridine; N,N-dimethyl-formamide for 3h;	84%

octadecyl isocyanate (112-96-9) + 3,5-di-tert-butylaniline (2380-36-1) → C33H60N2O

Conditions	Yield
In 1,2-dichloro-ethane at 70℃; for 23h; Inert atmosphere;	84%

octadecyl isocyanate (112-96-9) + (R,S)-methyl 3-hydroxy-2-(N-tritylamino) propionate (13515-76-9) → O-octadecylcarbamoyl-N-tritylserine methyl ester (126271-42-9)

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 16h;	83%
In ice-water; hexane; ethyl acetate; N,N-dimethyl-formamide	82.6%

octadecyl isocyanate (112-96-9) + 6,7-dihydroxy-4-thiaheptanoic acid t-butyl ester (167768-00-5) → 7-octadecylcarbamoyloxy-4-thiaheptanoic acid t-butyl ester

Conditions	Yield
With 2-(Dimethylamino)pyridine In 1,1-dichloroethane	83%

octadecyl isocyanate (112-96-9) + cyclohexanecarboxylic acid(4-aminophenyl)amide (351437-78-0) → N-[4-(3-octadecylureido)phenyl]cyclohexanecarboxamide

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	82%
In tetrahydrofuran for 2h; Heating;

octadecyl isocyanate (112-96-9) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,2-Dimethyl-3-(octadecylcarbamoyloxy)-1-propanol

Conditions	Yield
With sodium bicarbonate; sodium chloride; triethylamine In dichloromethane	82%
With sodium bicarbonate; sodium chloride; triethylamine In dichloromethane	82%

Upstream product

• 75-44-5 phosgene 
• 1838-08-0 octadecylamine hydrochloride 
• 108-88-3 toluene 
• 124-30-1 1-aminooctadecane 
• 503-38-8 trichloromethyl chloroformate 
• 646-30-0 nonadecanoic acid 
• 75-15-0 carbon disulfide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 77165-65-2 octadecanoyl azide 

Downstream Products

• 3891-29-0 aziridine-1-carboxylic acid octadecylamide 
• 10212-58-5 2-methyl-aziridine-1-carboxylic acid octadecylamide 
• 95851-33-5 N-octadecyl-lauramide 
• 25151-31-9 N,N'-dioctadecyl-adipamide 
• 35081-84-6 N,N'-dioctadecyl-decanediamide 
• 103045-26-7 3-(5-methyl-3-octadecyl-2,4-dioxo-imidazolidin-1-yl)-propionic acid 
• 2158-08-9 octadecylurea 
• 13276-08-9 N-(octadecanoyl)octadecylamide 
• 4051-66-5 N,N’-dioctadecyl urea 
• 6268-60-6 octadecyl-carbamic acid ethyl ester 
• 38428-58-9 Octadecyl-carbamic acid phenethyl ester 
• 38428-60-3 Octadecyl-carbamic acid 1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethyl ester 
• 14572-55-5 Octadecyl-carbamic acid 3,4,6-trichloro-2-nitro-phenyl ester 
• 14571-78-9 Octadecyl-carbamic acid 2,4-dichloro-6-nitro-phenyl ester 

Relevant articles and documents

Sensitized photolysis of stearic acid azide

In an IR-spectroscopic study of the sensitized photolysis of stearic acid azide in a solution of benzene, it was found that the introduction of Michler's ketone into the system decreased the efficiency of isocyanate formation by a factor of about 10. It was hypothesized that the azide photolysis in the presence of Michler's ketone can be explained by the formation of a complex of the acyl azide with the ketone in a triplet excited state, a displacement of electron density from the acyl azide group, and its degradation with the formation of a triplet acylnitrene, which is incapable of rearranging into isocyanate.

WATER-SOLUBLE POLYSACCHARIDE ETHERS AND THEIR USE

The invention relates to modified polysaccharide ethers having a weight-averaged molecular weight of 40000 to 50000 g/mole, zero shear viscosity of more than 10 Pas, and pseudoplasticity of more than 20, obtainable by reacting cellulose-based polysaccharide ether(s) with at least one mesogenic modification agent or modified polysaccharide ethers, obtainable by reacting polysaccharide ether(s) selected from the group consisting of hydroxypropylmethyl cellulose (HPMC), hydroxyethylmethyl cellulose (HEMC), methyl cellulose, and cellulose ethers with methyl and/or ethyl and/or propyl groups and mixtures thereof, with at least one mesogenic modification agent. Said substances can be used to produce gel-like to stable aqueous preparations having viscoelastic flow properties, which are suited for use in the human body, particularly within the scope of ophthalmologic procedures.

Phase change ink formulation

Colored waxes are made by reacting selected nucleophiles, including alcohol containing colorants with an isocyanate are disclosed. A phase change ink is made by blending the colored wax with a clear ink carrier composition. The clear ink carrier composition can be a fatty amide-based material and/or a combination of isocyanate-derived resins in which the order ofaddition of the isocyanate and the different nucleophiles can tailor the distribution of di-urethane, mixed urethane/urea, and/or diurea molecules in the final resin product. The colored wax materials are useful as ingredients with phase change ink carrier compositions to make phase change ink jet inks.