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Octadecyl isocyanate

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Name

Octadecyl isocyanate

EINECS 204-019-7
CAS No. 112-96-9 Density 0.87g/cm3
PSA 29.43000 LogP 6.58370
Solubility N/A Melting Point 15-16 °C(lit.)
Formula C19H37NO Boiling Point 317.7 °C at 760 mmHg
Molecular Weight 295.509 Flash Point 144.9 °C
Transport Information UN 2206 6.1/PG 3 Appearance Colorless and slightly turbid liquid
Safety 26-36/37-45 Risk Codes 20/21/22-36/37/38-43
Molecular Structure Molecular Structure of 112-96-9 (Octadecyl isocyanate) Hazard Symbols HarmfulXn
Synonyms

Isocyanicacid, octadecyl ester (6CI,7CI,8CI);1-Isocyanatooctadecane;1-Octadecylisocyanate;Baykanol OI;Millionate O;Mondur O;NSC 66466;ODI;Stearyl isocyanate;n-Octadecyl isocyanate;

Article Data 20

Octadecyl isocyanate Synthetic route

32315-10-9

bis(trichloromethyl) carbonate

124-30-1

1-aminooctadecane

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With sodium carbonate In dichloromethane at 20℃; for 2h;60%
In toluene at 20℃;
75-15-0

carbon disulfide

124-30-1

1-aminooctadecane

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With dihydrogen peroxide; diethylamine In tetrahydrofuran29%
75-44-5

phosgene

1838-08-0

octadecylamine hydrochloride

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With chlorobenzene
With xylene
With toluene
With chlorobenzene
108-88-3

toluene

124-30-1

1-aminooctadecane

503-38-8

trichloromethyl chloroformate

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
at 60 - 70℃;
75-44-5

phosgene

124-30-1

1-aminooctadecane

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With toluene at 340℃;
With toluene at 340℃;
124-30-1

1-aminooctadecane

503-38-8

trichloromethyl chloroformate

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With toluene anfangs bei 60-70grad,zuletzt bei Siedetemperatur;
1838-08-0

octadecylamine hydrochloride

503-38-8

trichloromethyl chloroformate

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With toluene anfangs bei 60-70grad,zuletzt bei Siedetemperatur;
646-30-0

nonadecanoic acid

112-96-9

octadecyl isocyanate

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In toluene
77165-65-2

octadecanoyl azide

A

112-96-9

octadecyl isocyanate

B

124-26-5

stearamide

Conditions
ConditionsYield
With anthracene at 20℃; Kinetics; Reagent/catalyst; Photolysis;
112-96-9

octadecyl isocyanate

168430-11-3

2-amino-1,6-dihydro-4-(4'-nitrophenyl)-6-oxopyrimidine

1-[6-(4-Nitro-phenyl)-4-oxo-1,4-dihydro-pyrimidin-2-yl]-3-octadecyl-urea

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

Octadecyl isocyanate Consensus Reports

Reported in EPA TSCA Inventory.

Octadecyl isocyanate Standards and Recommendations

DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD (UN 2207); DOT Class: 6.1; Label: Poison (UN 2206); DOT Class: 6.1; Label: Poison, Flammable Liquid (UN 3080); DOT Class: 3; Label: Flammable Liquid, Poison (UN 2478)

Octadecyl isocyanate Specification

The IUPAC name of Octadecyl isocyanate is 1-isocyanatooctadecane. With the CAS registry number 112-96-9, it is also named as Stearyl isocyanate. The product's categories are Intermediates of Dyes and Pigments; Isocyanates; Nitrogen Compounds; Organic Building Blocks. It is colorless and slightly turbid liquid which is toxic and flammable by fire. In addition, it will produce toxic nitrogen oxide fumes when buring. So the storage environment should be ventilate, low-temperature and dry. Keep this chemical separate from oxidant, acid and food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 9.86; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.86; (4)ACD/LogD (pH 7.4): 9.86; (5)#H bond acceptors: 2; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 17 ; (8)Index of Refraction: 1.464; (9)Molar Refractivity: 93.83 cm3; (10)Molar Volume: 339.6 cm3; (11)Polarizability: 37.19×10-24 cm3; (12)Surface Tension: 31.7 dyne/cm; (13)Enthalpy of Vaporization: 53.69 kJ/mol; (14)Vapour Pressure: 0.000704 mmHg at 25°C; (15)Rotatable Bond Count: 17; (16)Exact Mass: 295.287515; (17)MonoIsotopic Mass: 295.287515; (18)Topological Polar Surface Area: 29.4; (19)Heavy Atom Count: 21; (20)Complexity: 234.

Preparation of Octadecyl isocyanate: Octadecylamine reacts with phosgene in chlorobenzene to get octadecylamine chloride, and then we can get the product by thermal decomposition and vacuum distillation. The following are the reaction equations:
CH3(CH2)17NH2+COCl2→CH3(CH2)17NHCOCl+HCl
CH3(CH2)17NHCOCl→CH3(CH2)17NCO+HCl

Uses of Octadecyl isocyanate: It is used as synthetic raw material of printing and dyeing assistant and wool textile softener VS. It also can react with 1(2)H-tetrazol-5-ylamine to get 5-amino-tetrazole-1-carboxylic acid octadecylamide. This reaction needs solvent pyridine at ambient temperature. The reaction time is 3 hours. The yield is 38%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure.
1. SMILES:O=C=N/CCCCCCCCCCCCCCCCCC
2. 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 

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04505,

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