Basic information
- CAS
2877-26-1- Standard SMILES
CCCCCCCCCCCCCCCCCCN=C=S- InChIKey
VJIRSSFEIRFISD-UHFFFAOYSA-N- Molecular formula
- C19H37NS
- Average molar mass
- 311.6 g/mol
- Monoisotopic mass
- 311.26467136
Names & identifiers
- Preferred name
- Octadecane, 1-isothiocyanato-
- IUPAC
- 1-isothiocyanatooctadecane
- English name
- Octadecyl isothiocyanate
- Molecular formula
- C19H37NS
- Molecular weight
- 311.57
Names & synonyms
Octadecyl isothiocyanate2877-26-11-isothiocyanatooctadecaneOctadecane, 1-isothiocyanato-EINECS 220-722-1DTXSID0062680RefChem:855534DTXCID5037868220-722-1MFCD00041124Octadecane,1-isothiocyanato-C19H37NS
Show more names
Octadecyl isothiocyate1-isothiocyanato-octadecanN-OCTADECYL ISOTHIOCYANATEOCTADECYL ISOTHIOCYANATE 97%Octadecyl isothiocyanate,97%
VR5E4V8TRWSCHEMBL331790VJIRSSFEIRFISD-UHFFFAOYSA-NAKOS015839792NS00028540F009552
Database identifiers
- CAS
2877-26-1- PubChem CID
- 76140
- DTXSID
DTXSID0062680- UNII
- VR5E4V8TRW
- EC Number
- 220-722-1
- Nikkaji
- J306.797A
Properties
Computed structural properties
- XLogP
- 10.4
- Topological polar surface area
- 44.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 17
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 234
Physicochemical properties
- Melting point
- 29 · 29-33 °C
- Boiling point
- 140 · 140-142 °C(Press: 0.003 Torr)
- Density
- 0.9772 · 0.9772 (rough estimate)
- refractive index
- 1.53 · 1.5300 (estimate)
- InChI
- InChI=1S/C19H37NS/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-19-21/h2-18H2,1H3
- InChIKey
- VJIRSSFEIRFISD-UHFFFAOYSA-N
- SMILES
- C(N=C=S)CCCCCCCCCCCCCCCCC
- CAS DataBase Reference
- 2877 · 2877-26-1(CAS DataBase Reference)
- EPA Substance Registry System
- 1 · Octadecane, 1-isothiocyanato- (2877-26-1)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H335-H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
- Hazard Codes
- Xn
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
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- tsca
- TSCA listed
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37/39-26
- hazard_class
- IRRITANT
- Hazard statements
- H315-H335-H319
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationOctadecane, 1-isothiocyanato-: ACTIVE
Applications
UsesOctadecyl isothiocyanate is mainly used as a synthetic raw material for dyeing and printing auxiliaries and wool textile softener VS, and can also be used for surface treatment of waterproof fabrics.
Preparation methods
Preparationchemical synthesis method for Octadecyl isothiocyanate, using octadecylamine and bis(trichloromethyl) carbonate as raw materials, involves slowly adding a solution of octadecylamine dissolved in an organic solvent to a solution of bis(trichloromethyl) carbonate dissolved in the same organic solvent, while maintaining the reaction system temperature at 0–5°C. After the addition is complete, the mixture is stirred at room temperature for 0.5–5 hours, then heated to 35–150°C and reacted at this temperature for 0.5–10 hours. After the reaction is complete, the reaction solution is post-treated to obtain the Octadecyl isothiocyanate. The reaction equation is as follows: The molar ratio of octadecylamine to bis(trichloromethyl) carbonate is 1:1/3, the solvent is n-hexane, and the amount used is 2 mL/g based on the mass of octadecylamine. The specific steps are as follows: 29.7 g (0.1 mol) of bis(trichloromethyl) carbonate and 70 mL of n-hexane were added to a four-necked flask equipped with a mechanical stirrer, thermometer, constant-pressure dropping funnel, and reflux condenser. Stirring was started, and the mixture was cooled to 0–5 °C. A solution of 80.7 g (0.3 mol) of octadecylamine in 90 mL of n-hexane was added dropwise to the reaction system through the constant-pressure dropping funnel at a rate of approximately 1.5 mL/min. After the addition was complete, the mixture was stirred at room temperature for 0.5 h, then heated to 70 °C and reacted at 70–80 °C for approximately 2.5 h. After the reaction was complete, nitrogen gas was purged to purge hydrogen chloride gas. After recovering the n-hexane by vacuum distillation, 69.4 g of Octadecyl isothiocyanate was distilled off, yielding 78.2%. Gas chromatography determined the product purity to be 98.0%. Nuclear magnetic resonance (Bruke): ¹H NMR (300 MHz, CDCl₃): Δ (ppm) 3.28 (t, J = 6.68 Hz, 2H), 1.58–1.63 (m, 2H), 1.26–1.39 (m, 30H), 0.89 (t, J = 6.32 Hz, 3H); Infrared (AVATAR-370): IRvmax (KBr): 2925, 2854, 2270, 1462, 1356, 721 cm⁻¹.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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