ALLYL ISOCYANATE

• CAS: 1476-23-9
• Catalog Number: ACM1476239
• Category: Main Products
• Molecular Weight: 83.09
• Molecular Formula: C4H5NO
• Synonyms: 3-isocyanato-1-propen
• Boiling Point: 87-89 °C
• Density: 0.94 g/mL
• Appearance: Colorless liquid

Case Study

Allyl Isocyanate for the Preparation of Dex-AE Precursor for pH-Sensitive Biodegradable Hydrogels

Sun, Guoming, et al. Carbohydrate polymers, 2006, 65(3), 273-287.

In this study, polyethylene glycol-diacrylate (PEGDA) was chemically incorporated into dextran-allyl isocyanate-ethylamine (Dex-AE) by photocrosslinking, and a hybrid biodegradable hydrogel with pH sensitivity was successfully prepared. Dex-AE/PEGDA hydrogel demonstrated higher protein loading and sustained release capacity compared to pure PEGDA hydrogel, and that these was augmented with addition of Dex-AE component.
Preparation procedure of Dex-AE precursor
First, dextran reacted with allyl isocyanate (AI) in the presence of a DBTDL catalyst. Specifically, 2 g of dry dextran was dissolved in 24 mL of anhydrous DMSO under a dry nitrogen atmosphere at room temperature (22 °C). The DBTDL catalyst (0.73 mL) was added dropwise to the solution, followed by the dropwise addition of AI (1.09 mL). The reaction was stirred for 6 hours at 22 °C. The resulting polymer Dex-AI (with a degree of substitution of 0.25) was then used in the next step after precipitation, purification and drying.
Dex-AE was subsequently synthesized from Dex-AI to introduce free amine groups. At a predetermined temperature of 50 °C, 2.0 g of dry Dex-AI was dissolved in 20 mL of anhydrous DMSO under a dry nitrogen atmosphere. Triethylamine (11.2 mL) was added to this solution, followed by the dropwise addition of a DMSO solution of BEAHB (7.5 g in 10 mL). The mixture was stirred at 50 °C for set intervals (2, 4, 6, and 8 hours), and the resulting solution was filtered to eliminate the precipitated Et3NH4Br. The Dex-AE polymer was obtained by precipitating the filtered solution in excess cold isopropyl alcohol, followed by at least three purification cycles involving dissolution and precipitation with DMSO and cold isopropanol. The final product was dried overnight under vacuum at room temperature prior to further use.

Allyl Isocyanate Modified Graphene Oxide for Polyurethane Composites

Yoon, S. H., et al. Colloid and Polymer Science, 2011, 289, 1809-1814.

Waterborne polyurethane (WPU)/allyl isocyanate modified graphene oxide (iGO) nanocomposites were synthesized via UV curing. The results showed that iGO incorporated into WPU chains can act as a multifunctional cross-linker and reinforcing filler. When the iGO content reaches 1%, the mechanical properties and thermal stability of WPU are significantly improved. Above this content, the above properties decrease, which may be due to the auto-inhibitory effect of allyl compounds.
Preparation of Allyl iGO
· GO (1.2 g) was introduced into a 500 ml round-bottom flask equipped with a stirrer and placed under a nitrogen atmosphere. Anhydrous DMF (120 ml) was added to form an inhomogeneous suspension. Allyl isocyanate (3.99 g) was then incorporated and stirred for 5 days. After the reaction, the mixture was transferred to methylene chloride (2.4 L) to precipitate the product, which was subsequently filtered, washed, and dried via lyophilization.
Synthesis of Waterborne Polyurethane/iGO Nanocomposite
· PCL diol (Mn=530 g/mol) was placed in a 500 ml four-necked flask fitted with a mechanical stirrer, thermometer, and condenser with a drying tube. Molar excesses of IPDI and DMBA were reacted at 70 °C. The NCO-terminated polyurethane was end-capped with HEA at 55 °C, resulting in a polyurethane with a molecular weight of approximately 3,000. HEA-capped polyurethane and GO/iGO dissolved in DMF were added to the flask and allowed to cool to room temperature, whereupon the carboxylic acid groups were neutralized with TEA. Water was added to the mixture to achieve a solid content of around 30%, yielding the waterborne polyurethane (WPU). Finally, this mixture was cast onto a polyethylene film and partially dried before being cured under a UV lamp (365 nm, 8 W, Crosslink) for 2 hours at ambient conditions.

Custom Q&A

What is the molecular formula of allyl isocyanate?

The molecular formula of allyl isocyanate is C4H5NO.

What is the molecular weight of allyl isocyanate?

The molecular weight of allyl isocyanate is 83.09 g/mol.

What is the IUPAC name of allyl isocyanate?

The IUPAC name of allyl isocyanate is 3-isocyanatoprop-1-ene.

What is the InChI key of allyl isocyanate?

The InChI key of allyl isocyanate is HXBPYFMVGFDZFT-UHFFFAOYSA-N.

How many hydrogen bond acceptor counts does allyl isocyanate have?

Allyl isocyanate has 2 hydrogen bond acceptor counts.

What is the topological polar surface area of allyl isocyanate?

The topological polar surface area of allyl isocyanate is 29.4 Å2.

What is the heavy atom count of allyl isocyanate?

The heavy atom count of allyl isocyanate is 6.

Does allyl isocyanate have any defined atom stereocenter count?

No, allyl isocyanate does not have any defined atom stereocenter count.

What is the formal charge of allyl isocyanate?

The formal charge of allyl isocyanate is 0.

Is the compound canonicalized for allyl isocyanate?

Yes, the compound is canonicalized for allyl isocyanate.

Synthetic Use

Upstream Synthesis Route 1

• 1025-15-6

• 1476-23-9

Reference: [1]Patent: US2580468,1949,

Downstream Synthesis Route 1

• 1476-23-9

• 1025-15-6

Reference: [1] Organic Letters, 2004, vol. 6, # 25, p. 4679 - 4681
[2] Catalysis Communications, 2010, vol. 12, # 3, p. 226 - 230
[3] Journal of Organic Chemistry, 1994, vol. 59, # 17, p. 4931 - 4938
[4] Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1520 - 1524
[5] Tetrahedron, 2011, vol. 67, # 8, p. 1530 - 1535

Downstream Synthesis Route 2

• 1454-85-9
• 1476-23-9

• 102899-71-8

Reference: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1959,vol. 317,p. 43,46

Downstream Synthesis Route 3

• 1476-23-9

• 1801-72-5

Reference: [1]Perveen, Shahnaz; Abdul Hai, Syed M.; Khan, Rashid A.; Khan, Khalid Mohammed; Afza, Nighat; Sarfaraz, Tahira B.
[Synthetic Communications, 2005, vol. 35, # 12, p. 1663 - 1674]

* For details of the synthesis route, please refer to the original source to ensure accuracy.