Trichloroacetyl isocyanate

Base Information

• Chemical Name: Trichloroacetyl isocyanate
• CAS No.: 3019-71-4
• Deprecated CAS: 82631-56-9
• Molecular Formula: C3Cl3 N O2
• Molecular Weight: 188.397
• Hs Code.: 29291090
• European Community (EC) Number: 221-165-7
• UNII: QXV1P5J6JL
• DSSTox Substance ID: DTXSID7062790
• Nikkaji Number: J205.322E
• Wikidata: Q27287553
• Mol file: 3019-71-4.mol

Synonyms:CCl3CONCO;trichloroacetyl isocyanate

Chemical Property of Trichloroacetyl isocyanate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.677mmHg at 25°C
• Melting Point: 135-140 °C
• Refractive Index: n20/D 1.480(lit.)
• Boiling Point: 186 °C at 760 mmHg
• Flash Point: 65 ºC
• PSA: 46.50000
• Density: 1.581
• LogP: 1.21900
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with dichloromethane, ether, terahydrofuran and protic
• Water Solubility.: Decomposition
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 186.899461
• Heavy Atom Count: 9
• Complexity: 166

Purity/Quality:

99.9% ^*data from raw suppliers

2,2,2,-Trichloroacetyl isocyanate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 14-23/24-34-42-23/24/25-36/37/38
• Safety Statements: 23-26-36/37/39-45-8-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=NC(=O)C(Cl)(Cl)Cl)=O
• Uses: Trichloroacetyl isocyanate was used in catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrate. It was also used as a reagent for the conversion of alcohols to carbamates.

Technology Process of Trichloroacetyl isocyanate

There total 7 articles about Trichloroacetyl isocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

sodium isocyanate (917-61-3) + trifluoroacetyl chloride (76-02-8) → Trichloroacetyl isocyanate (3019-71-4)

Guidance literature:

In various solvent(s); at 130 - 170 ℃; for 7h;

DOI:10.1016/S0040-4020(01)89797-0

Reference yield: 52.0%

oxalyl dichloride (79-37-8) + trichloroacetamide (594-65-0) → Trichloroacetyl isocyanate (3019-71-4)

Guidance literature:

oxalyl dichloride; trichloroacetamide; at 70 ℃; for 24h;

at 100 - 140 ℃; for 25h;

Reference yield: 45.0%

tributyltin isocyanate (681-99-2) + trifluoroacetyl chloride (76-02-8) → Trichloroacetyl isocyanate (3019-71-4)

Guidance literature:

at 60 ℃; for 12h;

upstream raw materials:

oxalyl dichloride

trichloroacetamide

trichloroisocyanuric acid

trifluoroacetyl chloride

Downstream raw materials:

(2,2,2-Trichloro-acetyl)-thiocarbamic acid S-cyclohex-1-enyl ester

2-phenyl-1',3'-bis-trichloroacetyl-spiro[chromene-4,2'-[1,3]diazetidin]-4'-one

(2,2,2-Trichloro-acetyl)-carbamic acid 2-(2,2,2-trichloro-acetylcarbamoyl)-cyclohex-1-enyl ester

3-benzyl-2-phenyl-6-trichloromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one

Refernces

Chirality Transfer from a Chiral Primary Alcohol Equivalent Through Allyl Cyanate-to-Isocyanate Rearrangement: Synthesis of (+)-Geranyllinaloisocyanide

10.1055/s-0037-1612422

The research aims to develop a new approach for the construction of quaternary stereogenic centers bearing nitrogen substituents in an enantioselective manner. The strategy leverages the [1,3]-chirality transfer from a chiral primary alcohol equivalent through an allyl cyanate-to-isocyanate rearrangement. The efficiency of this approach was demonstrated in the eight-step synthesis of the marine natural product (+)-geranyllinaloisocyanide, achieving an overall yield of 43%. Key chemicals used in the process include chiral primary alcohol equivalent, allyl cyanate, isocyanate, and various reagents such as diethylzinc, trichloroacetyl isocyanate, potassium carbonate, trifluoroacetic anhydride, N,N-diisopropylethylamine, lithium triethylborohydride, and cesium fluoride, among others. The study concluded that the allyl cyanate-to-isocyanate rearrangement with enantiomerically enriched α-silyl allyl alcohol is a highly effective method for chirality transfer, showcasing its potential for further applications in the synthesis of nitrogen-containing natural products.

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