3729-19-9

Basic information

• Product Name: 3-Isocyanatopropanoylchloride
• Synonyms: 3-Isocyanatopropanoylchloride
• CAS NO: 3729-19-9
• Molecular Formula: C₄H₄ClNO₂
• Molecular Weight: 133.53306
• Mol File: 3729-19-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Isocyanatopropanoylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isocyanatopropanoylchloride(3729-19-9)
• EPA Substance Registry System: 3-Isocyanatopropanoylchloride(3729-19-9)

Safety Data

• Hazardous Substances Data: 3729-19-9(Hazardous Substances Data)

Usage

Preparation

Diphosgene is toxic. The reaction should be carried out in a well-ventilated hood. A 500-mL, twonecked flask was equipped with a thermometer and a reflux condenser protected at the top by a calcium chloride guard tube. A Teflon-coated magnetic stirring bar, anhydrous dioxane (250 mL), finely pulverized 3-aminopropanoic acid hydrochloride 1342 (b-alanine HCl) (12.6 g, 0.1 mol), and diphosgene (23.8 g, 14.4 mL, 0.12 mol) were placed in the flask in the order specified. The mixture was stirred and heated at 55–60 C°. After ca. 5 h, the solid had completely dissolved to give a clear solution. Heating was discontinued after a total of 7 h and the solvent was removed under reduced pressure. The residual oil was rapidly distilled under reduced pressure and a distillate amounting to 11.2–12.4 g (84–93%) was collected at 75–85 C°/20 mmHg. Redistillation afforded 10.5–11.8 g (79–88%) of 3-isocyanatopropanoyl chloride 1343 as a colorless liquid (bp 92–94 C°/25 mmHg). Comment: Although the reaction can be carried out with an equimolar amount of trichloromethyl chloroformate, a longer time (15–20 h) is required to reach completion, and the yield is somewhat reduced. If a 1.5–2.0-fold excess of trichloromethyl chloro-formate is used, the reaction time is decreased to ca. 5 h and the yield is increased to 90–95%. Organic acid chlorides have been prepared with diphosgene in the presence of DMF as a catalyst.

Upstream product

• 75-44-5 phosgene 
• 6057-90-5 β-alanine hydrochloride 
• 27762-02-3 N-Silyloxycarbonyl-β-alanin-trimethylsilylester 
• 503-38-8 trichloromethyl chloroformate 
• 107-95-9 3-amino propanoic acid 
• 3196-73-4 methyl 3-aminopropanoate hydrochloride 
• 4244-84-2 ethyl β-alaninate hydrochloride 

Downstream Products

• 5100-12-9 3-<3-(4-Aethoxy-phenyl)-ureido>-propionsaeure-p-phenetidid 
• 75-77-4 chloro-trimethyl-silane 
• 114503-07-0 3-Isocyanato-propionic acid 4-(3-isocyanato-propionyloxy)-butyl ester 
• 115345-78-3 3-Isocyanato-propionic acid phenyl ester 

Relevant articles and documents

Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is required after phosgeneation. Unusual generation of cynnamates and intramolecular N→O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic β-aminoacid esters were found. Pleiades Publishing, Inc., 2006.

The preparation of amino acid N-carboxyamhydrides (NCAs) from N-siloxycarbonyl amino acid trimethylsily esters

-