1487-43-0

Basic information

• Product Name: 2-chloroethyl formate
• CAS NO: 1487-43-0
• Molecular Formula: C₃H₅ClO₂
• Molecular Weight: 108.5236
• Mol File: 1487-43-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 137.2°C at 760 mmHg
• Flash Point: 52.3°C
• Density: 1.165g/cm³
• Vapor Pressure: 7.13mmHg at 25°C
• Refractive Index: 1.403
• CAS DataBase Reference: 2-chloroethyl formate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloroethyl formate(1487-43-0)
• EPA Substance Registry System: 2-chloroethyl formate(1487-43-0)

Safety Data

• Hazardous Substances Data: 1487-43-0(Hazardous Substances Data)

Usage

General Description

2-Chloroethyl formate is a chemical compound with the formula C3H5ClO2. It is a colorless liquid with a pungent odor, and it is primarily used as an intermediate in the production of pharmaceuticals and agricultural chemicals. 2-Chloroethyl formate is known to be highly flammable and may react violently with a variety of chemicals such as strong oxidizing agents and strong bases. Exposure to this compound can cause irritation to the eyes, skin and respiratory tract, and may also lead to more serious health effects if ingested or inhaled in large amounts. Due to its hazardous nature, 2-Chloroethyl formate must be handled and stored with caution, following appropriate safety measures to prevent accidents and minimize risks to human health and the environment.

Upstream product

• 109-94-4 formic acid ethyl ester 
• 83498-70-8 2-(hexyloxy)-1,3-dioxolane 
• 67-66-3 chloroform 
• 56-23-5 tetrachloromethane 
• 4544-20-1 2-ethoxy-1,3-dioxolane 
• 75-36-5 acetyl chloride 
• 646-06-0 1,3-DIOXOLANE 

Downstream Products

• 122814-46-4 2-(2-phenoxytetrafluoroethyl)-1,3-dioxolane 
• 199273-09-1 5-Bromo-2-N-Boc-Amino-Benzyl Alcohol 
• 17380-74-4 1-phenylcyclopentylamine 
• 64-18-6 formic acid 
• 107-07-3 2-chloro-ethanol 
• 63938-99-8 formylcholine 

Relevant articles and documents

Study of the Reaction Cl + Ethyl Formate at 700-950 Torr and 297 to 435 K: Product Distribution and the Kinetics of the Reaction C2H5OC(=O) → CO2 + C2H5

The kinetics and mechanism of the reaction of atomic chlorine with ethyl formate [Cl + CH3CH2O(C=O)H, reaction 1] have been examined. These experiments were performed at pressures of 760-950 Torr and temperatures from 297 to 435 K. Reactants and products were quantified by gas chromatography-flame ionization detector (GC/FID) analysis. The initial mixture contained ethyl formate, Cl2, and N2. Cl atoms were generated by UV photolysis of this initial mixture at 360 nm, which dissociates Cl2. The rate constant of reaction 1 was measured at 297 K relative to that of the reaction Cl + C2H5Cl (reaction 2), yielding the rate constant ratio k1/k2 = 1.09 ± 0.05. The final products formed from reaction 1 are ethyl chloroformate, 1-chloroethyl formate, and 2-chloroethyl formate. These products result from the reactions with Cl2 of the three free radicals formed by H atom abstraction from ethylformate in reaction 1. Based on the molar yields of these three chlorinated products, the yields of the three radicals formed from reaction 1 at 297 K are (25 ± 3) mole percent of CH3CH2O(C=O); (67 ± 5) mole percent of CH3CHO(C=O)H; and (8 ± 2) mole percent of CH2CH2O(C=O)H. A second phase of this experiment measured the rate constant of the decarboxylation of the ethoxy carbonyl radical [CH3CH2O(C=O) → CO2 + C2H5, reaction 4] relative to the rate constant of its reaction with Cl2 [CH3CH2O(C=O) + Cl2 → CH3CH2O(C=O)Cl + Cl, reaction 3a]. Over the temperature range 297 to 404 K at 1 atm total pressure, this ratio can be expressed by k4/k3a = 1023.56±0.22 e-(12700±375)/RT molecules cm-3. Estimating the value of k3a (which has not been measured) based on similar reactions, the expression k4 = 5.8 × 1012 e-(12700)/RT s-1 is obtained. The estimated error of this rate constant is ± a factor of 2 over the experimental temperature range. This rate expression is compared with recent ab initio calculations of the decarboxylation of the analogous methoxy carbonyl radical.

FREE-RADICAL CHLORINATION OF ACETALS AND ORTHO ESTERS

The chlorination of 1,3-dioxolane and ortho esters (trihexyloxymethane and 2-hexyloxy-1,3-dioxolane) in the presence of azobisisobutyronitrile was studied. 2-Chloroethyl formate is formed in the case of dioxolane and 2-chloroethyl formate, ethylene carbonate, and hexyl chloride are formed in the case of 2-hexyloxy-1,3-dioxolane.

FREE-RADICAL TRANSFORMATIONS OF 2-ALKOXY-1,3-DIOXOLANES IN POLYHALOGENOALKANES

The free-radical transformations of 2-ethoxy-1,3-dioxolane and 2-hexyloxy-1,3-dioxolane in bromoform and chloroform were investigated.The products from these transformations are alkyl 2-halogenoalkyl carbonates, 2-halogenoethyl formates, the corresponding cyclic and linear carbonates, aldehydes, and halogenoalkanes.A scheme of homolytic transormations is proposed for 2-alkoxy-1,3-dioxolanes in polyhalogenoalkanes.