5027-16-7

Basic information

• Product Name: ethyl (hydroxymethyl)-carbamate
• Synonyms: ethyl (hydroxymethyl)-carbamate;(Hydroxymethyl)carbamic acid ethyl ester;Carbamic acid, (hydroxymethyl)-, ethyl ester;Nsc20520
• CAS NO: 5027-16-7
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.11916
• EINECS: 225-717-8
• Mol File: 5027-16-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 53 °C
• Boiling Point: 229.4°Cat760mmHg
• Flash Point: 92.5°C
• Appearance: /
• Density: 1.141g/cm³
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: 1.439
• PKA: 11.27±0.46(Predicted)
• CAS DataBase Reference: ethyl (hydroxymethyl)-carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (hydroxymethyl)-carbamate(5027-16-7)
• EPA Substance Registry System: ethyl (hydroxymethyl)-carbamate(5027-16-7)

Safety Data

• Hazardous Substances Data: 5027-16-7(Hazardous Substances Data)

Usage

General Description

Ethyl (hydroxymethyl)-carbamate, also known as carbaryl, is a chemical compound commonly used as a broad-spectrum insecticide. It belongs to the carbamate class of pesticides and works by inhibiting the activity of acetylcholinesterase, an enzyme essential for the proper functioning of the nervous system in pests. As a result, carbaryl disrupts the transmission of nerve impulses, leading to paralysis and eventual death of the targeted insects. Due to its low toxicity to mammals and its effectiveness in controlling a wide range of pests, carbaryl has been widely used in agriculture, horticulture, and public health programs. However, it has been banned or restricted in some countries due to its potential harm to non-target organisms and its negative impact on human health and the environment.

InChI:InChI=1/C4H9NO3/c1-2-8-4(7)5-3-6/h6H,2-3H2,1H3,(H,5,7)

Upstream product

• 50-00-0 formaldehyd 
• 51-79-6 urethane 
• 79-22-1 methyl chloroformate 

Downstream Products

• 29272-72-8 2-ethoxy-5r-methyl-6t-phenyl-5,6-dihydro-4H-[1,3]oxazine 
• 3693-53-6 N,N'-methanediyl-bis-carbamic acid diethyl ester 
• 91644-82-5 (2-hydroxy-3,5-dimethyl-benzyl)-carbamic acid ethyl ester 

Relevant articles and documents

TIN TETRACHLORIDE-INDUCED ?-CYCLIZATIONS OF GLYCINE CATION EQUIVALENTS TO SUBSTITUTED PIPECOLIC ACID DERIVATIVES

Cationic ?-cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)acetoxyglycine esters induced by tin tetrachloride in dichloromethane are described.Reactions started and quenched with water at -78 deg C mainly yield cis-4-hydroxypipecolic esters, whereas reactions quenched after warm-up to room temperature provide trans-4-chloropipecolic esters as major products.A mechanistic scheme is advanced which adequately explains these results.The essentials are a rapid cationic aza-Cope equilibrium of the incipient iminium cation, and participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

Ethylideneaminooxyacetic acids and esters

Compounds of the formula STR1 wherein R1 is hydrogen, alkyl, cycloalkyl, phenylalkyl, alkoxyalkyl, alkoxyaryl, aryl or an agronomically acceptable cation; R2 and R3 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenylalkyl, carboxy, alkoxycarbonyl or phenyl group; X is hydrogen, fluoro, bromo, chloro or iodo atom; Y is a hydrogen, fluoro, bromo, chloro, iodo, alkyl, cycloalkyl, carboxy, alkoxycarbonyl, phenylalkyl, alkenyl and alkynyl group, wherein the alkyl, cycloalkyl, phenylalkyl and phenyl group may have up to three optional substituents; and B is hydrogen, carboxy, alkoxycarbonyl, methylene (--CH2 R4) or CZZ1 Z2 group wherein R4 is an alkyl or alkenyl group and Z, Z1 and Z2 are each independently a hydrogen, fluoro, bromo, chloro or iodo atom, provided that Z, Z1, Z2, X and Y are not all hydrogens.