Ethyl methanesulfonate

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Ethyl methanesulfonate[1]
Skeletal formula
Ball-and-stick model
IUPAC name
Other names
Ethyl mesylate
Ethyl methanesulphonate
Abbreviations EMS
62-50-0 YesY
ChEMBL ChEMBL338686 YesY
ChemSpider 5887 YesY
Jmol-3D images Image
KEGG C19239 N
PubChem 6113
Molar mass 124.16 g/mol
Appearance Clear colorless liquid
Density 1.1452 g/cm3 (22 °C)
Melting point < 25 °C
Boiling point 213 to 213.5 °C (415.4 to 416.3 °F; 486.1 to 486.6 K)
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Ethyl methanesulfonate (EMS) is a mutagenic, teratogenic, and possibly carcinogenic organic compound with formula CH3SO3C2H5. It produces random mutations in genetic material by nucleotide substitution; particularly by guanine alkylation. This typically produces only point mutations. It can induce mutations at a rate of 5x10−4 to 5x10−2 per gene without substantial killing. The ethyl group of EMS reacts with guanine in DNA, forming the abnormal base O-6-ethylguanine. During DNA replication, DNA polymerases that catalyze the process frequently place thymine, instead of cytosine, opposite O-6-ethylguanine. Following subsequent rounds of replication, the original G:C base pair can become an A:T pair (a transition mutation). This changes the genetic information, is often harmful to cells, and can result in disease.

EMS is often used in genetics as a mutagen. Mutations induced by EMS can then be studied in genetic screens or other assays.

See also[edit]


  1. ^ Merck Index, 11th Edition, 3782.