Benzyl iodide

Benzyl iodide
Names

Preferred IUPAC name (Iodomethyl)benzene
Other names Fraissite, iodotoluol, α-iodotoluene, phenylmethyliodide
Identifiers
CAS Number	620-05-3
3D model (JSmol)	Interactive image
ChemSpider	11601
ECHA InfoCard	100.009.659
PubChem CID	12098
UNII	859JV557EV^Y
CompTox Dashboard (EPA)	DTXSID6060715
InChI InChI=1S/C7H7I/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Key: XJTQJERLRPWUGL-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)CI
Properties
Chemical formula	C₇H₇I
Molar mass	218.037 g·mol⁻¹
Appearance	Low-melting crystals or colorless liquid
Melting point	24.5 °C
Boiling point	218 °C (424 °F; 491 K)
Solubility in water	Insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Flash point	86 °C (187 °F; 359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Benzyl iodide is an organic compound with the chemical formula C
₇H
₇I.^[1]^[2] The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes.

Synthesis

Benzyl iodide can be obtained via the Finkelstein reaction from benzyl chloride and sodium iodide in acetone.

Properties

Benzyl iodide forms colorless to yellow needles, melting at 24.5 °C.^[3] As a liquid, the compound has the high refractive index of 1.6334. Benzyl iodide is also a powerful lachrymator.^[4]^[5]

References

^ "BENZYL IODIDE". chemicalbook.com. Retrieved 8 June 2017.
^ "Benzyl iodide". NIST. webbook.nist.gov. Retrieved 8 June 2017.
^ CRC Handbook of Chemistry and Physics, 90. Edition, CRC Press, Boca Raton, Florida, 2009, ISBN 978-1-4200-9084-0, Section 3, Physical Constants of Organic Compounds, p. 3-306.
^ Bauta, William E. (2001). "Benzyl Iodide". Encyclopedia of Reagents for Organic Synthesis. onlinelibrary.wiley.com. doi:10.1002/047084289X.rb060. ISBN 978-0471936237.
^ Fieser, Louis F.; Fieser, Mary (1982). Organische Chemie (in German). ISBN 978-3-527-25075-2.

Blood agents

Blister agents

Arsenicals	Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3)
Sulfur mustards	Levinstein mustard (EA-229) T Q CEES
Nitrogen mustards	HN1 HN2 HN3 TL-301
Nettle agents	Phosgene oxime (CX)
Other	KB-16 Dibutylchloromethyltin chloride Selenium oxychloride

Nerve agents

G-agents	Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin
V-agents	EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7)
GV agents	GV (EA-5365)
Novichok agents	A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042
Carbamates	Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10)
Other	Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI
Precursors	Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG