594-02-5

Basic information

• Product Name: 1,1-diiodoethane
• Synonyms: 1,1-diiodoethane;Ethylidene diiodide;unsym-Diiodoethanee;1,1-Diiodoethane >=98.0% (GC)
• CAS NO: 594-02-5
• Molecular Formula: C₂H₄I₂
• Molecular Weight: 281.8621
• EINECS: 209-821-0
• Mol File: 594-02-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 63.01°C (estimate)
• Boiling Point: 223.38°C (estimate)
• Flash Point: 72.5°C
• Appearance: /
• Density: 2.7600
• Vapor Pressure: 2.05mmHg at 25°C
• Refractive Index: 1.6500
• Storage Temp.: ?20°C
• BRN: 1730848
• CAS DataBase Reference: 1,1-diiodoethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-diiodoethane(594-02-5)
• EPA Substance Registry System: 1,1-diiodoethane(594-02-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 594-02-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4476, 1951 DOI: 10.1021/ja01153a524

InChI:InChI=1/C2H4I2/c1-2(3)4/h2H,1H3

Upstream product

• 75-34-3 1,1-dichloroethane 
• 590-26-1 (Z)-1,2-diiodoethylene 
• 590-27-2 (E)-1,2-diiodoethene 
• 593-66-8 vinyliodide 
• 75-03-6 ethyl iodide 
• 74-86-2 acetylene 
• 759-73-9 N-Ethyl-N-nitrosourea 
• 593-60-2 Vinyl bromide 
• 10034-85-2 hydrogen iodide 
• 593-96-4 1-bromo-1-chloroethane 
• 75-11-6 diiodomethane 
• 917-54-4 methyllithium 

Downstream Products

• 26653-39-4 1-(buta-1,2-dien-1-yl)-4-bromobenzene 
• 32644-22-7 1-methyl-3-phenylallene 
• 4281-04-3 7-methyl-1,3,5-cycloheptatriene 
• 26653-38-3 1-(buta-1,2-dien-1-yl)-4-methylbenzene 
• 19781-63-6 4-Ethyl-(E)-2-hexen 
• 629-23-2 tetradecan-3-one 
• 120387-78-2 3-methoxy-2-tetradecene 
• 32400-17-2 1-[(E,Z)-2'-butenylidene]cyclohexane 
• 86597-36-6 (1-Methoxy-2-methyl-3-phenyl-cyclopropoxy)-trimethyl-silane 
• 122911-39-1 1-{3-[(E)-(1R,2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methoxy-2-methyl-hept-5-enyl]-2,5-dimethoxy-phenyl}-2,5-dimethyl-1H-pyrrole 
• 131685-49-9 (2R,3R,5E)-1-(benzyloxy)-3-methyl-5-hepten-2-ol 
• 131685-49-9 (Z)-(2R,3R)-1-Benzyloxy-3-methyl-hept-5-en-2-ol 
• 123826-96-0 (1α,2β,3β,5α)-3-<2<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-6-methylbicyclo<3.1.0>hexan-2-ol 
• 144514-35-2 3-(3,4-difluorophenyl)-4-methyl<1,3>thiazetidin-2-ylidenemalonate 

Relevant articles and documents

Studies on the synthesis of α-iodoaziridines and improved conditions for the synthesis of alkyl-α-iodoaziridines using ClMgCHI2

α-Iodoaziridines are unusual motifs and intriguing structures for further functionalisation of the intact aziridine. The preparation of N-protected α-iodoaziridines is achieved through an addition-cyclisation reaction of LiCHI2 with imines. The effects of varying the N-group and using different carbenoids are investigated. Excellent cis-stereochemistry is achieved, except for N-carbamates containing aryl groups. Using the mixed carbenoid LiCHICl, the iodide leaving group is selected for cyclisation affording chloroaziridines only, as a cis/trans mixture. More convenient and higher yielding conditions for the preparation of alkyl N-Ts α-iodoaziridines are developed, using ClMgCHI2. Additionally, the formation of the problematic primary alkyl α-iodoaziridines is achieved.