56798-08-4

Basic information

• Product Name: TRANS-1-BROMO-2-IODOETHENE 97
• Synonyms: TRANS-1-BROMO-2-IODOETHENE 97;TRANS-1-BROMO-2-IODOETHENE 97%;trans-1-Bromo-2-iodoethene;(E)-1-Bromo-2-iodoethylene
• CAS NO: 56798-08-4
• Molecular Formula: C₂H₂BrI
• Molecular Weight: 232.84575
• Mol File: 56798-08-4.mol

Chemical Properties

• Boiling Point: 63-77 °C100 mm Hg(lit.)
• Flash Point: 112 °F
• Appearance: /liquid
• Density: 2.605 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.6320(lit.)
• CAS DataBase Reference: TRANS-1-BROMO-2-IODOETHENE 97(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1-BROMO-2-IODOETHENE 97(56798-08-4)
• EPA Substance Registry System: TRANS-1-BROMO-2-IODOETHENE 97(56798-08-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 56798-08-4(Hazardous Substances Data)

Upstream product

• 74-86-2 acetylene 
• 540-49-8 cis+trans-dibromoethylene 
• 20244-70-6 1,2-diiodoethylene 

Downstream Products

• 7235-40-7 beta-carotene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 111-66-0 oct-1-ene 
• 71686-99-2 (7E,9E)-hexadeca-7,9-diene 
• 174365-91-4 (1E,3E)-1-bromo-1,3-decadiene 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 60606-71-5 (E)-1-(4'-cyanophenyl)-2-bromoethylene 
• 100-42-5 styrene 
• 188802-38-2 ((1E,3E)-4-bromobuta-1,3-dienyl)benzene 
• 4705-34-4 1,2-bis(4-methoxyphenyl)ethene 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 1058725-45-3 dimethyl (1E,3E,5E,7E,9E,11E,13E,15E,17E) 4,4'-(3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)-bis-(2,3-dimethylbenzoate) 
• 1333231-05-2 C₄₀H₄₆O₄ 
• 1021432-70-1 χ,χ-caroten-18,18-dioic acid 

Relevant articles and documents

The effect of vicinyl olefinic halogens on cross-coupling reactions using Pd(0) catalysis

(trans) 1-Chloro-2-iodoethylene (3), (trans) 1-bromo-2-iodoethylene (4), (trans) 1,2-diiodoethylene (5) and (cis and trans) 1,2-dibromoethylene (11) were reacted under Suzuki, Sonogashira and Negishi cross-coupling conditions using Pd catalysis to obtain mono coupled products. Only olefin template 3 provided the desired coupling products reliably under all reaction conditions. Compound 5 did not provide cross coupled products under any of the reaction conditions used. The Negishi reaction was the only one that worked for templates 4 and 11. Studies indicate that oxidative addition of the most reactive carbon-halogen bond to Pd(0) is followed by elimination of the second halide, when the second halide is a bromide or an iodide. This happens to a much lesser degree when the second halogen is a chloride. Graphical Abstract.

A novel, selective, and efficient route to carotenoids and related natural products via Zr-catalyzed carboalumination and Pd- and Zn-catalyzed cross coupling.

[structure: see text]. A highly efficient and stereoselective protocol for the syntheses of symmetrical and unsymmetrical carotenoids involving Zr-catalyzed carboalumination of conjugated oligoenynes and Pd- and Zn-catalyzed alkenyl-alkenyl coupling has been developed and applied to the syntheses of beta- and gamma-carotene and vitamin A. gamma-Carotene of > or =99% isomeric purity was prepared in three linear steps (five steps overall) from beta-ionone, enyne 8, (E)-ICH=CHBr, and (E)-Me3SiC triple bond CCH=CHBr in 32% overall yield.

An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-lodobromoethylene as a novel two-carbon synthon.

[structure: see text] Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized from commercially available (E)-1-bromopropene, acetylene, and propynoic acid in five steps (longest linear sequence) in 30% overall yield and >96% stereoselectivity. The preparation of (E)-iodobromoethylene and its use in the Pd-catalyzed cross coupling are two of the novel aspects of the synthesis reported herein.