62994-00-7

Basic information

• Product Name: 2-Butene-1,4-diol, 2,3-diiodo-, (2E)-
• Synonyms: 2,3-Dijod-but-2-en-1,4-diol;2,3-diiodo-but-2-ene-1,4-diol;2,3-diiodo-2-butene-1,4-diol
• CAS NO: 62994-00-7
• Molecular Formula: C4H6I2O2
• Molecular Weight: 339.899
• Mol File: 62994-00-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Butene-1,4-diol, 2,3-diiodo-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butene-1,4-diol, 2,3-diiodo-, (2E)-(62994-00-7)
• EPA Substance Registry System: 2-Butene-1,4-diol, 2,3-diiodo-, (2E)-(62994-00-7)

Safety Data

• Hazardous Substances Data: 62994-00-7(Hazardous Substances Data)

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 
• 854470-08-9 2-chloro-3-hydroxy-1-hydroxymethyl-propenylmercury ⁽¹⁺⁾; chloride 
• 67-66-3 chloroform 
• 7553-56-2 iodine 

Downstream Products

• 110-65-6 1,4-dihydroxybut-2-yne 

Relevant articles and documents

BUT-2-ENE-1, 4-DIOLS AND METHODS FOR THE PREPARATION THEREOF

Compounds are provided that are useful synthetic intermediates, particularly for the preparation of dialdehydes. The compounds have the formula (I): wherein Z is I, Br or CH2Ar2; Ar1 is 4-Y1C6H4

Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes

A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1=Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2-Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2=Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2-Ar1CH2(CHO)C=C(CHO)CH2Ar2, which in many cases undergo titanium(IV) chloride-induced double Bradsher closure, providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out.

Room-temperature carbonization of poly(diiododiacetylene) by reaction with Lewis bases

Poly(diiododiacetylene) (PIDA) is a conjugated polymer containing an all-carbon backbone and only iodine atom substituents. Adding a Lewis base to the blue PIDA suspension at room temperature leads first to rapid disappearance of the absorption peaks attributed to PIDA, followed more slowly by release of free iodine. The resulting solid material gives a Raman scattering spectrum consistent with graphitic carbon, and it has a much higher conductivity than PIDA itself. Further investigation has led to the discovery of a previously unreported transformation, the reaction of a Lewis base such as pyrrolidine with a trans-diiodoalkene to form the corresponding alkyne. The generality of this iodine elimination further suggests that reaction of PIDA with Lewis bases dehalogenates the polymer, presenting a new method to prepare carbon nanomaterials at room temperature under very mild conditions.