2936-44-9

Basic information

• Product Name: 1,2-Propadiene, 1-iodo-
• Synonyms: iodo-allene;1,2-Propadiene,1-iodo;allenyl iodide;iodopropadiene
• CAS NO: 2936-44-9
• Molecular Formula: C3H3I
• Molecular Weight: 165.961
• Mol File: 2936-44-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,2-Propadiene, 1-iodo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Propadiene, 1-iodo-(2936-44-9)
• EPA Substance Registry System: 1,2-Propadiene, 1-iodo-(2936-44-9)

Safety Data

• Hazardous Substances Data: 2936-44-9(Hazardous Substances Data)

Upstream product

• 10024-18-7 bromoallene 
• 106-96-7 propargyl bromide 
• 107-19-7 propargyl alcohol 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 52517-92-7 1-octyn-4-ol 
• 57649-52-2 octa-1,2-dien-4-ol 
• 1150518-82-3 N-benzyl-4-methyl-N-(3-methylbuta-1,2-dienyl)benzenesulfonamide 
• 6712-35-2 2-phenylpent-4-yn-2-ol 
• 136050-77-6 2-phenyl-3,4-pentdien-2-ol 
• 1743-36-8 1-phenylbut-3-yn-1-ol 
• 19135-08-1 1-(prop-2-ynyl)cyclohexanol 
• 34761-56-3 1-propa-1,2-dienylcyclohexan-1-ol 
• 55392-89-7 3-(1-hydroxycyclopentyl)propa-1,2-diene 
• 19135-07-0 1-(prop-2-ynyl)cyclopentanol 
• 5732-10-5 2,3-butadienoic acid 
• 2345-51-9 3-butynoic acid 
• 2749-79-3 4,5-hexadien-2-yn-1-hexanol 

Relevant articles and documents

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A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

Formation of Iodides and Esters from Alcohols and Tributyldiiodophosphorane and Diiodotriphenylphosphorane

Tributyldiiodophosphorane and diiodotriphenylphosphorane, prepared in situ from the corresponding phosphine and iodine, are generally able to convert primary and secondary alcohols into iodides at room temperature in diethyl ether or benzene containing two equivalents of hexamethylphosphoric triamide.Tertiary alcohols, as gauged by the lack of the reactivity of t-butyl alcohol, are, however, inert to this iodinating agents. 6-Hydroxyhexanoic acid yields a mixture of 6-iodohexanoic acid and 7-heptanolide.The first reagent also promotes facile condensation of secondaryand tertiary alcohols with carboxylic acids to form hindered esters in good yields.The phosphorane derived from tris(dimethylamino)phosphine and iodine, while less effective as an iodinating agent, rapidly converts 6-hydroxyhexanoic acid into 6-iodo-N,N-dimethylhexanamide, and hexanoic and benzoic acids into the corresponding N,N-dimethylamides in excellent yields at room temperature.Treatment of 3β-tosylocholest-5-ene with lithium iodide yields 3β-iodocholest-5-ene, and not 3α-iodocholest-5-ene, as previously reported.