24618-31-3

Usage

Synthesis Reference(s)

Synthesis, p. 483, 1972 DOI: 10.1055/s-1972-21907Tetrahedron Letters, 25, p. 527, 1984 DOI: 10.1016/S0040-4039(00)99928-3

InChI:InChI=1/C7H13BrO/c1-9-7-5-3-2-4-6(7)8/h6-7H,2-5H2,1H3

Upstream product

• 67-56-1 methanol 
• 560-95-2 bromotrinitromethane 
• 110-83-8 cyclohexene 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 1685-97-8 2,2-dibromo-indan-1,3-dione 
• 74307-85-0 2-bromo-1,3-dioxo-indan-2-carboxylic acid ethyl ester 
• 28078-73-1 methyl hypobromite 
• 598-91-4 dibromonitromethane 
• 464-10-8 bromopicrin 
• 37167-59-2 dimethyl dibromomalonate 
• 79-15-2 N-bromoacetamide 
• 21428-65-9 2,2-dibromo-5,5-dimethylcyclohexane-1,3-dione 
• 7726-95-6 bromine 
• 511-67-1 5,5-dibromobarbituric acid 

Downstream Products

• 2699-13-0 3-methoxycyclohexene 
• 1461-23-0 tributyltin bromide 
• 57431-42-2 2-(2-cyclohepten-1-yl)phenol 
• 822-67-3 Cyclohex-2-enol 

Relevant academic research and scientific papers

A useful propionate cofactor enhancing activity for organic solvent-tolerant recombinant metal-free bromoperoxidase (perhydrolase) from Streptomyces aureofaciens

The oxidative brominating activity of an organic solvent-tolerant recombinant metal-free bromoperoxidase BPO-A1 with C-terminal His-tag (rBPO-A1), from Streptomyces aureofaciens found to depend on various additives. These included carboxylic acids, used as cofactors and alcohols, used as water-miscible organic solvents. Enzyme activity was significantly enhanced by using propanoic acid (PA) as a cofactor, which had a high Log D at pH 5.0 and ethylene glycol with a low Log P. The positional specificity of oxidative hydroxybromination for olefins, using rBPO-A1 and PA in the presence of methanol, was higher compared to a non-enzymatic reaction using peracetic acid. The oxidative bromination step, occurring after enzymatic peroxidation step, is suggested to be pseudoenzymatic.

ELAECTROCHEMICAL OXIDATION OF CONJUGATED ARYLOLEFINS TO α-BROMOKETALS

Conjugated arylolefins electrolyzed in alcohols in the presence of alkali metal bromides are transformed into α-bromoketals.

COHALOGENATION DES OLEFINES : APPLICATION A LA SYNTHESE D'ALCOOLS ALLYLIQUES

Alkenes 1 a-f are converted in three steps into the ally alcohols 4 a-f ; the cohalogenation of alkenes by NBS in alcohols constitutes the first step of this synthesis.

The photochemical addition of N-haloamides to olefins: the influence of various factors on the competition between 1,2-addition and hydrogen abstraction

In the photodecomposition of N-haloamides (ZCONRX) in the presence of olefins, the 1,2-addition chain competes with the hydrogen abstraction chain(s) leading to the parent amide (the quantum yields for these processes are greater than unity).The following factors were shown to have an influence on this competition as measured by the yield of 1,2-addition and the yield of parent amide in methylene chloride solutions: (i) the N-halogen (higher yields of addition with X=Cl than with X=Br); (ii) the electronegativity of Z (increase of the yield of addition as the electronegativity of Z increases); (iii) the temperature (higher yields of addition at lower temperatures, and at -70 degC, better yields of addition (>90percent, R=H) for X=Br than for X=Cl); and (iv) the size of R (dramatic decrease of the yield of 1,2-addition in going from R=H to R=CH3).Surprisingly, the presence of a scavenger for HX had no influence on the yield of 1,2-addition.Both the size and electronegativity of Z had an effect on the stereochemistry of 1,2-addition to cyclohexene.High yields of addition to a variety of olefins were obtained with N-chloroamides such as ClCH2CONHCl, C2H5OCONHCl, CF3CONHCl.Their addition to enol ethers at -70 degC led to the synthesis of α-amido acetals or ketals (aldehydes or ketones) and to an α-amido glycoside in good yields.