2909-52-6

Usage

Uses

Used in Chemical Research:
Bromoform-D is used as a research compound for studying the properties and reactions of isotopically labeled molecules. Its application in this field aids in understanding the behavior of similar compounds and their interactions with other substances.
Used in Analytical Chemistry:
In analytical chemistry, Bromoform-D is used as a reference material or internal standard for various analytical techniques. Its isotopically labeled nature allows for accurate measurements and quantification of other compounds in complex mixtures.
Used in Pharmaceutical Industry:
Bromoform-D is used as a starting material or intermediate in the synthesis of isotopically labeled pharmaceutical compounds. These labeled compounds can be used for drug development, tracing metabolic pathways, and studying the pharmacokinetics and pharmacodynamics of drugs.
Used in Environmental Science:
Bromoform-D is employed in environmental science for tracing the transport and fate of bromine-containing compounds in the environment. Its isotopically labeled nature helps in understanding the behavior of these compounds in various environmental matrices, such as water, soil, and air.
Used in Material Science:
In material science, Bromoform-D can be used for studying the properties of isotopically labeled polymers and other materials. This information can be valuable for developing new materials with specific properties or for understanding the behavior of existing materials at the molecular level.

InChI:InChI=1/CHBr3/c2-1(3)4/h1H

Upstream product

• 115-17-3 bromal 
• 75-25-2 Bromoform 
• 75-96-7 tribromoacetic acid 
• 81193-49-9 butyl-di-t-butylbromophosphonium tribromomethanid 
• 18142-75-1 trimethyl-tribromomethyl-silane 
• 865-49-6 chloroform-d1 
• 67-64-1 acetone 

Downstream Products

• 120156-95-8 IrBr(CO)(P(C₆H₅)3)2(SC(CN)C(CN)S) 

Relevant academic research and scientific papers

Probing hyperconjugation experimentally with the conformational deuterium isotope effect

Hyperconjugation underlies many chemical phenomena of fundamental and practical importance. Owing to a great deal of interest in the anomeric effect, anomeric-like hyperconjugative effects have been thoroughly investigated in oxygen-containing systems. However, such interactions in the second- and third-row chalcogens are less well-understood and have generated some controversy. Here, we show that the conformational deuterium isotope effect, in combination with Saunders isotopic perturbation method, permits sensitive and direct experimental probing of the conformational equilibria in dioxane, dithiane, and diselenane analogues by variable-temperature, dynamic NMR spectroscopy. We find that the magnitude of the conformational deuterium isotope effect is 252.1, 28.3, and 7.1 J/mol (±10%) for the oxygen, sulfur, and selenium analogues, respectively. These results reveal the periodic trend for hyperconjugation in the chalcogens, which reflect a decreasing n x→σC-H(D) interaction throughout the period, as supported by IR spectroscopy and in agreement with DFT calculations and a natural bond order analysis.

Kinetic Isotope Effects for Proton Abstraction from Methanol by Polyhalogenomethyl Carbanions. Cleavage of Me3SiCHX2 and Me3SiCX3 by Base in Methanol.

The carbanions XxH(3-x)C- (X=Cl or Br; x=2 or 3) generated by base cleavage of Me3SiCH(3-x)Xx (or some related compounds) in MeOH, show a kinetic isotope kH/kD of ca. 1.1 in proton abstraction from methanol, as given by the product ratio XxH(3-x)CH/XxH(3-x)CD observed for reaction in MeOH-MeOD (1:1) at ca. 21 deg C.The low value of the isotope effect is attributed to the fact that the free electron pair in the carbanion is localized on the carbon centre; carbanions derived from acids of acidities comparable with those of X3CH and X2CH2 but in which the electron pair is conjugatively delocalized, show much larger isotope effects.

Carbene Rearrangements, XX. trans-2-(1,3-Butadienyl)cyclopropylidene: Generation and Reactive Behavior

1- and 2-Vinyl-1,3-cyclopentadiene (19 and 20) and trans-1,2,4,6-heptatetraene (21) are formed from trans-2-(1,3-butadienyl)cyclopropylidene(oid) (18), which is generated from the dibromocarbene adduct 17 with methyllithium at 0 deg C.The mechanisms of the rearrangements of 18 have been examined by 12C-labeling (12C >/= 99.95percent) in 17. 21 is formed from 18 by rupture of the distal bond B of the cyclopropylidene.Breakage of the lateral bond A in 18 induces a carbene-carbene rearrangement with 1,3-C migration.The rearranged carbene 28 stabilizes itself by three routes.The product ratio of the competing reactions in 18 is temperature dependent.At lower temperatures the carbene-carbene rearrangement 18 -> 20 predominates, at higher temperatures increased formation of 21 takes place. - If 18 is generated by pyrolysis of the organotin compound 34, the high temperature (260 deg C) necessary for the decomposition favors the allene formation and suppresses the carbene-carbene rearrangement. - 21 is also formed when 18 is released from the N-nitrosourea 36b. 19 and 20 decompose under the reaction conditions. - A new method for the generation of carben(oid)s is described.

1-BROMOBICYCLOBUTANES AND STRONG BASES: PRODUCTS AND MECHANISM

Treatment of the bromobicyclobutanes 4a - c with LDA led to the formation of the 1,2,3-butatrienes 6 which were isomerized by excess base to the alkynes 8.Reaction of 4c with LDA afforded 8d, indicating that bicyclobut-1(3)-ene 5 was not an intermediate.

CARBENE-CARBENE REARRANGEMENTS AS A ROUTE TO 1,5-DIHYDROPENTALENE

1,5-Dihydropentalene (4) is formed as the main product on treatment of trans-1,2-bis(2,2-dibromocyclopropyl)ethene 3 with methyllithium at -40 deg C.In addition the reaction affords 1- and 2-propadienylcyclopentadienes (5a) and (5b), and trans-1,2,4,6,7-octapentaene (6), new C8H8 isomers.Diels-Alder adducts of 4, 5a and 5b were obtained in the reaction with perfluorobut-2-yne.The formation of 1,5-dihydropentalene 4 is explained by a double ring expansion sequence involving consecutive carbene-carbene rearrangements with 1,3-carbon and subsequent 1,2-hydrogen shifts, supported by the reaction of double labelled ((13)C-depleted) 3.From readily available 3 at low temperatures formation and fusion of two 5-membered rings are achieved in one step.

Carbene-carbene rearrangements as a route to 1,5-dihydropentalene

1,5-Dihydropentalene (4) is formed as the main product on treatment of trans-1,2-bis(2,2-dibromocyclo-propyl)ethene 3 with methyllithium at -40°. In addition the reaction affords 1- and 2-propadienylcyclopentadienes (5a) and (5b), and trans-1,2,4,6,7-octapentaene (6), new CsHs isomers. Diets-Alder adducts of 4,5a and 5b were obtained in the reaction with perfluorobut-2-yne. The formation of 1,5-dihydropentalene 4 is explained by a double ring expansion sequence involving consecutive carbene-carbene rearrangements with 1,3-carbon and subsequent 1,2-hydrogen shifts, supported by the reaction of double labelled (13C-depleted) 3. From readily available 3 at low temperatures formation and fusion of two 5-membered rings are achieved in one step.

REACTIONS OF STERICALLY HINDERED PHOSPHINES WITH CARBON TETRAHALIDES: P-HALOGENYLIDS

1.A study has been made of the effects of steric factors on the reactions of tertiary phosphines with carbon tetrahalides.It is found that in the interaction of sterically hindered phosphine with carbon tetrabromide one gets the formation of bromophosphonium tribromomethylid, which exists at a low temperature, this being in an ionic pair containing the anion CBr3-.A sterically hindered phosphine having hydrogen at the α carbon atom forms P-halogenylids on reaction with carbon tetrahalides. 2.Unstabilized P-halogenylids with unsubstituted methylene and alkylidene gr oups have been synthesized, and also P-halogenylids with trimethylsilyl, methyl sulfide, phosphine, acyl, and aromatic groups on the ylid carbon atom. 3.A study has been made of the reactions of P-chlorylids with chlorine-bearing electrophilic reagents , which give rise to new P-halogenylids.