Tert-Butyl bromide

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tert-Butyl bromide
Tert-butyl bromide.svg
Tert-butyl-bromide-3D-balls.png
Names
Preferred IUPAC name
2-Bromo-2-methylpropane [1]
Other names
Identifiers
3D model (JSmol)
1730892
ChEMBL
ChemSpider
ECHA InfoCard 100.007.333 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-065-9
PubChem CID
RTECS number
  • TX4150000
UNII
UN number 2342
  • InChI=1S/C4H9Br/c1-4(2,3)5/h1-3H3 Yes check.svgY
    Key: RKSOPLXZQNSWAS-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)Br
Properties
C4H9Br
Molar mass 137.020 g·mol−1
AppearanceColorless liquid
Density 1.22 g mL−1 (at 20 °C) [2]
Melting point −16.20 °C; 2.84 °F; 256.95 K
Boiling point 73.3 °C; 163.8 °F; 346.4 K
log P 2.574
310 nmol Pa−1 kg−1
1.4279
Thermochemistry
165.7 J K mol−1
−133.4 kJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg
Danger
H225
P210
Flash point 16 °C (61 °F; 289 K)
Lethal dose or concentration (LD, LC):
  • 1.25 g kg−1(intraperitoneal, rat)
  • 4.4 g kg−1(intraperitoneal, mouse)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

tert-Butyl bromide (also referred to as 2-bromo-2-methylpropane) is an organic compound with the formula Me3CBr (Me = methyl). The molecule features a tert-butyl group attached to a bromide substituent. This organobromine compound is used as a standard reagent in synthetic organic chemistry. It is a colorless liquid.

Contents

Reactions

It is used to introduce tert-butyl groups. Illustrative is the tert-butylation of cyclopentadiene to give di-tert-butylcyclopentadiene: [3]

C5H6 + 2 NaOH + 2 Me3CBr → (Me3C)2C5H4 + 2 NaBr + 2 H2O

Other aspects

tert-Butyl bromide used to study the massive deadenylation of adenine based-nucleosides induced by halogenated alkanes (alkyl halides) under physiological conditions. 2-Bromo-2-methylpropane causes the massive deguanylation of guanine based-nucleosides and massive deadenylation of adenine based-nucleosides. [4]

Phase transition from orthorhombic Pmn21 phase III at low temperatures (measurements from 95 K), to a disordered rhombohedral phase II at 205-213 K. Phase II can exist from 213-223 K, partly coincident with an FCC phase I, which can be observed between 210-250 K. Phase transitions have also been studied at high pressure (up to 300MPa) [5]

Related Research Articles

Cyclopentadiene is an organic compound with the formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp.

<span class="mw-page-title-main">Protecting group</span> Group of atoms introduced into a compound to prevent subsequent reactions

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">1-Bromobutane</span> Chemical compound

1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is primarily used as a source of the butyl group in organic synthesis. It is one of several isomers of butyl bromide.

Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.

The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters:

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

Pivalic acid, also known as neovaleric acid, is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (t-BuC(O)) is Piv and for pivalic acid (t-BuC(O)OH) is PivOH. It is an isomer of valeric acid, the other two isomers of it are 2-Methylbutanoic acid and 3-Methylbutanoic acid.

tert-Butyl chloride is the organochloride with the formula (CH3)3CCl. It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds.

<span class="mw-page-title-main">Gallium(II) sulfide</span> Chemical compound

Gallium(II) sulfide, GaS, is a chemical compound of gallium and sulfur. The normal form of gallium(II) sulfide as made from the elements has a hexagonal layer structure containing Ga24+ units which have a Ga-Ga distance of 248pm. This layer structure is similar to GaTe, GaSe and InSe. An unusual metastable form, with a distorted wurtzite structure has been reported as being produced using MOCVD. The metal organic precursors were di-tert-butyl gallium dithiocarbamates, for example GatBu2(S2CNMe2) and this was deposited onto GaAs. The structure of the GaS produced in this way is presumably Ga2+ S2−.

tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.

2,6-Di-<i>tert</i>-butylpyridine Chemical compound

2,6-Di-tert-butylpyridine is an organic compound with the formula (Me3C)2C5H3N. This colourless, oily liquid is derived from pyridine by replacement of the two H atoms with tert-butyl groups. It is a hindered base. For example, it can be protonated, but it does not form an adduct with boron trifluoride.

The molecular formula C4H9Br, (molar mass: 137.02 g/mol, exact mass: 135.9888 u) may refer to:

Tetramethylbutane, sometimes called hexamethylethane, is a hydrocarbon with formula C8H18 or (H3C-)3C-C(-CH3)3. It is the most heavily branched and most compact of the many octane isomers, the only one with a butane (C4) backbone. Because of its highly symmetrical structure, it has a very high melting point and a short liquid range; in fact, it is the smallest saturated acyclic hydrocarbon that appears as a solid at a room temperature of 25 °C. (Among cyclic hydrocarbons, cubane, C8H8 is even smaller and is also solid at room temperature.) It is also the most stable C8H18 isomer, with a heat of formation 4.18 kcal/mol (17.5 kJ/mol) lower than that of n-octane, a fact that has been attributed to stabilizing dispersive interactions (electron correlation) between the methyl groups (protobranching).

<i>tert</i>-Butylthiol Chemical compound

tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

<span class="mw-page-title-main">Half sandwich compound</span> Class of coordination compounds

Half sandwich compounds, also known as piano stool complexes, are organometallic complexes that feature a cyclic polyhapto ligand bound to an MLn center, where L is a unidentate ligand. Thousands of such complexes are known. Well-known examples include cyclobutadieneiron tricarbonyl and (C5H5)TiCl3. Commercially useful examples include (C5H5)Co(CO)2, which is used in the synthesis of substituted pyridines, and methylcyclopentadienyl manganese tricarbonyl, an antiknock agent in petrol.

<span class="mw-page-title-main">Vinyllithium</span> Chemical compound

Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.

<i>tert</i>-Butyldimethylsilyl chloride Chemical compound

tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me3C)Me2SiCl (Me = CH3). It is commonly abbreviated as TBSCl or TBDMSCl. It is a silane containing two methyl groups, a tert-butyl group, and a reactive chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic synthesis. Examples can be found in the Nicolaou taxol total synthesis.

<span class="mw-page-title-main">Bulky cyclopentadienyl ligands</span>

In the area of organometallic chemistry, a bulky cyclopentadienyl ligand is jargon for a ligand of the type C
5
H
5−n
R
n
where R is a branched alkyl and n = 3 or 4. Representative examples are the tetraisopropyl derivative C
5
HiPr
4
and the tris(tert-butyl) derivative 1,2,4-C
5
H
2
tBu
3
. These ligands are so large that their complexes behave differently from the pentamethylcyclopentadienyl analogues. Because they cannot closely approach the metal, these bulky ligands stabilize high spin complexes, such as (C5H2tBu3)2Fe2I2. These large ligands stabilize highly unsaturated derivatives such as (C5H2tBu3)2Fe2N2.

Di-<i>tert</i>-butylcyclopentadiene Chemical compound

Di-tert-butylcyclopentadiene is an organic compound with the formula (Me3C)2C5H4, where Me = methyl. It is a colorless liquid that is soluble in organic solvents. The compound is the conjugate acid of the di-tert-butylcyclopentadienyl ligand, (Me3C)2C5H3 (sometimes abbreviated Cp). Two regioisomers of di-tert-butylcyclopentadiene exist, depending on the relative location of the double bonds.

References

  1. "2-Bromo-2-methylpropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 16 June 2012.
  2. CRC Handbook of Chemistry and Physics 65th Ed.
  3. Reiners, Matthias; Ehrlich, Nico; Walter, Marc D. (2018). "Synthesis of 1,3,5-Tri-tert-Butylcyclopenta-1,3-diene and Its Metal Complexes Na{1,2,4-(Me3C)3C5H2} and Mg{η5-1,2,4-(Me3C)3C5H2)2". Inorganic Syntheses. 37: 199. doi:10.1002/9781119477822.ch8.
  4. “2-Bromo-2-Methylpropane 135615.” H2NC6H4CO2C2H5, Drugs, www.sigmaaldrich.com/catalog/product/aldrich/135615?lang=en®ion=US.
  5. “2-Bromo-2-Methylpropane Structures.” The Cambridge Crystallographic Data Centre (CCDC), www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccvcqmj&sid=DataCite