1-chloro-1,1-dimethylethane
chlorotrimethylmethane
trimethylchloromethane
''t''-butyl chloride"},"Section1":{"wt":"{{Chembox Identifiers\n| ChEMBL_Ref ={{ebicite|correct|EBI}}\n| ChEMBL = 346997\n| StdInChI_Ref ={{stdinchicite|correct|chemspider}}\n| StdInChI = 1S/C4H9Cl/c1-4(2,3)5/h1-3H3\n| StdInChIKey_Ref ={{stdinchicite|correct|chemspider}}\n| StdInChIKey = NBRKLOOSMBRFMH-UHFFFAOYSA-N\n| CASNo = 507-20-0\n| CASNo_Ref ={{cascite|correct|CAS}}\n| UNII_Ref ={{fdacite|correct|FDA}}\n| UNII = JN2YO95TZ0\n| EC_number = 208-066-4\n| ChemSpiderID_Ref ={{chemspidercite|correct|chemspider}}\n| ChemSpiderID = 10054\n| PubChem = 10486\n| SMILES = ClC(C)(C)C\n| RTECS = TX5040000\n| UNNumber = 1127\n}}"},"Section2":{"wt":"{{Chembox Properties\n| Formula = C4H9Cl\n| MolarMass = 92.57 g/mol\n| Appearance = Colorless liquid\n| Density = 0.851 g/ml\n| MeltingPtC = −26\n| BoilingPtC = 51\n| Solubility = Sparingly soluble in water,miscible with alcohol and ether\n| VaporPressure = 34.9 kPa (20 °C)\n}}"},"Section3":{"wt":"{{Chembox Hazards\n| FlashPtC = −9\n| FlashPt_notes = (open cup)
−23 °C (closed cup)\n| AutoignitionPtC = 540\n| NFPA-H = 2\n| NFPA-F = 3\n| NFPA-R = 0\n| GHSPictograms ={{GHS02}}\n| GHSSignalWord = Danger\n| HPhrases ={{H-phrases|225}}\n| PPhrases ={{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}\n}}"},"Section8":{"wt":"{{Chembox Related\n| OtherFunction_label = [[alkyl halide]]s \n| OtherFunction = [[tert-Butyl bromide]]\n}}"}},"i":0}}]}" id="mwAw">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}
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Names | |||
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Preferred IUPAC name 2-Chloro-2-methylpropane | |||
Other names 1,1-dimethylethyl chloride 1-chloro-1,1-dimethylethane chlorotrimethylmethane trimethylchloromethane t-butyl chloride | |||
Identifiers | |||
3D model (JSmol) | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.334 | ||
EC Number |
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PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 1127 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C4H9Cl | |||
Molar mass | 92.57 g/mol | ||
Appearance | Colorless liquid | ||
Density | 0.851 g/ml | ||
Melting point | −26 °C (−15 °F; 247 K) | ||
Boiling point | 51 °C (124 °F; 324 K) | ||
Sparingly soluble in water, miscible with alcohol and ether | |||
Vapor pressure | 34.9 kPa (20 °C) | ||
Hazards | |||
GHS labelling: | |||
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Danger | |||
H225 | |||
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | −9 °C (16 °F; 264 K) (open cup) −23 °C (closed cup) | ||
540 °C (1,004 °F; 813 K) | |||
Related compounds | |||
Related alkyl halides | tert-Butyl bromide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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. [1]
tert-Butyl chloride is produced by the reaction of tert-butyl alcohol with hydrogen chloride. [1] In the laboratory, concentrated hydrochloric acid is used. The conversion entails a SN1 reaction as shown below. [2]
Step 1 | Step 2 | Step 3 |
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The acid protonates the alcohol, forming a good leaving group (water). | Water leaves the protonated t-BuOH, forming a relatively stable tertiary carbocation. | The chloride ion attacks the carbocation, forming t-BuCl. |
The overall reaction, therefore, is:
Because tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the step 2 allows the SN1 mechanism to be followed, whereas a primary alcohol would follow an SN2 mechanism.
When tert-butyl chloride is dissolved in water, it undergoes a hydrolysis to tert-butyl alcohol. When dissolved in alcohols, the corresponding t-butyl ethers are produced.
tert-Butyl chloride is used to prepare the antioxidant tert-butylphenol and the fragrance neohexyl chloride. [1]
In chemistry, an alcohol, is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.
In organic chemistry, ethers are a class of compounds that contain an ether group—a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group. They have the general formula R−O−R′, where R and R′ represent the organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism.
The unimolecular nucleophilic substitution (SN1) reaction is a substitution reaction in organic chemistry. The Hughes-Ingold symbol of the mechanism expresses two properties—"SN" stands for "nucleophilic substitution", and the "1" says that the rate-determining step is unimolecular. Thus, the rate equation is often shown as having first-order dependence on the substrate and zero-order dependence on the nucleophile. This relationship holds for situations where the amount of nucleophile is much greater than that of the intermediate. Instead, the rate equation may be more accurately described using steady-state kinetics. The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary and secondary alkyl halides, the alternative SN2 reaction occurs. In inorganic chemistry, the SN1 reaction is often known as the dissociative substitution. This dissociation pathway is well-described by the cis effect. A reaction mechanism was first introduced by Christopher Ingold et al. in 1940. This reaction does not depend much on the strength of the nucleophile, unlike the SN2 mechanism. This type of mechanism involves two steps. The first step is the ionization of alkyl halide in the presence of aqueous acetone or ethyl alcohol. This step provides a carbocation as an intermediate.
A transition metal alkoxide complex is a kind of coordination complex containing one or more alkoxide ligands, written as RO−, where R is the organic substituent. Metal alkoxides are used for coatings and as catalysts.
In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
Acetyl chloride is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.
tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.
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Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
In organic chemistry, alkyl nitrites are a group of organic compounds based upon the molecular structure R−O−N=O, where R represents an alkyl group. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds.
In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications.
Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. Two abbreviations for pivalic acid are t-BuC(O)OH and PivOH. The pivalyl or pivaloyl group is abbreviated t-BuC(O).
Oseltamivir total synthesis concerns the total synthesis of the anti-influenza drug oseltamivir marketed by Hoffmann-La Roche under the trade name Tamiflu. Its commercial production starts from the biomolecule shikimic acid harvested from Chinese star anise and from recombinant E. coli. Control of stereochemistry is important: the molecule has three stereocenters and the sought-after isomer is only 1 of 8 stereoisomers.
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Isopropyl alcohol is a colorless, flammable, organic compound with a pungent alcoholic odor.
In nitrile reduction a nitrile is reduced to either an amine or an aldehyde with a suitable chemical reagent.
Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.
tert-Butylthiol, also known as tert-butyl mercaptan (TBM), and abbreciated t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol has a strong odor. It is considered a flavoring agent.