53178-20-4

Basic information

• Product Name: (±)-sec-Butyl chloride
• Synonyms: dl-sec-Butyl chloride
• CAS NO: 53178-20-4
• Molecular Formula: C₄H₉Cl
• Molecular Weight: 0
• Mol File: 53178-20-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (±)-sec-Butyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-sec-Butyl chloride(53178-20-4)
• EPA Substance Registry System: (±)-sec-Butyl chloride(53178-20-4)

Safety Data

• Hazardous Substances Data: 53178-20-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(±)-sec-Butyl chloride is used as a solvent for facilitating various chemical reactions in organic synthesis.
Used in Chemical Production:
(±)-sec-Butyl chloride is used as a reagent in the production of different chemicals.
Used in Pharmaceutical Manufacturing:
(±)-sec-Butyl chloride is used as an intermediate in the manufacturing of pharmaceuticals.
Used in Pesticide Production:
(±)-sec-Butyl chloride is used as a component in the production of pesticides.
Used in Rubber Chemical Manufacturing:
(±)-sec-Butyl chloride is used in the manufacturing of rubber chemicals to enhance the properties of rubber products.
Note: Due to its flammability and harmful effects on the environment, exposure to (±)-sec-Butyl chloride should be limited, and necessary precautions should be taken when handling and using this chemical.

Upstream product

• 106-98-9 1-butylene 
• 107-01-7 butene-2 
• 106-97-8 n-butane 
• 123-86-4 acetic acid butyl ester 
• 78-76-2 s-butyl bromide 
• 78-92-2 iso-butanol 
• 543-20-4 succinoyl dichloride 
• 7719-09-7 thionyl chloride 
• 101-36-0 tri-n-butoxyboroxin 
• 7705-08-0 iron(III) chloride 
• 10026-13-8 phosphorus pentachloride 
• 7719-12-2 phosphorus trichloride 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 993-38-4 chlorodifluoromethansulfenylchloride 

Downstream Products

• 37172-15-9 3-sec-butyl-cyclohexanone 
• 1462-84-6 2,3,6-trimethylpyridine 
• 95652-44-1 acetyl-3 trimethyl-2,5,6 pyridine 
• 1595-16-0 1-sec-butyl-4-methylbenzene 
• 1595-06-8 2-sec-butyltoluene 
• 54932-77-3 2,5-di-(sec-butyl)phenol 
• 157432-87-6 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 
• 189832-67-5 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene 
• 68971-82-4 5,11,17,23,29,35,41,47-octakis(tert-butyl)-49,50,51,52,53,54,55,56-octakis(hydroxy)calix[8]arene 
• 106-98-9 1-butylene 
• 590-18-1 (Z)-2-Butene 
• 624-64-6 trans-2-Butene 
• 598-30-1 sec.-butyllithium 
• 7647-01-0 hydrogenchloride 

Relevant articles and documents

Hydrochlorination of Alkenes. 3. Reaction of the Gases Hydrogen Chloride and (E)- and (Z)-2-Butene

Mixtures of the gases hydrogen chloride and (E)-2-butene, hydrogen chloride and (Z)-2-butene, and hydrogen chloride and (Z)-2H2>-2-butene at total pressures up to 7 atm and temperatures between 283 and 313 K react to yield, exclusively, 2-chlorobutane (erythro- and threo-2H2>-2-chlorobutane in the case of the labeled alkene).Kinetic measurements for the reaction of all three gaseous alkenes with gaseous hydrogen chloride have been made by infrared spectroscopy.Elimination stadies were performed on the 2H2>-2-chlorobutane formed.It is concluded that sur face catalysis is required for product formation and that surface adsorption of both hydrohen chloride and butene is required to consummate the reaction.

METHOD FOR PRODUCING FLUORINATED HYDROCARBON

PROBLEM TO BE SOLVED: To provide an industrially advantageous method for producing a fluorinated hydrocarbon such as 2-fluorobutane useful as etching gas for a dry etching process. SOLUTION: There is provided a method for producing a fluorinated hydrocarbon represented by formula (3) by bringing an ether compound represented by formula (1) into contact with an acid fluoride represented by formula (2) in a halogenated hydrocarbon solvent in the presence of a metal halide represented by formula (4): MX3 (M represents a metal atom; X represents a chlorine atom or a bromine atom) (R1 and R2 each independently represent an alkyl group having 1-3 carbon atoms; R1 and R2 may be bonded to form a ring structure; R3 represents H, a methyl group or an ethyl group; R4 and R5 each independently represent a methyl group or an ethyl group.) SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Trichloroisocynuric acid/DMF as efficient reagent for chlorodehydration of alcohols under conventional and ultrasonic conditions

A new and efficient method for the chlorodehydration of alcohols utilizing TCCA/DMF is described. Various alcohols can be converted smoothly into their corresponding alkyl chlorides in high yields under mild conditions with short reaction times. Taylor & Francis Group, LLC.

The thermal and mass spectral fragmentation of N-butyl thiolo-, thiono-, and dithio-chloroformate

Thermal decomposition of n-butyl thiolochloroformate at 150C follows a similar pattern to that reported previously for n-butyl chloroformate, to give butyl chloride which is largely rearranged to the s-butyl isomer. An ion-pair mechanism, involving 1,2-and 1,3-hydride shifts, is proposed. The less stable thiono-and dithio-chloroformates decompose to give lower yields of butyl chlorides (mainly without rearrangement) together with numerous other byproducts, indicating the operation of a more complex combination of reaction pathways. The mass spectra of all three thio compounds exhibit molecular ions; the most prominent fragment ions in their spectra are the n-butyl cation, and the radical cations COS+ and CS2+. Numerous chlorine-containing ions of low intensity are also observed, and their mode of formation is discussed. Copyright Taylor &Francis Group, LLC.

Direct chlorination of alcohols with chlorodimethylsilane catalyzed by a gallium trichloride/tartrate system under neutral conditions

The reaction of secondary alcohols 1 with chlorodimethylsilane (HSiMe 2Cl) proceeded in the presence of a catalytic amount of GaCl 3/diethyl tartrate to give the corresponding organic chlorides 3. In the catalytic cycle, the reaction of diethyl tartrate 4a with HSiMe 2Cl 2 gives the chlorosilyl ether 5 with generation of H2. Alcohol-exchange between the formed chlorosilyl ether 5 and the substrate alcohol 1 affords alkoxychlorosilane 6, which reacts with catalytic GaCl 3 to give the chlorinated product 3. The moderate Lewis acidity of GaCl3 facilitates chlorination. Strong Lewis acids did not give product due to excessive affinity for the oxy-functionalities. Although tertiary alcohols were chlorinated by this system even in the absence of diethyl tartrate, certain alcohols that are less likely to give carbocationic species were effectively chlorinated using the GaCl3/diethyl tartrate system. The Royal Society of Chemistry.

FeCl3-activated oxidation of alkanes by [Os(N)O 3]-

Although the ion [OsVIII(N)(O)3]- is a stable species and is not known to act as an oxidant for organic substrates, it is readily activated by FeCl3 in CH2Cl2/CH 3CO2H to oxidize alkanes efficiently at room temperature. The oxidation can be made catalytic by using 2,6-dichloropyridine N-oxide as the terminal oxidant. The active intermediates in stoichiometric and catalytic oxidation are proposed to be [(O)3OsVIII≡N-Fe III] and [Cl4(O)OsVIII≡N-Fe III], respectively.

Gas-phase reactions of Cl atoms with propane, n-butane, and isobutane

Using the relative kinetic method, rate coefficients have been determined for the gas-phase reactions of chlorine atoms with propane, n-butane, and isobutane at total pressure of 100 Torr and the temperature range of 295-469 K. The Cl2 photolysis (λ = 420 nm) was used to generate Cl atoms in the presence of ethane as the reference compound. The experiments have been carried out using GC product analysis and the following rate constant expressions (in cm3 molecule-1 s-1) have been derived: (7.4 ±0.2) × 10-11 exp [-(70 ± 11)/T], Cl + C3H8 → HCl + CH3CH2CH2; (5.1 ± 0.5) × 10-11 exp [(104±32)/T], Cl + C3H8 → HCl + CH3CHCH3; (7.3±0.2) × 10-11 exp [-(68 ± 10)/T], Cl + n-C4H10 → HCl + CH3 CH2CH2CH2; (9.9 ± 2.2) × 10-11 exp [(106 ± 75)/T], Cl + n-C4H10 → HCl + CH3CH2CHCH3; (13.0 ± 1.8) × 10-11 exp [-(104 ± 50)/T], Cl + i-C4H10 → HCl + CH3CHCH3 CH2; (2.9 ± 0.5) × 10-11 exp [(155 ± 58)/T], Cl + i-C4H10 → HCl + CH3CCH3CH3 (all error bars are ±2ρ precision). The studies provide a set of reaction rate constants allowing to determine the contribution of competing hydrogen abstractions from primary, secondary, or tertiary carbon atom in alkane molecule.

Oxidative alkoxylation of zinc phosphide in alcoholic solutions of copper(II) chloride

Oxidative alkoxylation of Zn3P2 with the formation of valuable phosphoric and phosphorous acid esters occurred at a high rate and with a high selectivity in alcoholic solutions of CuCl2 under the action of oxygen at 30-60°C. Depending on the nature of the alcohol, two products were formed, namely, trialkyl phosphates (RO)3PO and dialkyl phosphites (RO)2HPO. Water favored the formation of dialkyl phosphates (RO)2(HO)PO. The kinetics and mechanism of the new catalytic reaction were studied, and the optimal conditions for conducting this reaction were found. The reaction proceeded in a topochemical mode by a separate redox mechanism.