54322-72-4

Basic information

• Product Name: Benzene, (1-chloro-3-butenyl)-
• Synonyms: 4-chloro-4-phenyl-1-butene;1-Chlor-1-phenyl-but-3-en;1-Chloro-1-phenyl-3-butene;(1-chlorobut-3-en-1-yl)benzene;Benzene,(1-chloro-3-butenyl)
• CAS NO: 54322-72-4
• Molecular Formula: C10H11Cl
• Molecular Weight: 166.65
• Mol File: 54322-72-4.mol

Chemical Properties

• CAS DataBase Reference: Benzene, (1-chloro-3-butenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (1-chloro-3-butenyl)-(54322-72-4)
• EPA Substance Registry System: Benzene, (1-chloro-3-butenyl)-(54322-72-4)

Safety Data

• Hazardous Substances Data: 54322-72-4(Hazardous Substances Data)

Upstream product

• 24850-33-7 allyltributylstanane 
• 120455-17-6 α-Methoxy-α-(phenylseleno)toluene 
• 153992-06-4 (Methoxy-methylselanyl-methyl)-benzene 
• 1793-90-4 allyltriethylgermane 
• 100-52-7 benzaldehyde 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 13865-07-1 (methoxy(phenylthio)methyl)benzene 
• 169172-96-7 α-Methoxy-α-(ethylthio)toluene 
• 22039-97-0 4-methoxy-4-phenyl-1-butene 
• 762-72-1 allyl-trimethyl-silane 
• 74472-22-3 allyl tert-butyldimethylsilane 
• 18752-21-1 allyltriphenylsilane 
• 33558-75-7 allyl(chloromethyl)dimethylsilane 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 54381-05-4 4-Phenyl-4-t-butoxybuten-1 
• 54322-74-6 4-cyclohexyl-4-phenyl-1-butene 

Relevant articles and documents

Iron catalyzed halogenation of benzylic aldehydes and ketones

A simple and efficient iron-catalyzed method for chlorination of aromatic carbonyl compounds is reported. By using 4-10 mol% Fe(iii) oxo acetate catalyst, prepared by solid state atmospheric oxidation of Fe(ii) acetate, in combination with triethylsilane and chlorotrimethylsilane, hydrosilylation of benzylic carbonyl compounds with subsequent chlorination is achieved within a few hours at room temperature. This new method is mild and rapid compared to the conventional two step approach involving reduction and chlorination reactions in separate stages. Development of synthetic methodology is also supplemented here by kinetic investigation of the reaction mechanism, which supports the tentative mechanisms suggested previously for similar reactions. This journal is

Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids

Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.

Boron trihalide mediated haloallylation of aryl aldehydes and its application to the preparation of (E)-1,3-dienes

In the presence of boron trihalides, aryl aldehydes couple readily with allylmetals to afford haloallylated products. The reactions tolerate a variety of functional groups. Simple aqueous workup of haloallylation reactions, followed by treatment with 1,8-

Unexpected Lewis acid mediated reactions of 1-arylbut-3-en-1-ols with trimethyl orthoformate - A new synthesis of homoallyl ethers and chlorides

1-Arylbut-3-en-1-ols react with trimethyl orthoformate in the presence of Lewis acids like InCl3, BiCl3, TiCl4, or BF3·OEt2 providing homoallyl ethers or homoallyl chlorides in high yields. Georg Thieme Verlag Stuttgart.

Boron trihalide mediated haloallylation of aryl aldehydes: Reaction and mechanistic insight

The reaction of aryl aldehydes with allylsilanes in the presence of boron trihalides produces haloallylated products. Mechanistic details are presented. The Royal Society of Chemistry.

Cyanuric chloride-mediated synthesis of allylic chloride - Ipso- versus tele-substitution

Synthesis of unsymmetrical allylic chlorides has been accomplished using cyanuric chloride in combination with DMF through ipso-substitution and tele-substitution by judicious choice of the substituents at appropriate positions of unsymmetrical allyl alcohols, taking care of their electronic and steric properties. Copyright Taylor & Francis Group, LLC.

Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane

On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides.This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated, or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used.In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of (O, S) mixed acetals are interpreted in terms of two major factors operating in opposite directions. 1H NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed.However, because of the much stronger C-O bond as compared to the C-Se bond, this latter (also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products.In contrast with BF3*OEt2, boron trichloride and boron tribromide were found to react with (O, Se) acetals to give the corresponding α-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.

Kinetics of the reactions of carboxonium ions and aldehyde boron trihalide complexes with alkenes and allylsilanes

Second order rate constants for the reactions of carboxonium ions Ar(MeO)CH+ and aldehyde-boron trihalide complexes ArCH=O→BX3 with allylsilanes and alkenes have been determined in CH2Cl2 solution. The relative reactivities of these electrophiles are almost independent of the nature of the π-nucleophiles, and it is possible to give an averaged reactivity order. For the electrophiles PhCH=O→BF3, PhCH=O→BCl3, Ph(p-MeOC6H4)CH+, and Ph(MeO)CH+, i.e., for PhCHX+ with X = F3BO-, Cl3BO-, p-MeOC6H4, MeO relative averaged reactivities of 1 : 5 × 102 : 1 × 104 : 4 ×105 (CH2Cl2, -70 °C) are determined indicating that the electrophilicities of aldehydeBHal3 complexes are only 3-6 orders of magnitude smaller than those of the corresponding carboxonium ions. The α-methoxy substituted benzyl cations Ar(MeO)CH+ are 3-16 times more reactive (CH2Cl2, 20 °C) than their phenylogous benzhydryl analogues Ar(P-MeOC6H4)CH+.

Halogenative Allylation and Reduction of Aromatic Acetals by Double Substitution of Alkoxyl Groups in Acetal

In the presence of excessive amount of acetyl halide along with a catalytic amount of tin(II) halide, aromatic acetals react with allyltrimethylsilane or triethylsilane to give α-allylbenzyl halides or benzyl halides, respectively, in good to excellent yields.