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ALPHA,ALPHA-DIMETHYLBENZYL CHLORIDE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 934-53-2 Structure
  • Basic information

    1. Product Name: ALPHA,ALPHA-DIMETHYLBENZYL CHLORIDE
    2. Synonyms: (1-Chloro-1-methylethyl)benzene;Benzene, (1-chloro-1-methylethyl)-;dimethylbenzylchloride;ALPHA,ALPHA-DIMETHYLBENZYL CHLORIDE;(α-CHLORO-ISOPROPYL)-BENZENE;a,a-Dimethyl-benzylchlorid;alpha, alpha-Dimethylbenzyl chloride 97%;A,A,- DIMETHYL BENZYL CHLORIDE
    3. CAS NO:934-53-2
    4. Molecular Formula: C9H11Cl
    5. Molecular Weight: 154.64
    6. EINECS: 213-284-8
    7. Product Categories: N/A
    8. Mol File: 934-53-2.mol
  • Chemical Properties

    1. Melting Point: -43.35°C (estimate)
    2. Boiling Point: 48-50°C 0,5mm
    3. Flash Point: 73°C
    4. Appearance: /
    5. Density: 1.0324 (estimate)
    6. Vapor Pressure: 0.468mmHg at 25°C
    7. Refractive Index: 1.5290
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: ALPHA,ALPHA-DIMETHYLBENZYL CHLORIDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: ALPHA,ALPHA-DIMETHYLBENZYL CHLORIDE(934-53-2)
    12. EPA Substance Registry System: ALPHA,ALPHA-DIMETHYLBENZYL CHLORIDE(934-53-2)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34-36
    3. Safety Statements: 26-36/37/39
    4. RIDADR: 3265
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 934-53-2(Hazardous Substances Data)

934-53-2 Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 1090, 1966 DOI: 10.1021/jo01342a024

Check Digit Verification of cas no

The CAS Registry Mumber 934-53-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 934-53:
(5*9)+(4*3)+(3*4)+(2*5)+(1*3)=82
82 % 10 = 2
So 934-53-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H11Cl/c1-9(2,10)8-6-4-3-5-7-8/h3-7H,1-2H3

934-53-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-chloropropan-2-ylbenzene

1.2 Other means of identification

Product number -
Other names 2-chloro2-phenylpropane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:934-53-2 SDS

934-53-2Relevant articles and documents

Carbocationic polymerization of isoprene using cumyl initiators: Progress in understanding side reactions

Ouardad, Samira,Wirotius, Anne-Laure,Kostjuk, Sergei,Ganachaud, Fran?ois,Peruch, Frédéric

, p. 59218 - 59225 (2015)

The cationic polymerization of isoprene using cumyl chloride/B(C6F5)3 and cumyl ether/TiCl4 systems was investigated in dichloromethane or in dichloromethane/methylcyclohexane mixtures varying the polymerization conditions. Polymerizations were performed in all cases in the presence of a large excess of a proton trap (2,6-di-tert-butyl pyridine, dtBP) compared to initiator in order to suppress any protic side reactions. As a consequence, no polymerization went to completion. Independently of the reaction conditions, trans-1,4-oligomers were exclusively obtained with mainly an olefinic terminal group. It was highlighted that an important loss of double bonds yielding saturated parts was observed, even in the absence of protons, assuming that a great amount of double bond loss generally observed in isoprene cationic polymerization could be due to intramolecular cyclization reactions. Nevertheless, under particular conditions (low temperature and/or low polarity medium), branching and cross-linking reactions were also found responsible for double bond loss.

First X-ray crystallographic study of a benzyl cation, cumyl hexafluoroantimonate(V), and structural implications

Laube, Thomas,Olah, George A.,Bau, Robert

, p. 3087 - 3092 (1997)

The crystal structure of the cumyl cation (1; 2-phenyl-2-propyl cation) has been determined at -124°C (as hexafluoroantimonate, 1.SbF6; R1 = 0.0502, wR2 = 0.1054). The cation 1 is nearly planar and has a short C+-C(ipso) bond (1.41(2) A?) and bond lengths in the phenyl ring which agree with strong benzylic delocalization. The weak but distinct shortening of the C+-CH3 bonds by 0.025(12) A? indicates weak C-H hyperconjugation. Nearly all H atoms are involved in H...F contacts to SbF6 anions, and one close C+...F contact (3.11 (2) A?) is observed. The phenyl rings form infinite stacks and are shifted against each other in the stack.

Thiourea-Mediated Halogenation of Alcohols

Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer

supporting information, p. 12901 - 12911 (2020/11/26)

The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.

Desulfurative Chlorination of Alkyl Phenyl Sulfides

Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.

, p. 918 - 921 (2017/02/26)

The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.

Mechanistic insight into the thermal 1,3-chlorine migrations of N-chloroacetanilides under neutral conditions

Cheng, Baoxiang,Xu, Jiaxi

, p. 518 - 525 (2017/05/01)

The mechanistic insight of the thermal 1,3-chlorine migration reactions of N-chloroacetanilides under neutral conditions has been investigated. The results indicate that the 1,3-chorinemigration reaction is initiated by the radical reaction of the homocleavage of the Cl-N bond and subsequent radical combination of the Cl-C bond on the aromatic rings. The radical mechanism was verified by the thermal rearrangement of Nchloro- N-(4-methylphenyl)acetamide in cumene. After generation of hydrochloric acid in the radical mechanism, the migrations occurred through the acid-catalyzed rearrangement as well as the acid-catalyzed Orton reaction. The current results provide a comprehensive understanding on the mechanistic insights in the Orton reaction under different conditions.

Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions

Ajvazi, Njomza,Stavber, Stojan

supporting information, p. 2430 - 2433 (2016/05/19)

A chemoselective method for the direct halogenation of different types of alcohols with halosilanes under catalyst- and solvent-free reaction conditions (SFRC) is reported. Various primary, secondary and tertiary benzyl alcohols and tertiary alkyl alcohols were directly transformed to the corresponding benzyl and alkyl halides, respectively, using chlorotrimethylsilane (TMSCl) and bromotrimethylsilane (TMSBr).

A Visible-Light-Induced α-H Chlorination of Alkylarenes with Inorganic Chloride under NanoAg@AgCl

Liu, Shouxin,Zhang, Qi,Li, Huiying,Yang, Yihua,Tian, Xia,Whiting, Andrew

supporting information, p. 9671 - 9675 (2015/06/30)

An efficient, photocatalytic chlorination of alkylarene α-H groups using NaCl/HCl as a chlorine source has been developed, which involves a radical mechanism under visible-light (including sunlight) conditions. A chlorine radical is proposed to be formed by an electron transfer from chloride ion to O2 in air through the bandgap hole of the semiconductor AgCl. The chlorination protocol is characterized by its use of natural sunlight or other visible light, mild conditions, cheap source of chlorine, green solvent, and high selectivity. The yield of benzylchloride is 95 % with a toluene conversion as high as 40 %, which rivals traditional chlorination methods.

Iron-catalyzed borylation of alkyl electrophiles

Atack, Thomas C.,Lecker, Rachel M.,Cook, Silas P.

supporting information, p. 9521 - 9523 (2014/07/22)

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

Solvolysis of 2-chloro-2(3,4-disubstituted) phenylpropanes: Validity of Hammett-Brown σ+ constants in assessing additive effects of substituents

Taha, Ahmed A.

scheme or table, p. 514 - 523 (2012/07/28)

The objective of this study is to test the suitability of the extended Hammett-Brown equation, log (kXX/kHH) = ρ+∑σ+, in depicting satisfactorily additive effects of electronegative atom-bearing substituents, which are known to possess diverse and multicomponent influences on the side chain reactions of polysubstituted benzenes. The equation has been used to correlate, for the first time, the additive effect of substituents in the specific rates of solvolysis of 2-chloro-2-phenylpropanes (3b-3f) having 3-F,4-Me, 3-Br,4-Me, 3-I,4-Me, 3-Me,4-Me, or 3-MeO,4-Me substituents. The rates were determined titrimetrically at 288, 298, and 308 K using 90% aqueous acetone as solvent. Measured additive effects of these substituents on the solvolysis rate and activation parameters of the parent cumyl chloride (2-chloro-2-phenylpropane) are found to be well correlated using the equation given above. Plots of log (kXX/k HH) of 3b-3f together with mainly di-, but also tri- and mono-substituted cumyl chlorides from previous studies against ∑σ+ give a linear correlation coefficient of 0.990 as a measure of the validity of the equation to depict such systems. The halogen substituents' extent of conformity with additivity reflected in their relative (kobsd/kcalcd) rate ratios is found to correlate with the steric size of substituents. Plots of rate ratios against Taft's steric factor of each halogen give a linear correlation coefficient of 0.994 for the 3-halo substituents. The 3,4-dimethyl substituents' relative rate ratio of 1.03 shows excellent additivity, whereas the 3-methoxy-4-methyl ratio of 1.43 shows the methoxy group to be far less deactivating than predicted. Similar trends were found for the free energy of activation (δG? - δG 0?) differences, which correlated linearly with a coefficient of 0.983 with Taft's steric factor of halogen atoms.

Hydrocarbon chlorination promoted by manganese and iron complexes with methylated derivatives of bis(2-pyridylmethyl)-1,2-ethanediamine

Goldsmith, Christian R.,Coates, Cristina M.,Hagan, Kenton,Mitchell, Casey A.

scheme or table, p. 24 - 30 (2011/04/22)

Non-heme iron halogenases, such as SyrB2 and CytC3, catalyze the regioselective chlorination and bromination of aliphatic C-H bonds. Reported here is the hydrocarbon chlorination promoted by manganese and iron complexes with methylated derivatives of bis(2-pyridylmethyl)-1,2-ethanediamine (bispicen). The reactions between these coordination compounds and meta-chloroperbenzoic acid generate oxidants capable of oxidizing weak C-H bonds to C-Cl bonds. This chemistry is regioselective, with a strong preference for activating C-H bonds on secondary carbons over weaker C-H bonds on tertiary carbons. The reactivity is consistent with the methyl groups on the ligands preventing more sterically encumbered substrates from accessing the reactive portions of a [MIV(LMen)(O)Cl2] oxidant. The iron compounds promote more hydrocarbon chlorination than their manganese analogs.

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