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4392-24-9

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4392-24-9 Usage

Chemical Properties

light yellow to beige cryst. low melting solid

Uses

Cinnamyl bromide, is used in the synthesis of naftifine.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 1697, 1987 DOI: 10.1016/S0040-4039(00)95397-8

Check Digit Verification of cas no

The CAS Registry Mumber 4392-24-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,9 and 2 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 4392-24:
(6*4)+(5*3)+(4*9)+(3*2)+(2*2)+(1*4)=89
89 % 10 = 9
So 4392-24-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H9Br/c10-8-4-7-9-5-2-1-3-6-9/h1-7H,8H2/b7-4+

4392-24-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C1109)  Cinnamyl Bromide  >98.0%(GC)(T)

  • 4392-24-9

  • 25g

  • 655.00CNY

  • Detail
  • Alfa Aesar

  • (L01420)  Cinnamyl bromide, predominantly trans, 95%   

  • 4392-24-9

  • 5g

  • 338.0CNY

  • Detail
  • Alfa Aesar

  • (L01420)  Cinnamyl bromide, predominantly trans, 95%   

  • 4392-24-9

  • 25g

  • 1088.0CNY

  • Detail
  • Alfa Aesar

  • (L01420)  Cinnamyl bromide, predominantly trans, 95%   

  • 4392-24-9

  • 100g

  • 2469.0CNY

  • Detail
  • Aldrich

  • (C81217)  3-Bromo-1-phenyl-1-propene  97%

  • 4392-24-9

  • C81217-5G

  • 321.75CNY

  • Detail
  • Aldrich

  • (C81217)  3-Bromo-1-phenyl-1-propene  97%

  • 4392-24-9

  • C81217-25G

  • 1,096.29CNY

  • Detail
  • Aldrich

  • (C81217)  3-Bromo-1-phenyl-1-propene  97%

  • 4392-24-9

  • C81217-100G

  • 3,707.73CNY

  • Detail

4392-24-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Cinnamyl bromide

1.2 Other means of identification

Product number -
Other names 3-PHENYLALLYLBROMID

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:4392-24-9 SDS

4392-24-9Relevant articles and documents

The Reactivity of Benzyl Lithium Species is Regulated by Intermediate Structures

Kroesen, Ulrike,Knauer, Lena,Strohmann, Carsten

, p. 6232 - 6235 (2017)

The reaction of benzyl lithiums is an important aspect in organic and organometallic synthesis. Reported herein are detailed insights into the reactivity of benzyl lithiums as regulated by intermediate structures. By discussing the carbometalation of allylamines and the reaction of the formed benzyl-lithium compounds with electrophiles, the influence of the metal as well as the solvent on the electronic structure of the intermediate is described. This molecular structure strongly influences the reactivity of these intermediates. By choosing the appropriate reaction conditions, the regioselectivity of reactions with electrophiles can be regulated. With trimethylchlorosilane in n-pentane a selective reaction at the para-position takes place. In contrast, selective reaction at the benzylic position, with trimethylchlorostannane in tetrahydrofuran (THF) as a solvent, is accomplished.

Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method

Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.

supporting information, p. 4176 - 4182 (2021/02/01)

Daptomycin (DAP) is a calcium (Ca2+)-dependent FDA-approved antibiotic drug for the treatment of Gram-positive infections. It possesses a complex pharmacophore hampering derivatization and/or synthesis of analogues. To mimic the Ca2+-binding effect, we used a chemoenzymatic approach to modify the tryptophan (Trp) residue of DAP and synthesize kinetically characterized and structurally elucidated regiospecific Trp-modified DAP analogues. We demonstrated that the modified DAPs are several times more active than the parent molecule against antibiotic-susceptible and antibiotic-resistant Gram-positive bacteria. Strikingly, and in contrast to the parent molecule, the DAP derivatives do not rely on calcium or any additional elements for activity.

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades

Wang, Hong-Fa,Guo, Lin-Na,Fan, Zhi-Bo,Tang, Tian-Hua,Zi, Weiwei

supporting information, p. 2676 - 2681 (2021/04/12)

A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.

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