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2-Bromo-5-fluorobenzyl bromide is an organic compound characterized by the presence of a bromine atom at the 2nd position and a fluorine atom at the 5th position on a benzene ring, with a bromomethyl group attached. It is a white to almost white solid and serves as a crucial intermediate in the synthesis of various pharmaceutical compounds.

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  • 112399-50-5 Structure
  • Basic information

    1. Product Name: 2-Bromo-5-fluorobenzyl bromide
    2. Synonyms: 1-Bromo-2-(bromomethyl)-4-fluorobenzene;5-FLUORO-2-BROMOBENZYL BROMIDE;2-BROMO-5-FLUOROBENZYL BROMIDE;2-Bromo-5-fluorobenzyl bromide 95%;2-Bromo-5-fluorobenzylbromide95%;Bromofluorobenzylbromide 25---;2-BroMo-5-fluorobenl broMide;1-Bromo-2-(bromomethyl)-4-fluorobenzene, alpha,2-Dibromo-5-fluorotoluene
    3. CAS NO:112399-50-5
    4. Molecular Formula: C7H5Br2F
    5. Molecular Weight: 267.92
    6. EINECS: -0
    7. Product Categories: Fluorine series;alkyl bromide| alkyl Fluorine
    8. Mol File: 112399-50-5.mol
  • Chemical Properties

    1. Melting Point: 34-35°C
    2. Boiling Point: 89-90°C 1mm
    3. Flash Point: 89-90°C/1mm
    4. Appearance: /
    5. Density: 1.923 g/cm3
    6. Vapor Pressure: 0.045mmHg at 25°C
    7. Refractive Index: 1.59
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. Water Solubility: Difficult to mix in water.
    11. Sensitive: Lachrymatory
    12. BRN: 4177658
    13. CAS DataBase Reference: 2-Bromo-5-fluorobenzyl bromide(CAS DataBase Reference)
    14. NIST Chemistry Reference: 2-Bromo-5-fluorobenzyl bromide(112399-50-5)
    15. EPA Substance Registry System: 2-Bromo-5-fluorobenzyl bromide(112399-50-5)
  • Safety Data

    1. Hazard Codes: C,Xn
    2. Statements: 34-36-52-22
    3. Safety Statements: 26-36/37/39-45
    4. RIDADR: 1759
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 8
    8. PackingGroup: III
    9. Hazardous Substances Data: 112399-50-5(Hazardous Substances Data)

112399-50-5 Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-5-fluorobenzyl bromide is used as a key intermediate in the synthesis of Benzazepines, a class of compounds with potential therapeutic applications. The alkylation of the β-amino ester 1a with 2-bromo-5-fluorobenzyl bromide results in the formation of Benzazepines as a white solid after purification through silica gel chromatography. This process highlights the importance of 2-Bromo-5-fluorobenzyl bromide in the development of new pharmaceutical agents.

Check Digit Verification of cas no

The CAS Registry Mumber 112399-50-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,3,9 and 9 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 112399-50:
(8*1)+(7*1)+(6*2)+(5*3)+(4*9)+(3*9)+(2*5)+(1*0)=115
115 % 10 = 5
So 112399-50-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H5Br2F/c8-4-5-3-6(10)1-2-7(5)9/h1-3H,4H2

112399-50-5 Well-known Company Product Price

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  • Alfa Aesar

  • (L09553)  2-Bromo-5-fluorobenzyl bromide, 97%   

  • 112399-50-5

  • 1g

  • 422.0CNY

  • Detail
  • Alfa Aesar

  • (L09553)  2-Bromo-5-fluorobenzyl bromide, 97%   

  • 112399-50-5

  • 5g

  • 1476.0CNY

  • Detail

112399-50-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Bromo-5-fluorobenzyl bromide

1.2 Other means of identification

Product number -
Other names 1-Bromo-2-(bromomethyl)-4-fluorobenzene

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:112399-50-5 SDS

112399-50-5Relevant articles and documents

Cross-coupling strategy for the synthesis of diazocines

Eleya, Nadi,Li, Shuo,Staubitz, Anne

supporting information, p. 1624 - 1627 (2020/03/13)

Ethylene bridged azobenzenes are novel, promising molecular switches that are thermodynamically more stable in the (Z) than in the (E) configuration, contrary to the linear azobenzene. However, their previous synthetic routes were often not general, and yields were poorly reproducible, and sometimes very low. Here we present a new synthetic strategy that is both versatile and reliable. Starting from widely available 2-bromobenzyl bromides, the designated molecules can be obtained in three simple steps.

STEREORETENTIVE CROSS-COUPLING OF BORONIC ACIDS

-

Paragraph 0112; 0195-0197, (2018/11/21)

The present disclosure provides tri-orthoalkylphenyl phosphine catalysts that are tuned electrically and sterically. Method of using the catalyst for cross-coupling of unactivated secondary boronic acids with near-perfect levels of site- and stereoretention are also provided.

Au-catalyzed biaryl coupling to generate 5- to 9-membered rings: Turnover-limiting reductive elimination versus π-complexation

Corrie, Tom J. A.,Ball, Liam T.,Russell, Christopher A.,Lloyd-Jones, Guy C.

supporting information, p. 245 - 254 (2017/05/29)

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes-substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to π-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the π-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

Au-Catalyzed Biaryl Coupling to Generate 5- To 9-Membered Rings: Turnover-Limiting Reductive Elimination versus ?-Complexation

Ball, Liam T.,Corrie, Tom J. A.,Lloyd-Jones, Guy C.,Russell, Christopher A.

supporting information, p. 245 - 254 (2021/09/04)

The intramolecular gold-catalyzed arylation of arenes by aryl-trimethylsilanes has been investigated from both mechanistic and preparative aspects. The reaction generates 5- to 9-membered rings, and of the 44 examples studied, 10 include a heteroatom (N, O). Tethering of the arene to the arylsilane provides not only a tool to probe the impact of the conformational flexibility of Ar-Au-Ar intermediates, via systematic modulation of the length of aryl-aryl linkage, but also the ability to arylate neutral and electron-poor arenes - substrates that do not react at all in the intermolecular process. Rendering the arylation intramolecular also results in phenomenologically simpler reaction kinetics, and overall these features have facilitated a detailed study of linear free energy relationships, kinetic isotope effects, and the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diaryl-gold(III) species. The turnover-limiting step for the formation of a series of fluorene derivatives is sensitive to the reactivity of the arene and changes from reductive elimination to ?-complexation for arenes bearing strongly electron-withdrawing substituents (σ > 0.43). Reductive elimination is accelerated by electron-donating substituents (ρ = -2.0) on one or both rings, with the individual σ-values being additive in nature. Longer and more flexible tethers between the two aryl rings result in faster reductive elimination from Ar-Au(X)-Ar and lead to the ?-complexation of the arene by Ar-AuX2 becoming the turnover-limiting step.

Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

Johnson, Kirsten F.,Schmidt, Adam C.,Stanley, Levi M.

supporting information, p. 4654 - 4657 (2015/10/12)

The development of a rhodium catalyst for endo- and enantioselective hydroacylation of ortho-allylbenzaldehydes is reported. A catalyst generated in situ from [Rh(COD)Cl]2, (R)-DTBM-SEGPHOS, and NaBARF promotes the desired hydroacylation reactions and minimizes the formation of byproducts from competitive alkene isomerization and ene/dehydration pathways. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in moderate-to-high yields (49-91%) with excellent enantioselectivities (96-99% ee).

Silver-catalyzed stereoselective [3+2] cycloadditions of cyclopropyl-indanimines with carbonyl compounds

Hung, Hsiao-Hua,Liao, Yi-Ching,Liu, Rai-Shung

supporting information, p. 1545 - 1552 (2013/06/27)

Silver-catalyzed stereoselective [3+2] cycloadditions between mono-substituted cyclopropyl-indanimines and aldehydes are reported. The stereochemical course of the reaction is rationalized with a cyclic transition state. The resulting indanimine cycloadducts are not readily hydrolyzed unless external aldehydes are present with the silver catalyst. Notably, this hydrolysis process leads to a change of stereochemistry for the resulting indanone products. Copyright

Atropoisomeric (P,N) ligands for the highly enantioselective Pd-catalyzed intramolecular asymmetric α-arylation of α-branched aldehydes

Nareddy, Pradeep,Mantilli, Luca,Guenee, Laure,Mazet, Clement

supporting information; scheme or table, p. 3826 - 3831 (2012/06/01)

Three-in-one: A short synthetic route readily gives access to a new class of chiral (P,N) ligands characterized by three distinct elements of chirality. These ligands are highly enantioselective in the challenging Pd-catalyzed intramolecular asymmetric α-

Palladium-catalyzed intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides

Shen, Zengming,Ni, Zhenjie,Mo, Song,Wang, Jing,Zhu, Yamin

supporting information; experimental part, p. 4859 - 4865 (2012/06/04)

Give me a ring? An efficient approach has been developed for the intramolecular decarboxylative coupling of arene carboxylic acids/esters with aryl bromides catalyzed by palladium (see scheme). From a synthetic viewpoint, this method is highly attractive because the catalyst loading is low, the optimized reaction conditions are mild, and the substrate scope is broad. Copyright

CERTAIN DIPEPTIDYL PEPTIDASE INHIBITORS

-

, (2011/07/08)

Provided are certain dipeptidyl peptidase inhibitors, pharmaceutical compositions thereof, and methods of use therefor.

A concise synthesis of 6,7-dihydro-5H-dibenz[c,e]azepin-5-one

Goh, Young-Hyoung,Kim, Guncheol,Kim, Bum Tae,Heo, Jung-Nyoung

experimental part, p. 669 - 677 (2010/04/29)

A concise and efficient strategy for the synthesis of dibenz[c,e]azepin-5-ones has been developed. The approach relies on a key transformation involving Suzuki-Miyaura coupling of 2-bromobenzyl azides with 2-(methoxycarbonyl)phenylboronic acid, followed b

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