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4-(Bromomethyl)-2-fluorobenzonitrile is an organic compound characterized by its bromomethyl and fluoro substituents on a benzonitrile framework. It is a synthetic intermediate with potential applications in the pharmaceutical and chemical industries due to its unique structural features.

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  • 222978-03-2 Structure
  • Basic information

    1. Product Name: 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE
    2. Synonyms: 4-CYANO-3-FLUOROBENZYL BROMIDE;4-(BROMOMETHYL)-2-FLUOROBENZONITRILE;4-Cyano-3-fluorobenzyl bromide 98%;4-Cyano-3-fluorobenzylbromide98%;4-(Bromomethyl)-2-fluorobenzonitrile 98%;4-Cyano-3-fluorobenzyl bromide, alpha-Bromo-2-fluoro-p-tolunitrile;Benzonitrile, 4-(bromomethyl)-2-fluoro-
    3. CAS NO:222978-03-2
    4. Molecular Formula: C8H5BrFN
    5. Molecular Weight: 214.03
    6. EINECS: N/A
    7. Product Categories: Fluorine series
    8. Mol File: 222978-03-2.mol
  • Chemical Properties

    1. Melting Point: 44-45 °C
    2. Boiling Point: 275.6 °C at 760 mmHg
    3. Flash Point: 120.5 °C
    4. Appearance: /
    5. Density: 1.59 g/cm3
    6. Vapor Pressure: 0.00505mmHg at 25°C
    7. Refractive Index: 1.564
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: Methanol (Slightly)
    10. Sensitive: Lachrymatory
    11. CAS DataBase Reference: 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE(222978-03-2)
    13. EPA Substance Registry System: 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE(222978-03-2)
  • Safety Data

    1. Hazard Codes: C,Xn
    2. Statements: 20/21/22
    3. Safety Statements: 36/37
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 222978-03-2(Hazardous Substances Data)

222978-03-2 Usage

Uses

Used in Pharmaceutical Industry:
4-(Bromomethyl)-2-fluorobenzonitrile is used as a building block for the preparation and optimization of BAY-876, a highly selective GLUT1 inhibitor. 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE plays a crucial role in the development of drugs targeting glucose transport, which can be beneficial for managing and treating various diseases related to glucose metabolism dysregulation.
Used in Chemical Synthesis:
4-(Bromomethyl)-2-fluorobenzonitrile can also be utilized as an intermediate in the synthesis of various chemical compounds, particularly those with potential applications in the pharmaceutical, agrochemical, and materials science industries. Its unique structural features make it a valuable component in the design and synthesis of novel molecules with specific biological activities or material properties.

Check Digit Verification of cas no

The CAS Registry Mumber 222978-03-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,2,9,7 and 8 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 222978-03:
(8*2)+(7*2)+(6*2)+(5*9)+(4*7)+(3*8)+(2*0)+(1*3)=142
142 % 10 = 2
So 222978-03-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H5BrFN/c9-4-6-1-2-7(5-11)8(10)3-6/h1-3H,4H2

222978-03-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(BROMOMETHYL)-2-FLUOROBENZONITRILE

1.2 Other means of identification

Product number -
Other names 2-fluoro-4-bromomethylbenzonitrile

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:222978-03-2 SDS

222978-03-2Relevant articles and documents

Mechanistic Studies into the Oxidative Addition of Co(I) Complexes: Combining Electroanalytical Techniques with Parameterization

Sandford, Christopher,Fries, Lydia R.,Ball, Tyler E.,Minteer, Shelley D.,Sigman, Matthew S.

, p. 18877 - 18889 (2019/11/28)

The oxidative addition of organic electrophiles into electrochemically generated Co(I) complexes has been widely utilized as a strategy to produce carbon-centered radicals when cobalt is ligated by a polydentate ligand. Changing to a bidentate ligand prov

Exploring the tetrahydroisoquinoline thiohydantoin scaffold blockade the androgen receptor as potent anti-prostate cancer agents

Xu, Xi,Ge, Raoling,Li, Lei,Wang, Jubo,Lu, Xiaoyu,Xue, Siqi,Chen, Xijing,Li, Zhiyu,Bian, Jinlei

, p. 1325 - 1344 (2017/11/13)

Prostate cancer (PC) is a major cause of cancer-related male death in worldwide and the identification of new and improved potent anti-PC molecules is constantly required. A novel scaffold of tetrahydroisoquinoline thiohydantoin was rationally designed based on the enzalutamide structures and our pre-work, leading to the discovery of a series of new antiproliferative compounds. Several new analogues displayed improved androgen receptor (AR) antagonistic activity, while maintaining the higher selective toxicity toward LNCaP cells (AR-rich) versus DU145 cells (AR-deficient) compared to enzalutamide. In fact, compound 55 exhibited promising in vitro antitumor activity by impairing AR unclear translocation. More importantly, 55 showed better pharmacokinetic properties compared to the compound 1 reported in our pre-work. These results demonstrate a step towards the development of novel and improved AR antagonists.

Optimization of Novel 1-Methyl-1 H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber's Pole Worm

Le, Thuy G.,Kundu, Abhijit,Ghoshal, Atanu,Nguyen, Nghi H.,Preston, Sarah,Jiao, Yaqing,Ruan, Banfeng,Xue, Lian,Huang, Fei,Keiser, Jennifer,Hofmann, Andreas,Chang, Bill C. H.,Garcia-Bustos, Jose,Jabbar, Abdul,Wells, Timothy N. C.,Palmer, Michael J.,Gasser, Robin B.,Baell, Jonathan B.

, p. 10875 - 10894 (2019/01/04)

A phenotypic screen of a diverse library of small molecules for inhibition of the development of larvae of the parasitic nematode Haemonchus contortus led to the identification of a 1-methyl-1H-pyrazole-5-carboxamide derivative with an IC50 of 0.29 μM. Medicinal chemistry optimization targeted modifications on the left-hand side (LHS), middle section, and right-hand side (RHS) of the scaffold in order to elucidate the structure-activity relationship (SAR). Strong SAR allowed for the iterative and directed assembly of a focus set of 64 analogues, from which compound 60 was identified as the most potent compound, inhibiting the development of the fourth larval (L4) stage with an IC50 of 0.01 μM. In contrast, only 18% inhibition of the mammary epithelial cell line MCF10A viability was observed, even at concentrations as high as 50 μM.

Optimization of Substrate-Analogue Furin Inhibitors

Ivanova, Teodora,Hardes, Kornelia,Kallis, Stephanie,Dahms, Sven O.,Than, Manuel E.,Künzel, Sebastian,B?ttcher-Friebertsh?user, Eva,Lindberg, Iris,Jiao, Guan-Sheng,Bartenschlager, Ralf,Steinmetzer, Torsten

, p. 1953 - 1968 (2017/11/22)

The proprotein convertase furin is a potential target for drug design, especially for the inhibition of furin-dependent virus replication. All effective synthetic furin inhibitors identified thus far are multibasic compounds; the highest potency was found for our previously developed inhibitor 4-(guanidinomethyl)phenylacetyl-Arg-Tle-Arg-4-amidinobenzylamide (MI-1148). An initial study in mice revealed a narrow therapeutic range for this tetrabasic compound, while significantly reduced toxicity was observed for some tribasic analogues. This suggests that the toxicity depends at least to some extent on the overall multibasic character of this inhibitor. Therefore, in a first approach, the C-terminal benzamidine of MI-1148 was replaced by less basic P1 residues. Despite decreased potency, a few compounds still inhibit furin in the low nanomolar range, but display negligible efficacy in cells. In a second approach, the P2 arginine was replaced by lysine; compared to MI-1148, this furin inhibitor has slightly decreased potency, but exhibits similar antiviral activity against West Nile and Dengue virus in cell culture and decreased toxicity in mice. These results provide a promising starting point for the development of efficacious and well-tolerated furin inhibitors.

Thio hydantoin ternary and circular androgen receptor antagonists and use thereof (by machine translation)

-

Paragraph 0068; 0070; 0071, (2017/08/02)

The invention relates to the field of pharmaceutical chemistry, and in particular relates to a category of thio hydantoin and indoline skeleton has the role of the anti-prostate cancer compound (I) and (II), a method for preparing these compounds, these c

SUBSTITUTED BENZOXAZOLES AND METHODS OF USE THEREOF

-

Page/Page column 51, (2014/09/29)

The invention provides compounds having the general formula (I): and pharmaceutically acceptable salts thereof, wherein the variables RA, subscript n, ring A, X2, L, subscript m, X1, R1, R2, R3, Rsup

PHENYLALANINE DERIVATIVES AND THEIR USE AS NON-PEPTIDE GLP-1 RECEPTOR MODULATORS

-

Page/Page column 32, (2012/01/14)

Provided herein are non-peptide GLP-1 receptor modulator compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of a metab

2-AMINOBENZAMIDE DERIVATIVE

-

Page/Page column 16, (2008/12/07)

To provide a novel and excellent agent for treating or preventing nociceptive pain, neuropathic pain, cancer pain, headache, bladder function disorder and the like, based on the inhibitory action on the capsaicin receptor VR1 activation. The present inven

Phenyl-1,2,4-Oxadiazolone Derivatives, Processes For Their Preparation and Methods For Their Use as Pharmaceuticals

-

Page/Page column 70, (2008/12/04)

The inventive compounds of the present invention are comprised of phenyl and pyridinyl-1,2,4-oxadiazolone derivatives and their physiologically acceptable salts and functional derivatives that are shown to provide peroxisome proliferator activator recepto

Design, synthesis, and biological evaluation of pyrazinones containing novel P1 needles as inhibitors of TF/VIIa

Trujillo, John I.,Huang, Horng-Chih,Neumann, William L.,Mahoney, Matthew W.,Long, Scott,Huang, Wei,Garland, Danny J.,Kusturin, Carrie,Abbas, Zaheer,South, Michael S.,Reitz, David B.

, p. 4568 - 4574 (2008/02/11)

Herein is described the design, synthesis, and enzymatic activity of a series of substituted pyrazinones as inhibitors of the TF/VIIa complex. These inhibitors were designed to explore replacement and variation of the P1 amidine described previously [J. Med. Chem. 2003, 46, 4050]. The P1 needle replacements were selected based upon their reduced basicity compared to the parent phenyl amidine (pKa ~ 12). A contributing factor towards the oral bioavailability of a compound is the ionization state of the compound in the intestinal tract. The desired outcome of the study was to identify an orally bioavailable TF-VIIa inhibitor.

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