344-18-3

Basic information

• Product Name: 2,6-Dibromo-4-fluoroaniline
• Synonyms: 2,6-DIBROMO-4-FLUOROANILINE;1-AMINO-2,6-DIBROMO-4-FLUOROBENZENE;2,6-Dibromo-4-Tluoroaniline;2,6-Dibromo-4-fluoroaniline 98%;2,6-Dibromo-4-fluoroaniline98%;2,6-DIBROMO-4-FLUOROANLINE;4'-fluoro-[1,1'-biphenyl]-2-carbonitrile;2,6-Dibromo-4-fluoro
• CAS NO: 344-18-3
• Molecular Formula: C₆H₄Br₂FN
• Molecular Weight: 268.91
• Product Categories: Miscellaneous;Anilines, Amides & Amines;Bromine Compounds;Fluorine Compounds;Amines;C2 to C6;Nitrogen Compounds
• Mol File: 344-18-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 64-66 °C(lit.)
• Boiling Point: 265.2 °C at 760 mmHg
• Flash Point: 114.2 °C
• Appearance: grey-purple to brown crystalline powder, needles
• Density: 2.0271 (rough estimate)
• Vapor Pressure: 0.139mmHg at 25°C
• Refractive Index: 1.4640 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 0.54±0.10(Predicted)
• BRN: 3246923
• CAS DataBase Reference: 2,6-Dibromo-4-fluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dibromo-4-fluoroaniline(344-18-3)
• EPA Substance Registry System: 2,6-Dibromo-4-fluoroaniline(344-18-3)

Safety Data

• Hazard Codes: Xn,T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 344-18-3(Hazardous Substances Data)

Usage

Description

2,6-Dibromo-4-fluoroaniline is an organic compound characterized by the presence of two bromine atoms at the 2nd and 6th positions and a fluorine atom at the 4th position on an aniline (aminobenzene) backbone. This unique structure endows it with specific chemical properties that make it a valuable intermediate in the synthesis of various pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Industry:
2,6-Dibromo-4-fluoroaniline is used as a key intermediate in the asymmetric synthesis of prostaglandin D2 receptor antagonists. These antagonists are crucial for the development of medications aimed at treating allergic rhinitis, a common condition characterized by inflammation of the nasal passages. 2,6-Dibromo-4-fluoroaniline's specific substitution pattern allows for the creation of targeted therapies with fewer side effects, improving patient outcomes and quality of life.

InChI:InChI=1/C6H4Cl2FN/c7-4-1-3(9)2-5(8)6(4)10/h1-2H,10H2

Upstream product

• 393-42-0 2-amino-5-fluorobenzenesulfonic acid 
• 371-40-4 4-fluoroaniline 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 351-83-7 4'-fluoroacetanilide 

Downstream Products

• 576-82-9 1,2,3-tribromo-5-fluorobenzene 
• 38366-77-7 2,6-dibromo-4-fluorothioanisole 
• 38366-78-8 2,6-Dibrom-4-fluorothiophenol 
• 117336-04-6 2,6-diethyl-4-fluorobenzenamine 
• 828932-39-4 2-[(1R)-cyclopent-2-en-1-yl]-N-(2,6-dibromo-4-fluorophenyl)acetamide 
• 898127-99-6 1,3-dibromo-5-fluoro-2-nitrosobenzene 
• 946197-48-4 1-N-allyl-2,6-dibromo-4-fluoroaniline 
• 899369-58-5 4-(3,5-dibromo-4-nitrosophenyl)morpholine 
• 828932-42-9 (3aR,6aS)-1-(2,6-dibromo-4-fluorophenyl)-3,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2(1H)-one 
• 571170-92-8 [4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester 
• 571170-77-9 laropiprant 
• 62720-29-0 1,3-dibromo-5-fluoro-2-iodobenzene 
• 401631-93-4 C₁₀H₁₂Br₂FN₃ 
• 119664-62-9 2-bromo-N-(2,6-diethyl-4-fluoro-phenyl)-acetamide 

Relevant articles and documents

A Practical Procedure for Regioselective Bromination of Anilines

A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.

Method of catalytically synthesizing polybromo-aniline in water phase

The invention discloses a method of catalytically synthesizing polybromo-aniline in a water phase. The method comprises following steps: adding a catalytic amount of a free radical initiator, aniline derivatives, cheap and low-toxic bromine salts, and water into a reactor; carrying out reactions in a photocatalytic reaction instrument under power of 5W at a room temperature; after a while, extracting the reaction product by ethyl acetate, and carrying out recrystallization to obtain polybromo-aniline; wherein the free radical initiator is eosin, sodium persulfate, or potassium persulfate. The power of the incandescent lamp of the photocatalytic reaction instrument is 5W. The free radical initiator and bromine salts are cheap and easily available. The method is an ideal synthesis method of polybromo-aniline. Cheap and low-toxic bromine salts are used to replace liquid bromine. The cheap and easily available free radical initiator is used to replace unstable and explosive hydrogen peroxide. After 4 to 10 hours of reactions under the power of 5W, polybromo-aniline can be synthesized, the yield and the reaction selectivity are high, the byproducts are few, and the post treatment is simple.

Pyrrolidine-3-carboxylic acids as endothelin antagonists. 4. Side chain conformational restriction leads to ET(B) selectivity

When the dialkylacetamide side chain of the ETA-selective antagonist ABT-627 is replaced with a 2,6-dialkylacetanilide, the resultant analogues show a complete reversal of receptor selectivity, preferring ETB over ETA. By optimizing the aniline substitution pattern, as well as the alkoxy group on the 2-aryl substituent, it is possible to prepare antagonists with subnanomolar affinity for ETB and with selectivities in excess of 4000-fold. A number of these compounds also show promising pharmacokinetic profiles; a useful balance of properties is found in A-192621 (38). Pharmacology studies with A-192621 serve to reveal the role of the ETB receptor in modulating blood pressure; the observed hypertensive response to persistent ETB blockade is consistent with previous postulates and indicates that ETB-selective antagonists may not be suitable as agents for long-term systemic therapy.