2-Bromo-6-chlorobenzaldehyde

Base Information

• Chemical Name: 2-Bromo-6-chlorobenzaldehyde
• CAS No.: 64622-16-8
• Molecular Formula: C7H4BrClO
• Molecular Weight: 219.465
• Hs Code.: 2913000090
• European Community (EC) Number: 816-695-6
• DSSTox Substance ID: DTXSID80542897
• Nikkaji Number: J2.941.314B
• Wikidata: Q82419698
• Mol file: 64622-16-8.mol

Synonyms:2-Bromo-6-chlorobenzaldehyde;64622-16-8;2-CHLORO-6-BROMOBENZALDEHYDE;Benzaldehyde, 2-bromo-6-chloro-;AKOS MSC-0782;MFCD00266792;SCHEMBL611923;2-bromo-6-chloro-benzaldehyde;DTXSID80542897;NUGMENVSVAURGO-UHFFFAOYSA-N;CS-M3138;AKOS004115241;AM62292;GS-3934;MB01095;2-Bromo-6-chlorobenzaldehyde, AldrichCPR;AC-28682;SY019134;EN300-131417;AR-362/43519160;J-508438;Z1269187937

Chemical Property of 2-Bromo-6-chlorobenzaldehyde

Chemical Property:

• Vapor Pressure: 0.013mmHg at 25°C
• Melting Point: 74-76℃
• Boiling Point: 258.819oC at 760 mmHg
• Flash Point: 110.33oC
• PSA: 17.07000
• Density: 1.698g/cm3
• LogP: 2.91500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 217.91341
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

99%, ^*data from raw suppliers

2-Bromo-6-chlorobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Br)C=O)Cl
• Uses: 2-Bromo-6-chlorobenzaldehyde plays an important role as a linker, which provides higher selectivity and reactivity in the Buchwald C-N bond forming reaction in order to prepare Bruton's tyrosine kinase inhibitor.

Technology Process of 2-Bromo-6-chlorobenzaldehyde

There total 6 articles about 2-Bromo-6-chlorobenzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

ortho-bromobenzaldehyde (6630-33-7) → 2-bromo-6-chlorobenzaldehyde (64622-16-8)

Guidance literature:

With N-chloro-succinimide; palladium diacetate; silver trifluoroacetate; anthranilic acid; trifluoroacetic acid; In 1,2-dichloro-ethane; at 60 ℃; for 24h; Sealed tube;

DOI:10.1021/jacs.6b11188

Reference yield: 96.0%

2-chloro-benzaldehyde (89-98-5) → 2-bromo-6-chlorobenzaldehyde (64622-16-8)

Guidance literature:

With N-Bromosuccinimide; palladium diacetate; silver trifluoroacetate; toluene-4-sulfonic acid; trifluoroacetic acid; 4-Nitroanthranilic acid; In 1,2-dichloro-ethane; at 90 ℃; for 24h; Sealed tube;

DOI:10.1021/jacs.6b11188

Reference yield: 87.0%

1-bromo-3-chlorobenzene (108-37-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-bromo-6-chlorobenzaldehyde (64622-16-8)

Guidance literature:

1-bromo-3-chlorobenzene; With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃;

N,N-dimethyl-formamide; In tetrahydrofuran; water; Acidic conditions;

DOI:10.1021/op4001077

upstream raw materials:

2-bromo-6-chlorotoluene

1-bromo-3-chlorobenzene

N,N-dimethyl-formamide

2-chloro-benzaldehyde

Downstream raw materials:

3-chloro-2-carbaldehyde phenylboronic acid

1-bromo-3-chloro-2-(2,2-dibromovinyl)benzene

Refernces

• 1、 Yong, Qiyun,Sun, Bing,Zhang, Fang-Lin. "Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy". supporting information. . Retrieved 2019/11/03.
• 2、 Dou?ová, Hana,R??i?ková, Zdeňka,?im?nek, Petr. "Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling". supporting information. p. 670 - 684. Retrieved 2018/01/22.