4-Bromo-3,5-dimethylaniline

Base Information

• Chemical Name: 4-Bromo-3,5-dimethylaniline
• CAS No.: 59557-90-3
• Molecular Formula: C8H10BrN
• Molecular Weight: 200.078
• Hs Code.: 2921430090
• European Community (EC) Number: 893-009-1
• DSSTox Substance ID: DTXSID00495578
• Nikkaji Number: J2.702.400I
• Wikidata: Q72454845
• Mol file: 59557-90-3.mol

Synonyms:4-bromo-3,5-dimethylaniline;59557-90-3;(4-Bromo-3,5-dimethylphenyl)amine;Benzenamine, 4-bromo-3,5-dimethyl-;4-bromo-3,5-dimethylbenzenamine;MFCD07780648;Benzenamine, 4-?bromo-?3,?5-?dimethyl-;EN300-100804;Bromo-3,5-dimethylaniline;SCHEMBL525424;4-bromo-3,5-dimethyl-aniline;AMY845;4-bromanyl-3,5-dimethyl-aniline;DTXSID00495578;OGBPXDJLNYCSJH-UHFFFAOYSA-N;4-Bromo-3,5-dimethyl-phenylamine;BDBM625957;BCP21244;4-Bromo-3 pound not5-dimethylaniline;AKOS005133404;CS-W020003;SB78466;AS-18438;SY026358;BB 0258072;FT-0683270;A832367;J-514709

Chemical Property of 4-Bromo-3,5-dimethylaniline

Chemical Property:

• Melting Point: 73-74 °C
• Boiling Point: 260.992 °C at 760 mmHg
• PKA: 4.14±0.10(Predicted)
• Flash Point: 111.644 °C
• PSA: 26.02000
• Density: 1.425 g/cm³
• LogP: 3.22930
• Storage Temp.: Room temperature.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 198.99966
• Heavy Atom Count: 10
• Complexity: 104

Purity/Quality:

98% ^*data from raw suppliers

4-Bromo-3,5-dimethylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1Br)C)N

Technology Process of 4-Bromo-3,5-dimethylaniline

There total 12 articles about 4-Bromo-3,5-dimethylaniline 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%

3,5-dimethylaminoaniline (108-69-0) → 4-bromo-3,5-dimethylaniline (59557-90-3)

Guidance literature:

3,5-dimethylaminoaniline; With acetic anhydride; triethylamine; In chloroform; at 20 ℃; for 4h;

With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 12h;

With hydrogenchloride; water; In ethanol; for 6h; Heating;

DOI:10.1021/jo049571q

Reference yield: 80.0%

N-(4-bromo-3,5-dimethylphenyl)acetamide (64835-48-9) → 4-bromo-3,5-dimethylaniline (59557-90-3)

Guidance literature:

With sodium hydroxide; In ethanol; for 6h; Heating;

DOI:10.1021/ja0177657

Reference yield:

2-Bromo-m-xylene (576-22-7) + neopentyl N-fluoro-N-(fluorosulfonyl)carbamate → 4-bromo-3,5-dimethylaniline (59557-90-3) + 3-bromo-dimethylaniline (66314-77-0)

Guidance literature:

2-Bromo-m-xylene; With 6,6'-dimethyl-2,2'-bipyridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate; calcium carbonate; In dichloromethane; for 0.166667h; Inert atmosphere; Schlenk technique;

neopentyl N-fluoro-N-(fluorosulfonyl)carbamate; In dichloromethane; at 30 - 40 ℃; for 12h; Irradiation; Inert atmosphere; Schlenk technique;

With lithium borohydride; In tetrahydrofuran; at 60 ℃; for 2h; Overall yield = 14.6 mg; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.1c13569

upstream raw materials:

2-bromo-1,3-dimethyl-5-nitrobenzene

3,5-dimethylaminoaniline

N-(4-bromo-3,5-dimethylphenyl)acetamide

2,6-dimethyl-4-nitro phenol

Downstream raw materials:

2,5-dibromo-1,3-dimethylbenzene

tert-butyl (4-bromo-3,5-dimethylphenyl)carbamate

C₂₁H₂₆BrNO

N-(4-bromo-3,5-dimethylphenyl)acetamide

Refernces

• 1、 Adachi, Akiya,Aikawa, Kohsuke,Hashimoto, Takuya,Ishibashi, Yuichiro,Oe, Yuno,Okazoe, Takashi,Tanaka, Airi,Yoshida, Ryuhei. "An N-Fluorinated Imide for Practical Catalytic Imidations". supporting information. . Retrieved 2022/02/10.
• 2、 Oubaha, Hamid,Demitri, Nicola,Rault-Berthelot, Jo?lle,Dubois, Philippe,Coulembier, Olivier,Bonifazi, Davide. "Photoactive Boron-Nitrogen-Carbon Hybrids: From Azo-borazines to Polymeric Materials". supporting information. p. 9101 - 9116. Retrieved 2019/08/12.