4-Bromo-N,N-dimethylaniline

Base Information

• Chemical Name: 4-Bromo-N,N-dimethylaniline
• CAS No.: 586-77-6
• Deprecated CAS: 508191-89-7
• Molecular Formula: C8H10BrN
• Molecular Weight: 200.078
• Hs Code.: 29214290
• European Community (EC) Number: 209-582-2
• NSC Number: 8056
• UNII: K49ZS2E9KX
• DSSTox Substance ID: DTXSID2060414
• Nikkaji Number: J55.361A
• Wikidata: Q72454838
• ChEMBL ID: CHEMBL3098160
• Mol file: 586-77-6.mol

Synonyms:4-Bromo-N,N-dimethylaniline;586-77-6;4-Dimethylaminobromobenzene;N,N-Dimethyl-p-bromoaniline;p-Bromo-N,N-dimethylaniline;Benzenamine, 4-bromo-N,N-dimethyl-;N,N-Dimethyl-4-bromoaniline;1-Bromo-4-(dimethylamino)benzene;p-(Dimethylamino)phenyl bromide;p-Dimethylaminobromobenzene;p-Bromo(dimethylamino)benzene;p-N,N-Dimethylaminobromobenzene;4-(Dimethylamino)phenyl bromide;Aniline, p-bromo-N,N-dimethyl-;ANILINE, 4-BROMO-N,N-DIMETHYL-;NSC 8056;MFCD00000093;EINECS 209-582-2;N-(4-bromophenyl)-N,N-dimethylamine;K49ZS2E9KX;NSC-8056;(4-bromophenyl)dimethylamine;4-bromo-n,n-dimethyl aniline;4-bromo-N,N-dimethyl-aniline;(4-bromo-phenyl)-dimethyl-amine;UNII-K49ZS2E9KX;4-dimethylaminophenyl bromide;SCHEMBL59844;WLN: ER DN1&1;4-dimethylamino-1-bromobenzene;4-Bromo-N,N-dimethylbenzenamine;CHEMBL3098160;DTXSID2060414;NSC8056;BCP30666;4-Bromo-N,N-dimethylaniline, 97%;AKOS005256709;CS-W010495;SB77477;AC-22962;DS-14421;LS-19611;SY013736;A8294;AM20060845;B0585;FT-0617904;EN300-19549;D70593;AC-509/25001966;W-105368;F9995-1667;N,N-Dimethyl-p-bromoaniline pound>>4-Dimethylaminobromobenzene pound>>p-Bromo-N,N-dimethylaniline

Chemical Property of 4-Bromo-N,N-dimethylaniline

Chemical Property:

• Appearance/Colour: white to light grey powder
• Vapor Pressure: 0.00996mmHg at 25°C
• Melting Point: 52-54 °C(lit.)
• Refractive Index: 1.586
• Boiling Point: 264 °C at 760 mmHg
• PKA: 4.23(at 25℃)
• Flash Point: 104.7 °C
• PSA: 3.24000
• Density: 1.393 g/cm³
• LogP: 2.51510
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 198.99966
• Heavy Atom Count: 10
• Complexity: 95.4

Purity/Quality:

99% ^*data from raw suppliers

4-Bromo-N- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/38-33-22
• Safety Statements: 26-36-45-37-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CN(C)C1=CC=C(C=C1)Br
• Uses: 4-Bromo-N,N-dimethylaniline is used as an internal standard in the determination of iodine present as iodide (as in pharmaceuticals), iodate (as in iodized table salt) and covalently bound to organic compounds (as in milk and vegetables).

Technology Process of 4-Bromo-N,N-dimethylaniline

There total 109 articles about 4-Bromo-N,N-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: 99.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) → 4-bromo-N,N-dimethylaniline (586-77-6)

Guidance literature:

With methanol; tetraethylammonium chloride; bromine; In dichloromethane; at 35 ℃; other substituted anilines: regioselectivity of bromination;

DOI:10.1016/S0040-4039(00)60359-3

Reference yield: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-bromo-aniline (106-40-1) → 4-bromo-N,N-dimethylaniline (586-77-6)

Guidance literature:

With sodium cyanoborohydride; acetic acid; at 0 - 65 ℃; for 3.42h;

DOI:10.1021/acs.orglett.8b02318

Reference yield: 97.0%

4-Bromo-N,N-dimethylaniline N-oxide (22710-09-4) → 4-bromo-N,N-dimethylaniline (586-77-6)

Guidance literature:

With phenylboronic acid; In dichloromethane; at 20 ℃; for 0.0833333h; Reagent/catalyst; Solvent;

DOI:10.1016/j.tetlet.2017.01.051

upstream raw materials:

formaldehyd

2,4,6-tribromoaniline

5,5-dibromobarbituric acid

ethanol

Downstream raw materials:

5-bromo-2-dimethylamino-benzyl alcohol

5-bromo-2-dimethylamino-benzoic acid

1-(4-N,N-dimethylaminophenyl)propane

5-Hydroxy-5-(p-dimethylamino-phenyl)-10,11-dihydro-dibenzocyclohepten

Refernces

• 1、 Cerichelli, Giorgio,Luchetti, Luciana,Mancini, Giovanna. "Surfactant control of the ortho/para ratio in the bromination of anilines. 3". . p. 2465 - 2470. Retrieved 1996.
• 2、 Shang, Xiao,Liu, Xuan,Sun, Yujie. "Flexible on-site halogenation paired with hydrogenation using halide electrolysis". supporting information. p. 2037 - 2043. Retrieved 2021/03/26.
• 3、 Liu, Jianguo,Ma, Longlong,Song, Yanpei,Zhang, Mingyue,Zhuang, Xiuzheng. "Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions". supporting information. p. 4604 - 4617. Retrieved 2021/06/30.