4-Bromoaniline

Base Information

• Chemical Name: 4-Bromoaniline
• CAS No.: 106-40-1
• Molecular Formula: C6H6BrN
• Molecular Weight: 172.024
• Hs Code.: 29214210
• European Community (EC) Number: 203-393-9
• ICSC Number: 1226
• NSC Number: 7085
• UN Number: 2811
• UNII: 0RR61TC330
• DSSTox Substance ID: DTXSID7021867
• Nikkaji Number: J47.028G
• Wikipedia: 4-Bromoaniline
• Wikidata: Q412773
• ChEMBL ID: CHEMBL57376
• Mol file: 106-40-1.mol

Synonyms:4-bromoaniline;4-bromoaniline conjugate acid;4-bromoaniline hydrochloride;4-bromoaniline monophosphate salt;p-bromoaniline

Chemical Property of 4-Bromoaniline

Chemical Property:

• Appearance/Colour: brown crystals
• Vapor Pressure: 0.0843mmHg at 25°C
• Melting Point: 56-62 °C(lit.)
• Refractive Index: 1.5680 (estimate)
• Boiling Point: 225.9 °C at 760 mmHg
• PKA: 3.86(at 25℃)
• Flash Point: 90.4 °C
• PSA: 26.02000
• Density: 1.594 g/cm³
• LogP: 2.61250
• Storage Temp.: Store below +30°C.
• Solubility.: ethanol: soluble0.5g/10 mL, clear, colorless to almost colorless
• Water Solubility.: <0.1 g/100 mL at 23℃
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 170.96836
• Heavy Atom Count: 8
• Complexity: 66.9
• Transport DOT Label: Poison

Purity/Quality:

>99% ^*data from raw suppliers

4-Bromoaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R36/37/38:
• Safety Statements: S26:; S36/37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC(=CC=C1N)Br
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in the formation of methaemoglobin.
• Uses: 4-Bromoaniline is a brominated aniline used as a building block in the preparation or pharmaceutial and organic compounds. In preparation of azo dyes; condensed with formaldehyde in preparation of dihydroquinazolines. 4-Bromoaniline is used as a precursor in the production of azo dyes and dihydroquinazolines. It is also used as carbon and nitrogen supplement in the culture medium of Moraxella sp. strain G. Further, it is employed in the preparation of para-bromobiphenyl through Gomberg-Bachmann reaction. In addition to this, it is used as a building block in the preparation or pharmaceutical and organic compounds.

Technology Process of 4-Bromoaniline

There total 270 articles about 4-Bromoaniline 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: 93.0%

C24H19AsBrClN2 (120261-37-2) → diphenylarsinic acid (4656-80-8) + o-chloroaniline (95-51-2) + 4-bromo-aniline (106-40-1)

Guidance literature:

With water;

Reference yield: 87.0%

aniline (62-53-3) → 4-bromo-aniline (106-40-1) + 2-bromoaniline (615-36-1)

Guidance literature:

With dihydrogen peroxide; potassium bromide; In water; acetonitrile;

DOI:10.1016/j.poly.2012.09.036

Reference yield: 60.0%

7-methyl-1,2,3,4-tetrahydroquinoline (58960-03-5) + para-nitrophenyl bromide (586-78-7) → 7-methylquinoline (612-60-2) + 4-bromo-aniline (106-40-1)

Guidance literature:

With nickel-nitrogen-doped carbon framework; In water; at 145 ℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/c9gc04358f

upstream raw materials:

O-Methylhydroxylamin

(4-bromophenyl)magnesium bromide

N-benzyloxyamine

4-Bromobenzoic acid

Downstream raw materials:

2-(4-bromophenylamino)ethan-1-ol

N-(4-bromophenyl)-4,6-dimethyl-2-pyrimidinamine

N⁴-(4-bromo-phenyl)-6-methyl-pyrimidine-2,4-diamine

3-[(4-bromophenyl)amino]-3-oxopropanoic acid

Refernces

• 1、 Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.. "Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones". . p. 6001 - 6009. Retrieved 2019.
• 2、 Liu, Yang-Yang,Wu, Chuan-De,Zhan, Guo-Peng. "In situcreation of multi-metallic species inside porous silicate materials with tunable catalytic properties". . p. 6185 - 6188. Retrieved 2021.
• 3、 Shankaraiah, Nagula,Markandeya, Nagula,Espinoza-Moraga, Marlene,Arancibia, Claudia,Kamal, Ahmed,Santos, Leonardo Silva. "One-pot microwave-assisted selective azido reduction/tandem cyclization in condensed and solid phase with nickel boride". . p. 2163 - 2170. Retrieved 2009.
• 4、 Hahn, Gabriela,Ewert, Julia-Katharina,Denner, Christine,Tilgner, Dominic,Kempe, Rhett. "A Reusable Mesoporous Nickel Nanocomposite Catalyst for the Selective Hydrogenation of Nitroarenes in the Presence of Sensitive Functional Groups". . p. 2461 - 2465. Retrieved 2016.
• 5、 Cerichelli, Giorgio,Luchetti, Luciana,Mancini, Giovanna. "SURFACTANT CONTROL OF THE ORTHO/PARA RATIO IN THE BROMINATION OF ANILINES". . p. 6209 - 6210. Retrieved 1989.
• 6、 Zeynizadeh, Behzad,Setamdideh, Davood. "NaBH4/charcoal: A new synthetic method for mild and convenient reduction of nitroarenes". . p. 2699 - 2704. Retrieved 2006.
• 7、 Han,Jang. "Montmorillonite catalyzed reduction of nitroarenes with hydrazine". . p. 1181 - 1182. Retrieved 1990.
• 8、 Ramdar, Moosa,Kazemi, Foad,Kaboudin, Babak. "A photocatalytic green system for chemoselective reduction of nitroarenes". . p. 1155 - 1163. Retrieved 2017.
• 9、 Jiang, Xuefeng,Li, Yiming,Lu, Lingling. "Visible-light-promoted oxidative halogenation of (hetero)arenes". . p. 5989 - 5994. Retrieved 2020.
• 10、 Wu, George,Huang, Mingsheng,Richards, Monique,Poirier, Marc,Wen, Xin,Draper, Richard W.. "Novel ZnX2-modulated Pd/C and Pt/C catalysts for chemoselective hydrogenation and hydrogenolysis of halogen-substituted nitroarenes, alkenes, benzyl ethers, and aromatic ketones". . p. 1657 - 1660. Retrieved 2003.