4-Bromoaniline

4-Bromoaniline Chemical Properties
Melting point 56-62 °C (lit.)
Boiling point 230-250 °C
density 1.497
refractive index 1.5680 (estimate)
Fp 222-224°C
storage temp. Store below +30°C.
solubility ethanol: soluble0.5g/10 mL, clear, colorless to almost colorless
form crystalline
pka3.86(at 25℃)
color white to light yellow
OdorSweetish
Water Solubility <0.1 g/100 mL at 23 ºC
Merck 14,1404
BRN 742031
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, peroxides, acids, acid chlorides, acid anhydrides, chloroformates. May be air sensitive.
InChIKeyWDFQBORIUYODSI-UHFFFAOYSA-N
CAS DataBase Reference106-40-1(CAS DataBase Reference)
NIST Chemistry Reference4-Bromoaniline(106-40-1)
EPA Substance Registry Systemp-Bromoaniline (106-40-1)
Safety Information
Hazard Codes Xn
Risk Statements 21/22-36/37/38-20/21/22
Safety Statements 26-36/37-36/37/39
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS BW9280000
8-9-23
Hazard Note Harmful
TSCA Yes
HazardClass 6.1
PackingGroup III
HS Code 29214210
Hazardous Substances Data106-40-1(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 456 mg/kg LD50 dermal Rat 536 mg/kg
MSDS Information
ProviderLanguage
p-bromophenylamine English
SigmaAldrich English
ACROS English
ALFA English
4-Bromoaniline Usage And Synthesis
Chemical Propertiesbrown crystals
Uses4-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.
Uses4-Bromoaniline is a brominated aniline that is commonly used as a building block in the preparation of pharmaceutical and organic compounds. It is used in the preparation of azo dyes and is condensed with formaldehyde to prepare dihydroquinazolines. In addition, 4-Bromoaniline is also used as an intermediate in the production of other chemicals such as metobromuron, a herbicide, and resorantel, an antiparasitic agent.
Preparation4-bromoaniline can be made by reacting aniline with bromine with a protection with acetyl chloride.
Synthesis Reference(s)The Journal of Organic Chemistry, 40, p. 1867, 1975 DOI: 10.1021/jo00900a053
Synthetic Communications, 19, p. 3047, 1989 DOI: 10.1080/00397918908052699
General DescriptionP-bromoaniline is a brown solid with a sweet odor. (NTP, 1992)
Air & Water Reactions4-Bromoaniline is sensitive to prolonged exposure to air. Vapor may form highly reactive mixtures in air . Insoluble in water.
Reactivity ProfileVapor may form highly reactive mixtures in air.
Fire HazardFlash point data are not available for 4-Bromoaniline, but 4-Bromoaniline is probably combustible.
Purification MethodsCrystallise the aniline (with appreciable loss) from aqueous EtOH. The benzoyl derivative has m 204o (from EtOH). [Beilstein 12 IV 1497.]
2-BENZOYLACETANILIDE Sulfanilic acid N-Methylaniline 4-Amino-benzenesulfonic acid monosodium salt 2,5-Dibromobenzenamine 2,6-Dibromoaniline Bromobenzene 4-Aminophenylacetic acid p-Anisidine N,N-Dimethylaniline POLYANILINE Diphenylamine 4-Fluoroaniline 4-Chloroaniline p-Toluidine M-BROMOANILINE,3-BROMOANILINE,BROMOANILINE(3-) 4-Bromoaniline 4-Nitroaniline

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