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479152

Sigma-Aldrich

4-Bromobenzylamine

96%

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About This Item

Linear Formula:
BrC6H4CH2NH2
CAS Number:
3959-07-7
Molecular Weight:
186.05
EC Number:
223-559-4
MDL number:
MFCD00047931
UNSPSC Code:
12352100
PubChem Substance ID:
24871602
NACRES:
NA.22

Assay

96%

bp

110-112 °C/30 mmHg (lit.)

mp

25 °C (lit.)

density

1.473 g/mL at 25 °C (lit.)

SMILES string

NCc1ccc(Br)cc1

InChI

1S/C7H8BrN/c8-7-3-1-6(5-9)2-4-7/h1-4H,5,9H2

InChI key

XRNVSPDQTPVECU-UHFFFAOYSA-N

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General description

4-Bromobenzylamine (BBA), also known as p-bromobenzylamine, is an aryl bromide. The selective formation of nitrile or imine from BBA in the presence of red copper has been reported. The formal [4+4] reaction of BBA to form 2,6,9-triazabicyclo[3.3.1]nonane derivatives has been investigated.

Application

4-Bromobenzylamine (p-Bromobenzylamine) may be used to synthesize 7-[(p-bromobenzyl)ureido]-7,8-dihydro-α-bisabolene.
It may be used to synthesize the following 4-biphenylmethylamine derivatives:
  • (4′-fluoro-4-biphenyl)methylamine
  • (4′-methoxy-4-biphenyl)methylamine
  • (2′-methoxy-4-biphenyl)methylamine
  • (3′-cyano-4-biphenyl)methylamine

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

>230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jiaqing Wang et al.
Chemical communications (Cambridge, England), 50(42), 5637-5640 (2014-04-16)
A novel, efficient, convenient and environmentally friendly approach for the synthesis of nitriles and imines from primary amines has been developed. Using commercially available red copper as the catalyst, ammonium bromide as the co-catalyst and molecular oxygen as the sole
Jing Zhuang et al.
Nanoscale, 11(31), 14553-14560 (2019-07-26)
An all-inorganic CsPbI2Br perovskite with excellent phase stability and thermal stability has been considered to be a promising candidate for photovoltaic application. However, low efficiency and high moisture sensitivity hinder its advancement. In this work, we exploit 4-bromobenzylamine hydriodate post-treatment
Silvia Galiano et al.
Bioorganic & medicinal chemistry, 15(11), 3896-3911 (2007-04-05)
We have designed and synthesized two novel series of MCH-R1 antagonists based on a substituted biphenylmethyl urea core. SAR was explored, suggesting that optimal binding with the receptor was achieved when the biphenylmethyl group and the linker were substituted on
Nitrogenous bisabolene sesquiterpenes from marine invertebrates.
Gulavita NK, et al.
The Journal of Organic Chemistry, 51(26), 5136-5139 (1986)
Efficient synthesis of 2,6,9-triazabicyclo [3.3.1] nonanes through amine-mediated formal [4+4] reaction of unsaturated imines.
Tanaka K, et al.
Tetrahedron Letters, 53(44), 5899-5902 (2012)
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