4-Bromobenzylamine hydrochloride

4-Bromobenzylamine hydrochloride Property

Melting point:

274-276 °C(lit.)

refractive index 

1,5855-1,5875

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Soluble in water.

Sensitive 

Hygroscopic

BRN 

3693458

InChI

InChI=1S/C7H8BrN.ClH/c8-7-3-1-6(5-9)2-4-7;/h1-4H,5,9H2;1H

InChIKey

BVYUYDBWQMSOKM-UHFFFAOYSA-N

SMILES

C1(CN)=CC=C(Br)C=C1.Cl

CAS DataBase Reference

26177-44-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-21/22

Safety Statements 

26-37/39-36/37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29214900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Bromobenzylamine hydrochloride Chemical Properties,Usage,Production

Chemical Properties

OFF-WHITE TO BEIGE CRYSTALLINE POWDER

Uses

4-Bromobenzylamine hydrochloride is used to study the characteristics of C-terminal polyamine modification in the presence of protease and amine. Further, it is used to prepare 1-(4-Brombenzyl)-pyrrole by reacting with 2,5-dimethoxy-tetrahydro-furan.

Synthesis

General procedure: in a glove box, to a flame-dried GLC vial fitted with a magnetic stirring bar was added [3a] + [BArF4]? (1.0 mol%) and Me2PhSiH(2a) (2.1 or 5.0 equivalents). The specified 4-bromobenzonitrile was added to the glove box (in case of solid material) or via a microsyringe outside the glove box. The resulting reaction mixture was kept at room temperature for the indicated time. Upon completion of the reaction, a mixture of cyclohexane and tert-butyl methyl ether (90:10) containing 4% Et3N (0.5 mL) was added to quench the reaction. The resulting solution was filtered through a diatomaceous earth pad coated with a small amount of silica gel, and a solution of cyclohexane and tert-butyl methyl ether (90:10) containing 4% Et3N (3-4 mL) was used as the eluent. The solvent was removed under reduced pressure and the residue was dissolved in Et2O (1 mL), followed by the addition of HCl (2M in Et2O, 1.0 mL, 2.0 mmol, 10 equiv). The resulting suspension was stirred for 1 h and filtered to give 4-bromobenzylamine hydrochloride as a white to yellow solid.

References

[1] Synlett, 2017, vol. 28, # 18, p. 2411 - 2414
[2] Tetrahedron, 2014, vol. 70, # 4, p. 975 - 983
[3] Tetrahedron Letters, 2009, vol. 50, # 50, p. 7005 - 7007
[4] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8809 - 8814
[5] ACS Catalysis, 2018, vol. 8, # 10, p. 9125 - 9130