| Identification | More | [Name]
2-Bromophenethylamine | [CAS]
65185-58-2 | [Synonyms]
2-BROMOPHENETHYLAMINE
BENZENEETHANAMINE, 2-BROMO-
RARECHEM AL BW 0201
2-(2-bromophenyl)ethanamine
2-bromophenylethyl amine | [Molecular Formula]
C8H10BrN | [MDL Number]
MFCD01529874 | [Molecular Weight]
200.08 | [MOL File]
65185-58-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to slightly yellow liquid | [Boiling point ]
253 °C(lit.) | [density ]
1.396 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5770(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Store under Nitrogen | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [pka]
9.52±0.10(Predicted) | [color ]
Clear colorless to slightly yellow | [Sensitive ]
Air Sensitive | [InChI]
1S/C8H10BrN/c9-8-4-2-1-3-7(8)5-6-10/h1-4H,5-6,10H2 | [InChIKey]
ITRNQMJXZUWZQL-UHFFFAOYSA-N | [SMILES]
NCCc1ccccc1Br | [CAS DataBase Reference]
65185-58-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2735 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
8 | [PackingGroup ]
Ⅱ | [HS Code ]
29214990 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to slightly yellow liquid | [Uses]
2-(2-Bromophenyl)ethylamine is used as a pharmaceutical intermediate. | [General Description]
May darken in storage | [Synthesis]
The general procedure for the synthesis of o-bromophenethylamine from o-bromobenzyl cyanide was as follows: 1 M borane-tetrahydrofuran complex (BH3-THF, 200 mL, 0.2 mol) was slowly added dropwise to a solution of 2-bromobenzyl cyanide (20.0 g, 0.1 mol) in tetrahydrofuran (THF, 100 mL) at 0 °C for 30 min. Subsequently, the reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the reaction was quenched with methanol (MeOH, 50 mL) and 6 M hydrochloric acid (HCl, 50 mL) at 0 °C, and then the mixture was heated and refluxed again for 4 hours. The reaction solution was concentrated under reduced pressure and the residue was diluted with distilled water (H2O, 300 mL) and washed with ethyl acetate (EA, 75 mL × 2). The aqueous layer was neutralized with 15% sodium hydroxide (NaOH) solution and then extracted with ethyl acetate (EA, 75 mL × 2). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford the target product o-bromophenethylamine (2a) as a yellow oil (17.4 g, 85.2% yield). High-resolution mass spectrometry (HRMS) calculated value C8H11NBr [M + H]+ 200.0069, measured value 200.0068. nuclear magnetic resonance hydrogen spectrum (1H NMR, 500 MHz, CDCl3) δ 7.58 (d, J = 8.0 Hz, 1H), 7.35-7.31 (m, 2H), 7.15 (t, J = 7.0 Hz, 1H). 2.79 (m, 4H), 1.18 (m, 2H). Nuclear magnetic resonance carbon spectrum (13C NMR, 125 MHz, DMSO-d6) δ 139.8,132.9,131.6,128.6,128.2,124.3,42.4,40.3. | [References]
[1] Journal of Organic Chemistry, 2008, vol. 73, # 24, p. 9627 - 9632
[2] Patent: US2002/198251, 2002, A1
[3] Tetrahedron, 1996, vol. 52, # 21, p. 7525 - 7546
[4] Tetrahedron, 1998, vol. 54, # 25, p. 7121 - 7126
[5] ChemCatChem, 2014, vol. 6, # 2, p. 538 - 546 |
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