| Identification | More | [Name]
4-Bromobenzyl chloride | [CAS]
589-17-3 | [Synonyms]
4-BROMO-ALPHA-CHLOROTOLUENE
4-BROMOBENZYL CHLORIDE
P-BROMOBENZYL CHLORIDE
1-Bromo-4-(chloromethyl)benzene
4-Bromobenzyl chloride/4-Bromo-alpha-chlorotoluene
4-Bromobenzylchloride,97%
Benzene, 1-bromo-4-(chloromethyl)-
4-bromo-à-chlorotoluene
α-Chloro-4-bromotoluene | [EINECS(EC#)]
209-638-6 | [Molecular Formula]
C7H6BrCl | [MDL Number]
MFCD00040867 | [Molecular Weight]
205.48 | [MOL File]
589-17-3.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow crystal powder to light yellow liqui | [Melting point ]
36-40 °C | [Boiling point ]
136-139 °C (27 mmHg) | [density ]
1.3431 (rough estimate) | [refractive index ]
1.5750 (estimate) | [Fp ]
106-107°C/10mm | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Powder and Granules | [color ]
White | [Water Solubility ]
Insoluble in water. | [Merck ]
14,1410 | [BRN ]
6123220 | [InChI]
InChI=1S/C7H6BrCl/c8-7-3-1-6(5-9)2-4-7/h1-4H,5H2 | [InChIKey]
BSIIGUGKOPPTPZ-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC=C(CCl)C=C1 | [CAS DataBase Reference]
589-17-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzene, 1-bromo-4-(chloromethyl)-(589-17-3) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R36/37:Irritating to eyes and respiratory system .
R34:Causes burns. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S25:Avoid contact with eyes . | [RIDADR ]
3261 | [WGK Germany ]
3 | [Hazard Note ]
Corrosive/Lachrymator | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29039990 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow crystal powder to light yellow liqui | [Uses]
4-Bromobenzyl chloride is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals. | [Synthesis]
General procedure for the synthesis of 4-bromobenzyl chloride from 4-bromobenzyl alcohol: 4-bromobenzyl alcohol (0.6 g, 0.6 mmol) and dichloromethane (5 mL) were added to a round bottom flask. After stirring for 10 min, oxalyl chloride or oxalyl bromide (0.6 mmol) was slowly added. The reaction mixture was magnetically stirred at room temperature. After the gas was released, 4-bromobenzyl alcohol (0.5 mmol) was added and the reaction mixture was heated to reflux. The progress of the reaction was monitored by TLC and after completion of the reaction, the mixture was cooled to room temperature and filtered. The solid on the funnel was washed with dichloromethane (3 x 10 mL), the filtrate was combined and concentrated under reduced pressure. The purity of the resulting 4-bromobenzyl chloride was confirmed by 1H NMR and 13C NMR spectral analysis. | [Purification Methods]
Crystallise the chloride from EtOH and distil it in a vacuum. [Beilstein 5 IV 832.] LACHRYMATORY. | [References]
[1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[2] Organic Letters, 2013, vol. 15, # 1, p. 108 - 111
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4016 - 4024
[4] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3434 - 3436
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064 |
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