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9-Bromoanthracene

9-Bromoanthracene structure

CAS No:
1564-64-3
Formula:
C14H9Br
Chemical Name:
9-Bromoanthracene
Synonyms:
Anthracene,9-bromo-;9-Bromoanthracene;9-Anthracyl bromide;NSC 803;9-Anthracenyl bromide;10-Bromoanthracene;2417309-91-0
Categories:
Organic Chemistry > Hydrocarbons and Derivatives

Description

white to light yellow crystal powder9-bromoanthracene is a kind of bromine-derived anthracene. It is known to be able to reversibly photodimerize in a head-to tail fashion upon irradiation by long-wavelength ultraviolet light. The photodimers of 9-bromoanthracene are suitable to be used as alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions. It is also used as the intermediate for the preparation of the 9-substitued form of the polycyclic aromatic hydrocarbon (P

9-Bromoanthracene Basic Attributes

Molecular Weight：

257.13

Exact Mass：

257.13

BRN：

1869747

EC Number：

216-359-3

UNII：

4KA5657H57

NSC Number：

803

DSSTox ID：

DTXSID6049224

HScode：

29049090

Characteristics

PSA：

XLogP3：

5.2

Appearance：

Yellow Powder

Density：

1.4251 (rough estimate)

Melting Point：

99-101 °C

Boiling Point：

212-215 °C @ Press: 4 Torr

Flash Point：

190.3±13.7 °C

Refractive Index：

1.6404 (estimate)

Water Solubility：

Insoluble in water.

Storage Conditions：

0-6°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

22-24/25

Marks：

Hazard note：

Irritant

Precautionary statement(s)：

P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (66.67%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

9-Bromoanthracene Use and Manufacturing

anthracene(356mg, 2mmol), potassium bromide (143mg, 1.2mmol), A mixed solution of 9 ml of acetic acid, 1 ml of water, and 5 ml of methylene chloride was sequentially added to a three-necked flask equipped with a condenser and a thermometer, and transferred to a thermostatically heated magnetic stirring water bath.The ZnAl-BrO3-LDHs (1.8 g, 1.8 mmol) were slowly added in batches over 15 min. The reaction temperature was controlled at 40 °C. The TCL was followed by the progress of the reaction. After 5 h, the solution was washed with sodium sulfite solution, followed by dichloromethane (3× 10ml) extraction, combined organicPhase, add two scoops of column chromatography silica gel (200-300 mesh) in methylene chloride phase, and evaporate the organic solvent under vacuum to passColumn chromatography (petroleum ether:ethyl acetate = 15:1 as eluent) was isolated to give 468 mg of the desired product. Light yellow solid, yield91percent.A thermometer was placed on a 500-ml three-necked round bottom flask and 8.9 g (50 mmol) of hydrazine and 200 ml of dichloromethane were added.After cooling to zero degrees Celsius, a solution of 40percent hydrobromic acid (17.6 ml, 60 mmol) was added. After stirring evenly, 5 ml (50 mmol) of hydrogen peroxide (30percent) was added dropwise over 15 minutes. After completion of the addition, the solution was incubated for 30 minutes, and then warmed to room temperature and stirred for 12 hours.The reaction solution was washed with water, dried and spin-dried. 60 ml of dioxane was added to the solid.After filtration, the filtrate was concentrated and added to methanol to precipitate a pale yellow solid, 9-bromoanthraquinone, 11.6 g, yield 91percent.Into a 250 mL two-neck round bottom flask was added 8.9 g (50 mmol) of hydrazine.Then 200mL of dichloromethane was added to dissolve. After stirring for 30min, 22.7mL of 40percent hydrobromic acid was added. The temperature of the ice bath was controlled at 10-15°C. A constant pressure dropping funnel was added dropwise with 5mL of 30percent aqueous hydrogen peroxide solution. Warm to room temperature and continue stirring magnetically. About 19 hours were completed. The reaction solution was washed with water and the organic phase was dried over anhydrous magnesium sulfate, filtered, and spin-dried. The spin-dried solid was added to 35 mL of 1, 4-dioxane, filtered, and the filtrate was concentrated. Concentration to 10 mL was carried out. Carefully, anhydrous methanol was added to precipitate a yellow solid to give 9-bromoanthraquinone.

Computed Properties

Molecular Weight:257.12
XLogP3:5.2
Exact Mass:255.98876
Monoisotopic Mass:255.98876
Heavy Atom Count:15
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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