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2-BROMOINDAN

2-BROMOINDAN structure

CAS No:
17623-96-0
Formula:
C9H9Br
Chemical Name:
2-BROMOINDAN
Synonyms:
2-BROMOINDAN;2-BROMO-2,3-DIHYDRO-1H-INDENE;2-BroMo-2,3-dihydroindene;β-BroMoindane;1H-Indene, 2-broMo-2,3-dihydro-
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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2-BROMOINDAN Basic Attributes

Molecular Weight：

197.07

Exact Mass：

195.98900

DSSTox ID：

DTXSID90450055

HScode：

2903999090

Characteristics

PSA：

XLogP3：

Density：

1.483±0.06 g/cm3(Predicted)

Boiling Point：

249.2±29.0 °C(Predicted)

Safety Information

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

2-BROMOINDAN Use and Manufacturing

Methods of Manufacturing

In a 250 ml dry three-necked flask, 22.0 g of bromo compound I, 0.67 g of 5percent palladium on carbon, Add ethanol 250ml, into the hydrogen, the reaction pressure control at 2.5MPa, Bromide compound I and hydrogen molar ratio of 1:50, room temperature stirring reaction 24h, The palladium carbon was recovered by filtration and the solvent was evaporated. To give 18.5 g of the oily compound II as an oil. Yield 90percent.In a 250 ml dry three-necked flask, 22.0 g of bromo compound I, 0.67 g of 5percent palladium on carbon, Add ethanol 250ml, into the hydrogen, the reaction pressure control at 2.5MPa, Bromide compound I and hydrogen molar ratio of 1:50, room temperature stirring reaction 24h, The palladium carbon was recovered by filtration and the solvent was evaporated. To give 18.5 g of the oily compound II as an oil. Yield 90percent.In a 500 ml dry three-necked flask, 21.0 g of phthalimide potassium salt, 18.5 g of bromo compound II and 250 ml of dry N, N-dimethylformamide were added.Heating to 80 C stirring reaction 6h, natural cooling to room temperature, vacuum distillation solvent was crude.The crude product was dissolved in 200 ml of ethanol, and 7.05 g of 80% hydrazine hydrate (dissolved in 50 ml of ethanol) was added dropwise at 50 C, After completion of the dropwise addition, the reaction was refluxed for 2 h, the solid was filtered off and the solid was washed twice with ethanol. The filtrate was removed under reduced pressure to give crude product.The crude product was dissolved in 100 ml of 20% dilute hydrochloric acid and stirred for 0.5 h. The aqueous layer was washed twice with 80 ml of ether, The pH of the aqueous layer was adjusted to 12-13 with 20% sodium hydroxide solution and the target product was filtered to give 11.3 g of a white solid. Yield 90.4%.

Uses

Used in the synthesis of Αtipamezole, a potential PET ligand for the α2-adrenergic receptor in the brain.

Computed Properties

Molecular Weight:197.07
XLogP3:3
Exact Mass:195.98876
Monoisotopic Mass:195.98876
Heavy Atom Count:10
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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