Tear gas and rubber bullets have been fired during violent clashes outside Hong Kong's parliament as protesters stormed the building.
Angry demonstrators confronted police as anger grows over plans to allow extradition to mainland China.
Dramatic video shows tear gas being fired at crowds after bricks and bottles were reportedly hurled at riot police.
Protesters – mostly dressed in black – charged police with umbrellas, and ambulances were seen heading toward the protest area.
Masked demonstrators have been in a stand-off with authorities for days, with thousands blocking access to government buildings.
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This morning a debate on the controversial extradition bill was postponed after a number of politicians failed to arrive.
Despite calls to disperse, defiant demonstrators said they will not stop until the bill is withdrawn.
Hong Kong's Legislative Council (LegCo) is widely expected to allow extradition to the mainland on June 20 – a move critics warn could be used to target dissidents.
Tens of thousands of protesters had gathered peacefully in the Chinese-ruled city before tempers flared, some charging police with umbrellas.
Police warned them back, saying: "We will use force."
On Sunday, activists claim a million people took to the street to protest against the controversial proposals, which would see suspected criminals extradited to China.
Authorities claim the move is necessary after a man accused of murdering his pregnant girlfriend in Taiwan fled to Hong Kong.
The protesters, most of them young people dressed in black, put up barricades in preparation for a long demonstration.
Similar pro-democracy protests by the Occupy campain gridlocked the former British colony in 2014.
Protesters rallied in and around Lung Wo Road, a main east-west artery near the offices of embattled Hong Kong Chief Executive Carrie Lam.
Hundreds of armed riot police, some with plastic shields, warned them to stop advancing.
"Didn't we say at the end of the Umbrella movement we would be back?" pro-democracy lawmaker Claudia Mo said – referring to the name often used for the "Occupy" demonstrations, whose trademark was the yellow umbrella.
"Now we are back!" she said as supporters echoed her words.
The government said debate on the bill that was due to take place in the city's 70-seat Legislative Council on Wednesday would be delayed until further notice.
The legislature is controlled by a pro-Beijing majority.
"We won't leave till they scrap the law," one young man wearing a black mask and gloves told Reuters.
"Carrie Lam has underestimated us. We won't let her get away with this."
Businesses have closed in solidarity with the protesters, while hotels have opened their doors to allow demonstrators to shower and sleep.
More than 4,000 teachers have said they will strike.
The Hong Kong National Front has threatened to storm the legislative council and remain there "indefinitely" until the bill is withdrawn.
Hong Kong's government has claimed legally binding safeguards to prevent human rights abuses by China have been secured.
Beijing has been accused of torture and obtaining forced confessions by activists.
Hong Kong was a British colony between 1841 and 1997, when sovereignty was returned to China.
It has its own judicial system, government and currency, and basic human rights are protected under the mini-constitution established at the time.
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