Wall Street resumed its sell-off Wednesday after oil hit another record and a bearish analyst report renewed concerns that General Motors could run out of cash.

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NEW YORK — Wall Street resumed its sell-off Wednesday after oil hit another record and a bearish analyst report renewed concerns that General Motors could run out of cash.

The Dow Jones industrial average fell 166.75 to 11,215.51, the lowest close since August 2006.

Microsoft, one of the 30 Dow stocks, sank 99 cents to close at $25.88 a share. Boeing, also a Dow stock, fell $1.55 to $63.90.

Broader stock indicators also posted big losses after showing gains for much of the morning. The Standard & Poor’s 500 index fell 23.39 to 1,261.52, and the technology-laden Nasdaq composite index fell 53.51 to 2,251.46.

The stock market’s pullback, which accelerated in the final hours of the week’s last full trading day, left the Dow officially in bear-market territory, with the blue chips having fallen more than 20 percent from their October highs.

The S&P is just shy of the 20 percent pullback that signals a bear market. While the Nasdaq is also in bear-market territory, it hit that mark in March, moved higher and has now returned to a bear level.

Crude oil hit a record $144.32 a barrel in after-hours trading after reaching a record settlement of $143.57, an advance of $2.60 on the New York Mercantile Exchange.

The Energy Department reported Wednesday that U.S. crude-oil supplies fell more than expected last week.

Businesses are also struggling with elevated energy costs, and demand is weakening for autos, heavy machinery and steel.

The Commerce Department said Wednesday that factory orders rose by 0.6 percent in May. The result was in line with a consensus of Wall Street economists surveyed by Thomson Financial, but was much smaller than the gain of 1.3 percent for April.

Worries that GM could go so far as to declare bankruptcy only added to investors’ worries.

The stock fell to its lowest level since September 1954 as investors shrugged off better-than-expected sales figures from June and worried about the company’s cash needs.

GM closed down $1.77, or 15.1 percent, at $9.98.