Spurs submitted a £40 million offer for Conor Gallagher earlier on Friday but in the final few hours of the summer transfer window, the club have made a fresh enquiry for Chalobah.
The Chelsea defender has not featured in any of the club’s three Premier League games so far this season and was expected to leave Stamford Bridge before Friday’s 11pm deadline.
Bayern Munich had held talks with Chelsea over a deal but were unable to reach an agreement before their window closed at 5pm GMT on Friday afternoon.
According to Fabrizio Romano, Tottenham have asked Chelsea about the possibility of signing Chalobah on loan for the remainder of the season.
However, Chelsea could be reluctant to strengthen a rival and may block Spurs’ approach.
Chelsea have also received a £25m bid from Nottingham Forest for Chalobah but the 24-year-old has turned down a move to Steve Cooper’s side.
Spurs, meanwhile, are set to miss out on Gallagher after Pierre-Emile Hojbjerg failed to complete his move to Atletico Madrid on deadline day.
When asked about Gallagher’s future on Friday, Mauricio Pochettino said: ‘All players in the squad are in our plans. After is a decision of two parts of the club and the player.
‘Conor is a consistent player than can play in different positions. We are happy with him.
‘Circumstances happen in the past, we can say nothing, we can only say our feeling from day one and he has shown great commitment to the club, he was captain two days ago, he is an important player but the future I don’t know.
‘If you are the best you are going to play, even if we spend big money on a player, that is football.
‘All players in the squad know they are going to play if they deserve to play. That is the thing that is happening with the squad.
‘Just because we spent big money on a player does not mean he is guaranteed to play. We are so happy with Conor, we hope he stays with us.’
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