In this paper we study natural generalizations of the first order Calderón commutator in higher dimensions d≥2. We study the bilinear operator Tm which is given byTm(f,g)(x):=∬R2d[∫01m(ξ+tη)dt]fˆ(ξ)gˆ(η)e2πix⋅(ξ+η)dξdη. Our results are obtained under two different conditions of the multiplier m. The first result is that when K∈S′∩Lloc1(Rd∖{0}) is a regular Calderón-Zygmund convolution kernel of regularity 0<δ≤1, TKˆ maps Lp(Rd)×Lq(Rd) into Lr(Rd) for all 1<p,q≤∞, 1r=1p+1q as long as r>dd+1. The second result is that when the multiplier m∈Cd+1(Rd∖{0}) satisfies the Hörmander derivative conditions|∂ξαm(ξ)|≤Dα|ξ|−|α| for all ξ≠0, and for all multi-indices α with |α|≤d+1, Tm maps Lp(Rd)×Lq(Rd) into Lr(Rd) for all 1<p,q≤∞, 1r=1p+1q as long as r>dd+1. These two results are sharp except for the endpoint case r=dd+1. In case d=1 and K(x)=1/x, it is well-known that TKˆ maps Lp(R)×Lq(R) into Lr(R) for 1<p,q≤∞, 1r=1p+1q as long as r>1/2. In higher dimensional case d≥2, in 2016, when Kˆ(ξ)=ξj/|ξ|d+1 is the Riesz multiplier on Rd, P. W. Fong, in his Ph.D. Thesis [9], obtained‖TKˆ(f,g)‖r≤C‖f‖p‖g‖q for 1<p,q≤∞ as long as r>d/(d+1). As far as we know, except for this special case, there has been no general results for the off-diagonal case r<1 in higher dimensions d≥2. To establish our results we develop ideas of C. Muscalu and W. Schlag [18,19] with new methods.