With the gradual completion of the split-share structure reform, private placement has gradually become the mainstream of refinancing. One of the points that the practical and theoretical circles are widely concerned about is that the private placement price is often higher than the market price at the time of the private placement. High discounts are often accompanied by the transmission of benefits, and the increase in insider information will lead to the risk of a stock market crash? This paper intends to use the data of A-share listed companies from 2006 to 2015 to empirically study the relationship between the discount on private placements and the risk of stock market crash. At the same time, this paper examines whether the degree of information asymmetry plays a regulatory role in the relationship between the discount on private placements and the risk of stock market crash. This paper provides a certain reference for the regulatory authorities to improve the relevant laws and regulations in the private placement, and to provide a certain reference for the protection of the interests of small and medium-sized investors.