From b6d32d96616761af575f69ed7ff02dde0def2a20 Mon Sep 17 00:00:00 2001
From: Patrick Hoefler <61934744+phofl@users.noreply.github.com>
Date: Fri, 24 Mar 2023 17:55:14 -0400
Subject: [PATCH] Backport PR #52180: BUG: to_sql raises when arrow dtype has
 missing values

---
 pandas/core/arrays/arrow/array.py |  2 +-
 pandas/tests/io/test_sql.py       | 16 ++++++++++++++++
 2 files changed, 17 insertions(+), 1 deletion(-)

diff --git a/pandas/core/arrays/arrow/array.py b/pandas/core/arrays/arrow/array.py
index 390eb33d6eefe..81d8183a79bc1 100644
--- a/pandas/core/arrays/arrow/array.py
+++ b/pandas/core/arrays/arrow/array.py
@@ -2077,7 +2077,7 @@ def _dt_round(
     def _dt_to_pydatetime(self):
         data = self._data.to_pylist()
         if self._dtype.pyarrow_dtype.unit == "ns":
-            data = [ts.to_pydatetime(warn=False) for ts in data]
+            data = [None if ts is None else ts.to_pydatetime(warn=False) for ts in data]
         return np.array(data, dtype=object)
 
     def _dt_tz_localize(
diff --git a/pandas/tests/io/test_sql.py b/pandas/tests/io/test_sql.py
index 40cd011a1dd62..2504794384038 100644
--- a/pandas/tests/io/test_sql.py
+++ b/pandas/tests/io/test_sql.py
@@ -570,6 +570,22 @@ def test_dataframe_to_sql_arrow_dtypes(conn, request):
         df.to_sql("test_arrow", conn, if_exists="replace", index=False)
 
 
+@pytest.mark.db
+@pytest.mark.parametrize("conn", all_connectable)
+def test_dataframe_to_sql_arrow_dtypes_missing(conn, request, nulls_fixture):
+    # GH 52046
+    pytest.importorskip("pyarrow")
+    df = DataFrame(
+        {
+            "datetime": pd.array(
+                [datetime(2023, 1, 1), nulls_fixture], dtype="timestamp[ns][pyarrow]"
+            ),
+        }
+    )
+    conn = request.getfixturevalue(conn)
+    df.to_sql("test_arrow", conn, if_exists="replace", index=False)
+
+
 @pytest.mark.db
 @pytest.mark.parametrize("conn", all_connectable)
 @pytest.mark.parametrize("method", [None, "multi"])