diff --git a/prism/diagnostic.c b/prism/diagnostic.c
index bf89ca781a..815a2b2a6c 100644
--- a/prism/diagnostic.c
+++ b/prism/diagnostic.c
@@ -261,6 +261,7 @@ static const pm_diagnostic_data_t diagnostic_messages[PM_DIAGNOSTIC_ID_LEN] = {
     [PM_ERR_RESCUE_TERM]                        = { "expected a closing delimiter for the `rescue` clause", PM_ERROR_LEVEL_FATAL },
     [PM_ERR_RESCUE_VARIABLE]                    = { "expected an exception variable after `=>` in a rescue statement", PM_ERROR_LEVEL_FATAL },
     [PM_ERR_RETURN_INVALID]                     = { "invalid `return` in a class or module body", PM_ERROR_LEVEL_FATAL },
+    [PM_ERR_SINGLETON_FOR_LITERALS]             = { "cannot define singleton method for literals", PM_ERROR_LEVEL_FATAL },
     [PM_ERR_STATEMENT_ALIAS]                    = { "unexpected an `alias` at a non-statement position", PM_ERROR_LEVEL_FATAL },
     [PM_ERR_STATEMENT_POSTEXE_END]              = { "unexpected an `END` at a non-statement position", PM_ERROR_LEVEL_FATAL },
     [PM_ERR_STATEMENT_PREEXE_BEGIN]             = { "unexpected a `BEGIN` at a non-statement position", PM_ERROR_LEVEL_FATAL },
diff --git a/prism/diagnostic.h b/prism/diagnostic.h
index 33123262b5..8f09fb9099 100644
--- a/prism/diagnostic.h
+++ b/prism/diagnostic.h
@@ -259,6 +259,7 @@ typedef enum {
     PM_ERR_RESCUE_TERM,
     PM_ERR_RESCUE_VARIABLE,
     PM_ERR_RETURN_INVALID,
+    PM_ERR_SINGLETON_FOR_LITERALS,
     PM_ERR_STATEMENT_ALIAS,
     PM_ERR_STATEMENT_POSTEXE_END,
     PM_ERR_STATEMENT_PREEXE_BEGIN,
diff --git a/prism/prism.c b/prism/prism.c
index aaa0035104..2f54e9ee93 100644
--- a/prism/prism.c
+++ b/prism/prism.c
@@ -2743,6 +2743,45 @@ pm_constant_write_node_create(pm_parser_t *parser, pm_constant_read_node_t *targ
     return node;
 }
 
+/**
+ * Check if the receiver of a `def` node is allowed.
+ */
+static void
+pm_check_def_receiver(pm_parser_t *parser, pm_node_t *receiver) {
+    switch (receiver->type) {
+        case PM_BEGIN_NODE: {
+            pm_begin_node_t *begin_node = (pm_begin_node_t *)receiver;
+            pm_check_def_receiver(parser, (pm_node_t *) begin_node->statements);
+            break;
+        }
+        case PM_PARENTHESES_NODE:
+            pm_check_def_receiver(parser, ((pm_parentheses_node_t *) receiver)->body);
+            break;
+        case PM_STATEMENTS_NODE: {
+            pm_statements_node_t *statements_node = (pm_statements_node_t *)receiver;
+            pm_check_def_receiver(parser, statements_node->body.nodes[statements_node->body.size - 1]);
+            break;
+        }
+        case PM_ARRAY_NODE:
+        case PM_FLOAT_NODE:
+        case PM_IMAGINARY_NODE:
+        case PM_INTEGER_NODE:
+        case PM_INTERPOLATED_REGULAR_EXPRESSION_NODE:
+        case PM_INTERPOLATED_STRING_NODE:
+        case PM_INTERPOLATED_SYMBOL_NODE:
+        case PM_INTERPOLATED_X_STRING_NODE:
+        case PM_RATIONAL_NODE:
+        case PM_REGULAR_EXPRESSION_NODE:
+        case PM_SOURCE_ENCODING_NODE:
+        case PM_SOURCE_FILE_NODE:
+        case PM_SOURCE_LINE_NODE:
+        case PM_STRING_NODE:
+        case PM_SYMBOL_NODE:
+        case PM_X_STRING_NODE:
+            pm_parser_err_node(parser, receiver, PM_ERR_SINGLETON_FOR_LITERALS);
+    }
+}
+
 /**
  * Allocate and initialize a new DefNode node.
  */
@@ -2771,6 +2810,10 @@ pm_def_node_create(
         end = end_keyword->end;
     }
 
+    if ((receiver != NULL) && PM_NODE_TYPE_P(receiver, PM_PARENTHESES_NODE)) {
+        pm_check_def_receiver(parser, receiver);
+    }
+
     *node = (pm_def_node_t) {
         {
             .type = PM_DEF_NODE,
diff --git a/test/prism/errors_test.rb b/test/prism/errors_test.rb
index 62e72ea16a..c65fff5167 100644
--- a/test/prism/errors_test.rb
+++ b/test/prism/errors_test.rb
@@ -2087,6 +2087,52 @@ module Prism
       assert_errors expression(source), source, errors, compare_ripper: false
     end
 
+    def test_singleton_method_for_literals
+      source = <<~'RUBY'
+        def (1).g; end
+        def ((a; 1)).foo; end
+        def ((return; 1)).bar; end
+        def (((1))).foo; end
+        def (__FILE__).foo; end
+        def (__ENCODING__).foo; end
+        def (__LINE__).foo; end
+        def ("foo").foo; end
+        def (3.14).foo; end
+        def (3.14i).foo; end
+        def (:foo).foo; end
+        def (:'foo').foo; end
+        def (:'f{o}').foo; end
+        def ('foo').foo; end
+        def ("foo").foo; end
+        def ("#{fo}o").foo; end
+        def (/foo/).foo; end
+        def (/f#{oo}/).foo; end
+        def ([1]).foo; end
+      RUBY
+      errors = [
+        ["cannot define singleton method for literals", 5..6],
+        ["cannot define singleton method for literals", 24..25],
+        ["cannot define singleton method for literals", 51..52],
+        ["cannot define singleton method for literals", 71..72],
+        ["cannot define singleton method for literals", 90..98],
+        ["cannot define singleton method for literals", 114..126],
+        ["cannot define singleton method for literals", 142..150],
+        ["cannot define singleton method for literals", 166..171],
+        ["cannot define singleton method for literals", 187..191],
+        ["cannot define singleton method for literals", 207..212],
+        ["cannot define singleton method for literals", 228..232],
+        ["cannot define singleton method for literals", 248..254],
+        ["cannot define singleton method for literals", 270..277],
+        ["cannot define singleton method for literals", 293..298],
+        ["cannot define singleton method for literals", 314..319],
+        ["cannot define singleton method for literals", 335..343],
+        ["cannot define singleton method for literals", 359..364],
+        ["cannot define singleton method for literals", 380..388],
+        ["cannot define singleton method for literals", 404..407]
+      ]
+      assert_errors expression(source), source, errors, compare_ripper: false
+    end
+
     private
 
     def assert_errors(expected, source, errors, compare_ripper: RUBY_ENGINE == "ruby")